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Holiday Rentals in Key West, FL

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 24
    5 of 5 stars (9) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 21
    4.5 of 5 stars (35) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    1 / 27
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    1 / 28
    5 of 5 stars (3) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    CASA GRANDE: Located on a quaint lane steps from Duval Street with room to park 2 vehicles off-street. Built for entertaining from the wide open floor plan that encompasses the spacious living room and grand kitchen to the magnificent pool. Master bedroom with bath ensuite shares first floor with... View all property information
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    Key West, Florida Keys
    1 / 9
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    Steps from the Ocean, Esprit du Vent is a spacious catamaran within minutes of Key West on Stock Island in a yacht club setting with a pool, beach and restaurant. The catamaran has 3 cabins, 1 head, and is bright, airy and spacious. Fully equipped with galley kitchen, oven, stove, coffee maker,... View all property information
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    Key West, Florida Keys
    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Note, this is a monthly rental only. We do not rent our home out for less than 30 days. Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features... View all property information
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    Key West, Florida Keys
    1 / 13
    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... View all property information
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    Key West, Florida Keys
    1 / 30
    4.5 of 5 stars (59) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    All new luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in NEW 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 from Duval St. and 2... View all property information
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    Key West, Florida Keys
    1 / 31
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Key West, Florida Keys
    1 / 26
    5 of 5 stars (33) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community... View all property information
    Location Information
    Key West, Florida Keys
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    1 / 25
    4.5 of 5 stars (54) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    AMELIA HOME - 2 bedroom 2.5 bath home with sparkling private pool only four blocks from the Atlantic Ocean and one block from Duval Street entertainment. Kitchen complete with everything to create a gourmet meal. Large open dining and living area. Lush garden with private pool that gives one a... View all property information
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    Key West, Florida Keys
    1 / 6
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    This is an amazing summer rental. Available during June and part of July only for either long weekends or by the week. Stunning location within the old town of Key West, over two levels, full kitchen, bbq, 2 bedrooms, shared pool. (Only between 4 houses) It just doesn't get better than this This... View all property information
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    Key West, Florida Keys
    1 / 20
    4.5 of 5 stars (47) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    DUVAL SEA TURTLE: This townhome has 2 bedrooms and 2.5 baths with a balcony off the master bedroom and the living room. Covered, gated parking space, WIFI, 3 TVs, free long distance calls King mattress, washer/dryer, and living room furniture new in March 2014. There is a community pool area to... View all property information
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    Key West, Florida Keys
    1 / 24
    4.5 of 5 stars (27) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked for a Key West vacation rental Florida. Fabulous artwork, fun collectibles, beautiful stained glass all give this cottage the unique feel that keeps... View all property information
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    Key West, Florida Keys
    1 / 23
    5 of 5 stars (10) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    ISLAND WIND: When balmy breezes beckon and tropical retreats call your name, Island Wind will be just the escape you need. Located in the pristine gated community of Windward Park this 2 bedroom, 2 bath Bahamian-style townhome is surrounded by lush landscaping and views of a sparkling swimming... View all property information
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    Key West, Florida Keys
    1 / 24
    4.5 of 5 stars (56) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    DUVAL BREEZE: 2 bedroom 2.5 bath townhome in Duval Square. 1st floor offers an open floor plan with a well stocked kitchen, spacious living room, dining room, half bath and French doors to your own private balcony. 2nd floor has 2 bedrooms with bath ensuite. Master bedroom has a private balcony.... View all property information
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    Key West, Florida Keys
    1 / 18
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Location! Style! Elegance! This beautiful home is the fabulous combination of everything a great vacation property should be. One half block to Duval Street in the historic district, the location can't be beat. The home's history is rich; neighboring the historic Gato Cigar factory which is now... View all property information
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    Key West, Florida Keys
    1 / 26
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    BLOOM'N PARADISE: Private residence with 3 bedrooms and 3 bathrooms in the main house plus a pool house with 1 bedroom 1 bath in Truman Annex, a prestigious gated community in Old Town. Surrounded by tropical greenery in a beautiful quiet gated community 2 blocks from Duval Street and Mallory... View all property information
