Home Vacation Home Rentals By Owner In Key West, FL

Showing 320 Of 878 Vacation Rentals
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Exceptional(5)

$727.88

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Private Vacation Home

A Wave From It All at The Truman Annex in Key West

Key West, Florida, United States

Searching for the perfect vacation home away from it all Your hunt ends in here! A Wave from it All is an updated and tastefully decorated 2-story townhome with its own private pool that epitomizes island living at its finest while offering all the comforts of home. Best of all, this home is nestled in a palm tree lined residential community with many historic buildings including the Truman Little Whitehouse, walking distance to many of Key West’s finest dining establishments, two blocks from the world-famous Duval Street, two blocks from the nightly sunset celebration at Mallory Square, and less than a half mile from the beach at Fort Zachary Taylor State Park. Break away from the ‘high seas’ of everyday life while you settle into for what’s sure to be a memorable Key West vacation!brbrThe double set of sliding glass doors on the back of the home open up to provide a private spacious tropical oasis of indoor/outdoor living space with a private pool. A large flat screen HD SMART TV hangs on the wall in front of comfortable seating options. The fully equipped kitchen has all the appliances and tools needed to prepare meals at home, on those nights that you chose to dine home with your pick of indoor or outdoor dining.brbrTruman Annex is the most exclusive private residence community in Old Town Key West. Located just off the main drag of Duval Street, The Truman Annex is an oasis of calm, quiet palm tree lined streets with many historic homes, 24-hour staff and restricted access in the evenings where you can use the entry gate keys to come and go on foot.brbrProperty includes..brCentral Heat and A/C, Ceiling Fans, Flat Screen TVs in Living Room & All Bedrooms, Fully Equipped Kitchen, Laundry Room with full size Washer and Dryer, Starter supply of paper products & cleaning supplies, Linens and Towels provided, Wireless high-speed Internet access & full cable included.brbr** Fully Fenced & Lushly Landscaped Private Yard with Poolbrbr** Designated Covered Off-Street Parking (one space)brbr** This property will accommodate up to 4 adultsbrbr** No Pets Allowedbrbr**Gas GrillbrbrPlease note: This property has a 28 night minimum stay
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Bath 2

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Sleep 4

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$220.07

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Private Vacation Home

Paradise Point by AvantStay | Golf Course Living

Key West, Florida, United States

*Please note that this home is available for 28+ night stays only.*brbrParadise Point is a charming retreat sitting right on the course of the Key West Golf Club! Enjoy unobstructed green views right from your private covered patio, complete with comfortable seating and a fan for airflow on balmy days. Inside, this chic home features a cozy living room, a fully-equipped kitchen, and two comfortable bedrooms, with the primary featuring balcony access. You'll be on Stock Island, a tropical haven just outside the main island of Key West, with dining options and convenient grocery shopping all nearby. The Gulf is calling, and Paradise Point is ready to welcome you!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!brbrKey West is a place unlike any other in the United States. Connect with marine life through diving or fishing, or sightsee along the beautiful turquoise beaches. Nature is abundant, and so are the bars! Known for its nightlife, you will play as hard as you work in Key West, although it remains a wonderful destination for families and solo travelers alike. Make sure to chow down on some of the local seafood or Cuban-influenced cuisine—the country is only about 100mi away. 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- 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 two shared pools.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:brThere's street parking in the community.brGuest will receive 1 parking pass to park on the street.brbr---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 2

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Bath 1

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Sleep 4

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Exceptional(192)

