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Key West House Rentals

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    2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 of 5 stars (1) Very good
    Studio, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 of 5 stars (1) Very good
    1 Bedroom, 1 Bathroom, Sleeps 4
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    About this property
    Part of Conch Republic Cottages 'Porchside Paradise' is located in the front section of the 'Conch Republic Cottages'. This beautiful 'home away from home' features an inviting and spacious front porch - great for people watching - as well as a private two person hot tub. The unit is gated off... View all property information
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    Key West, Florida Keys 33040
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    1 / 28
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    ISLAND BREEZE: Located in the exclusive Sanctuary within the Key West Golf Club, this is a spacious home with 3 bedrooms and a sleeper sofa. Enter an open floor plan of kitchen, dining room, half-bath and living room, with French doors leading outside to the private deck. Upstairs offers the... View all property information
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    Key West, Florida Keys 33040
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    1 of 5 stars (1) Terrible
    Studio, 1 Bathroom, Sleeps 2
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    Part of Conch Republic Cottages Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get the most bang for their buck. You have everything you need in this cozy, studio-style unit, including a fully-stocked kitchen, cable TV, free... View all property information
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    Key West, Florida Keys 33040
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    3 of 5 stars (2) Average
    1 Bedroom, 1 Bathroom, Sleeps 4
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    Part of Conch Republic Cottages Welcome to sweet paradise! Located at 510 Petronia, the 'Orange Blossom Suite' is in close proximity to all the fun-filled action of Duval St, however, it is private enough to not hear any of it! 'Orange Blossom Suite' shares a huge back patio with one other suite... View all property information
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    Key West, Florida Keys 33040
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    1 / 31
    4.5 of 5 stars (39) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    About this property
    Located inside the Villas known as Old Town Garden Villas Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite.Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (25) Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    About this property
    Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 3 Bathrooms, Sleeps 4
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    About this property
    KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo. It's not Bermuda or the Bahamas but better, a... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (20) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6
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    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute blocks 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,... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (35) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6
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    About this property
    One half of the group unit Tradewinds Opposite Windward Isle , the Leeward Isle sits at 529 Olivia Street, right in the center of Old Town Key West, just 1/2 block from Duval Street. This superb example of shotgun style architecture is complimented with original Dade County pine floors and... View all property information
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    Key West, Florida Keys 33040
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    1 / 27
    4 of 5 stars (19) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4
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    About this property
    Located inside the Villas known as Old Town Garden Villas Little Havana suite is a bi-level suite with a very spacious bedroom upstairs with king bed, down pillows, tv/dvd player, cordless telephone, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, a/c... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (36) Very good
    Studio, 1 Bathroom, Sleeps 2
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    • Internet Access
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    About this property
    Romantic Retreat features a king pillow-top bed, Tommy Bahama furniture, flat screen TV and tropically inspired original fine art. The recently renovated kitchen includes granite counter tops, under counter refrigerator, microwave, toaster/oven, coffee maker, blender and soft mood lighting under... View all property information
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    Key West, Florida Keys 33040
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    $3,086
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    1 / 28
    1 Bedroom, 2 Bathrooms, Sleeps 2
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    About this property
    COCONUT COTTAGE: The perfect escape if you’re looking to get away from it all. Located in a quiet neighborhood of Old Town Key West, this 1 bedroom 2 bath cottage is a gorgeous spot to rest your head in our island city. Enter the property in a cozy sitting room. The living room and kitchen are... View all property information
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    Key West, Florida Keys 33040
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    $6,312
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6
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    • Satellite TV
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The main dwelling includes a beautiful, newly-renovated kitchen, a master bedroom with en-suite, a second bedroom with twin beds (which can be made into a king upon request), a full guest bathroom including... View all property information
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    Key West, Florida Keys 33040
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    $292
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    1 / 24
    4.5 of 5 stars (19) Very good
    Studio, 1 Bathroom, Sleeps 2
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    • Deck
    • DVD Player
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    • Internet Access
    • Patio
    • Hot Tub
    • Air Conditioning
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • x
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    About this property
    Part of 4 exclusive units at Abbey Road, renovated January, 2010, this free standing historic cottage at 918-920 Center Street, features a king pillow-top bed, 2 lushly padded swivel chairs and a full kitchen which includes a full stove, refrigerator with ice-maker, microwave, dishwasher and soft... View all property information
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    Key West, Florida Keys 33040
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    1 / 25
    4.5 of 5 stars (15) Very good
    Studio, 1 Bathroom, Sleeps 2
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    Part of 4 exclusive units at Abbey Road, The state-of-the-art kitchen includes granite counter tops, a Jenn-Air 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft mood lighting under and above the cabinets. There is also an ice-maker on site for fresh ice to prepare your... View all property information
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    Key West, Florida Keys 33040
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    $1,175
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    1 / 25
    6 Bedrooms, 5 Bathrooms, Sleeps 16
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    • Grill
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    • Stereo System
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    • x
