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Key West House Rentals

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    4 of 5 stars (40) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    4.5 of 5 stars (15) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    4.5 of 5 stars (45) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    4.5 of 5 stars (31) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    Located on one of old town's prettiest historic streets, Frances Street. Casa Serendipity is one of the finest examples of the 'conch cottage' style architecture that Key West is famous for. Designed to accommodate a family, this three-bedroom home has two full baths, one full bath upstairs and... View all property information
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    Key West, Florida Keys 33040
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    1 / 5
    1 Bedroom / 5 Bathrooms / Sleeps 2
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    • Balcony
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    About this property
    We are a young couple with a private cabin on a two cabin sailboat in a Key West marina with a number of amenities (restaurant, bar, gym, lounge). The cabin holds two people comfortably (one double bed). We live on the boat as well in the second cabin. Restrooms and showers are at the bathhouse at... View all property information
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    Key West, Florida Keys 33040
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    1 / 31
    4.5 of 5 stars (7) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    One half of the group unit Tradewinds and Opposite Leeward Isle The style is common throughout the islands. Our shotgun offers original Dade County pine floors and sandblasted walls that reflect the antiquity of design. The Webster Dictionary dates windward back to 1549; defined as, the side... View all property information
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    Key West, Florida Keys 33040
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    1 / 16
    4.5 of 5 stars (38) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story... 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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    1 / 14
    4.5 of 5 stars (43) Very good
    Studio / 1 Bathroom / Sleeps 2
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    About this property
    Perfect for two, this Bali-style studio cottage has it all: comfort, privacy and location. 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... 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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    About this property
    Located on a quiet residential street in the beautiful Key West neighborhood of Casa Marina, A Low Key Paradise has a beautiful open layout, with views of the large private patio and pool visible as soon as you enter. Guests can walk to nearby Higgs beach, and Higgs beach dog park— perfect for your... View all property information
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    Key West, Florida Keys 33040
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    1 / 31
    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 / 36
    4.5 of 5 stars (3) Very good
    4 Bedrooms / 2 Bathrooms / Sleeps 12
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    About this property
    Tradewinds is comprised of the Leeward Isle and Windward Isle Two Cigar Maker’s Cottages, side-by-side, located ½ block off Duval Street. These two cottages are a favorite of our guests who like to relax in the private, quiet, beautiful garden areas with large spas that are behind each house.... View all property information
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    Key West, Florida Keys 33040
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    1 / 13
    4.5 of 5 stars (14) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    The Pineapple Cottage is tucked away and totally private, yet it is only a half a block from Duval Street. This two story 'cottage' offers a first floor bedroom that opens through french doors to the private pool and gardens. A second floor suite includes a bedroom and bath plus a seperate living... View all property information
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    Key West, Florida Keys 33040
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    $512
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    1 / 18
    4.5 of 5 stars (32) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 10
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    • Air Conditioning
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    • x
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront... View all property information
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    Key West, Florida Keys 33040
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    $768
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    1 / 9
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Air Conditioning
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    • Gym
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    • Ocean Views
    • Satellite TV
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    • Waterfront
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    • Pets allowed
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    About this property
    Price includes taxes. cleaning fee and sunset sail (weather willing). For six or less adults only. You have the use of three of four private cabins each with its own marine style bathroom and queen like bed. Captain Charles and wife Deborah use one cabin.The 'ANAA B' is 41ft long and 24ft wide... View all property information
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    Key West, Florida Keys 33040
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    1 / 24
    4.5 of 5 stars (3) Very good
    Studio / 1 Bathroom / Sleeps 2
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    About this property
    Part of TROPICAL VILLAGE Where else can you find resort style accommodations at motel pricing? Poolside Paradise @ Tropical Village, features all the amenities needed for a quick weekend getaway vacation at an affordable nightly rate. Once the winter vacation suite of Pulitzer Prize winning... View all property information
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    Key West, Florida Keys 33040
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    $253
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    4.5 of 5 stars (29) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    • Air Conditioning
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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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! Andros Suite is a bi-level suite with a very spacious bedroom upstairs with a... View all property information
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    Key West, Florida Keys 33040
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    $535
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    1 / 29
    4.5 of 5 stars (50) Very good
    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • x
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    About this property
    Tropical Retreat, at 519 Catherine Street, is on a quiet lane half a block off the upscale Upper end of Duval St. where there are many sophisticated restaurants, high-end art galleries and shops. Downtown Duval St. is within easy walking distance from Tropical Retreat to enjoy the exciting... View all property information
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    Key West, Florida Keys 33040
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    $7,036
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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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.*** 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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    1 / 25
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    Just like its name, Petunia is a happy place. Open the picket gate, pull your bags down the short, bricked walk and open the massive wood door with a grin from ear to ear. You’ve come home. This two-story, two-bedroom home with a beautifully updated, second-floor bath offers the kinds of privacy... View all property information
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    Key West, Florida Keys
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    1 / 25
    4.5 of 5 stars (15) Very good
    Studio / 1 Bathroom / Sleeps 2
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    • Air Conditioning
    • Balcony
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    • Hot Tub
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    • Pets allowed
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    • 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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    $1,008
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    1 / 24
    4 of 5 stars (1) Very good
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    About this property
    Located at 729 Whitehead St, 'Southern Palms' is the group property consisting of the following homes Coconut Palm formerly Island Oasis Traveler's Palm formerly Palm Isle Royal Palm formerly Little Palm which can all be booked individually. All together, these three units have 5 separate... View all property information
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    Key West, Florida Keys 33040
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    1 / 53
    5 of 5 stars (14) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 16
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    • Pets allowed
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    • Suitable for children
    • x
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    About this property
    Almost Southernmost Retreat is made up of Part of ALMOST SOUTHERNMOST and Part of ALMOST SOUTHERNMOST TOOon the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker... View all property information
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    Key West, Florida Keys 33040
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    1 / 17
    5 of 5 stars (1) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Pets allowed
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    • x
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    About this property
    Three story townhouse with master bedroom, deck and full bath on second floor and guest bedroom and full bath on third floor. Kitchen, great room, and half bath on first floor as well as deck and garden. Outdoor grill on deck. Please note that I have a licensed real estate broker in Key West who... View all property information
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    Key West, Florida Keys 33040
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    $535
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    3 Bedrooms / 4 Bathrooms / Sleeps 8
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    • Air Conditioning
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    • Pets allowed
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    • x
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    About this property
    Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene hideaway is just moments away from Duval Street and the most exciting spots the southernmost... View all property information
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    Key West, Florida Keys 33040
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    $394
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    4.5 of 5 stars (13) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
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    • Suitable for children
    • x
    • x
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    • ?