$716.07

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Private Vacation Home

Jasmine Place - Right there with Hemingway - 2BD/2Bath - Private Pool

Key West, Florida, United States

WELCOME TO JASMINE PLACE!brbrbrJasmine Place is a beautiful and enchanting home conveniently located next door to the Ernest Hemingway Home and Museum and just across the street from the Key West Lighthouse.brbrYou are marveled with the grandeur and history that is so well maintained when looking at this home from the street. The two-story home, behind a white picket fence has brick steps leading to a large front porch and grand balcony that perfectly overlooks the Lighthouse.brbrUpon entrance, the Jasmine Place celebrates original carpenter hard wood flooring beneath the open concept features of a family friendly, entertaining home. The spacious living and dining areas lead directly outside through kitchen’s French Doors. The inviting light makes this home a perfect place to relax or entertain.brbrThe first floor serves as living space, kitchen space, and has one full bathroom that access the outside patio. The bathroom is also equipped with a washer dryer unit. The clean, white kitchen has the perfect view of this spacious backyard. This allows the tropical breeze in while watching friends and family outside grilling, swimming or lounging.brbrUp the original wooden stairs, the second floor of the home has two bedrooms and one full bath. The first bedroom has a queen size bed, and large windows. The second bedroom has a king bed and also has large windows to allow that natural tropical light in. The balcony on the second story has a perfect view of the Key West Lighthouse and overlooks Whitehead Street. The entry to the balcony is through a common area hallway and has chairs for relaxing.brbrThe backyard is landscaped with a tropical, local plants. The deck and private pool allow plenty of space for lounging, grilling, and outdoor dining. Plenty of outdoor seating can accommodate all your friends and family!brbrThe proximity to Duval Street, shopping, restaurants and the many activities Key West has to offer are walking distance. Although there is no need for a car, there is a private, gated, narrow off street driveway for your use only. Small cars only, SUV's will have a hard time parking here).brbrImportant Notice: Some booking platforms may not correctly display our security deposit requirements. This contract is based on a $125 non-refundable damage protection plan in place of a $5000.00 refundable security deposit; if you prefer to pay the $5000.00 deposit instead, please let us know. brbrGuests are subject to a 2% credit card processing fee. In order to avoid that fee, we encourage you to pay by check. br brThis is not a shared pool and not heated. brPets accepted with non refundable depositbrbrbr**PLEASE NOTE: THE HEMINGWAY HOUSE HOSTS EVENTS THERE AND MUSIC TILL 10 PM OR LATER SOMETIMES.brVirtual Tour Url: https://my.matterport.com/show/ m=KTTMKmULBc5
Bed 2

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Bath 1

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Sleep 4

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Exceptional(1)

$301.46

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Private Vacation Home

Key Haven 3bedroom 2bath canal front home w/boat dock, private pool, parking

Key West, Florida, United States

AGE REQUIREMENT:brEveryone must be 25 years or older. Families are welcome as long as children are accompanied with their parents and primary renters are 25 years or older. We do not accommodate bachelor parties, bachelorette parties, student groups or construction workers-NO EXCEPTIONSbrbrThis property is a 30 night minimum. brbrFEATURES:brBedrooms: 3 (1 king, 1 queen, and 1 queen)brBathrooms: 2brLocation: Key HavenbrSquare Feet: 1870brParking: Off street parking behind gated driveway (NO garage access) and parking along fencebrAmenities: Wifi, TVs, in-unit laundry, boat trailer parking, dock space for 1 boat about 33 feet, private pool, outdoor bar area, outdoor showerbr*The pool has been resurfaced, and the outdoor grill area has been redone*brbrTHINGS TO KNOW: brRestrictions/Rules: No smoking. No Pets.brbrCheck in: 4PM - We do not guarantee an early check in request will be granted because we need to give the housekeepers time to ready the units for check-in, however, should your unit be ready early, we will notify you from this number that you can check-in. No units will be able to accommodate a check-in earlier than 12pm. brbrCheck out: 10AM - We do not accommodate late check outs. brbrItems provided: All linens, bath towels and beach towels are provided for your convenience. You are provided an initial supply of bath soap, dish washing liquid, toilet paper, laundry detergent and paper towels. Additional supplies are the responsibility of the renter, or once the initial supply is used.brbrPool heating is $100 per week and must be requested in advance
Bed 3

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Bath 2

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Sleep 6

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$354.44

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Private Vacation Home

Fairway Oasis

Key West, Florida, United States

Summary:brbrLuxury monthly rental with private pool in The Sanctuary at Key West Golf ClubbrbrbrbrThe Space:brbrExperience island living at its finest in this beautifully updated 3 bedroom, 2.5 bathroom residence located in the exclusive Sanctuary enclave within the Key West Golf Club community. This sophisticated two-story home offers the perfect blend of modern comfort, elegant design, and resort-style surroundings — ideal for an extended stay in paradise.brbrbrbrStep inside to a bright, open floor plan where the living, dining, and kitchen spaces flow seamlessly together. The chef-inspired kitchen features premium appliances, quartz waterfall island with seating, and custom cabinetry — perfect for preparing meals or entertaining. The adjoining living area is flooded with natural light, opening through floor-to-ceiling sliding doors to a private backyard oasis. Relax by the sparkling private pool and waterfall surrounded by lush tropical landscaping, accent lighting and peaceful garden paths.brbrbrbrThe main floor includes a versatile den or home office space, which can be closed off for privacy when needed. Upstairs, the primary suite boasts vaulted ceilings, a luxurious ensuite bath, and a private covered balcony overlooking the golf course. Two additional bedrooms share a stylish full bath and a charming covered porch shaded by palms. Additional features include a covered carport, high-speed WiFi and an in-unit washer and dryer.brbrbrbrGuests enjoy access to Key West Golf Club amenities, including:brbr- Two resort-style heated swimming poolsbrbr- Modern fitness centerbrbr- 24-hour gated securitybrbr- 18-hole Rees Jones-designed championship golf coursebrbr- Community walking pathsbrbrbrbrRental details:brbr- Available for monthly rental (30-day minimum)brbr- No pets and no smoking permittedbrbr- Primary renter must be 25 or olderbrbr- Proper state and county taxes collected regardless of booking platformbrbrbrbrEnjoy the peaceful setting of the Golf Club while just minutes from Key West’s attractions, bars, restaurants and waterfront. Whether you’re seeking a relaxing retreat or an extended island adventure, this home offers the ultimate Key West lifestyle.
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Bath 2

