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Key West Vacation Rentals

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    1 of 5 bubbles
    1 Review
    StudioSleeps 4Quick View
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    4.5 of 5 bubbles
    47 Reviews
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    4 of 5 bubbles
    30 Reviews
    2 BedroomsSleeps 4Quick View
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    About this property
    Havana Lane hearkens back to a time when cigar makers lived in the neighborhood, gathering on porch stoops to pass on the latest news. Near the notorious Key West Cemetery, this classic conch cottage embodies the essence of rustic charm while offering modern amenities and style. Centrally located...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4.5 of 5 bubbles
    6 Reviews
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    About this property
    Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this Secret Courtyard Cottage hideaway, you'll never know you're right in the center of Old Town Key West. Situated at the end of a little walking lane, this charming cottage, with private Jacuzi,  is made...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bathroom, Sleeps 5
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    About this property
    To tee, or not to tee: that is the question ... But whether or not golf is your game, the Key West Golf and Country Club promises a stay in one of the most esthetical residential neighborhoods in the Florida Keys. Beyond the masterfully designed 18 hole golf course, here you’ll enjoy the 200 acres...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bathrooms, Sleeps 6
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    Located in Bahama Village is the hidden gem we like to call Havana Daydream. You will definitely have to pinch yourself after walking into this little slice of paradise. As you walk in, you are welcomed by the colorful living space featuring a top of the line sleeper sofa that was made for ultimate...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    2 Reviews
    4 BedroomsSleeps 7Quick View
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    About this property
    The house is a traditional Key West cottage that has undergone a complete renovation in 2012. The charm and historic features have been retained, while all the luxuries of today have been added. There is a master bedroom, with king bed and full bath, on the first floor. Additionally, there is a...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    5 of 5 bubbles
    9 Reviews
    1 BedroomSleeps 4Quick View
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    About this property
    Location combined with history and design makes Coral Condo a prize piece of vacation real estate. This cozy one bedroom is located in the heart of Old Town just one block off Duval Street, where you'll find many of the attractions visitors come to the island to enjoy. This large corner condo is on...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    • Waterfront
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    About this property
    Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a...
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    Key West, Florida Keys 33040
    Rental Home - 6 Bathrooms, Sleeps 12
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    About this property
    Located just minuets from Duval St in a quiet mid-town neighborhood this attached 2 story house has everything you could want to enjoy your stay in Key West. It was remodeled in 2005 and has been upgraded constantly since. This house has 3br/3ba and the perfect layout for family and guests alike....
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4.5 of 5 bubbles
    21 Reviews
    2 BedroomsSleeps 6Quick View
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    • Balcony
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    About this property
    Enjoy the resort-style amenities of 1800 Atlantic Condominiums while relaxing in a residential setting amongst neighbors. 1800 Atlantic sits on 400 feet of oceanfront property. An expansive pool and spa sits oceanside surrounded by a lushly landscaped garden of native Key West plants and trees....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Hot Tub
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    About this property
    Fantastic 3rd floor ocean-view condominium. Unit features a full size fully equipped kitchen. Washer dryer. King in the master bedroom, 2 twins in the guest bedroom and a queen size sleeper sofa in the living room. The place is close to nightlife, the city center, the airport, and parks. You’ll...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    7 Reviews
    StudioSleeps 10Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    About this property
    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bathrooms, Sleeps 10
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    5 of 5 bubbles
    3 Reviews
    StudioSleeps 8Quick View
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    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice  vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bathrooms, Sleeps 8
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    4 of 5 bubbles
    3 Reviews
    StudioSleeps 6Quick View
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    About this property
    Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary. A spacious ocean front balcony provides the perfect setting...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bathrooms, Sleeps 6
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    1 of 5 bubbles
    1 Review
    2 BedroomsSleeps 6Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Sunrise Suites Resort is an island paradise. Complimentary hourly shuttle service from 9:15 AM - 5:30 PM daily between the Resort, beaches, airport, ferry terminal, & downtown make this resort's location ideal. Spend sun-filled days pampered by our warm and friendly staff. Pull up a lounge chair...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 of 5 bubbles
    22 Reviews
    2 BedroomsSleeps 6Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of Old Town, convenient to everything. These newer townhomes are in Duval Square's brick, tree lined courtyard that includes shops and restaurants. These units offer well equipped kitchens and living rooms that open to a patio, or porch, two bedrooms and two baths. There is a shared...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    About this property
    The shell of a Nautilus provides a home for this ocean animal, making Nautilus House your home away from home. So leave your worries behind and lounge by the private pool or swing in the hammock. The 3 bedrooms and 2 bathrooms comfortably accommodates all that stay. A well stocked kitchen allows...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 of 5 bubbles
    2 Reviews
    1 BedroomSleeps 3Quick View
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    Smoking allowed
    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The second floor unit "Treetop" sleeps up to 2...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Pet friendly
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    Smoking allowed
    About this property
    Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bathrooms, Sleeps 6
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    4 of 5 bubbles
    3 Reviews
    2 BedroomsSleeps 6Quick View
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    About this property
    Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    Steps to the Beach and Sunrise Nature's boutique offer you an exceptional view of key west's native birds right from your private balcony. It is furnished with all of the comforts of home. Large flat screen tv, ensuite bath, full laundry center, fully stocked kitchen, assigned parking bay and...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    38 Reviews
