Vacation Rentals By Owner In Key West, FL

$311.45

Tumi's Time Out by AvantStay | Heart Of Old Town w/ Shared Pool

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrTumi’s Time Out is a 2-bedroom, 2-bathroom townhome in the sought-after Windward Park community. A secluded compound that is a tropical hideaway, surrounded by lush palms and balmy breezes. When you enter the gated compound, you will be greeted by a sparkling swimming pool to relax in or lounge poolside and sun the day away.brbrThe main level features an open floor plan with living room, dining area and a full kitchen to whip up your island creations. French doors lead to a sizeable private outdoor patio. The downstairs bathroom has a queen-size bed and a full bathroom with adjoining access from the living area. Upstairs the master bedroom has a king size bed with an ensuite bathroom. Relax in the cozy lounge area with vaulted ceilings overlooking the main floor. The second-floor master balcony looks down over the pool providing tropical breezes and greenery.brbrTumi’s Time Out is an ideal location in the heart of Old Town, less than 2 blocks from Duval Street. You will be able to walk to all the sites and activities that Key West is famous for. Stroll the streets for fabulous music, dining, and adventures galore, or return home at the end of the day to a private compound.brbrThe property comes complete with all the amenities desired to make this your perfect home away from home, full size washer/dryer set, all linens and towels, 1 reserved parking space, Wi-Fi, and cable TV.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- This property has been recently updated with brand-new flooring in the upstairs bedroom and fresh paint in both bedrooms.br- This home has access to a shared pool and is part of a gated community.br- Pool heat is not available between 4/1 and 10/1.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brOne assigned parking spacebrbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / Queen bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$622.35

/ Nightly

Villa

Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool

Key West, Florida, United States

Coral Palm is a lovely 3 bedroom, 3 bathroom, 2 story townhome located in the private gated community of Coral Hammock on Stock Island. The property is less than 5 miles from downtown Key West allowing you to live in a quiet tropical paradise while still being close to all that Key West has to offer.brbrEntering the property you will feel immediately at home. The first floor has an elegant living space with a dining table for six and a vibrant living room. The french doors open up to the private porch overlooking the palms with an additional outdoor dining space. There is a guest bedroom off of the main living area with two twin beds and a full bathroom just down the hall. The full kitchen is equipped with updated appliances and everything you will need for your gourmet meals.brbrBoth bedrooms on the second floor have a king bed with an en suite full bathroom. The french doors in the master bedroom open to a spacious balcony overlooking the property. The washer and dryer set in the upstairs hall also add to the convenience of the home.brbrCoral Palm is conveniently located just down the street from Hurricane Hole Restaurant and Marina where you can explore kayaking, paddle boarding, and fishing excursions. Walk to some of Key West's best restaurants including Roostica, Hog Fish Bar and Grill, Chico’s Cantina, El Siboney, Croissant De France Bakery, and The Dolphin Deli.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Pool heat is not available between 4/1 and 10/1.br- This home has access to a shared pool and is part of a gated community.br- This home also features a sleeper sofa in the downstairs living room.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrPets:br- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet. br- We LOVE pets, however- Certain breeds typically have to have an additional owner or HOA approval. If your pet falls under any typical breed restrictions (breed, size, weight) please let us know so that we can confirm!brbrParking Details:brOff-street parking is available.brBoats, Jet Skis, buses, campers, trailers, motor homes, recreating vehicles, mobile homes, and commercial vehicles are notbrallowed to park on the association property (except for deliveries).brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / King bedbrBedroom 3 / Two twin bedsbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

3

Bed

3

Bath

6

Sleeps

$305.72

/ Nightly

Private Vacation Home

Serenity by AvantStay | Guest House in Old Town w/ Shared Pool

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrLocated in Bahama Village, a quaint neighborhood in Old Town Key West, this beautifully renovated conch home is a romantic island getaway. This rental is a guest house situated in the backyard of a private residence.brbrThe guest house is a two-story cottage, with one bedroom, one bathroom, and a bonus loft space. The high ceilings allow for the bright Key West sun to shine throughout this charming cottage. There is a full kitchen with hand-painted cabinets, marble counters, a dishwasher, a range, and a microwave.brbrMagnificent glass doors on both sides of the cottage open to a luscious tropical garden with a shared pool on the property. The backyard offers a secluded space for you to unwind on the lounge chairs, relax in the heated pool, or cool off in the open outdoor shower. The living spaces in and around this cottage really allow you to enjoy the laid-back, calming vibe that this home delivers. Serenity fully encompasses its meaning in this perfect backyard oasis.brbrPerfect for couples looking for a romantic retreat. This cottage is just 3 blocks from Duval Street allowing for you to be both close to the action yet hidden from the outer world.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- This guest home has access to a shared pool.br- Pool heat is not available between 4/1 and 10/1.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$284.77