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Sleep 6

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Exceptional(2)

$351.16

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Private Vacation Home

**DANCE OF THE BUTTERFLIES @ SOUTHERNMOST** New Home & Pool + LAST KEY SERVICES.

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrFor a month in Key West it is ideal to harness the comforts of new construction similar to the luxuries of your own home, but keeping the true spirit of Old Town Key West and the magical surprises around every corner. This brand newly constructed home, located a stone's throw from the Southernmost Point, also backs up to the famous Butterfly Museum and welcomes the delicate neighbors who flutter to the pool area for a visit each day. In addition to a unique mix of modern & classic luxuries, this home boasts these premium amenities:brbr• Rooftop Sundeck Overlooking Ocean & Old Townbrbr• Private Heated Pool brbr• Designated Off-Street Parkingbrbr• Fully-Equipped Kitchen brbr• Indoor & Outdoor DiningbrbrCombined with Last Key Realty's Five-Star Guest Services, DANCE OF THE BUTTERFLIES is the ideal mix of fresh, top-of-the-line construction and the simple pleasures of Old Town Key West.brbrTHE LOCATION...brbrThis home is located at the very end of Whitehead Street, just steps from The Southernmost Point of the United States and the iconic Buoy, in a private gated community of all newly built homes. You couldn't be any closer to the nightlife and attractions on Duval Street, yet this home is tucked away just far enough from the hustle and bustle. Just two short blocks from the Southernmost Beach and any number of well known Key West restaurants - you won't need a car to get around, but should you decide to bring one there is a designated off-street parking space available.brbrTHE PRIVATE POOL and DECKS...brbrThrough the large sliding doors in the living room is the pool area. The private pool can be heated and is perfect for a dip after a day at the beach or with a cocktail for happy hour. Relax in the sun or shade in the comfortable chaise lounges located on the pool deck. These is outdoor dining for 6 under a shady umbrella and a BBQ grill for a poolside cookout.brbrTake the stairs up to the third floor to discover the most unique feature of this home: a Rooftop Sun Deck with splendid views of the Ocean and Old Town. There is a dining table set up on the rooftop deck with an umbrella, making this the perfect place for a sunrise breakfast or a sunset happy hour you won't soon forget.brbrTHE LIVING AREAS and KITCHENS...brbrDANCE OF THE BUTTERFLIES offers top of the line living and kitchen amenities including:brbr• Open Floorplanbrbr• Large Flat Screen SMART TVbrbr• Comfortable Queen Sleeper Sofabrbr• Fully-Equipped Kitchen with State-of-the-Art Appliancesbrbr• Dining Area with Extra Bar SeatingbrbrTHE ACCOMMODATIONS...brbrThis home has a total of three bedrooms (one downstairs and two upstairs), each with a flat screen TV and plenty of closet space. The bedroom layout is as follows:brbr• First Bedroom: Located on the First Floor with Two Twin beds OR One Kind bed and an en-suite bathroom.brbr• Master Suite: Located on the Second Floor with a King bed, balcony access, and an en-suite bathroom.brbr• Third Bedroom: Located on the Second Floor with a King bed and an en-suite bathroom.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr• Washer and Dryerbr• Central Heat and A/Cbr• Ceiling Fans Throughoutbr• Flat Screen HD TVs in Living Room and Bedroomsbr• Fully-Equipped Kitchenbr• Basic Stock of Spicesbr• Starter supply of paper productsbr• Starter set of cleaning productsbr• Linens and Towels providedbr• Wireless high-speed Internet access and full cable is includedbr• Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr• Electric Parking Gate with Security Codebr• Private Heated Poolbr• Propane BBQ Grillbr• Queen Sized Sleeper Sofabr• Off-Street ParkingbrbrOther Notes:brbr• In person welcome br• All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br• Additional interim cleanings availablebr• This property will accommodate 6-8 adultsbr• Pets Considered - Max of 2 and if approved an additional fee of $200 per pet will be assessed
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Sleep 8

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Exceptional(9)

$284.04

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Private Vacation Home

~ MY HAPPY PLACE ~ A charmingly beautiful treasure in a perfect location!