    3 BedroomsSleeps 6Quick View
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    Smoking allowed
    About this property
    An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    12 Reviews
    StudioSleeps 6Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    2 Reviews
    3 BedroomsSleeps 8Quick View
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    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 of 5 bubbles
    41 Reviews
    4 BedroomsSleeps 8Quick View
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    About this property
    Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    About this property
    28 DAY MINIMUM RENTAL TERM ONLY Kali Zoi is Greek for “good life.” That's what you'll have when you book a stay in this large, classic conch style house in historical Old Town. This 1,960 square foot, 2 story house has all of the charm of a 19th century home but was actually built in 1988 so it...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 of 5 bubbles
    1 Review
    1 BedroomSleeps 2Quick View
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    Location, location, location!<BR><BR>Situated in the heart of the Cuban district, steps from arguably the best 'con leche' in Key West, this monthly rental is minutes from everything on the island. No cars are necessary, bikes and beach chairs are provided.<BR><BR>This property will meet all of the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    About this property
    Beautifully renovated 2 bedroom 2 bath penthouse overlooking the Atlantic Ocean and Smathers Beach. Fabulous kitchen with stainless appliances and granite counter tops. Enjoy the amazing sunrise from the balcony of Awaken to Morning reflections. Recently renovated the master suite has a luxurious...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 of 5 bubbles
    2 Reviews
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    About this property
    THE MARTHA SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET Each...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5 of 5 bubbles
    4 Reviews
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    About this property
    Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the moment you step onto the front porch and into the cool, sun-dappled living area, your stress will drop away and your creativity will soar. This one-bedroom, one-bath unit is located on a...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    About this property
    Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 of 5 bubbles
    42 Reviews
    3 BedroomsSleeps 6Quick View
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    About this property
    Whitehead House is a unique two-story single family attached home nestled beside the Audubon House in Old Town Key West. Hidden behind the most photographed "prohibition fence" in Key West, this three bedroom, two bathroom home includes a large sunny pool and patio as well as off street parking (1...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4.5 of 5 bubbles
    47 Reviews
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    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bathrooms, Sleeps 12
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    4.5 of 5 bubbles
    9 Reviews
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    Welcome To Paradise!!! Located in the heart of Key West this charming 3 bedroom, 2 bathroom house has been completly renovated and includes 50", 42", and 27" flat screen TVs, DVR, and wireless high speed internet. The interior has just been furnished with custom designer furniture by Domestic Home...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 of 5 bubbles
    6 Reviews
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    • Hot Tub
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    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bathrooms, Sleeps 10
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    5 of 5 bubbles
    9 Reviews
    2 BedroomsSleeps 5Quick View
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    • Washer
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    7 day minimum please Key West Vacation Rental This fully furnished newly updated getaway! It is so close to all the Beach, our pool and the local Key West bars & restaurants and museums just take a short stroll or jump on a bike and a way you go... Our gated pool is climate controlled with plenty...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    • Shared Outdoor Pool (Unheated)
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    28 DAY MINIMUM RENTAL .... NO PETS ACCEPTED Break away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path,...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 BedroomsSleeps 6Quick View
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    Stay in a beautifully restored Century Old Conch Home by the Southernmost Point, the beach and Duval Street. Enjoy the nightlife of what Key West has to offer without the need to drive or take a taxi. No detail was left undone through- out this home featuring lots of dade county pine and...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pet friendly
    Kid friendly
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    About this property
    Our Key West condominium, Casa Tropico is a 2 bedroom, 1 bath ground floor condominium. The master bedroom has a queen size bed, the second bedroom has 2 twins. A double set of French doors in the living room open onto the rear deck. The deck overlooks a quiet walking lane. Outfitted with table,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 of 5 bubbles
    13 Reviews
    3 BedroomsSleeps 6Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    “Southard Comfort” is true Island living in downtown Historic Old Town Key West. Two story, 3 bedroom, 2.5 bath plus outdoor shower Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3.5 of 5 bubbles
    6 Reviews
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    This wonderful unit that has been completely remodeled in July 2013 has a private entrance in to the quaint efficiency on the back side of the complex. Featuring hardwood floors, Dade County Pine walls and a high-end, fully stocked kitchenette, this secluded hideaway offers the finest of...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    4.5 of 5 bubbles
    7 Reviews
    StudioSleeps 8Quick View
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    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time.  But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bathrooms, Sleeps 8
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    5 of 5 bubbles
    1 Review
    3 BedroomsSleeps 5Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 5
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    • Satellite TV
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    • Private Yard
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    Kid friendly
    Smoking allowed
    About this property
    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with...
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    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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    2 BedroomsSleeps 6Quick View
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    About this property
    Beautifully renovated duplex in Old Town. 2 bed/1.5 bath. Sleeps 4-6. There is a private stairway to apartment/loft upstairs. Upstairs unit is a massive 1100 sq ft with cathedral ceilings and loft (2nd bdrm). There is a king bed in the master, full bed in the loft and a pull-out sofa. Fully...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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