/ Nightly

Private Vacation Home

Lazy Gecko by AvantStay | Walk to Duval St in Key West! | Month Long Stays Only

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrGrab your bike and head for some fresh seafood at the Historic Seaport. Walk four blocks to bustling Duval Street to find the perfect t-shirt or enjoy a cold brew and people watch at a street view table. Check out the history and architecture of Old Town. All these options and many more are yours while staying at the charming Lazy Gecko.brbrLocated in a large historic home surrounded by a white picket fence, this recently remodeled 2 bed/1.5 bath downstairs condo offers the best of all worlds. Enter from a quiet lane into the newly painted and furnished living/dining/kitchen space. Lots of windows and French doors let in the abundant sunshine and lead to a private courtyard – a perfect spot to enjoy your morning coffee. Shiny hardwood floors add to the urban feel.brbrBehind another set of French doors is the master queen bedroom, decorated in low-key pastels with a unique bathroom en-suite. The tucked away, crisp hall bathroom has access to the tub/shower through its own private door and is appointed with white cabinetry. Spiral stairs lead you up to the guest queen bedroom, offering lots of privacy at night.brbrA gleaming kitchen with appliances and a granite counter has everything you'll need in your home away from home. The Lazy Gecko - your perfect location to explore the Conch Republic!brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- This home features a sleeper sofa for additional sleeping options.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brStreet parking only.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Queen bedbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$188.99

/ Nightly

Private Vacation Home

Bogey's Retreat by AvantStay | Golfer's Retreat w/ Shared Pool! |

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrWelcome to your home away from home in Key West. This lovely townhome is located in the Key West Golf Club Community and allows you to enjoy all that Key West has to offer while staying in a relaxing environment.brbrBogey's Retreat offers a cozy, comfortable vacation home, updated from top to bottom with new stainless kitchen appliances, beds, and furnishings. When you're not out on Duval Street, enjoy all the comforts of the home like lounging in the backyard or patio.brbrTwo bedrooms located on the 2nd floor can accommodate 4 guests. The rear bedroom with a queen bed overlooks the golf course, while the front guest bedroom with a full-size bed has French doors opening to its sunny balcony. The full bathroom is upstairs located between the two bedrooms.brbrThe fully stocked kitchen and BBQ grill offer to dine any way you like in your home away from home. A few doors away from the community pool and clubhouse make this the perfect location for a month (or two) of peace and serenity. But you're still only a short drive to Old Town Key West with all its exciting site-seeing and dining opportunities. Enjoy the additional outdoor space on your wrap-around porch and large bricked patio that this home has to offer.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- This home has access to a shared pool and is part of a gated community.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brSpace for two vehicles permittedbrbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Full bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$271.0

/ Nightly

Private Vacation Home

Breezy Bungalow | Close 2 Zachary Taylor State Park & Beach | Month-Long Stays

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrWhen a name says it all you know you have made the perfect choice for your Key West island escape.brbrBright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Breezy Bungalow. This 2-story spacious sanctuary will make this your best adventure yet.brbrThe main level consists of an open floor plan complete with a large kitchen area ideal for preparing your island fare, dining area with seating for 6, half bath, living room and double glass French doors that swing wide to a spacious outside deck. Tropical foliage surrounds the deck making this a secluded retreat with outside seating, the ideal location to sip your morning coffee or entertain with margaritas.brbrTake the staircase upstairs to find 2 bedrooms with full size baths en-suite, the master bath has a queen size bed and 2 twin beds in the second bedroom that can be converted to a king bed. Each bedroom has glass doors that open to a private hideaway, a balcony perfect for hiding away as the sunrises or reading a good book in your own private space.brbrThe shared Truman Annex pool is only a short walkway away and is the ideal location to spend sunny afternoons cooling off in the crystal waters or lounging pool side. And to complete it all you have the quintessential location of Truman Annex, only a few short walking blocks to Duval Street, Mallory Square or Ft. Zachary Taylor State Park and Beach. Nightly entertainment, shopping , fabulous restaurants and water adventures are all at your feet within easy walking or biking. Enjoy all the island offers and never use a vehicle the entire time you are here.brbrBreezy Bungalow also comes complete with the modern amenities of home with high speed WiFi, expanded cable TV service, full size washer/dryer set and 1 reserved parking space.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home has access to a shared pool and is part of a gated community.br- Unfortunately, pets are not allowed in this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Two twin bedsbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$284.35