Key West, Florida, United States

MONTHLY RENTAL: Requires a minimum stay of 28 nights occurring within the same month. Stay a month and live like a local!brbrTHE PROPERTY: From its delightful mosaic-tiled, covered front porch to its back yard dip pool, this Key West home will surprise you! Petite yet grand, this home is walkable to many attractions. brbrAs you enter the home via the living room, you will be surrounded by comfortable furnishings, hardwood floors, a vaulted ceiling and plenty of natural light. Proceed down the Dade County Pine hall to the guest bedroom and hall bath. Further down the hall is the primary bedroom and en-suite bath. Continue through the French doors towards the back of the home, to the well-appointed kitchen with vaulted ceiling. White cabinets and countertops, stainless-steel appliances, and a small island make this kitchen a dream to cook in. If hor d’ oeuvres and cocktails are more your style, you will love preparing them in the kitchen while enjoying a pool view.brbr Stroll beyond the kitchen’s double glass doors onto the covered deck and patio. Here you will find your private dip pool, lounge chairs, table with umbrella and additional seating as well as a grill. The backyard area is secluded and beautifully landscaped. Your own washer and dryer are housed in a spacious outdoor room near the pool. After a day strolling about Key West, this beautiful and classic home offers you a unique opportunity to relax and unwind, like you have been yearning for. brbrBED CONFIGURATION: The primary bedroom boasts a king size bed, ensuite bath and closet. The second includes a queen size bed and hall bath. Both bedrooms have TVs, ceiling fans, and ample closets. brbrOUTDOOR AMENITIES: With your own dip-pool and fenced-in yard, this home provides Key West privacy and tranquility. The pool is heated seasonally (November through April) for an additional fee which will be assessed at the time of booking. Enjoy morning coffee and people-watching from the covered front porch. brbrPARKING: No designated parking space. There is free on-street neighborhood parking. brbrLOCATION: Being in the heart of Old Town makes this a fabulous choice for access to all that Key West has to offer. Just 3 blocks to Duval Street and conveniently located near restaurants, groceries, shops and galleries, this home is walkable to attractions including Mallory Square and The Wharf. brbrPETS: This home is NOT pet friendly. (If you have pets, please browse through our many homes that are pet-friendly).brbrSMOKING: This is a non-smoking home and property. brbr***Guests must be 25 years of age or older unless accompanied by an adult.brbr***Please note that the cleaning fee includes a full mid-stay clean***brbr***Managed by Historic Key West Vacation Rentals***
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Bath 2

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Sleep 4

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$943.46

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Private Vacation Home

**VILLA PARADISO @ CASA EAST** Private Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrWelcome to VILLA PARADISO, an elegant single-story home meticulously furnished in the classic British Colonial style. The moment you walk in the front door, you’ll feel the embrace of its Old World comfort as you pass through the bright and airy living room into the updated kitchen, and out back to your private backyard oasis. No expense was spared in the design and completion of this beautiful vacation home, which can be seen at every turn. VILLA PARADISO is located in a very quiet residential neighborhood just minutes from Higgs beach and from Old Town. All three bedrooms have their own dedicated bathroom and provide direct access to the pool area. Best of all, your stay at VILLA PARADISO includes Last Key Realty’s prestigious Guest Services & In-house Concierge, ensuring your time in Key West will be unforgettable!brbrTHE LOCATION...brbrThe Casa Marina East district of Key West is a quiet, mostly residential neighborhood on the southern side of the island. Just a quick three block walk from the start of Higgs Beach at White Street, and just down the street from Smathers Beach, VILLA PARADISO is a dream for beach-lovers who prefer to pack their coolers and towels and walk down to the sand and water. Watch the sunset from Smathers Beach or the White Street pier just around the corner. Take the short stroll to Salute Ristorante for a beach-side meal, or ride bikes down to Duval Street or the Historic Seaport for the most popular Key West attractions.brbrTHE LIVING AREA & KITCHEN…brbrThe open plan living area is surrounded by French doors to allow in plenty of natural light and to let the tropical breezes flow through the home. The living room offers comfortable seating options that surround the large flat screen TV. The fully-equipped kitchen features stainless steel appliances and all the tools needed to prepare meals at home. The dining area is in the vaulted attached pavilion with access to the kitchen via the French doors and a convenient window passthrough. brbrTHE POOL...brbrHead into the backyard to find your true paradise -- the fully fenced backyard with a private heat-optional pool and ample seating, perfect for lounging in the South Florida sun. The pool can be heated to your liking, so no matter the temperature, the pool is the right place to be. After a dip, soak up some sun in one of the chaise lounges on the pool deck. Enjoy a poolside BBQ using the propane grill and outdoor dining area.brbrTHE ACCOMMODATIONS...brbrAll three bedrooms in this lovely home are located on the first floor. No stairs necessary!brbr** Master Bedroom: King bed, large flat screen TV, walk-in closet, multiple French Doors that open to the pool, and en suite bathroom with a walk-in shower.brbr** Second Bedroom: King bed, flat screen TV, closet, direct access to a private patio and to the pool area, and en suite bathroom with a walk-in shower.brbr** Third Bedroom: Two Twin beds OR One King bed, flat screen TV, direct access to walkway that leads around to the pool area, and access to the hall bathroom with a shower and tub combo.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced & Lushly Landscaped Private Yardbr** Private Pool with Available Pool Heatbr** Propane BBQ Grillbr** Off-Street Parking for Multiple VehiclesbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 6 adultsbr** Pets Allowed br** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
Bed 3

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Bath 3

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Sleep 6

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Exceptional(1)

$740.11

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Private Vacation Home

**INFINITE HORIZONS @ BIG COPPITT** Waterfront Home & Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrAs if a vacation to the Florida Keys wasn’t memorable enough, the million-dollar views from INFINITE HORIZONS are ones you’ll never forget. Located about 10 minutes north of Key West on Big Coppitt Key, INFINITE HORIZONS sits on an oversized, open water lot with a private pool and beach placed against the stunning backdrop of the gorgeous Gulf of Mexico that stretches to the infinite horizon beyond. The fully renovated interior is equally as spacious and impressive. At over 3,000 sq ft and featuring 6 bedrooms, this large, elevated home offers plenty of space for everyone in your group to spread out. In addition to the spacious layout and amazing amenities, a month at INFINITE HORIZONS also includes Last Key Realty's Five Star Guest Services & In-house Concierge, known for elevating Florida Keys vacations to the next level.brbrTHE LOCATION…brbrINFINITE HORIZONS is located at Mile Marker 10 on Big Coppitt Key. You'll be only a 10-minute drive or Uber ride from Key West, and the commute is beautiful: sapphire blue waters on either side of the road. Best of all, you have restaurants and entertainment options within minutes of your front door. Karlita’s Cafe is located just a short stroll or bike ride away for breakfast or a cup of Cuban coffee. You’ll also be within a few minutes of local Keys’ favorite restaurants Geiger Key Fish Camp and Bobalu’s.brbrTHE PRIVATE POOL & GROUNDS... brbrFrom floating around in the private pool to laying out on the private beach to boat days at the sandbar, INFINITE HORIZONS is a sun worshiper’s dream home! The 13 x 38 pool gets plenty of sun all day long and is surrounded by chaise lounges. The private beach is the perfect place to lay out and provides swimming and fishing access to the surrounding shallow waters. There’s also a small craft ramp for launching your boat or kayaks and paddleboards (both included with the rental) right from your back yard. Snipes Key and Marvin Key sandbars are located less than 10 minutes away. The floating boat dock is approx. 16 ft long and is located on the canal, which is approx. 5 ft deep.brbrTreat your group to a poolside BBQ using the propane grill and outdoor dining table that seats 6. For a shaded poolside meal, there are two picnic tables located under the tiki hut. The grounds also include a regulation sized pickleball court, ample parking for multiple vehicles, an RV, boat trailer, and more. Guests can also use the deep freezer, corn hole, wiffle ball set, and bikes at the house. Water shoes in every size (child to adult) are also available for guest use.brbrTHE LIVING AREA & KITCHEN...brbrThe spacious, modern living room has been furnished and decorated with comfort in mind. The plush sofa and recliner sits in front of a large flat screen TV. The fully equipped gourmet kitchen includes stainless steel appliances and every tool you’ll need to prepare meals at home. The kitchen offers a dining table with seating for 6, plus 2 extra seats at the island. There's also a formal dining room with a large dining table that seats 8. The back covered porch overlooking the Gulf provides yet another dining option, with seating for 6. Incredible views can be appreciated from every window of the living room and kitchen.brbrTHE ACCOMMODATIONS...brbr** Primary Suite – Located on the First Floor with a King bed, a flat screen TV, closet, desk and chair, couch, and an en-suite bathroom with a garden tub, and a walk-in shower.brbr** Bedroom #2 - Located on the Second Floor with a King bed, a flat screen TV, double closets, and direct access to the jack-n-jill bathroom with a walk-in shower.brbr** Bedroom #3 – Located on the Second Floor with a King bed, a flat screen TV, double closets, direct access to the shared balcony, and direct access to the jack-n-jill bathroom with a walk-in shower.brbr** Bedroom #4 - Located on the Second Floor with a King bed, a flat screen TV, double closets, direct access to the shared balcony, and direct access to the jack-n-jill bathroom with a walk-in shower.brbr** Bedroom #5 – Located on the Second Floor with Full sized bunk beds and a twin trundle (not photographed), a flat screen TV, double closets, and direct access to the jack-n-jill bathroom with a walk-in shower.brbr** Bedroom #6 - Located on the First Floor with a Queen bed, a flat screen TV, closet, and access to the first floor half bathroom in the hall.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer & Dryerbr** Central A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Fully Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and YouTubeTV is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced Private Yardbr** Private Poolbr** Propane BBQ Grillbr** Boat Dockage (max boat length 30 ft)br** Fish Cleaning Stationbr** Deep Freezerbr** Kayaks w/ Paddles & Life Jacketsbr** Pickleball Courtbr** Paddleboards w/ Paddles & Life Jacketsbr** Bicyclesbr** Corn Holebr** Wiffle Ball Set w/ Basesbr** Ample Off-Street ParkingbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 13 adultsbr** Max of 2 Pets Allowed with Additional Fee of $200 per pet
Bed 6

