Vacation Condo Rentals By Owner In Key West, FL

Make your special trip to paradise most memorable with a stay in your bright and airy Shipyard Unit. Located within Truman Annex, Key West's most premier address, you are only a minute from the fine restaurants, shops, and galleries of Duval Street. Sit on your 40 foot veranda and cool off in the gentle trade winds as you watch the world go by. Your unit has central air, washer/dryer, updated furnishings, HDTV, queen size bed, and beautiful hardwood floors. Quiet and peaceful, your 1 bedroom/1 bath unit, is unique in the Shipyard and will be the perfect accommodation as you savor the paradise that Key West offers. brPlease note: This property will require a minimum of a 28 night stay.

Marlin Blue at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$291.38

Welcome to Cozy Key West Cottage !!!brA REAL ISLAND GATAWAY IN KEY WEST!!!brbrStay just around the corner from Duval Street and walk to everything Key West has to offer. brAfter a day out, relax in your own private space in a great Old Town location.brbrPerfect for two guests who want to be close to everything.brbrNested in the heart of Key West, Cozy Key West Cottage, welcomes you to a sanctuary of comfort and convenience. brbrAs your host , we're delighted to extend our warmest greeting and ensure your stay is nothing short of exceptional.

Hidden Key West Cottage - Walk to Duval !!!

Key West, Florida, United States

Bed

Bath

Sleeps

$451.94

Summary:brbrExperience the best of Key West from Sky Loft, your perfect weekend getaway! Just one block from the iconic Duval Street, this top-floor gem puts you right at the heart of the action. From vibrant bars and restaurants to must-see local attractions, adventure is just steps away.brbrbrbrUnwind by the inviting pool, complete with cozy lounge chairs, and soak in the island vibes.brbrbrbrBright, airy, and perfectly located, Sky Loft offers incredible value for couples or friends looking to enjoy the ultimate Key West experience!brbrbrbrThe Space:brbrThis bright and airy 1-bedroom, 1-bathroom space features an open-concept living area, a private balcony, and all the comforts of home. The fully equipped kitchen has stainless steel appliances, including a refrigerator, microwave, and stove. With AC, free WiFi, a private washer and dryer, and access to a shared pool, Sky Loft has everything you need for a relaxing stay.brbrbrbrBed and Bathroom Layout:brbrbrbr1 King-size bedbrbr1 Queen sleeper sofabrbrPerfect for couples or small groups, Sky Loft offers comfort, convenience, and a touch of island charm.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code 3 days prior to check-in to enter the unit.brbrbrbrShared community features: shared pool, lounge chairs and seating areabrbrbrbrHow to access: This unit is accessed by 2 flights of stairsbrbrbrbrThe Neighborhood:brbrThis unit is located on the highly touted Southard Street, just steps away from the world-famous Duval St, the Historic Seaport, and a variety of restaurants, coffee shops, and bars.brbrbrbrGetting Around:brbrParking Information: Unfortunately, there is no on-site parking for this unit. brbrbrbrFor overnight parking, here are some parking lot options:brbr• Fleming Street Pay-to-Park Lot (This is Closest to you!)brbr• 204 Simonton Streetbrbr• Caroline Street Outdoor Parking Lotbrbr• Park N Ride Old Town GaragebrbrbrbrStreet parking information:brbr• There are pay-to-park spots and meters - it is free from 12am - 8pm. There is a 3 day limit.brbr• The neighborhoods of Old Town offer some free parking spaces, but be aware that many of the spots are marked “Residential Only” and visitors are NOT permitted to park in them.brbrbrbrThere are a variety of great ways to explore Key West including by bicycle, scooter, golf cart, Uber, Taxi, or by feet. As this unit is located in downtown Key West, many attractions are within walking distance.brbrbrbrOther Things to Note:brbr- One block from Duvalbrbr- Private washer/dryer in unitbrbr- This unit is on the 3rd floor of the complex and is not recommended for guests with mobility issuesbrbr- This unit is about 10 minutes from the airportbrbr- This unit is not pet friendly

