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House Rentals and Vacation Home Rentals in Florida Keys, FL

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    1 / 32
    4.5 of 5 bubbles (3) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 12
    4.5 of 5 bubbles (11) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    1 / 6
    4.5 of 5 bubbles (6) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 30
    4 of 5 bubbles (1) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    One-half block off world famous Duval Street sits the beautifully renovated home in the 500 block of Olivia Street. The updated kitchen features granite counter tops and beautiful wooden floors. Your bathroom offers a large walk-in tiled shower. A semi-private pool with waterfall feature(shared... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 26
    4 of 5 bubbles (25) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    The location is ideal in that it is just two blocks from the action of Duval street, yet has the tranquility and peacefulness to nap on the outside deck. This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (4) Excellent
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the... View all property information
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    Key West, Florida Keys 33040
    1 / 39
    4.5 of 5 bubbles (16) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Located at Papa's Hideaway, the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best... View all property information
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    Key West, Florida Keys
    1 / 14
    4 of 5 bubbles (16) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    4.5 of 5 bubbles (79) Very good
    Key West
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (8) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    One half of the group unit Tradewinds and opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side or... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 22
    5 of 5 bubbles (2) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    4.5 of 5 bubbles (25) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Part of the Nightly group unit Tres Flores You won't find a better private off-street parking is just outside your door. Turn down 'Free School House Lane' (1/2 block from the Marquesa Hotel & Restaurant) and you are home! Featuring a queen pillow-top bed with light weight down comforter, the... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    5 of 5 bubbles (1) Excellent
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    THE MOON BAY PENTHOUSE located beautiful Key Largo. This beautiful Penthouse condo is on the Florida Bay side of Key Largo at Moon Bay Condos just one mile from John Pennekamp State Park. The Penthouse condo is 1 of 2 original, top floor, large Penthouse units that includes 2 parking garages that... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 22
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    This beautiful motor yacht is available for your exquisite Key West vacation! . Huge Salon, Large galley, gorgeous teak throughout. One queen bedroom and one full bedroom with bathrooms for each one. Forward on the bow are 2 very comfortable loungers with pillows for relaxing. The upper deck is... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    4 of 5 bubbles (5) Very good
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    VILLAGE OF ISLAMORADA REQUIRES MINIMUM OF 29 NIGHT STAY Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 33
    4.5 of 5 bubbles (4) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Part of Southernmost Sanctuary Suites People looking for a vacation getaway in Key West are thrilled when they find a hidden gem like The Seagull Suite - located in the gardens of a private compound called The Sanctuary. Location, charm, and island appeal - the Seagull Suite is located in the back... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 33
    4.5 of 5 bubbles (3) Very good
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Welcome to your home away from home! “Bel Cielo” is a beautiful two-story condo in the quaint community of Moon Bay, located at mile marker 104 in Key Largo. (Moon Bay was recently featured on HGTV's Beach Front Bargain Hunt!) Featuring 1,146 square feet of living space with handsome furnishings,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 24
    5 of 5 bubbles (14) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    If you want peace and quiet and disconnect from the daily stresses of life, this is the place to be! Come enjoy all that the Florida Keys has to offer in this 'home away from home' Your reservation includes so many amenities! Great for a well-deserved get-away or Mini-vacation! Located in the... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 33
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Part of Banana's Foster Guest House This spacious 2 bedroom apartment takes up the first floor of this historic Key West home located on the corner of Caroline St and Simonton Dt. From the off street parking and shared courtyard entrance off Simonton opening into the kitchen to the private front... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    5 of 5 bubbles (4) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Porch
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    • x
    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
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    Key West, Florida Keys 33040
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    1 / 13
    4.5 of 5 bubbles (3) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This beautifully refurbished 4th floor condo has great marina and ocean views from the living room, master bedroom & balcony! Gorgeous wood floors throughout and new furnishings lend an elegant atmosphere with lots of comfort in mind. Master bedroom has a king-sized bed, while guest bedroom has 2... View all property information
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    Key Largo, Florida Keys 33037
    1 / 10
    5 of 5 bubbles (9) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This 2 bedroom 2 bath ground level home with a glassed in Florida room, is on a boating canal with only 1/4 mile to open water. In five minutes at idle speed you have immediate access to the Atlantic or the Gulf of Mexico via Bogie Channel. The Canal has 50 feet of concrete seawall with bumpers... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 39
    4.5 of 5 bubbles (10) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amelia House is surrounded by fine restaurants, art galleries, and fine shopping. The living room incorporates a sofa and chairs, in a colorful Caribbean print, which compliments the soft peach wall color. Included are rattan tables to complete the comfortable ambiance of the great room which... View all property information
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    Key West, Florida Keys
    1 / 9
    5 of 5 bubbles (5) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This spacious 2/2 has a giant deck for lounging with pool, shuffleboard and horse shoes on property. Boat slips available and just 10 minutes by boat to the reef. Walk to Sharkeys pub for some awesome food. Dive and Charter boats are just 5 minutes away on foot! This is THE place to stay in Key... View all property information
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    Key Largo, Florida Keys 33037
    1 / 23
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Canal-front house, quiet and in the nicest of neighborhoods (Plantation Key Colony). Situated on the bayside on Mile Marker 90. All remodeled,white tiled floor, furnished in wicker/rattan and decorated with the ocean & beach ambiance in mind. Boat dockage in the back and easy access to few boat... View all property information
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    Islamorada, Florida Keys 33070
    1 / 69
    4.5 of 5 bubbles (16) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Clean one bedroom and one bathroom cottage. Full size kitchen ,dinning room, sleeping couch on family room. Cable and internet are included., great location walking distance to swim with the dolphins .and 2 mile to the world famous John penny Camp State National Park. close to restaurants and... View all property information
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    Key Largo, Florida Keys 33037
    1 / 34