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    Key West, Florida Keys
    1 / 29
    4.5 of 5 stars (11) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    CORAL VILLA: A beautiful 3-bedroom townhome in the gated community of Coral Hammock. Just off U.S. 1, across from the golf course, and minutes from some of Key West locals' favorite restaurants, marinas, Smathers Beach and the airport. Fully equipped kitchen, HDTVs, WIFI and off-street parking for... View all property information
    Location Information
    Key West, Florida Keys
    1 / 24
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    THE DOLPHIN HOUSE: Two houses with the comfort of one. The Dolphin House comprises a main house and a guesthouse with pool and outdoor living space comfortably nestled in between. Enter the main house into the spacious, open and airy great room with vaulted ceilings and a wall of French doors that... View all property information
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    Key West, Florida Keys
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    1 / 22
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
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    • x
    About this property
    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local... View all property information
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    Key West, Florida Keys
    1 / 17
    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as... View all property information
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    Key West, Florida Keys
    1 / 20
    4 of 5 stars (28) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    PARADISE PLACE: Ground level 1-bedroom 1-bath condo in the Palm Gardens compound only 6 blocks from Duval Street and the White Street Pier in the other direction. Walk or bike to any Old Town or beach adventure you imagine. Completely renovated, this lovely property offers hardwood floors and... View all property information
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    Key West, Florida Keys
    1 / 12
    3.5 of 5 stars (3) Average
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key... View all property information
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    Key West, Florida Keys
    1 / 17
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Well maintained townhouse in the Truman Annex of Key West. The house has a beautiful garden that you will enjoy. A short walk to Duval and Mallory Square. All quality furnishings. Margaret' s Park is the choice in Key West. Two master suites with private balconies. The house is fully equipped... View all property information
    Location Information
    Key West, Florida Keys
    1 / 29
    4.5 of 5 stars (26) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    KEY WEST CHARMING: Downstairs 2 bedroom 1 bath home in Truman Annex, a secluded gated community in Old Town Key West. Living/dining area opens to the large back deck that is one of the best spots on the island to relax. Master bedroom has queen bed; 2nd bedroom has 2 twins. Well-equipped kitchen... View all property information
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    Key West, Florida Keys
    1 / 17
    5 of 5 stars (22) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Forget that "been there, done that" hotel room; enjoy the comforts of home in Old Town Key West at the Seashell Cottage. Located on a quiet lane, just 1 block to Duval Street, walk to the grocery store, restaurants, museums, beach, and "Sunset Celebration". The original local artwork throughout... View all property information
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    Key West, Florida Keys
    1 / 9
    6 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    About this property
    Why stay in a cramped hotel when you can relax in a private, quiet, and peaceful 2-acre estate! We are now running an special discounted offer for the Fall of 2016 WHITE IBIS INN - LOCATED ONLY A 15 MINUTE DRIVE FROM KEY WEST OR THE WORLD-FAMOUS BAHIA HONDA BEACH. Sometimes we run a special... View all property information
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    Key West, Florida Keys
    1 / 27
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    CITY CAY: City Cay is our 1-bedroom 1-bath upstairs condo in Truman Annex that has been lovingly renovated and furnished in a sleek modern style. Stay connected in the living room with high-end electronics including HDTV, WIFI and an over-the-top stereo system. Relax on the covered back balcony... View all property information
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    Key West, Florida Keys
    1 / 9
    5 of 5 stars (8) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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... View all property information
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    Key West, Florida Keys
    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    Coral Casita - Weekly Vacation Rental Completely Re-Designed, Re-Decorated and Ready for your island adventures! When Key West is calling your name and nothing else will do, Coral Casita is the perfect mix of location, price and room for your large group to gather. A spacious 3 bedroom townhome... View all property information
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    Key West, Florida Keys
    1 / 16
    4.5 of 5 stars (48) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    This charming one bedroom cottage is the perfect hideaway. 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. Within 2 blocks you'll find Key West classics like The Bull, Sloppy... View all property information
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    Key West, Florida Keys
    1 / 27
    5 of 5 stars (52) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    SHIPYARD TREASURE: 2 bedroom 1 bath Shipyard condo has it all. Located in Truman Annex, there is a shared pool, off street parking and 24 hour security. Shipyard Treasure is a 2nd floor condo with private full-length balconies front and rear. This property has an open and airy feeling and is one... View all property information