Sky Loft - Steps from Duval Street & Shared Pool

Key West, Florida, United States

1

Bed

1

Bath

4

Sleeps

$326.17

Life is best lived from the balcony of this tranquil oceanfront condo. Feel like your feet are touching the sand, but yet your balcony is a floor above the actual sand with both sunrise and White St Pier views. This is a new unit to the rental program and therefore doesn't have reviews yet! Don't let that stop you from renting!brbrThis oceanfront oasis is located in the Key West Beach Club, an upscale, gated community with two oceanfront pools, pavilion area, workout room and tennis court. The Key West Beach Club is one of the very few condo communities on the island that sits directly on the coastline.brbrEnter the open living, dining, kitchen with your eye drawn immediately to the view. The living room has light blue walls with dark wood flooors and features a modern sectional leather sofa with leather accent chairs & natural wood accent tables. The dining area has a spacious natural wood Room and Board dining table for 6. The kitchen features a full wall of cabinets and stainless appliances The coffee bar is a nice feature to enhance the kitchen. It is the counter height table in the kitchen that steals the show, with its surfboard inspired design and bar stools as another dining space or perfectly used as a serving area.brbrThe Primary Bedroom has been updated with a king tropical style bed and new mattress. The ensuite bath has a long vanity and large walk in shower. A concealed window in the shower allows you to see the ocean while showering, but the view is obscured from the bedroom for privacy. The guest room features a queen bed and desk for multi-purpose use of the space. A hallway door between the guest room and guest bath will close to allow the large bathroom with walk-in shower to serve as a second ensuite.brbrThe balcony offers a lounge area, outdoor dining and chaise lounge chairs for relaxing oceanside. brbrUnit Features:brCentral A/C, Wi-Fi, washer/dryer, security entry, garage parking and elevator access.brbrCommunity Amenities: Resort-type amenities include two oceanside pools (heated), tennis court, outside cooking facilities and pavilion, fitness center and sauna. Since the shoreline is natural, beach access is best at the public beaches on either side of the community. Smather’s Beach is around the corner to the right when exiting the property and Higgs Beach is just past White Street Pier to the left. There are plenty chaise lounges around the pool areas as well as the covered pavilion to enjoy during those sunny island afternoons.brbrAdditional things to know:brThe Key West Beach Club Condo Association requires additional registration, which includes providing copies of photo IDs for everyone over the age of 17, in advance of your arrival. Details will be provided along with your RKWV rental agreement.brbr*Disclaimer: Due to the property's oceanfront location, please be aware that Key West experiences seasonal occurrences of fermenting turtle grass along the south shore of the island brought on by our southern winds in the late spring and summer. This is a natural phenomenon that is outside of our control.brbrPlease note: This is a Monthly vacation rental with a minimum stay of 29 days, excluding February.

Oceanfront living in Key West by Rent Key West Vacations

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Shipyard Condominiums are located in the prestigious gated community of Truman Annex in Key West’s old town area. The condos are located 2 blocks from Duval Street and all the Old Town Key West attractions. The properties are also ¼ mile from Fort Zachary Taylor State Park. The property is outfitted with washer/dryer, pots/pans, towels, linens, have central air conditioning, off street parking, and pool access. This Shipyard home is a single level condominium on the 2nd floor with balconies. This property also has an awning for coverage from the sun. brPlease note: This property is monthly rental - the minimum rental period is 28 nights