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Bath 3

Bath

Sleep 12

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Exceptional(7)

$408.71

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Private Vacation Home

CLOUD 9 ~ 4 Bedroom, 3.5 Bathroom with Off Street Parking and Pool!

Key West, Florida, United States

NO PASSPORT REQUIRED…brA lovingly restored island retreat with luxurious coastal flair, this home’s aesthetic beauty draws you in to a world of tranquility. This home is also known as Hunter House in the name of Blake Hunter for his generous donation to a local organization. Spacious by design with 4 bedrooms and 3.5 bathrooms, a lifetime of memories await as your loved ones come together in this gem set a world apart from reality. br***PRIMARY GUEST MUST BE AT LEAST 25 YEARS OF AGEbrbrDETAILS & AMENITIES…brAn adorable glance to your picture-perfect getaway catches your eye as you pull up to 2 off street parking with views of your long awaited dream home. A quaint sunroom begins your journey with seating for your 5 o’clock happy hour. Step foot into an attractive, open Great Room area with cozy furnishings, a flat screen TV and rich hard wood flooring throughout. A crisp, gourmet kitchen follows with ample lighted cabinetry, a gas stove, granite counters, stainless steel appliances and bar seating for 4. Dining for 6 lies just beyond overlooking your outdoor tropical oasis. brbrSLEEPING ARRANGEMENTS…brTwo comfortable bedrooms occupy the first level of the home sharing a full bathroom with a walk in shower. The first bedroom comes with a queen bed and the other with a king bed. The private king master suite lies up the stairs equipped with a large walk in closet, writing desk and en suite full bathroom with double vanity sinks, a walk in shower and clawfoot tub. Soak up the pristine backyard views from the master suite’s very own balcony with seating for two. Visiting guests can experience a poolside cottage featuring a queen bed, mini fridge and en suite full bathroom with a shower. Additional sleeping arrangements can be found on the sofa sleeper downstairs with a powder room just off the dining area. Apple TV's are provided in guest rooms so you can log in to catch up on all your Netflix favorites! brbrOUTDOOR LIVING…brSunny days are best spent out on the spacious outdoor deck surrounding a sparkling, heated pool and natural beauty of swaying palms all around. Cool off under the retractable awning and enjoy your fresh catch al fresco with seating for 6. Just a short distance to the sandy beaches of Key West and all the adored attractions, this home is the ideal destination for island perfection. brbrPARKING...brTwo off street parking spaces are available for this home.brbrPETS...brOne pet per reservation, 30 pound non-shedding dogs are considered. No kitties please! Please either inquire prior to booking, or make sure to check the box that you are bringing a pet when booking, AND include size, breed, and age of the pet in Comments/Special Requests. A pet fee is required.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)brbrBOOKING DATES...brThis home is only available 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. 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% refund. brbrCancellations 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). brbrA TROPICAL DREAM…
Bed 4

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Bath 3

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Sleep 10

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Exceptional(6)

$698.28

/ Nightly
Private Vacation Home

The Jasmine House Just a 2 minute walk to Duval and restaurants and bars

Key West, Florida, United States

Enjoy your tropical vacation, whether work-free or not, in this Old Town home only a couple of minutes from Duval and Whitehead Streets and loads of restaurants, bars, and entertainment. The quiet lane is so small and discrete that even most locals would need a map to find it. But if you do know the area, you know this home is close to all of the action in Old Town. In addition, nearby City and County bus stops are very close to aid your transportation needs on the island. brbrThe home has a heated pool, modern kitchen, and entertaining areas, both inside and out near the pool. The main level has a very large living/dining/kitchen area with French doors opening out onto a spacious deck and a very private pool and rear garden area with beautiful tropical landscaping. The first level also has several closets and a half bath. On the second level, there are two identical bedrooms with a shared bath and porches overlooking the front yard and quiet street. In addition, the upstairs master bedroom is more than ample with a walk-in closet, private bath, and its own covered porch overlooking the pool and rear garden area. There is plenty of room for two cars in the gated off-street parking area in front of the house. The house also has cable TV and high speed internet.brThe property has been newly repainted and decorated! Please check out our YouTube video by copying/paste this link: https://youtu.be/nUBKtLvcmfk to see the completion!brbrPlease note, if you have a large party of guests and need additional space, the house immediately next door has common ownership and might also be available for rent at the same time. See our other VRBO properties listing numbers 2784733 and 2232811!
Bed 3