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    About this property
    Located at Papa's Hideaway , the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best... View all property information
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    Key West, Florida Keys
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    $496
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    4.5 of 5 stars (20) Very good
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • x
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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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    1 / 26
    4.5 of 5 stars (2) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    • ?
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** The master bedroom features a king-size bed, flat screen television, en suite bathroom and french doors leading you out to the private side deck. The second bedroom features a queen-size bed and flat screen... View all property information
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    Key West, Florida Keys
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    $240
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    1 / 28
    4.5 of 5 stars (21) Very good
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • x
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    About this property
    Located inside the Villas known as Old Town Garden Villas With 1 bedroom 1 bath this Townhouse with shared heated pool will be your favorite. 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... View all property information
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    Key West, Florida Keys 33040
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    $704
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    1 / 15
    4 of 5 stars (7) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one... View all property information
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    Location Information
    Key West, Florida Keys 33040
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    $1,279
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    1 / 24
    5 of 5 stars (19) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 12
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    • Air Conditioning
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    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    About this property
    Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (8) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    About this property
    THIS PROPERTY IS A MONTHLY ONLY RENTAL Casa Mañana at 800 Virginia Street is perfectly situated for the discriminating guest who wants to enjoy Key West at its finest. Located just two blocks from Duval Street, home of world famous watering holes, shopping and dining, you are steps away from... View all property information
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    Key West, Florida Keys 33040
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    4 of 5 stars (30) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    About this property
    Thoughtfully restored, 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... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (13) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    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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    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    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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    4.5 of 5 stars (47) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Inside, you will find all of the comforts of home and This two-story 1880's Cigar Maker's Cottage has been completely renovated and has a living room with 42' flat screen TV/DVD, Queen sleeper sofa, kitchen with dishwasher, dining room and bath (with outdoor shower) on the ground floor.... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, beautifully furnished... View all property information
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    Key West, Florida Keys 33040
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    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    Part of TROPICAL VILLAGE Southern Cross: Sitting next to the lily pond with fountain or lounging in the shade of your own Royal Poinciana tree, Southern Cross is the perfect place to relax in paradise. This one and a half story vacation cottage is surrounded by exotic gardens, and situated in... View all property information
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    Key West, Florida Keys 33040
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    $253
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    4 of 5 stars (19) Very good
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    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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    $240
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    1 Bedroom / 1 Bathroom / Sleeps 4
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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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    $317
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    4 of 5 stars (9) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    Part of POOLSIDE PARADISE One-half block off world famous Duval Street sits the beautifully renovated home on the 500 block of Olivia Street. A semi-private pool with waterfall (shared with Poolside Retreat) and Private Off-Street Parking makes this the ideal Old town location. Enjoy nearby... View all property information
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    Key West, Florida Keys 33040
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    $330
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    4.5 of 5 stars (35) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    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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    $1,087
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    4.5 of 5 stars (15) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
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    Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways, meandering by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (8) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    ***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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    $448
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    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Waterfront
    • Water Views
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    BETTER THEN ANY HOTEL IN KEY WEST HANDS DOWN :) As the name suggests Key West Livin' this is the only way To truly experience what Key West is all about. Stay aboard this 50 foot Ocean Super Sport Yacht instead of a hotel room in Beautiful Harbor Yacht Club located on the ocean with Beach ,... 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
    1 Bedroom / 2 Bathrooms / Sleeps 4
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels lays the Paradise Suite. Paradise Suite (renovated for January 2013) is a bi-level suite with one... View all property information
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    Key West, Florida Keys 33040
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    $576
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    4.5 of 5 stars (35) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    About this property
    This mid-town Key West home is newly renovated and beautifully decorated in jewel tones of the Mediterranean. It features three bedrooms and three baths. The open living/kitchen area is decorated with rich tones with tropical accents and soft fabrics. The dining room is outside in the attached... View all property information
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    Key West, Florida Keys 33040
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    $8,699
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    4.5 of 5 stars (2) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 1116 Curry Lane. This home is situated in the heart of Old... View all property information
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    Key West, Florida Keys 33040
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    4.5 of 5 stars (4) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Tobago House is just steps from restaurants, night life, Hemingway's House, and the 'Southernmost Point' of the United States. This home offers an open, airy floor plan with old style pine walls and floors,... View all property information
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    Key West, Florida Keys 33040
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    $345
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    4 of 5 stars (43) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    About this property
    The best of Key West, in the middle of Historic Old Town and a half block from Duval Street and the gates to Bahama Village, a perfect location for visitors to our Island. Guests can stroll to Mallory Square, Fort Zachary Beach or the sunset piers which are all within easy walking distance of this... View all property information
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    Key West, Florida Keys 33040