Tropical Breezes at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$574.13

The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Condo in Truman AnnexbrbrWelcome to your sunny escape in paradise! Nestled in the charming and secure Shipyard Condominium community—part of the iconic Truman Annex in Old Town Key West—this two-bedroom, two-bath, two-story condo blends island comfort with unbeatable location.brbrStep inside and feel instantly at home. The living room is spacious and inviting, with cozy furnishings, a dedicated work area, and a sleeper sofa for extra guests. Sunlight pours through the glass doors, which open onto a private outdoor deck surrounded by lush tropical foliage. Whether you're sipping morning coffee or enjoying a meal at the outdoor dining set for four, you'll love the relaxing Key West vibes.brbrThe compact kitchen is thoughtfully equipped with everything you need for your stay—stove, refrigerator with ice maker, dishwasher, and more. A breakfast bar and dining table provide seating for four, perfect for casual meals before heading out to explore.brbrDownstairs, you’ll find a convenient bedroom with a Smart TV and sleeper sofa, ideal for kids or guests. Upstairs, the entire second floor is a peaceful retreat featuring two queen-size beds, a full bathroom, and another Smart TV.brbrThis condo comes with all the extras to make your stay easy and carefree: in-unit washer and dryer, front porch with comfortable seating for people-watching, and an assigned parking spot located right outside your door for effortless arrival and unpacking.brbrWhen it’s time to explore, you’re just a short stroll from the famous Duval Street—home to five-star dining, eclectic shops, vibrant art galleries, and world-class entertainment. The stunning Fort Zachary Taylor State Park is also nearby, offering a beach, shaded picnic areas, and grills for a perfect day by the sea. Little ones will love the Truman Annex splash pad and playground, and everyone can enjoy the Shipyard’s own heated pool and sun loungers.brbrWhether you're here for adventure, relaxation, or a little bit of both, this beautifully maintained condo offers the perfect launchpad for your Key West getaway.brbrBook your stay today and let the island life welcome you home.

The Conchtail Club a Tropical Oasis in the Heart of Old Town – Shipyard Complex

Key West, Florida, United States

Bed

Bath

Sleeps

$298.58

The Grand Turk | Key West Condo with Pool, Hot Tub & Private BalconybrbrWelcome to The Grand Turk, a spacious and inviting 2-bedroom, 2-bathroom condo located in the serene Sunrise Suites community on Key West's southeast side. Just one mile from the beach and 10 minutes from the excitement of Duval Street, this island retreat combines resort-style amenities with the comfort of home—perfect for families, couples, and friends seeking a relaxing yet well-connected Key West getaway.brbrThe Ambiance:brStep inside The Grand Turk and enjoy a bright, coastal-inspired space designed for comfort and easy island living. This thoughtfully laid-out condo sleeps up to six guests, featuring a king-size primary bedroom with an en-suite bathroom, a queen bedroom with convenient hallway-access bath, and a queen pull-out sofa in the living room. The open living area is ideal for unwinding after a day of adventure, complete with TV, cable, complimentary WiFi, and central air conditioning. The fully equipped kitchen includes all cooking essentials, a dishwasher, and a Keurig coffee maker—perfect for casual meals or morning coffee. Step out onto your private balcony to enjoy poolside breezes, afternoon lunches, or a quiet moment to relax.brbrGuest Access:brEnjoy a smooth, stress-free arrival with our contactless check-in process. Guests will receive a personalized access code prior to arrival for easy entry.brbrGuests also have access to Sunrise Suites' shared amenities, including:br- Communal heated pool and hot tubbr- Tennis courtsbr- Scenic walking paths and biking trailsbr- Shared washer and dryer facilitiesbr- Convenient elevator and stair access to the unitbrbrLocation Highlights:brLocated within the peaceful Sunrise Suites Resort, The Barbados is just minutes from Smathers Beach, Higgs Beach, and the energy of Duval Street. Explore Key West's vibrant dining, nightlife, and attractions, then return to your quiet retreat to unwind. The Key West International Airport is only a few minutes away for easy travel access.brbrGetting Around:brWith parking available, you'll have easy access to explore the island by car. If you prefer to travel by bike, scooter, or golf cart, rentals are nearby for your convenience. Key West's walkability means many attractions are just a short stroll away, and for longer distances, taxis and rideshare services are readily available.brbrOther Things to Note:br- Pet-Friendly Policy: Pets are welcome!br- Maximum weight: 40 lbs per petbr- $20/night per pet (2-pet maximum)br- Please notify us if you plan to bring your furry friend!br- Guests must be 25 years of age or older to reserve this property.brbrCheck-In: 3:00 PMbrCheck-Out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

The Grand Turk | Spectacular Sunset View, Private

Key West, Florida, United States

Bed

Bath

Sleeps

$192.25

Shipyard Condominiums are located in the Truman Annex Complex which is located 2 blocks from Duval Street and all of the Old Town Key West attractions. The properties are also located ¼ mile from one of the best beaches on the island. The Shipyard units are single level condominiums which have private courtyards on the first level. All properties are outfitted with washer/dryer, pots; pans, towels linens, have central air conditioning, off street parking and pool access. This property is a garden level condo and has recently been refreshed! New additions include all new flat screen TVS, linens, and housewares.brPlease note: This property requires a 28 night minimum stay.