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Bath 2

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Exceptional(69)

$1034.09

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Private Vacation Home

**THE TOASTED COCONUT @ OLD TOWN** Fully Restored + Pool + LAST KEY SERVICES…

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrThroughout Key West you'll find subtle touches of coconuts; from the towering coconut palms nestled throughout the streets of Old Town to folks sipping from fresh coconuts while soaking up the sun, and now, you can add THE TOASTED COCONUT to that list. THE TOASTED COCONUT is a rare gem in the heart of Old Town Key West that captures the essence of classic Key West in a fully renovated modern design and includes all of the coveted amenities of a vacation home: a spacious living area, an ideal bedroom and bathroom layout, a private pool, and plenty of space to stretch out or come together as a group. In addition to the fabulous layout and desirable amenities, this home has an unmatched location. THE TOASTED COCONUT combined with Last Key Realty's Five-Star In-Home Guest Services is sure to make your group's stay in Key West an extraordinary one.brbrNeed more space Rent both THE ZESTY LIME and THE TOASTED COCONUT together as THE LIME AND THE COCONUT - two side-by-side private homes that can sleep a total of 16 guests with two private pools.brbrTHE LOCATION...brbrImagine being just steps from all of the shops, restaurants, and sites of Key West. Walk just one block to reach the world-famous Duval St, or take a short stroll down Simonton St to watch sunsets from the Historic Seaport. Not only will you be within walking distance of restaurants and entertainment, but you'll also be within a mile of Fort Zachary Taylor State Park, home to Key West's best beach.brbrTHE LIVING AREA AND KITCHEN...brbrThis home's classic Key West architecture is apparent from the street, with the gingerbread trim and a whimsical porch swing that define Old Town conch homes. Upon entering, you'll be pleasantly welcomed into a newly restored version of a Key West conch home. The living area boasts a large flat screen SMART TV, which can be viewed from the comfort of the plush living room furniture. The brand-new kitchen features stainless-steel appliances as well as all the tools needed to prepare a meal at home. The indoor dining table seats 4 and there's additional seating for 2 at the kitchen bar. There's also a convenient powder room just off the kitchen.brbrYOUR PRIVATE POOL...brbrPrepare your favorite beverage of choice (perhaps a Pina Colada or a Toasted Coconut Daiquiri) and head out the back door to the lovely pool area, which is fully fenced for privacy. The private 6' x 9' dipping pool can be heated to your liking and has a soothing waterfall. Comfortable patio furniture on the pool's deck provides outdoor lounging options for everyone in your group. The pool area is complete with an outdoor dining set that will comfortably seat 6.brbrTHE ACCOMMODATIONS...brbrEach of the three bedrooms in THE TOASTED COCONUT is a suite with a private en-suite bathroom. brbr** First Master Suite: Located on the First Floor with a King bed and an en-suite bathroom with a shower and tub combo. brbr** Second Master Suite: Located on the Second Floor with a King bed and an en-suite bathroom with a shower and tub combo. brbr** Third Master Suite: Located on the Second Floor with Two Twins OR One King bed and an en-suite bathroom with a spacious walk-in shower.brbrALL LAST KEY VACATION HOMES INCLUDE:brbr** Washer and Dryerbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen Cable TVs in Living Room and All Bedroomsbr** Fully-Equipped Kitchenbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access and full cable is includedbr** Full Time Concierge ServicebrbrIn addition, this fully stocked home also includes, but is not limited to the amenities on this list:brbr** Fully Fenced and Landscaped Backyardbr** Private Pool with Available Pool HeatbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 8 adultsbr** Pets Considered - Max of 2 allowed and if approved an additional fee of $200 per pet will applybr** This home does not include designated parkingbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
Bed 4