/ Nightly

Private Vacation Home

Bahamian Reed | Walk to Everything! w/ Pool Access | Month-Long Stays

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrWelcome to Bahamian Reed, your dream vacation home that has undergone a complete makeover! Look no further for those special moments that will create lasting vacation memories. This is the perfect place for you to return to time and time again.brbrThis two-bedroom, 2.5-bathroom, 2-story townhome located in scenic Truman Annex in Old Town is conveniently located near all the reasons you came to Key West yet offers a quiet respite for relaxation and comfort.brbrBahamian Reed offers a gourmet kitchen, a bright cheery dining area, and a living room (with a queen sleeper sofa) with two sets of French doors that open to a private deck for al fresco enjoyment. Upstairs is the master suite with a king bed and twins in the guest bedroom (that converts to king). Balconies off both bedrooms let you feel the tropical breezes as you sit with a cup of tea or afternoon cocktail. The shared full bathroom has a large vanity and two sinks for easy access.brbrThe community pool is a short stroll away for sunbathing or cooling off. Or grab some Cuban sandwiches at a nearby deli and head to Ft. Zachary Taylor State Park to picnic under the pines. And don’t forget your snorkeling equipment for the best spot on the island.brbrLater, walk a couple of blocks to Duval Street for some shopping, people-watching, and dining at a white tablecloth, ethnic or casual restaurant. Listen to some live music at a variety of bars or head to the waterfront for a gorgeous sunset at Mallory Square.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home has access to a shared pool.br- This home is located in a gated community.br- This home offers a sleeper sofa as an additional sleeping option.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bedbrBedroom 2 / Two twin bedsbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce it. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$684.05

/ Nightly

Villa

Coral Villa by AvantStay | Close 2 DT Key West | Shared Pool & Patio!

Key West, Florida, United States

Welcome to Coral Villa by AvantStay!brbrSpacious, beautifully decorated, and rare in all the right ways — Coral Villa offers 3 bedrooms, 3 bathrooms, and off-street parking for two vehicles, a genuine luxury in Key West. Tucked inside the gated community of Coral Hammock just off U.S. 1, this townhome sits directly across from the Key West Golf Course and puts you minutes from the local-favorite restaurants, marinas, Smathers Beach, and the airport.brbrStep inside to an easy, open first floor where the living and dining areas flow into a fully stocked kitchen ready for family breakfasts, sunset cocktails, and everything in between. A main-floor bedroom with a full bathroom sits just off the living space, opening to a back patio and balcony made for morning coffee or a quiet nightcap.brbrUpstairs, the primary suite and a second guest bedroom each come with their own en-suite bathroom — ideal for families or friends traveling together. Soft earth tones carry through every room, creating a calm, grounded feel that makes it easy to settle in. The home comfortably sleeps up to 8.brbrWhen you're ready to cool off, the community pool and clubhouse are just a short walk away. And when you want the energy of downtown Key West and Duval Street, you're only about 3 miles from the action — close enough to dip in whenever the mood strikes, far enough to retreat to your own private corner of the island when it's time to unwind.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home has access to a shared pool.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- This home offers a sleeper sofa for additional sleeping arrangements.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brOff-street parking for 2 cars.brBoats, Jet Skis, buses, campers, trailers, motor homes, recreating vehicles, mobile homes, and commercial vehicles are notbrallowed to park on the association property (except for deliveries).brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / Queen bedbrBedroom 3 / Two twin bedsbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$241.44

/ Nightly

Private Vacation Home

Place to Relax by AvantStay | Shared Pool | 3 Miles to Smather's Beach

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrLocated in the Sanctuary of the gated community in the Key West Golf Club, this spacious single-family home welcomes you to the laid-back island life with the ease of everything on one floor. You and your guests will enjoy being close to the best that Key West has to offer, yet far enough away to relax and unwind in this quiet community.brbrThe spacious and well-equipped kitchen at Place to Relax has everything you need to prepare and enjoy your meals in the open dining area. This home-away-from-home offers three comfy bedrooms (a king, queen, and twin beds) making it comfortable for up to six guests.brbrThe back bedroom with king bed has its own en suite bathroom. The French doors from this bedroom open up to the backyard. The two front bedrooms with queen and two twin beds share the second full bathroom. This property is one level making it easy for a family with small children or families traveling with a senior family member to get around.brbrA special feature at Place to Relax is the large back patio with a BBQ grill and plenty of space for entertaining just overlooking the golf course. Guests also have access to a beautiful lagoon-style pool and 24-hour gym. Private parking is conveniently located under the adjacent car-port.brbrPlace to Relax is perfect for family getaways. The property is a monthly rental and has everything that you and your family need to enjoy time together in paradise. Just a few miles to Smather's Beach and downtown Duval Street where you will enjoy all the local attractions, restaurants, shops and more.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- This home has access to a shared pool. br- Unfortunately, pets are not allowed at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brSpace for two cars to park.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / Queen bedbrBedroom 3 / Two twin bedsbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$250.71

/ Nightly

Private Vacation Home

Communal Pool | Gated Community | Month-Long Stays | Key West Charming

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrPLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests. *The rates for the month of August have already been discounted to reflect the loss of the amenity.*brbrLocated at the Shipyard Condominiums downtown Key West, this first floor, 2 bedroom, 1 bathroom home has been lovingly cared for by the owners. The living and dining area opens to a large wooden deck in the backyard to relax and soak up the sun in privacy.brbrThe master bedroom has a queen-size bed. The second bedroom has 2 twins. The bathroom is conveniently located in the hallway between the two. A well-equipped kitchen makes any meal you prepare a breeze.brbrKey West Charming offers the benefit of a great downtown location, within walking distance to all the sights and attractions including Fort Zachary Taylor State Park with one of the nicest beaches on our island. The property is just minutes from Duval Street with restaurants, bars, galleries, tourist attractions, and Sunset Celebration at Mallory Square.brbrRide your bike or walk through the beautiful Truman Annex. Play all day out and around town or soak up the afternoon sun at the community swimming pool. Perfect for a couple or a small family.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbr*Home Truths:*br- This home has access to a shared pool.br- This home is part of a gated community.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.br- PLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Two twin bedsbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$254.29

/ Nightly

Condo

Discounted Rates! • 2 Blocks to Duval St • Pool | Shipyard Treasure by AvantStay

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrPLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests. *The rates for the month of August have already been discounted to reflect the loss of the amenity.*brbrShipyard Treasure brings an easygoing Key West feel to a bright, oversized second-floor condo in the heart of Old Town. Set within the sought-after Shipyard community, this two-bedroom retreat pairs a walkable Historic District location with breezy balconies, tropical surroundings, and the relaxed charm that makes Key West so memorable.brbrInside, the home feels sunny, comfortable, and thoughtfully refreshed. The open living and dining area is filled with natural light from multiple French doors, creating an airy space to gather after a day at the beach or exploring nearby Duval Street. A cozy seating area, TV, and dining table make nights in feel easy, while the updated kitchen features stainless steel appliances, bright cabinetry, cheerful blue tile, and everything needed for simple breakfasts, happy-hour snacks, or relaxed dinners at home.brbrTwo queen bedrooms offer comfortable sleeping arrangements for up to four guests. Both bedrooms open to the front balcony, making it easy to step outside for a quiet morning moment or enjoy the island breeze before heading out for the day. A full bathroom, central air conditioning, high-speed internet, and an in-unit washer and dryer add convenience throughout your stay.brbrOutdoor living is a highlight here, with two spacious covered balconies to enjoy. The front balcony is ideal for people-watching, morning coffee, or catching the energy of Old Town, while the back balcony offers a quieter spot to unwind with a drink after a day in the sun.brbrWhen you’re ready to cool off, follow the palm-lined paths and white picket fences to the community pool. You’ll also have one designated parking space, though the location makes it easy to explore by foot or bike.brbrFrom Shipyard Treasure, you’re close to Fort Zachary Taylor State Park, Duval Street, Green Parrot Bar, the Hemingway House, Truman Waterfront Park, Blue Heaven, Mallory Square, and some of Key West’s best dining, history, nightlife, and waterfront adventures. Whether you’re here for beach days, sunset strolls, or a classic Old Town escape, this condo puts the best of Key West right within reach.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrLocal Attractions: Key West Shipwreck Treasure Museum, Hemingway Home and Museum, Mel Fisher Maritime Museum, Harry S. Truman Little White House, Conch Tour Train, Dry Tortugas National Park, Lazy Dog Adventures, Dolphin encounters, Ghosts & Gravestones Tour, Old Town Trolley, Sloppy Joe’s Bar, Audubon House & Tropical Gardens, Florida Keys Eco-Discovery Center, Bike Tours, Seaplane adventures, Key West Aquarium, Sebago Day Tours, Private boat charters, Sportfishing, Rick’s Entertainment Complex, Duval Street (shop strips, shops, bar, and cafes), Mallory Square (waterfront plaza), Key West Garden Club, Sunset Pier, Grand, Cafe Key West, Island House, El Meson de Pepé, Cafe Sole.brbr*Home Truths:*br- This unit is located on the upper floor.br- This home has access to a shared pool.br- This home is part of a gated community.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.br- PLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bedbrBedroom 2 / Queen bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

2

Bed

1

Bath

4

Sleeps

$238.45

/ Nightly

Private Vacation Home

Dune Wind South by AvantStay | Gated Community | Close to Beach

Key West, Florida, United States

*Prior to booking, please note:*brPool and Jacuzzi resurfacing is scheduled from July 6 through August 30, weather permitting. During this time, the pool and Jacuzzi area will be fully closed and unavailable for guest use.brbr*Please note that this home is available for 28+ night stays only.*brbrThis two-bedroom, two-bath condominium is located oceanfront in a gated community with a direct view of the Atlantic Ocean. Enjoy amazing views from this waterfront condo of the sparkling blue waters from your private balcony while relaxing in the tropical breezes and sipping a margarita. Put your feet up and know this is the vacation home you have been looking for.brbrWhen you enter this waterfront condo, you will find a fully equipped kitchen with everything you need to cook up your fresh catch, dine in the dining area, and relax in the spacious living room that opens to a private balcony with those unlimited ocean views. Pictures do not begin to tell the story of Dune Wind South, this beautifully renovated end unit located in La Brisa Condominiums. Enjoy sunrise ocean views from the large balcony while enjoying morning coffee.brbrComplete with two spacious bedrooms, each with its own full bathroom. A large walk-in closet is great for long stays in your new home-away-from-home, along with ample storage space for all of your necessities. Marble floors are throughout the main living areas, including the balcony and bathrooms. The fully renovated designer kitchen is complete with marble counters, stainless steel appliances, and a temperature-controlled red wine fridge.brbrDune Wind South evokes luxury style living in the heart of offbeat Key West, offering the best of both worlds. Enjoy walking on Smathers Beach every morning, right across the street from your luxurious condo. Perfect for couples looking to spend a much-needed stay in paradise with the option of having a guest bedroom available for visitors.brbrLa Brisa offers your own covered parking space with additional guest parking. A secure gated building, tennis courts, pool, Jacuzzi, clubhouse, and BBQ picnic areas are among the common grounds.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- This home has access to a shared pool & hot tub.br- This home is part of a gated community.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.br- The elevator is currently out of order. At this time, there is no estimated timeframe for when it will be operational.brbrParking Details:br- 1 covered parking spacebr- All vehicles permitted to park within the La Brisa Community must not be over 20 feet in length, including any attachments to the vehicle, not over 8 feet in width, and not over 7.5 feet in overall height.br- Trailers, boats, jet skis, and boat trailers, with or without boats or jet skis, are not permitted in the La Brisa Community.br- Kayaks, canoes, and paddleboards are permitted but must be kept on top of the vehicle at all times.br- Unauthorized vehicles will be towed at the owner or operator's expensebrbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brBedroom 2 / Queen bedbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$246.03

/ Nightly

Private Vacation Home

Linger Longer | Near Key West, Gated Community, Shared Pool | Month-Long Stays

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrEnjoy a carefree vacation in a 2 bedroom 1.5 bath, 2-story townhome, located on Southard Court in the Truman Annex, downtown Key West. This home is situated right in front of the community pool.brbrThe first floor has an open floor plan with a full kitchen, dining area, and living area which opens to a beautiful backyard patio. There is also a half bath on the first floor. French doors from the living room open to the back deck with grill and exit gate right onto Thomas Street, giving easy access to and from downtown. This townhome is conveniently located poolside and just a short walk to the many restaurants, attractions, and shopping that Old Town Key West has to offer.brbrThe second floor has two bedrooms and a full bathroom. One bedroom has a queen bed and the second guest bedroom has two twin beds. The sofa in the living room pulls out into a queen.brbrLinger Longer is a great place to get away from it all and enjoy our tropical climate, exploring the tiny lanes and exotic byways that make Key West famous.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home has access to a shared pool and is part of a gated community.br- This home also features a sleeper sofa.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / 2 twin bedsbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$242.87

/ Nightly

Private Vacation Home

Parrot Perch by AvantStay | Old Town Key West w/ Shared Pool | Month-Long Stays

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrPLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests. *The rates for the month of August have already been discounted to reflect the loss of the amenity.*brbrUnbeatable location at a great price! The Parrot Perch is in the gated Shipyard Community of the prestigious Truman Annex. You’ll find being part of “Old Town” Key West will make your vacation special, only a block to the infamous Green Parrot bar, a few blocks to Mallory Square to catch the nightly sunset or a short walk to one of the nicest beaches on the island -- yet still in a secluded, quiet community.brbrThis vacation rental is a second-floor 2 bedroom 2 bathroom condo with a balcony off the living room offering a view of the neighborhood. Feel immediately relaxed in the soft blues of the living room with a queen sleeper adding flexible accommodations for a group of 5. The inviting master bedroom has a queen bed with bathroom en-suite and the guest bedroom comes with twin beds that can be converted to a king.brbrThe gleaming white kitchen is well equipped to prepare culinary delights when you're not sampling the many amazing restaurants on the island. Just two short blocks to Duval Street, you're in walking and biking distance to shopping, restaurants, and entertainment, Fort Zachary Taylor State Park, and all the attractions of Key West.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home has access to a shared pool and is part of a gated community.br- This home also features a sleeper sofa.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.br- PLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Two twin bedsbrQueen sleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$242.65

/ Nightly

Private Vacation Home

La Casita by AvantStay | Steps to Duval Street | Month Long Stays Only

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrThe location of La Casita cannot be beaten -- right in the heart of Old Town yet on a quiet lane, only steps to Duval Street. This property is a monthly rental only. Sleeps 4 people.brOnce here, you can settle in like a local as everything is within walking or biking distance. Imagine walking around the corner to grab a delectable key lime pie at Blue Heaven. Turn the corner and you’re ready for a tour of the famous Ernest Hemingway home. Cross the street to climb the Key West lighthouse for a bird’s eye view of the city.brbrThis charming 2-bedroom, 1-bath cottage is a perfect vacation home away from home. Do not feel like trying a new restaurant every single night The property offers a fully equipped kitchen for the evenings when you decide to let your inner chef come out. There is plenty of dining space indoors or out in the tropical landscaped courtyard. Enjoy a cold Mojito lounging on the sofa or cooking up some Key West pinks on the grill at the end of the day.brbrLa Casita can accommodate four people, the master bedroom has a queen-sized bed, and the guest bedroom has two twins. There is a queen sleeper sofa in the living room for the occasional extra guest. Tasteful, eclectic artwork and decorative touches adorn your tropical getaway.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbrHome Truths:br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home features a sleeper sofa as an additional sleeping option.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brStreet parking only.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Two twin bedsbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$310.55

/ Nightly

Apartment

Key West Casa | Pool Access | BBQ & Patio | Near Duval Street | Month-Long Stays

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrPLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests. *The rates for the month of August have already been discounted to reflect the loss of the amenity.*brbrThis spacious 3-bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West's most popular restaurants.brbrBeautiful and spacious Shipyard condo, Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigious Truman Annex community just 2 blocks from famous Duval Street and within walking distance to shopping, restaurants, and attractions that make Key West the perfect tropical vacation.brYou enter into the newly renovated kitchen with granite countertops and fully stocked from cookware to dishes. The downstairs bedroom is just to your left and offers 2 twin beds. The living room is comfortable and welcoming, and French doors open onto the back porch. There’s also a full bath downstairs.brbrUpstairs you will find spacious bedrooms, the front-facing bedroom has a queen bed and the rear-facing bedroom offers a queen bed and another set of French doors that open onto a balcony that overlooks the backyard.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- This home has access to a shared pool.br- This home is part of a gated community.br- This is a two-story condo.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.br- PLEASE READ PRIOR TO BOOKING THIS PROPERTY:brThe Shipyard Pool will be closed beginning August 1, 2026, for the Pool Deck Replacement Project. The project is expected to take 30 days, with the goal of having the work completed and the pool reopened by September 1, 2026. During this time, no pool will be available to the guests.brbrParking Details:br- One parking space per unit, no guest parking.br- No vehicle over 18’ long or 80” wide allowed.br- No large trucks, trailers, mobile homes, vans, campers or similar vehicles shall be parked in the Truman Annex.br- Motorcycles and scooters must be parked in the parking lot and not on sidewalks or porches.br- All vehicles parked within the community must either have a permanent parking sticker or a temporary parking pass (obtained at the Security Guardhouse).br- All others will be subject to ticketing and towing.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Queen bedbrBedroom 3 / Two twin bedsbrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking.brbrWe report and prosecute all Credit Card Fraud.

3

Bed

2

Bath

6

Sleeps

$258.16

/ Nightly

Private Vacation Home

Boat House by AvantStay | Character Cottage | Central Location Month Long Stays

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrStep into a tranquil community on a quiet lane and discover the Boat House, a nautically themed treasure in Old Town Key West.brbrFor anyone with an affinity for the sea, everywhere you turn is a reminder of the water – from sailboat replicas of every shape and size; to prints of fish and sailor knots; to a mermaid toilet and a leaping dolphin faucet. This bohemian cottage features a master bedroom with a therapeutic king-sized bed, flat-screen TV, gleaming hardwood floors, and white-washed paneled walls. A spacious wheelchair-accessible bathroom comes complete with a walk-in shower and a separate tub with navy and white checked tiles.brbrThe airy galley kitchen is equipped with stainless steel appliances and is ready for the chef at your party to prepare delicious meals. Sit and savor at the dining room as you overlook the soothing landscaped outdoor area or step into the bricked courtyard and contemplate life on a bench overlooking the tranquil lagoon pool. The Boat House has a large private covered deck, just perfect for enjoying an afternoon cocktail or a good book, overlooking a shared pool.brbrSpend some time relaxing and dream of days on the ocean at the Boat House, but remember you are within two blocks of the excitement of Duval Street with shops, bars, restaurants and art galleries all waiting to be explored!brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrNeed even more room for your group The Boat House is just next door to the Midnight Cowboy compound, which includes the three spaces that can also be rented together: Monkey House (a 2BR space), the Main House (1 king bedroom) plus the Hibiscus Suite (studio-style space with a queen bed) at Tennessee Williams. All spaces share access to the central pool area.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- If you require more space, this listing is also available as part of a buyout called Midnight Cowboy which has a total of 4 bedrooms. br- There is also a 2-bedroom listing located on the same compound called Tennessee Williams. Please reach out to the team to enquire about availability.br- This home has access to a shared pool.br- Pool heat is available for an additional fee but must be requested at least 48 hours before your stay.br- Pool heat is not available between 4/1 and 10/1.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brDriveway Parking for two car.brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed brbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$255.7

/ Nightly

Private Vacation Home

Southard Getaway | Covered Patio, Great Location, Shared Pool | Month Long Stays

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbr“Amazingly Perfect!” That is how one of our delighted guests reviewed Southard Getaway and we’re sure you’ll agree. Imagine arriving in Key West to this beach-like home within walking distance of all that Key West has to offer.brbrLocated in the exclusive gated community of the Truman Annex, this tropical gem is decorated in hues of blue and green that remind you of the ocean. Fort Zachary Taylor Beach is only a short bike ride away.brbrSouthard Getaway is a 2-bedroom, 1.5-bathroom, 2-story townhome with upper and lower decks. Two queen bedrooms upstairs with a full bath between each, open to their own shaded decks to sit, relax, and while away the hours. Enjoy a meal out back on your private patio or take a dip in the sparkling community pool. Furnished with a full kitchen, washer/dryer, and your own convenient parking spot, and the excitement of Mallory Square and Duval Street a mere two blocks away - this truly is paradise.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbr*Home Truths:*br- Smoking is not allowed anywhere on the premises. br- This home has access to a shared pool.br- This home is part of a gated community.br- This home features a sleeper sofa.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:brParking for one vehicle.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bedbrBedroom 2 / Queen bedbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$639.61

/ Nightly

Condo

Ocean-View Condo • Shared Pool + Near Beach | Gated Community | Brisa Del Mar

Key West, Florida, United States

*Prior to booking, please note:*br- The building is currently undergoing an exterior spalling project, which may result in construction noise and occasional elevator closures. The stairwell remains open, and the property is located on the second floor. Work is scheduled Monday through Saturday from 8:00 AM to 5:00 PM.br- Pool and Jacuzzi resurfacing is scheduled from July 6 through August 30, weather permitting. During this time, the pool and Jacuzzi area will be fully closed and unavailable for guest use.brbr*Please note that this home is available for 3+ night stays only.*brbrBrisa Del Mar brings the best of Key West right to your balcony, with ocean views, tropical breezes, and easy access to the laid-back island lifestyle. Set in the oceanfront gated community of La Brisa across from Smathers Beach, this 2-bedroom, 2-bath condo is made for slow mornings, sunny beach days, and sunset drinks with the Atlantic as your backdrop.brbrInside, the condo keeps things bright, comfortable, and relaxed. The living area opens directly to the private balcony, letting the ocean views flow into the space, while the fully equipped kitchen makes it easy to prep breakfast, beach snacks, or a fresh-catch dinner after a day on the water. A dining area and cozy seating give you plenty of room to unwind between adventures.brbrThe primary bedroom features a queen bed, ensuite bathroom, and direct balcony access, so you can wake up to salty air and sparkling water views. The second bedroom includes two twin beds that can be converted into a king, offering flexible sleeping arrangements for couples, friends, or families. A second full bathroom adds extra convenience for easy beach-to-dinner transitions.brbrStep outside and Key West is yours to enjoy. Spend the day across the street at Smathers Beach, where you can lounge in the sun, rent chairs and umbrellas, try paddleboarding or kayaking, or simply stroll along the shoreline. Back at La Brisa, cool off in the community pool, relax in the hot tub, or enjoy a friendly match on the tennis and pickleball courts.brbrWith ocean views, resort-style amenities, and easy access to beach days, watersports, dining, and the colorful energy of Key West, Brisa Del Mar is a breezy island home base for guests who want comfort, convenience, and that unmistakable Keys feeling.brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrLocal Attractions: Key West Shipwreck Treasure Museum, Hemingway Home and Museum, Mel Fisher Maritime Museum, Harry S. Truman Little White House, Conch Tour Train, Dry Tortugas National Park, Lazy Dog Adventures, Dolphin encounters, Ghosts & Gravestones Tour, Old Town Trolley, Sloppy Joe’s Bar, Audubon House & Tropical Gardens, Florida Keys Eco-Discovery Center, Bike Tours, Seaplane adventures, Key West Aquarium, Sebago Day Tours, Private boat charters, Sportfishing, Rick’s Entertainment Complex, Duval Street (shop strips, shops, bar, and cafes), Mallory Square (waterfront plaza), Key West Garden Club, Sunset Pier, Grand, Cafe Key West, Island House, El Meson de Pepé, Cafe Sole.brbr*Home Truths:*br- This home has access to a shared pool.br- This home is part of a gated community.br- This home features a sleeper sofa for the maximum occupancy of 6. The maximum occupancy is strictly enforced.br- Please note that max occupancy includes infants.br- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- All bookings 28 days or longer require a security deposit to be charged after booking.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that if requested, the two twin beds can be converted into one king bed with bedding for a fee of $75. Please ensure you make this request at least 48 hours in advance.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrParking Details:br- 1 covered parking spacebr- All vehicles permitted to park within the La Brisa Community must not be over 20 feet in length, including any attachments to the vehicle, not over 8 feet in width, and not over 7.5 feet in overall height.br- Trailers, boats, jet skis, and boat trailers, with or without boats or jet skis, are not permitted in the La Brisa Community.br- Kayaks, canoes, and paddleboards are permitted but must be kept on top of the vehicle at all times.br- Unauthorized vehicles will be towed at the owner or operator's expensebrbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / King bed w/ ensuitebrBedroom 2 / Two twin bedsbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