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    About this property
    Located in the luxury townhome complex 'Echo Gardens,' 'Escape 2 Paradise' consists of two homes, units #3 and #4 - A Key Escape and Absolutely Paradise - which are right next door to each other. Equipped with two private pools, two private parking spaces, and enough room to sleep 16 people,... View all property information
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    Key West, Florida Keys 33040
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    $2,665
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    1 / 24
    4 of 5 stars (2) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2
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    About this property
    IBIS - 1 bedroom 1 bath condo 2 blocks from Duval Street, part of The Colony compound.Simple but comfortable, kitchenette opens onto the living area with a flat screen TV. The bedroom has a queen bed with TV and bath ensuite.WIFI, flatscreen TV, community coin-op laundry and swimming poolQ/Qslpr... View all property information
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    Key West, Florida Keys 33040
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    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    ***BRAND NEW POOL TO BE COMPLETED BY SEPTEMBER 2015*** Tucked into a quiet residential neighborhood, this renovated home is the perfect getaway for a family or group of friends looking to experience the Key West island life! This 3 bedroom home is on Patricia St, just a block from the scenic... View all property information
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    Key West, Florida Keys 33040
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    $839
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    1 / 35
    4 Bedrooms, 5 Bathrooms, Sleeps 10
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    About this property
    'Simonton Court Cottages' consists of the 4 nightly units 'Audubon House,' 'Truman Efficiency,' 'Monroe Efficiency,' and 'Mallory Efficiency.' In total, this group rental sleeps 8 - 10 comfortably. Perfect for cost-conscious, larger, groups who are looking for great a location. Take advantage... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (6) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    About this property
    Part of ALMOST SOUTHERNMOST RETREAT Almost Southernmost Too in the 400 block of Truman Avenue is the perfect location, located between Duval Street and Whitehead St. Just around the corner from Hemingway's House and the Historic Lighthouse Museum, Almost Southernmost Too is a perfect example of... View all property information
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    Key West, Florida Keys 33040
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    4 Bedrooms, 5 Bathrooms, Sleeps 12
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    • x
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    About this property
    Island Oasis The beaches of the Atlantic Ocean are less than a 7 minute blocks 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... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Terrace
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    About this property
    A LITTLE SLICE OF PARADISE (monthly rental): Secluded community, steps from the golf course, minutes from the beach, airport and some of the locals' favorite restaurants. 2 bedrooms, 1 full bath upstairs; open floor plan downstairs with sleeper sofa for guests, half bath, and screened porch.... View all property information
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    Key West, Florida Keys 33040
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    $586
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    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Deck
    • Air Conditioning
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    • Private Outdoor...
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    • Satellite TV
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    • Pet-friendly
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    About this property
    A Key Escape 3 br 2.5 bath w/ private heated pool. Professionally decorated in a Coastal Living style, this elegant yet very comfortable custom built 3 bedroom, 2.5 bath, 3 story home has a living room (Q sleeper sofa) with rose hardwood floors, a gourmet kitchen with granite countertops and... View all property information
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    Key West, Florida Keys 33040
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    2 Bedrooms, 1 Bathroom, Sleeps 4
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    Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing,... View all property information
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    Key West, Florida Keys 33040
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    $544
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    2 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Beach Boys on one of their many trips to Key West (they are Mojito buds with Jimmy Buffett) stayed at our vacation rental called Havana Hideaway, where they wrote the song Kokomo - according to a very reliable source at the Pink Cab Company. This vacation rental is a modern two-story, built in... View all property information
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    Key West, Florida Keys 33040
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    1 / 29
    4.5 of 5 stars (2) Very good
    Studio, 1 Bathroom, Sleeps 4
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    About this property
    Part of Southernmost Sanctuary Suites Located on Historic Simonton Street, these suites are the perfect cozy escape you've been looking for! An adorable front porch to watch the people biking, walking or scooting along. Start your mornings on the porch with your Cuban coffee and a good book... View all property information
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    Key West, Florida Keys 33040
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    3.5 of 5 stars (2) Average
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    About this property
    WIND SWEPT: 2 bedroom 1.5 bath townhome which includes kitchen, dining alcove, living room and screened-in sitting room. A few doors away from the community pool and clubhouse makes this the perfect location for a month (or two) of peace and serenity at Key West Golf Club.Upstairs you will find... View all property information
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    Key West, Florida Keys 33040
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    $278
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    5 of 5 stars (2) Excellent
    Studio, 1 Bathroom, Sleeps 4
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    Part of Southern Palms Traveler's Palm (formerly Palm Isle) - a room ahead of its time - A truly 'green unit'. Your roommate, or in this case, 'suite mate' is a giant Sapodilla tree that provides the ambiance and shade to your private hot tub and tree-top hammock. The second-story studio... View all property information
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    Key West, Florida Keys 33040
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    $264
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    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2
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    Part of Southern Palms ROYAL PALM (formerly Little Palm) - What an idyllic setting! Picture the most perfect romantic getaway cottage with all the must have's for a great Key West vacation - in a setting that nature provided in the late 1800's - the hardwood canopy is stunning! The Tommy Bahama... View all property information
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    Key West, Florida Keys 33040
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    $1,442
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    5 Bedrooms, 6 Bathrooms, Sleeps 14
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    • Patio
    • Satellite TV
    • Private Outdoor...
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    • Grill
    • Refrigerator
    • Air Conditioning
    • Deck
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    About this property
    When rented as a group, Banana’s Foster includes- Sweet Caroline - Banana Split - Key Lime Cottage Creme Brûlée All together this grouping has 5 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool.... View all property information
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    Key West, Florida Keys 33040
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    $180
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    Studio, 1 Bathroom, Sleeps 2
    other traveller has booked this property
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    • Internet Access
    • Terrace
    • Balcony
    • Linens Provided
    • Air Conditioning
    • Satellite TV
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    • Grill
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    • Pet-friendly
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    About this property
    Part of Banana's Foster Guest House This comfortable 2nd floor studio right on the corner of Caroline and Simonton, just a block off Duval, is a great spot for 2 guests wanting to be in the thick of things! After entering the compound from the shared off street parking into the courtyard with... View all property information
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    Key West, Florida Keys 33040
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    $3,787
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    2 Bedrooms, 3 Bathrooms, Sleeps 4
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    • Hairdryer
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    • Pet-friendly
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    GREEN ORCHID: Situated on a narrow lane in one of the last historic Old Town neighborhood, this 2-bedroom 2.5 bath home has it all!Living room has French doors opening to let in the tropical breezes. Modern, stainless kitchen. Outdoor shower on the lushly landscaped walkway. Guest bedroom with... View all property information
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    Key West, Florida Keys 33040
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    $586
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    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Pet-friendly
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    • x
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    Absolutely Paradise! That's what you will think the moment that you arrive at this luxurious, tropical retreat. Located in the heart of Old Town Key West, this beautiful home will entice, entertain, and excite even the most discriminating traveler. This spacious (almost 2000 sq ft) three story, 3... View all property information
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    Key West, Florida Keys 33040
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    $250
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    Studio, 1 Bathroom, Sleeps 4
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    About this property
    Part of Southernmost Suites The Pelican Suite is located in The Southernmost Suites on historic Simonton Street. Tucked back within the garden the Spoonbill Suite offers a serene escape from the hustle and bustle. The Pelican Suite has 2 Queen Beds and a kitchenette for you to enjoy meals in... View all property information
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    Key West, Florida Keys 33040
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    $376
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    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Part of TROPICAL VILLAGE Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is... View all property information
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    Key West, Florida Keys 33040
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    $264
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    1 / 23
    5 of 5 stars (4) Excellent
    Studio, 1 Bathroom, Sleeps 2
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    • Air Conditioning
    • Internet Access
    • Grill
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    • Satellite TV
    • Hot Tub
    • Deck
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • Elder access
    • x
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    About this property
    The kitchen offers an under-counter fridge, microwave, coffee maker, toaster, blender and everything to cook, prepare and enjoy a light meal…and don’t forget the BBQ grill and Ice-maker by the pool! This very comfortable unit also has a very sexy two-person custom shower with glass door,... View all property information
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    Key West, Florida Keys 33040
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    $877
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    4.5 of 5 stars (24) Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8
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    • DVD Player
    • Air Conditioning
    • Private Outdoor...
    • Grill
    • Balcony
    • Internet Access
    • TV
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    BAHAMA HOUSE: Conveniently located in the heart of Old Town 1/2 block from shops, restaurants and nightlife on Duval Street. 3 bedrooms with private baths on 3 floors. Main level with gourmet kitchen, dining area, half bath, and sitting room with a wall of French doors to the deck and private... View all property information
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    Key West, Florida Keys 33040
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    $264
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    1 Bedroom, 1 Bathroom, Sleeps 4
    other travellers have booked this property
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    • Internet Access
    • Satellite TV
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    • Grill
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    • Pet-friendly
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    • Child-friendly
    • ?
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    Part of POOLSIDE PARADISE 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... View all property information
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    Key West, Florida Keys 33040
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    $194
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    Studio, 1 Bathroom, Sleeps 2
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    • x
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    About this property
    Perhaps the best value in the Curry House, Room four is simply stunning. The walls have remained unpainted, revealing the solid construction of native, Dade County pine which is naturally resistant to the adverse effects of the local environment. Room Four shares a bathroom with Room 3. The... View all property information
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    Key West, Florida Keys 33040
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    $250
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    Studio, 1 Bathroom, Sleeps 2
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    • x
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    About this property
    Room 5 is on the ground floor with a King-sized bed, private bathroom & has access to a wraparound porch. The Curry House is an historic piece of Old Key West. Pearl Curry originally opened her home as 'Curry's Rooms' in the mid-1900's. Now the inn offers nine beautiful guestrooms and the... View all property information
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    Key West, Florida Keys 33040
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    $3,507
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    1 / 23
    1 Bedroom, 1 Bathroom, Sleeps 6
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    • Air Conditioning
    • Patio
    • Deck
    • DVD Player
    • Shared Outdoor Pool...
    • Internet Access
    • Satellite TV
    • Grill
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
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    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in tropical, flowering gardens, the Providence Suite is perfectly located, 1/2 block from Duval Street Downstairs is the living room with Queen sleeper sofa, dining room and fully equipped... View all property information
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    Key West, Florida Keys 33040
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    $877
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    4.5 of 5 stars (24) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8
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    • Balcony
    • TV
    • Grill
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Parking
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • ?
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    About this property
    DUVAL PENTHOUSE: Fabulous location, beautiful furnishings and plenty of space, suited to the casual lifestyle here in Key West. 2nd and 3rd story of the building; 3 bedrooms 2.5 bathrooms and an open floor plan. Living room, kitchen and master suite on the 2nd floor; French doors open from... View all property information
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    Key West, Florida Keys 33040
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    $8,416
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    1 / 24
    5 Bedrooms, 3 Bathrooms, Sleeps 18
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    • Internet Access
    • Patio
    • Waterfront
    • Grill
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    • Pet-friendly
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    • ?
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    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of... View all property information
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    Key West, Florida Keys
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    $418
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    2 Bedrooms, 1 Bathroom, Sleeps 4
    other travellers have booked this property
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    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Linens Provided
    • Grill
    • Deck
    • Satellite TV
    • Refrigerator
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    • Pet-friendly
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    • Child-friendly
    • ?
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    • x
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    About this property
    Duval Hideaway features all the comforts of home, and then some! A full kitchen with everything needed to prepare a gourmet meal including washer/dryer, glass top stove, dishwasher, blender, toaster, coffee maker and radio/CD player. Each of the queen bedrooms has a 24' LCD TV, spacious closets... View all property information
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    Key West, Florida Keys 33040
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    $5,611
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    1 / 26
    4.5 of 5 stars (8) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Private Outdoor...
    • Internet Access
    • DVD Player
    • Patio
    • Satellite TV
    • Air Conditioning
    • Grill
    • Deck
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The superb location at the top of Solares Hill, three blocks to the Historic Seaport and Duval Street, one block to the Public Library; Casa 625 will amaze you with the detailing, decorating and attention to... View all property information
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    Key West, Florida Keys 33040
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    $530
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    1 / 29
    5 of 5 stars (13) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
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    • Private Outdoor...
    • Grill
    • Patio
    • Satellite TV
    • Deck
    • Internet Access
    • Refrigerator
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • x
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    About this property
    This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
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    Key West, Florida Keys 33040
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    $295
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    4.5 of 5 stars (23) Very good
    1 Bedroom, 1 Bathroom, Sleeps 2
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    • Hairdryer
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Grill
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
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    • Elder access
    • ?
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    About this property
    ISLAND PEARL: Loft bedroom 1-bath cottage, complete with living room and kitchen. French doors open to deck. Located behind a needlepoint store in Old Town Key West. This is a wonderful place to experience the 'real' Key West in a secure Old Town setting. Steps away from Duval Street, Old Town... View all property information
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    Key West, Florida Keys 33040