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Bath 3

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Sleep 8

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$305.73

/ Nightly
Private Vacation Home

Casa del Sol

Key West, Florida, United States

Summary:brbrSpacious Retreat with Pool & Guest CottagebrbrbrbrThe Space:brbrWelcome to your tropical escape in one of Key West’s most sought-after neighborhoods — Casa Marina, where laid-back island living meets comfort and style. Just a short bike ride from the beaches, restaurants, and all the excitement of downtown, this beautiful home offers the perfect balance of serene privacy and convenient access to everything Key West has to offer.brbrbrbrThis spacious four-bedroom, four-bathroom main house features an open-concept living space with a bright and airy living room and a fully equipped kitchen, ideal for easy entertaining and gathering with family and friends. On the main floor, you’ll find two inviting guest bedrooms, each with its own private bathroom. Upstairs, the primary suite with a king-size bed serves as a luxurious retreat, complete with a private bathroom. A second upstairs guest bedroom and a cozy lounge area provide even more space to unwind.brbrbrbrStep outside into your own tropical paradise — a lush garden with a huge pool and comfortable seating area, perfect for lazy afternoons, poolside cocktails, and evening barbecues. Please note POOL IS NOT HEATEDbrbrbrbrAn added bonus is the private guest cottage, featuring a bedroom, bathroom, and kitchenette — ideal for visiting friends, extended family, or anyone who enjoys a little extra privacy.brbrbrbrSet in a peaceful residential area just far enough from the bustle of downtown, this home offers a tranquil retreat while still keeping you close to Key West’s best beaches, dining, and entertainment. Whether you’re planning a family getaway or a group escape, this Casa Marina oasis has everything you need for an unforgettable stay in paradise.
Bed 6

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Bath 4

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Sleep 12

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Exceptional(21)

$1036.13

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Private Vacation Home

A contemporary island gem that was formerly used as a bottling plant,

Key West, Florida, United States

A contemporary island gem that was formerly used as a bottling plant, this modern and spacious home is now a desirable tropical retreat loctated in the heart of Key West. Having received a prestigious Ceramic Star for Architectural Preservation Excellence, Casa Amor captivates historic essence while luring you in with the finest of amenities.brbrStep into an open and bright space boasting high ceilings and natural lighting flowing into this island getaway. Polished concrete floors on the lower level and rosewood and travertine marble on the upper level keeps you cool on a steamy summer afternoon. The updated and fully equipped kitchen comes with granite counters and bar seating for 4 with an indoor dining table to seat 6 for group mealtime. Adjoining the kitchen is an open concept living area featuring cozy furnishings, a flat screen TV, and views through the floor to ceiling sliding doors of the lush backyard area, making this a great indoor/outdoor space to be enjoyed for entertaining. An additional table for 4 is located in the center of the home for card games or a happy hour before a night out on the town. Youtube TV service is available in this home.brbrTwo large guest rooms occupy the first level with comfortable king beds and flat screen TVs, and one of these rooms also includes a bunk bed. There is a nearby full bathroom with a shower and another half bathroom on this level making it convenient for those utilizing the sofa sleeper. Travel up the spiral staircase to the master suite that comes with a king size bed, a flat screen TV, walk in closet and an ensuite full bathroom with a soaking tub and shower.brbrThe lush backyard oasis is the epitome of Key West living! The covered and airy patio has plenty of room for lounging on a lazy day overlooking the lap pool which can be heated during the winter months and features a waterfall. Enjoy the convenience of your own outdoor shower and high walls outlining the home creating ideal privacy. An outdoor gas grill is available for your fresh catch of the day! Located blocks from all the fun Key West has to offer, you're sure to experience the true island lifestyle at Casa Amor.brbrOff street parking is available for one vehicle.brbrEnjoy 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!
Bed 4

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Bath 2

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Sleep 8

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Exceptional(1)

$239.96

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Private Vacation Home

Prime Old Town Location w/ Pool, Walk to Duval Steet | Blue Heron by AvantStay

Key West, Florida, United States

*This condo is available for 28+ day stays only, and the pool area is shared with 3 other condos.*brbrLocated at 906-2 Truman Avenue, Blue Heron is a charming two-bedroom, two-bath condo nestled in the vibrant heart of Key West. Just steps from the island’s most beloved attractions, this cozy retreat combines comfort, convenience, and a touch of island flair—perfect for your next sun-soaked escape.brbrInside, the living room features two plush sofas and board games for rainy days. Whip up meals in the fully equipped kitchen, and make your morning brew with the Keurig coffee maker. The primary bedroom features a king bed, TV, and direct access to the patio and pool area, while the second bedroom offers a plush queen, making it easy for everyone to unwind in privacy. brbrStep outside to the serene shared patio, where lush landscaping sets the scene for total island relaxation. Take a dip in the sparkling pool and soak up the sun with plenty of poolside lounge space, or opt for the shady hammock. An outdoor kitchenette and grill await for the perfect evening BBQ.brbrWhen you're ready to explore, you're just steps away from Duval Street, the Hemingway House, beaches, and a local grocery store. Whether you're here to explore Old Town’s rich history, sip cocktails at sunset, or simply recharge in paradise, Blue Heron puts you in the perfect place to experience it all!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.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- 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- Please note that the pool and outdoor area are shared with 3 other condos. This home does not have a balcony. The balcony seen in the photo gallery belongs to another unit.br- The hammock, bbq, and laundry facilities are private amenities for this unit.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:brNo onsite parking.brStreet parking only.brbr---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 2

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Bath 2

Bath

Sleep 4

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