Bed

Bath

Sleeps

$234.38

/ Nightly

Private Vacation Home

Land Of Love by AvantStay | Pets Allowed! Shared Pool! Great Location!

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrYour perfect escape to Key West awaits you in the Land of Love.brbrNestled on a desirable Historic street in Old Town Key West, this two-story private home is a special hidden gem. The property sits in a gated compound with a shared pool and a private patio area with a table and grill. This two-story home is able to accommodate dogs under 50lbs.brbrThe first floor of the home is an open floor plan with living, dining, kitchen, and a half bath. A spiral staircase leads to the second floor where you will find two bedrooms and one full bathroom.brbrThis property is for those who are extremely laid back and want to enjoy all that Key West has to offer including dining out at all the fabulous restaurants or eating take-out by the pool.brbrWhile the Kitchen is equipped with a cooktop for lite meals, there is no oven or dishwasher at the property.brbrKey West is the place to visit the lively nightlife and relax in the historic charm, flamboyance, and conch-style architecture that early Bahamian settlers made famous. It embodies a clash of the past and the present, and every building (including this rental) in Key West reflects this eclectic ambiance!brbrAvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!brbr*Home Truths:*br- Please note that all bookings 28 days or longer will require a security deposit of $2000 which will be collected after the booking has been made. Multiple months reservations might be subject to a higher security deposit fee.br- Any reservations 28 days or longer will require additional clean/cleans to be scheduled. Additional payment will be collected and the amount of cleans will depend on the length of your stay.br- This home has access to a shared pool and is part of a gated community.br- This home features a sleeper sofa for additional sleeping options.br- This home is on a monthly pest control schedule. The area of Key West is home to many insects such as termites, no-see-ums, and mosquitos. Pest control can not eliminate these insects during the swarming season. You may also encounter geckos, lizards, iguanas, frogs, and chickens during your stay in the area.br- Key West is a resort island where renovation of existing historic properties, new construction, and road repair sometimes occur without forewarning. AvantStay is not liable for any guest inconveniences caused due to construction in the area.br- Please note that max occupancy includes infants.br- Please be advised that documentation may be necessary for ESA/service animals to gain entry.brbrPets:br- This home allows pets for a fee. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet. br- We LOVE pets, however- Certain breeds typically have to have an additional owner or HOA approval. If your pet falls under any typical breed restrictions (breed, size, weight) please let us know so that we can confirm!brbr---brbrThe room configuration is as follows:brbrPrimary Bedroom / Queen bed brBedroom 2 / Full bedbrSleeper sofabrbr---brbrThis is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.brbrAs part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation. brbrEvents or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees. brbrThere is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.brbrAs a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.brbrIDs will be requested for verification after booking. brbrWe report and prosecute all Credit Card Fraud.

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