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    Key West, Florida Keys
    1 / 26
    4 of 5 stars (15) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. The huge oceanfront balcony can be accessed from both the living/dining... View all property information
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    Key West, Florida Keys
    1 / 26
    4 of 5 stars (27) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    ARTIST GARDEN : 2 bedroom 2.5 bath located in the prestigious Admirals Lane neighborhood of Truman Annex. Open floor plan on the main level with kitchen opening into the dining and living areas. French doors to a large deck with plenty of space to unwind and enjoy the fabulous 2 bedrooms and 2... View all property information
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    Key West, Florida Keys
    1 / 38
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    28 DAY MINIMUM STAY, PLEASE DO NOT SEND REQUESTS FOR SHORTER PERIODS! Enjoy the amenities of a luxury hotel in the privacy of our home for a fraction of the cost. Located on the sunset side of Shark Key island, a 10 minute drive from Key West. With 2800 sq. ft., three bedrooms, three and a half... View all property information
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    Key West, Florida Keys
    1 / 12
    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... View all property information
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    Key West, Florida Keys
    1 / 25
    5 of 5 stars (1) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Key West, Florida Keys
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    4.5 of 5 stars (84) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    BAHAMA DREAMING: One Of At Home In Key West's Most Popular Rentals! Bahama Dreaming is a traditional 3-bedroom Conch cottage located just steps from Duval Street. With it's fantastic location and amenities this home offers it all. The main level has 2 bedrooms, one containing a comfy queen size... View all property information
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    Key West, Florida Keys
    1 / 31
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is... View all property information
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    Key West, Florida Keys
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Hyatt Sunset Harbour Residence Club. *2016 Certificate of Excellence Winner TripAdvisor* 1 week rental 9/25/16 to 10/02/16. Location, Location, Location. 2 bedroom 2 bath. Full kitchen, dining table and living room includes sofa bed. TV's are in bedrooms as well as living room. . Great resort in... View all property information
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    Key West, Florida Keys
    1 / 15
    5 of 5 stars (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven.... View all property information
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    Key West, Florida Keys
    1 / 18
    4.5 of 5 stars (55) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    TROPICAL DREAMING: This tropical 2-bedroom home with classic art features, hardwood floors, tall ceilings, new appliances, new furnishings and a true Key West feel. One block from Duval Street , it is close to restaurants, shops, galleries and clubs. The Atlantic Ocean is only 4 blocks away. The... View all property information
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    Key West, Florida Keys
    1 / 22
    4 of 5 stars (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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... View all property information
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    Key West, Florida Keys
    1 / 29
    4.5 of 5 stars (23) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    PARROT PERCH: Great location and great value for a great vacation. Parrot Perch is an upstairs 2 bedroom 2 bath condo with a balcony from the living room offering a view of the neighborhood. The best priced 2 bedroom 2 bath condo in Truman Annex with a queen bed and bathroom ensuite; guest... View all property information
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    Key West, Florida Keys
    1 / 28
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    Breezy Bungalow - Weekly Rental When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside breezes to flow openly into Breezy Bungalow. Two levels of... View all property information
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    Key West, Florida Keys
    1 / 9
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    President’s Walk is perfectly located in the Truman Annex. A quick stroll to Duval Street and minutes from Fort Zachary Taylor State Park and its beach, this gated community offers lush gardens and a beautiful community pool at your doorstep. For Key West history buffs, Truman's Little White House... View all property information
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    Key West, Florida Keys
    1 / 63
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Allinclusivecharter provides the perfect getaway on your own private crewed luxury motor yacht in the Florida Keys area. Being the only guests on our board, you are treated like royalty. Do what you really want, when you want. Your voyage is personalized and is a customized vacation tailored to you... View all property information
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    Key West, Florida Keys
    1 / 20
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Relax in paradise amongst all the comforts of home in the Sailor House. Just a half a block off the world famous Duval Street, the Sailor House offers the ultimate in privacy and luxurious island living. Families and couples traveling together rave about their tropical “home away from home.” Its... View all property information
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    Key West, Florida Keys
    1 / 23
    4 of 5 stars (19) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Shared Outdoor Pool...
    • Air Conditioning
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys