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Holiday Rentals in Key West, FL

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    Travellers to Key West are booking April dates now. Secure your holiday rental today, and have the perfect trip.
    1 / 18
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    4 of 5 bubbles (19) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4.5 of 5 bubbles (18) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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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... View all property information
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    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    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 33040
    1 / 25
    4.5 of 5 bubbles (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Stay on our fabulous 3 bedroom houseboat and you'll have a vacation that will challenge your imagination! This spacious vacation rental on the water comfortably sleeps up to 8 guests and is completely air-conditioned and heated to keep you comfortable even on the hottest days! Your full kitchen... View all property information
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    Key West, Florida Keys 33140
    1 / 23
    4 of 5 bubbles (42) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick 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... View all property information
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    Key West, Florida Keys 33040
    1 / 38
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Spectacular 2 bedroom 2 bath ocean-view overlooking the famous Smathers Beach, Enjoy the balmy ocean breezes from your private balcony and watch the world go by. This unit features 2 bedrooms, one king and one queen. For your convenience there are 2 roll-away beds for extra guests. Full size... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 bubbles (6) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    About this property
    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... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca is the perfect get-a-way vacation rental for two! Key West Casablanca is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a... View all property information
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    Key West, Florida Keys 33040
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    1 / 31
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    4 of 5 bubbles (10) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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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. This comfortable 2 bedroom unit features a huge oceanfront balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 24
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
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    • Porch
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    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated Conch house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described as... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    2.5 of 5 bubbles (3) Poor
    Studio, 3 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Perched just above the fun and frolic of Duval Street at the City Island View vacation rental suite, you're sure to capture the "island beat" that stirs this tiny tropical island of Key West, Florida. This extraordinary Key West vacation rental features the original 2nd floor front porch that spans... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 13
    5 of 5 bubbles (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Shared Outdoor Pool...
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    • x
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    • x
    About this property
    In the heart of Old Town, with the beautiful community of private homes and condominium of Truman Annex, this Shipyard Condominium is great access to Zachary State Park Beach as well as the Historic Old Town Key West. This beautifully decorated first floor condominium on Southard Street has two... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    5 of 5 bubbles (7) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    28 Night Minimum - Monthly Rentals Only Can you say “perfectly adorable”? We thought so. Now picture “perfectly adorable” and you have found Poppy. Poppy is a one-bedroom, one-bath home that is perfect for one or a couple. The front porch is perfect for people watching and chatting with locals... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    5 of 5 bubbles (39) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 32
    4.5 of 5 bubbles (16) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Pineapple Cottage is a two bedroom, two bathroom home with a private pool in Old Town Key West. There is total privacy and charm throughout this island home and the proximity to all things Key West is unbeatable (one block from Duval Street). Behind an enclosed, white wooden gate there is tropical... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • x
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    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities... View all property information
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    Key West, Florida Keys 33040
    1 / 16
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    La Brisa Condominiums is located on S. Roosevelt Blvd. across from Smathers beach the largest beach in Key West. Only 5 minutes from Duval Street & Mallory Square. La Brisa is a two bedroom two bath condo on the third floor. The master bedroom has a king size bed with a walk in closet, a desk... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots. All the rooms have ceiling fans and air conditioners. Modern conveniences include a new... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    4.5 of 5 bubbles (14) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • x
    About this property
    Come stay aboard our FABULOUS houseboat Libra! Docked in one of Key West's most exclusive yacht club marinas, our guests have free access to a host of "members only" amenities including an infinity-edge swimming pool, private beach, tiki bar, fitness facility, sauna, clubhouse, onsite restaurant,... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4 of 5 bubbles (30) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Grill
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    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 10
    5 of 5 bubbles (41) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Terrace
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    • x
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    • 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. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2... View all property information
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    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 bubbles (25) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    • 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
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    Key West, Florida Keys 33040
    1 / 29
    5 of 5 bubbles (17) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Beautiful Poolside Townhome - Perfect for family or Travel with Friends! The Best of Everything! 'Island Days' has it all: Large heated resort style pool with Tiki Hut right outside your French doors. Lush landscaping and off street parking steps to your door complete the resort feel all in a... View all property information
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    Key West, Florida Keys 33040
    1 / 11
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    About this property
    Take advantage of our "Tax Free Holiday"! Reserve any available 2017 week and we will pay the taxes on your Key West vacation getaway (12.5% discount) Hurry! Book now for best available dates. Offer Expires April 18, 2017 (Limited exclusions. Contact Owner-Tracy for details) Location,... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    5 of 5 bubbles (21) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Shared Garden
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    • x
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    About this property
    Romantic, Private, Boutique Guesthouse with only 2 suites in Key West, Florida steps away from the Beach and Ocean and the Key West Wildlife Center. Reserve 1 room for a couple or both rooms to accommodate up to 4. The owners Capt. Steve and Kayla offer Snorkeling, Sunset trips, eco-adventure... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 bubbles (33) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    • x
    About this property
    It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment. From your private and expansive... View all property information
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    Key West, Florida Keys 33040
    1 / 13
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • x
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    About this property
    Make your next Key West vacation on the Lion's Paw, a roomy monohull sailboat located in Key West premier marina resort - the Key West Harbour Marina. Three night to seven day vacation packages have options for half day, full day, and overnight sails. The yacht club has it's own private beach and... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    4 of 5 bubbles (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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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. Bright, tropical colors and tile floors provide an island ambience to... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    4.5 of 5 bubbles (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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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... View all property information
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    Key West, Florida Keys 33040
    1 / 18
    5 of 5 bubbles (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
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    • x
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    About this property
    One of the very few & one of the largest Ocean Front Suites in Key West. 2200 sq. ft living area. This place is really incredible! it's one of the largest oceanfront suites in Key West. 3 bedroom, 2 bath, 2200 square ft .You are literally 20 yards from the oceans edge. The wrap around balcony... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 bubbles (8) Very good
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street in Old Town Key West. It is indeed rare to find a cottage property... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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... View all property information
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    Key West, Florida Keys 33040
    1 / 20
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Grill
    • DVD Player
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 25
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Parking
    • Grill
    • DVD Player
    • Patio
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    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Perfectly located 1/2 block from Duval St this 1 bed 1 bath bilevel property is nestled in a quiet gated compound with lush flowering gardens, songbirds, gazebo, and a shared heated pool. Downstairs is the living room with Queen sleeper sofa, dining room, and fully equipped kitchen. On the front... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 19
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located on a quiet street in Key West, a tranquil residential neighborhood located just behind the Key West Historical district. Close to downtown and the beaches. Perfect for two couples looking for Old Town and peace and quiet. This home offers a two bedroom, two bathroom and was nicely... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 30
    4 of 5 bubbles (39) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    • Terrace
    • Satellite TV
    • Shared Outdoor Pool...
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    • Internet Access
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    • Balcony
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    • 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 33040
    1 / 13
    5 of 5 bubbles (1) Excellent
    7 Bedrooms, 6 Bathrooms, Sleeps 18 | Quick View
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    • Grill
    • Balcony
    • Satellite TV
    • Patio
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    • Private Outdoor...
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    Our unique property consists of 3 suites (a total of 7 bedrooms and 6 baths) with 2 sparkling lagoon style dipping pools in one compound in the luxurious Casa Marina area of Old Town Key West. We can accommodate groups up to 18 guests. The breakdown of the 3 suites which are being rented... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 31
    4 of 5 bubbles (2) Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • Private Outdoor...
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    • Satellite TV
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    • DVD Player
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    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof.... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 14
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Private Outdoor...
    • Air Conditioning
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    • Washer
    • Wi-Fi
    • Patio
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 20
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Grill
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool...
    • Parking
    • Satellite TV
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 18
    Studio, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Grill
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Washer
    • Balcony
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 37
    5 of 5 bubbles (1) Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Parking
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    • Private Outdoor...
    • Satellite TV
    • Grill
    • Balcony
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Welcome to your quiet and relaxing Key West vacation! The Key West Beach Club stretches along the Atlantic Ocean shores. This top floor penthouse has it all: 15 foot vaulted ceilings, a well equipped kitchen, huge oceanfront balcony, four bedrooms and three baths. Enjoy breathtaking views of the... View all property information
    Location Information
    Key West, Florida Keys
    1 / 9
    4.5 of 5 bubbles (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • ?
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    • x
    About this property
    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
    Location Information
    Key West, Florida Keys 33040
    1 / 23
    4.5 of 5 bubbles (41) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Internet Access
    • Parking
    • Satellite TV
    • Hot Tub
    • Patio
    • DVD Player
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens leads to a... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    4.5 of 5 bubbles (40) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Satellite TV
    • Balcony
    • Shared Outdoor Pool...
    • Air Conditioning
    • Patio
    • Internet Access
    • Terrace
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Great, popular, quiet townhouse in the well-liked Duval Square complex in the heart of Old Town. One off-street parking space per unit. Easy walking distance to all downtown attractions. Bank, convenience store, health club, hair salon and fine restaurants in the complex. Families are... View all property information
    Location Information
    Key West, Florida Keys 33040