ISLAND TIME at The Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$254.29

*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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

$639.61

*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.

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

Key West, Florida, United States

Bed

Bath

Sleeps

$451.79

*Please read before booking:*brConstruction on the Annex Building spalling project will begin on April 1st. The project is expected to take approximately four to five months to complete. Please be advised that work may be noisy at times, and scaffolding will be erected in front of certain units. Please exercise caution while crews are active on the property.brbr*Please note that this home is available for 28+ night stays only.*brbrView passing ships and sunsets from your own balcony in the Truman Annex’s most prestigious building!brbrBalmy breezes, brilliant sunrises, and magnificent sunsets await you at Sundown Refuge, located in the exclusive Harbour Place condominium complex. You'll spend most of your time overlooking Florida Bay in one direction and Truman's Little White House in the other from the privacy of your own spacious deck.brbrThe living and dining areas are decorated in soothing tones of green and beige and tastefully furnished with a plethora of local artwork with all the necessities of home. You'll wonder how you'll ever leave!brThe master bedroom with a king bed and bathroom en-suite and the queen guest bedroom opens to the deck, offering lots of opportunities to congregate with a large group or keep it intimate with your morning coffee.brbrOnce you do leave the comforts of this home, anything you'll want to do is close by – the nightly Sunset Celebration at Mallory Square, dining and shopping galore on Duval Street, and many historic attractions within easy walking distance. Spend time relaxing by the refreshing pool or ride your bike to Ft. Zachary Taylor State Park for some swimming and snorkeling at Key West’s nicest beach. Life is good at Sundown Refuge!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- 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- The Harbor Place HOA is doing extensive renovations on the exterior of the Condominiums. They are attempting to soundproof the noise the best they can, and at times part of the deck adjacent to your rental may be unavailable for use. This will affect reservations between August and December 2023.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 bed w/ ensuitebrBedroom 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.

Sundown Refuge | Top Location w/ Outdoor Dining & Shared Pool | Month Long Stays

Key West, Florida, United States

Bed

Bath

Sleeps

$297.76

*Please read before booking:*brConstruction on the Annex Building spalling project will begin on April 1st. The project is expected to take approximately four to five months to complete. Please be advised that work may be noisy at times, and scaffolding will be erected in front of certain units. Please exercise caution while crews are active on the property.brbr*Please note that this home is available for 28+ night stays only.*brbrIt’s hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. But either way, you can enjoy breathtaking sunsets with a glass of wine from your own private porch.brbrThis lovely Truman Annex condo rental in the exclusive Harbour Place condominium complex offers all the comforts of home with the special touches that make it a vacation worth remembering.brbrThe colorfully decorated living room/dining room area, showcases tropical art. A fully equipped kitchen has everything at hand if you decide to cook. A whimsical wall mural of dogs enjoying water sports adorns the master bedroom with king bed along with a cozy sitting area, perfect for curling up with a good book. A queen guest bedroom and a second bathroom with tub and shower are provided.brbrEnjoy the large shared pool with a spectacular view or head to close-by Fort Zachary Taylor State Park for a swimming/snorkeling adventure or a shady picnic by the sea.brbrTruman Annex is a gated community within the Old Town section of Key West within walking distance of anything you'll want to do while visiting -- Sunset Celebration at Mallory Square; Duval Street with its bars, restaurants, art galleries, and shopping; historic attractions such as the Hemingway House, Lighthouse Museum, Customs House, and the Mel Fisher Museum. So many options, so little time!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 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- The Harbor Place HOA is doing extensive renovations on the exterior of the Condominiums. They are attempting to soundproof the noise the best they can, and at times part of the deck adjacent to your rental may be unavailable for use. This will affect reservations between August and December 2023.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 bed w/ ensuitebrBedroom 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.