    Big Pine Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Beautiful home very centrally located in the heart of Big Pine key this 3 bedroom 2 bathroom home is close to everything that lower keys has to offer, Bahia Honda State Park which has one of the most beautiful beaches in the country is only 3.5 miles away as well as 29 miles away from Key West and... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 27
    4 of 5 bubbles (4) Very good
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hotel. If you have many people in your party, or big family, or want to have some privacy from your friends or... View all property information
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    Tavernier, Key Largo 33070
    1 / 18
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    BOOK BY NOVEMBER 15 TO RECEIVE 10% OFF YOUR STAY Condo has just been updated to include new mattresses, carpet, paint, linens, pots/pans and dinnerware. You will not find a cleaner unit in such a great location. This unit is in sought after Building #4 which is the closest to the ocean, offering... View all property information
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    Tavernier, Key Largo 33070
    1 / 15
    4.5 of 5 bubbles (2) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Located in the middle of Duval St, you are a 15 minute walk in one direction to the Atlantic Ocean and the Southernmost Point, and the same distance to the Gulf of Mexico and Mallory Square. Shopping, nightlife and the best restaurants are outside your front door. Hemingway House is 2 blocks away!... View all property information
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    Key West, Florida Keys 33040
    1 / 7
    Islamorada
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 27
    4.5 of 5 bubbles (21) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute walk away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (31) Very good
    Key West
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    The Monroe Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    4.5 of 5 bubbles (5) Very good
    Key Largo
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    This fully furnished 4 Bedroom, 3 1/2 Bath Canal Front Home is the ideal Escape to Paradise. One thing that cannot be seen through photos is the amount of privacy this location has, at the end of the Cul-de-sac with the canal and mangroves surrounding the home. Double Boat Dockage, Large Tiki Hut... View all property information
    Location Information
    Key Largo, Florida Keys 330037
    1 / 28
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-style complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    5 of 5 bubbles (2) Excellent
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
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    • x
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    • x
    About this property
    Enjoy your own private paradise and have fun in the Keys! This beautiful, clean, spacious and airy vacation rental home is locate in Key Largo "Diving Capital of the World." Key Largo is the first island of the Florida Keys, south of the Florida mainland. The house has three wonderfully decorated... View all property information
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    Key Largo, Florida Keys 33037
    1 / 26
    4.5 of 5 bubbles (42) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    With world class nightlife, shopping and restaurants all within walking distance, you are in the center of the best that Key West has to offer. Located on the second floor of a lovely Victorian-styled complex, this 1 bedroom/1 bathroom condominium features a full kitchen, high ceilings and a... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Resort in Key Largo, located in the town of Tavernier, Florida, is at the southern tip of Key Largo island Enjoy a resort in southern Florida's subtropical zone, with easy water access, a hotel bar and restaurant, and fun Florida Keys town nearby. This location is keen for those who like to get out... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    1 / 23
    4.5 of 5 bubbles (22) Very good
    Key West
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
    About this property
    AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a living... View all property information
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    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 bubbles (29) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details.... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    5 of 5 bubbles (7) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach and a... View all property information
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    Islamorada, Florida Keys 33036
    1 / 25
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set... View all property information
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    Islamorada, Florida Keys 33036
    1 / 43
    5 of 5 bubbles (2) Excellent
    Key Largo
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Mariner's Club 606 in Key Largo is one of a kind with it's resorts style pools and amenities that will meet the expectations of anyone looking for a high end, high quality place to stay and truly enjoy this beautiful part of the world! It is a private community tucked away in between palm trees,... View all property information
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    Key Largo, Florida Keys 33037
    1 / 9
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Yard
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    • Pet-friendly
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    • x
    About this property
    Neat, clean and perfect for a family vacation. This 2 bedroom, 2 bathroom home sits on a wide, deepwater canal Comfortable beds and furniture. Plenty of parking and room for a boat trailer onsite Optional access to a pool at the Glunz Ocean beach club $12 per person per day Outside Covered... View all property information
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    Key Colony Beach, Florida Keys 33051
    1 / 10
    4 of 5 bubbles (1) Very good
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • x
    • x
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    • x
    About this property
    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... View all property information
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    Key West, Florida Keys 33040
    1 / 33
    Key West
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    Welcome to "Duval Street Retreat" - The perfect vacation rental for large groups looking to be around all the Duval St action! Duval St. Retreat consists of two separate two-bed, one-bath condos located at 1124 Duval St. The property is only a couple steps (or stumbles) away from fine dining,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    5 of 5 bubbles (1) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Balcony
    • Satellite TV
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Huge screened in terrace. Spacious and extremely clean.. Peaceful and away from the highway. Sleeps 4-6 people. Enjoy the tennis courts, large pool on the ocean, beach-side BBQ grills. Relax, dine and drink under one of the tiki huts or visit one of the many water-front restaurants and bars nearby.... View all property information
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    Islamorada, Florida Keys 33070
    1 / 23
    5 of 5 bubbles (3) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    • x
    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    4 of 5 bubbles (2) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Resort in Key Largo 'located in the town of Tavernier' at the southern edge of Key Largo island, along the designated scenic drive on US Hwy 1. This is a perfect location for those who love to get out onto the water, or to observe the local wildlife. The tropical birds in this area are amazing.... View all property information
    Location Information
    Key Largo, Florida Keys 33070
    1 / 28
    4 of 5 bubbles (2) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Terrace
    • Satellite TV
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    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 and bask by our lagoon-shaped pool surrounded... View all property information
    Location Information
    Key West, Florida Keys 33040
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