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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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    Luxurious Cozy Studio 2 Blocks From Duval Street1 / 20
    (1)Average
    Studio, 1 Bathroom, Sleeps 3 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Louisa House: A comfortable four bedroom vacation hideaway1 / 27
    (41)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca Too is the perfect get-a-way vacation rental for two! Casablanca Too is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
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    About this property
    Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Poinciana Place Garden: First Floor, Hot Tub, Walk to Beach & Downtown!1 / 24
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    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 Garden at Poinciana Place is a cozy and...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
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    28 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-style design with large doors and windows that let in the natural sunshine. The large living area is decorated in charming vintage wallpaper and bright, tropical colors. To the left...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    This newly renovated unit is located just two blocks from world famous Duval Street surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway. The bungalow features an one level open space living/dining area, full kitchen and a spacious...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Central Heating
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    Pet friendly
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    Smoking allowed
    About this property
    This property can only be rented by the month. This estate has it all waterfront, luxury,pool,jacuzzi and dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
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    About this property
    Have this recently surveyed 150 thousand dollar yacht all to yourself, at safe harbour marina dock ,and get free captained sunset Trip during your stay ,yacht has a large bed in the bow stateroom and two single beds for smaller people in the other ,,perfect for kids in the other stateroom. The...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Tee by the Sea - Luxury 2/3 condo - 7 Bikes FREE1 / 30
    (67)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    About this property
    Very nice luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in very well maintained gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    ROBERT FROST COTTAGE1 / 10
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill. At 410 Caroline Street is...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Duval Square Penthouse: A large, beautiful condo steps from the action1 / 24
    (8)Very good
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Terrace
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    • Shared Outdoor Pool (Unheated)
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    Key West, Florida Keys 33040
    Condo/Apartment - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    Poinciana Place Treetop: Second Floor, Hot Tub, Walk to Beach & Downtown!1 / 31
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Satellite TV
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    Pet friendly
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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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    Shipyard1 / 24
    (25)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
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    Pet friendly
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    About this property
    END OF SUMMER DISCOUNT! 10% OFF already discounted prices for open dates AUGUST - SEPTEMBER 2017! Please call our office for details. This cozy two-bedroom, one-bath condo lies hidden behind wrought iron gates and down a winding pathway. The Shipyard, part of the Truman Annex neighborhood named...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
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    Smoking allowed
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    About this property
    A great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    This delightful 2 Bedroom Cigar Maker's Cottage at 1008 Whitehead was built in the 1880's, where there was once a Cigar Factory across the street on Truman Ave. It's history also includes the previous owner, David Kaufelt, a well-known Key West writer. Quaint and charming, with a view of the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Chick-a-Pea's Cottage: Pet-Friendly with Fenced Yard! Parking & Private Pool1 / 28
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
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    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    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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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
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    Pet friendly
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    Smoking allowed
    About this property
    Beautiful home in the desirable canal front community of Key Haven. At the end of a quiet street this 3/2 home features a 2010 renovated kitchen, gorgeous enclosed back porch for relaxing, 2 boat lifts on the canal. The home is set deeply off the street for privacy, and has a long driveway for 2+...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building.  Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    About this property
    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Atlantis House Master Suite1 / 22
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
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    About this property
    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Luxury 1 Bedroom with Full Kitchen - Sleeps 3 - Walk to the Beach & Nightlife1 / 20
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Terrace
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    About this property
    THE BESS 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 - Recently...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    About this property
    2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ellen's Retreat, Key West, MONTHLY RENTALS ONLY1 / 19
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    About this property
    This beautiful home offers you contemporary luxury combined with exquisite historical charm of Old Town Key West. The open and spacious downstairs floorplan has an abundance of natural light and opens onto a fabulous pool area with an expansive deck. Entertaining your family and friends is...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    About this property
    This unit has a king in both bedrooms. 1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City Beach with a variety of watersports activities available. The property itself features assigned secure parking spaces, 3 lighted tennis courts, one of which is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Margarita Suite Treat yourself! Amazing condo with pool and hot tub access!1 / 24
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West condo! Bring your own boat!1 / 20
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Come down and take part in in Key West's many fishing tournaments! No docking fees at this condo where you can park your boat in the spacious lot and keep your car covered in your reserved spot under the building. Make memories the whole family will cherish in this great family friendly condo in...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing Florida Retreat1 / 23
    (32)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Balcony
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    • Shared Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Key West 2bd/2ba Condo - Monthly1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    ***Due to licensing restrictions, this Key West Condo rental requires minimum stay of 30 nights*** MONTHLY RENTAL ONLY - NO PETS ALLOWED - NO SMOKING - NO EXCEPTIONS Seaside Breeze is a true Key West island paradise. It is a wonderful two bedroom two bath, newly renovated condo decorated in light...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Whitehead House: A unique two story home beside the Audubon House1 / 23
    (42)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
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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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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    This efficiency is located on the 5th floor of the Galleon Resort. One of only two efficiencies with both a king size bed and a balcony (resort view). This unit has a brand new kitchenette featuring new wood cabinets, granite countertop and new stainless appliances including a mini-refrigerator,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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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 - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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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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    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Smoking allowed
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping....
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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    Pet friendly
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    Smoking allowed
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    This 4 Bedroom Key Haven open-water home has it all!! Enjoy the custom in-ground pool, barbeque and dine in at your waterside gazebo. You can relax upstairs in the custom finished open porch which features a beautiful open water view. This home also offers a downstairs porch which includes a bar...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Escape1 / 26
    (84)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Sunshine, beaches, and ocean breezes at Ocean Vista (La Brisa #403E)1 / 18
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
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    La Brisa beach condominiums offer a Florida charm that is relaxing, easy and captivating. Named for the ocean breezes that flow around the pretty blue and white buildings, La Brisa is an ideal spot to enjoy your Keys vacation. Located on South Roosevelt Boulevard, this secure gated community is...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Atlantica: A studio condo on the Atlantic shore of Key West1 / 10
    (35)Very good
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Satellite TV
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    Located just steps from the White Street Pier and Higgs Beach, Casa Atlantica truly lives up to its name: a home perched on the very edge of the turquoise waters of the Atlantic. Located on the quiet end of a waterfront townhome community, this property features simply the best views you will...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Havana Hideaway1 / 25
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Smoking allowed
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    Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing tall ships,...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stunning 2 bedroom ocean-view oasis vacation rental at the fabulous 1800 Atlantic in Key West. Our family owned unit has a new King in the master suite 2 twins in the guest bedroom and a queen sleeper sofa in the living room. The property has a Mexican tile floor in the living area's adding to the...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    "Not Big Enough"1 / 32
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, Location, Location! Ocean View, Lagoon Beach Front. This 83' Luxury Houseboat is located at 6000 Peninsular Ave. Key West, FL 33040, slip 25. The property is furnished and includes: linens, towels, 3 bedrooms, 3 beds, 2 full baths, 1 Large pull-out couch, all kitchen appliances,...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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