Truman's Hideaway | Top Location w/ Patio, Pool Access & BBQ | Month Long Stays

Key West, Florida, United States

Bed

Bath

Sleeps

$264.8

*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 cozy and charming vacation rental in Truman Annex is guaranteed to make you feel right at home.brbrA beautiful 2 bedroom, 2 bath ground level condo located in the gated Shipyard Condominium area of the prestigious Truman Annex community. You will find everything here you want to make your Key West vacation spot a home away from home and more.brbrBeach House Condo has the perfect back deck to sip a cafe con leche in the morning or read a book in the afternoon. The property has an open floor plan with a fully equipped kitchen that allows the cook to remain in the gathering, a dining area with seating for 4 and a comfortable living room that opens to the large private deck. The bright and cheerful master bedroom suite has a queen-size bed and private bathroom while the second bedroom has two twin beds and a bathroom just outside the door.brbrThe shared swimming pool is steps away from the property, the perfect place to sun, relax, enjoy a good book or cool down after a busy day enjoying the sights of Key West. Reserved parking and WIFI complete the amenity package for this property.brbrTruman Annex is a secure gated community in the midst of historic Old Town Key West, one of the most requested locations for travelers to Key West. Located at the entrance to Fort Zachary Taylor State Park with one of our finest beaches and only 2 blocks from infamous Duval Street with shops, galleries, bars and restaurants from the Gulf of Mexico to the Atlantic Ocean, this spot is the ideal beach rental in the Florida Keys. Walk to Truman's Little White House, the Hemingway House, Lighthouse Museum or the Sunset Celebration at Mallory Square. Everything is within easy reach; you'll never want to leave.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 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 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 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. 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.

Beach House Condo | Pool Access, Gated Community, Top Location| Month Long Stays

Key West, Florida, United States

Bed

Bath

Sleeps

$1106.95

Get ready to relax in this 2-bedroom Hyatt condo in Key West. You are welcome to use all available Hyatt onsite amenities.The space features a king bed and a queen bed, plus a cozy living room with a sofa bed for extra guests. Two bathrooms include both a shower and a bathtub. There is a full kitchen and seating for 6 making your stay comfortable and convenient. Guests can enjoy a cool, pleasant atmosphere throughout the condo, perfect for unwinding after a day of exploring Duvall Street and Mallory Square. Whether you’re lounging inside or spending time together, this condo offers an enjoyable retreat. Book now and enjoy everything this condo has to offer.brbrThere may be other unlisted dates and smaller suites, 1bedroom or studios. Inquire with dates and suite size.

Hyatt Sunset Harbor 2Bedroom 2Bath Sleeps6 Special March Dates

Key West, Florida, United States

Bed

Bath

6

Sleeps

$255.69

Charming first floor 2-Bedroom, 1-Bathroom Shipyard Condo in Historic Truman Annex - Key WestbrbrEscape to the heart of Key West with this beautifully appointed 2-bedroom, 1-bathroom condo in the prestigious Shipyard community of Truman Annex. Perfectly located just steps from the island's top attractions, this condo offers the ideal blend of comfort, convenience, and style for your next tropical getaway.brbrProperty Highlights:brbrPrime Location: Nestled in the tranquil and secure Truman Annex, you’ll be just a short stroll from the famous Duval Street, historic Old Town, and the scenic Waterfront. Explore the vibrant culture, lively nightlife, and charming cafes of Key West, all within walking distance.brbrSpacious Living Area: This light-filled, open-concept condo boasts a cozy living room with comfortable seating and a flat-screen TV for relaxation after a day of adventure.brbrFully Equipped Kitchen: Whether you’re preparing a quick breakfast or a gourmet dinner, the modern kitchen has everything you need, including stainless steel appliances, cookware, and ample counter space.brbrComfortable Bedrooms: The two cozy bedrooms feature plush bedding, ceiling fans, and ample closet space. Perfect for a restful night’s sleep after enjoying the island’s activities.brbrPrivate Outdoor Space: Step outside onto your private patio with convenient awning to unwind with a drink, enjoy the warm tropical breeze, and take in the beautiful surroundings of Truman Annex. Also, just steps from the pool.brbrCommunity Amenities: Guests can take advantage of the Shipyard’s heated pool, lush tropical landscaping, and secure, gated entry. Enjoy the serenity of this peaceful community while being just moments away from all the excitement of Key West.brbrWhy You'll Love It:brbrPerfect for couples or small families seeking a relaxing and convenient escape in Key West.brbrSteps away from the Key West Historic Seaport, Mallory Square, and Sunset Celebration.brbrPrivate parking and secure access provide peace of mind.brbrThe perfect blend of modern amenities and island charm in one of the most sought-after locations in Key West.brbrWhether you're looking to explore Key West’s iconic attractions or simply relax in the comfort of your Shipyard condo, this vacation rental offers the ideal home base for your tropical retreat.brThis property has a 28 night minimum stay

A & E's Tranquil Tides at the Truman Annex in Key West

Key West, Florida, United States

Bed

Bath

Sleeps

$300.3

The Barbados | Key West Condo with Pool, Hot Tub & Private BalconybrbrWelcome to The Barbados, a welcoming 2-bedroom condo nestled in the peaceful Sunrise Suites community on the southeast side of Key West. Designed for relaxation and easy island living, this charming retreat offers resort-style amenities, a private balcony, and a prime location close to beaches, biking trails, and the best of downtown—making it an ideal home base for your Key West getaway.brbrThe Ambiance:brStep inside The Barbados and enjoy a laid-back island atmosphere that feels instantly inviting. This comfortable condo features an open living space perfect for unwinding after a day in the sun, with plenty of room to relax, dine, and recharge. The fully equipped kitchen makes it easy to prepare meals or snacks, while the living area offers a cozy spot to kick back with TV, WiFi, and cool central air conditioning. Step out onto your private balcony to enjoy the tropical breeze, morning coffee, or a quiet evening after a day by the pool.brbrGuest Access:brEnjoy a smooth and stress-free arrival with contactless check-in—your personalized access code will be provided prior to arrival. During your stay, you'll have access to all Sunrise Suites community amenities, including:brbrGuests also have access to Sunrise Suites' shared amenities, including:br- Communal heated pool and hot tubbr- Tennis courtsbr- Scenic walking paths and biking trailsbr- Shared washer and dryer facilitiesbr- Convenient elevator and stair access to the unitbrbrLocation Highlights:brLocated within the peaceful Sunrise Suites Resort, The Barabados is just minutes from Smathers Beach, Higgs Beach, and the energy of Duval Street. Explore Key West's vibrant dining, nightlife, and attractions, then return to your quiet retreat to unwind. The Key West International Airport is only a few minutes away for easy travel access.brbrGetting Around:brWith parking available, you'll have easy access to explore the island by car. If you prefer to travel by bike, scooter, or golf cart, rentals are nearby for your convenience. Key West's walkability means many attractions are just a short stroll away, and for longer distances, taxis and rideshare services are readily available.brbrOther Things to Note:br- Pet-Friendly Policy: Pets are welcome!br- Maximum weight: 40 lbs per petbr- $20/night per pet (2-pet maximum)br- Please notify us if you plan to bring your furry friend!br- Guests must be 25 years of age or older to reserve this property.brbrCheck-In: 3:00 PMbrCheck-Out: 11:00 AMbrbrTo enhance guest safety and security, this property is equipped with exterior security cameras for safety and monitoring purposes. Cameras are located around the perimeter, including entrances, walkways, pool, parking areas, and common outdoor areas. No cameras are placed in private or interior spaces.brbrAt Colocada Vacation Rentals, we're dedicated to providing a relaxing and memorable Key West experience. If you have any questions or need recommendations, don't hesitate to reach out! We're here to help make your stay as special as possible.

The Barbados | Private Balcony, Pool View!

Key West, Florida, United States

Bed

Bath

Sleeps

$205.32

PLEASE BE AWARE:brThis community is currently undergoing balcony repair property-wide potentially through May 2026. A 12 person crew will be working section-by-section from 8am-6pm, 5 days a week, and Saturdays will be weather make-up days as-needed. Please understand there will most likely be some amount of noise heard throughout the community. Your specific unit's balcony repair is currently scheduled for 12/11/25 -2/6/26. This is subject to change depending on how the project progresses. Our rentals have been priced to offset noise issues or any other inconvenience due to the construction project.brbrUNWIND IN PARADISE…brLet you worries wash away in this peaceful retreat located within the 1800 Atlantic community offering endless amenities. This 2 bedroom, 2 bathroom gem is the ideal setting to take advantage of your time in Paradise while having every luxury at your fingertips!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brGreeted by an open space filled with comfortable furnishings with nautical décor, this charming abode pulls you into your alternate reality. Enjoy a large, fully equipped kitchen with stainless steel appliances for meal prep that can be enjoyed at the dining table for 4. Occupy the living area for movie and card night as you continue to create your Key West story together. The unit is accessible by an elevator or the stairs. brbrSLEEPING ARRANGEMENTS…brSleep comfortably in a cozy queen bedroom with a TV and hallway bathroom with a shower tub combination. The primary king suite comes with a TV and en suite bathroom with a walk in shower and ample closet space. Both rooms conveniently open up to a balcony overlooking a lush, vibrant courtyard with a sliver of the sparkling ocean from the distance. Enjoy a sofa sleeper to accommodate visiting guests in town.brbrOUTDOOR LIVING…brTake advantage of the sweet island breeze as you craft up your 5 o’clock cocktail on the balcony with blissful views beyond. A heated, saltwater community pool is equipped with plenty of loungers and views of the sparkling ocean. Tennis courts reside on property as well as a community grill and fitness center. Enjoy being located in these peaceful surroundings with just a short ride into town! brbrPARKING...brDesignated garage parking space included as well as overflow parking in front lots (first come first serve). brbrBOOKING DATES...brThis home is offered only as a monthly rental (28 night minimum). We prefer to book by the calendar month (first day of the month to the last). We may consider alternate dates if the calendar allows or if the owner will make an exception. brbrPETS...brThis is not a pet-friendly home.brbrMULTI MONTH RESERVATIONS... brFor monthly reservations, the following fees will be added PER MONTH: brMid-stay cleanbrPool/hot tub heating fee (if applicable)brPet fee (if applicable)brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 90 days before the start of stay will receive a 100% refundbrbrCancellations inside of 90 days may receive a refund if we are able to re-rent any or all of the dates of the stay. The refund amount is dependent upon the rate of the new reservation. For multi-month reservations for January through March, a refund will only be offered in the event we are able to re-rent. The refund amount is dependent upon the rate of the new reservation(s). brbrCOME GET ON ISLAND TIME…

ALMOST HEAVEN ~ Stunning 2 Bedroom, 2 Bathroom Condo with Community Pool!

Key West, Florida, United States

Bed

Bath

Sleeps

$881.95

When you do not need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key West, you can rent Stars, the first floor condo of the Stars & Stripes compound.br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrINSIDE AND SLEEPING ARRANGEMENTS...brThis home offers four bedrooms, a living room with indoor dining for four, a fully equipped chef’s kitchen and a tiled bath with clawfoot tub and walk-in glass shower. The first bedroom has a comfortable king bedroom with armoire, flat screen TV and is right next to the bathroom. The second bedroom is just across the hall is the twin room with armoire and flat screen (twins convert to a king). The third bedroom has an adjoining door from the twin bedroom with a queen bed. And the fourth bedroom is a private suite that may be adjoined to the third bedroom, or from the outside if you prefer more privacy. The suite is like having your own unit; perfect for a couple or a family with kids. There is a full bath with shower/tub combo, wet bar with mini fridge and microwave in between the 3rd and 4th bedrooms.brbrThere is also a sofa sleeper in the living room for additional guests.brbrOUTDOOR LIVING...brIf you walk out the kitchen’s beautiful French doors to the deck there is a four-top outdoor dining table. The compound has a heated pool that is shared by the other condo on the premises (Stripes; levels 2 & 3). All guests have access to the laundry area, grill and grounds.brbrPARKING...brOne parking space is available that is first-come-first-serve with the unit above. You can find non-residential parking spaces in the surrounding area, or there is also The Old Town Garage a few blocks away. But this home is in an ideal location, and you don't need a car as you can walk or bike to almost anywhere you will want. If you need a ride, Ubers and Lyfts are readily available. The grocery is just a couple of blocks away, and you can also have groceries delivered or the fridge stocked by our concierge prior to arrival!brbrDISTANCES TO BEACHES...brSimonton Beach is 0.4 mibrFort Zachary Taylor Beach is 1.4 mibrSouth Beach is 1.1 mibrHiggs Beach is 1.3 mibrSmathers Beach is 2.3 mibrbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrPARADISE AWAITS...

STARS ~ 4 bedroom, 2 Bath Condo, Shared Heated Pool, Downtown Location!

Key West, Florida, United States

4

Bed

Bath

10

Sleeps

$810.88

When you don't need the entire compound but still want to enjoy this magnificent property in the heart of Old Town Key West.... rent Stripes, the second and third floor condo with tree top views and beautiful balconies!br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrINSIDE AND SLEEPING ARRANGEMENTS...brThe unique layout of this property allows your group to be together under one roof but have separate levels offering privacy and your own space! brbrThe second level offers a living room, dining for eight where one four top table is located inside and the other four top table is outside on the back balcony. There is a full gourmet kitchen and a large bathroom with walk-in shower. brbrThe second level bedrooms include a room with a full size bed, another room with two twin beds, and a bunk room with a trundle that's perfect for a kids room! The bunk room top mattress is a twin, the bottom mattress is a full, and the trundle is a twin mattress. All rooms offer storage for clothing and a flat screen TV. brbrThe third level is equipped with a small living room with flat screen TV, full kitchen, full bath with shower/ tub combo and a bedroom. The bedroom offers a queen and a twin, as well as a dresser for storage and a flat screen TV. brbrShould you want only one adult per double bed there is a sleeper sofa on each floor but we do not allow more than 10 guests in the condo at one time as there are only two baths. brbrOUTDOOR LIVING...brThe compound has a heated pool that is shared by the other condo on the premise (Stars; level one). All guests have access to the laundry area, grill and grounds. brbrPARKING...brOne parking space is available that is first-come-first-serve with the unit below. You can find non-residential parking spaces in the surrounding area, or there is also The Old Town Garage a few blocks away. But this home is in an ideal location, and you don't need a car as you can walk or bike to almost anywhere you will want. If you need a ride, Ubers and Lyfts are readily available. The grocery is just a couple of blocks away, and you can also have groceries delivered or the fridge stocked by our concierge prior to arrival!brbrDISTANCES TO BEACHES...brSimonton Beach is 0.4 mibrFort Zachary Taylor Beach is 1.4 mibrSouth Beach is 1.1 mibrHiggs Beach is 1.3 mibrSmathers Beach is 2.3 mibrbrCANCELLATION...brBookings canceled at least 30 days before the start of stay will receive a 100% refund. Bookings canceled at least 14 days before the start of stay will receive a 50% refund.brbrCONCIERGE SERVICES...brEnjoy our concierge service to assist you with planning activities for your trip, from bike/scooter/golf cart rentals to any excursion you can think of including snorkeling and sunset cruises, jet ski rentals, parasailing, kayaking, fishing, paddle boarding and much more. They can also have your fridge stocked with all the necessities in advance of your arrival!brbrPARADISE AWAITS...

STRIPES ~ Delightful Condo w/Shared Pool in the Heart of Old Town Key West!

Key West, Florida, United States

4

Bed