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Bonair Suite

Key West Florida

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  •  Home
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 6
  • $100 to $250 Per Night
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Our Bonaire Suite is a bi-level suite decorated in a rich contemporary Palm Tree motif with two beds in the upstairs bedroom. The upstairs bath features a custom tumbled marble shower with glass door....
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Orchid Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Family House

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  1.5 Baths
  •  Sleeps 6
  • Over $250 Per Night
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Steps from Duval Street, on a quiet hidden lane two blocks long, The Family House is hidden in a tropical oasis, a gated compound. The view from the front door is a fish/lily pod with the relaxing sou...
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Esperanza Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  2 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Nestled in tropical, flowering gardens, the Esperanza Suite is PERFECT FOR YOUR EXTENDED HONEYMOON OR A ROMANTIC MONTH, STEPS FROM DUVAL STREET! Esperanza Suite is a bi-level suite with a very spacio...
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Oceania Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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A Key Escape

Key West Florida

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  •  Home
  •  3 Bedrooms
  •  2.5 Baths
  •  Sleeps 8
  • Over $250 Per Night
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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 gou...
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Casa Key West

Key West Florida

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  •  Condo
  •  3 Bedrooms
  •  2 Baths
  •  Sleeps 8
  • Over $250 Per Night
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Located in Duval Square (between Duval Street and Simonton Street) where fine and varied dining abounds (Square One, Origami Sushi Restaurant and New York Garden Cafe), Casa Key West is a second story...
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Fishtail Hideaway

Key West Florida

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  •  Home
  •  1 Bedrooms
  •  2 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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This cottage features a cozy master suite which encompasses the entire 2nd floor. This bedroom features a pillow top King bed, large flat screen TV, en-suite bath with shower. The living room has ...
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The Casa de Mango

Key West Florida

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  •  Condo
  •  2 Bedrooms
  •  2.5 Baths
  •  Sleeps 6
  • Over $250 Per Night
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Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa de Mango is a second story paradise just steps from the sights...

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Mermaids Cove

Key West Florida

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  •  Home
  •  4 Bedrooms
  •  4 Baths
  •  Sleeps 10
  • Over $250 Per Night
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Located at 1219 Duval Street, you won’t find a better location for fun and activities in Key West! Next to Banana Café, across from the Coffee & Tea House, 1 block from the Butterfly ...
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Garden House

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  2 Baths
  •  Sleeps 6
  • Over $250 Per Night
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Perfectly located only a block from all the fun and activities of Duval Street, enjoy the unique Garden House in the sanctuary of your own 25 foot heated private pool surrounded by lush gardens. This ...
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The Bahama Breeze

Key West Florida

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  •  Condo
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • Over $250 Per Night
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Less than one block from Duval Street, this delightful, spacious two Queen bedroom suite welcomes you with amenities usually not found at this price point! Bahama Breeze features all the amenities of...
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Poolside Suite

Key West Florida

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  •  Duplex
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • Over $250 Per Night
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One-half block off world famous Duval Street sits the beautifully renovated (2005) home at 517 Olivia Street. At the corner of Olivia and Center Streets, this suite features granite counter tops, beau...
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Windward Isle

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 6
  • Over $250 Per Night
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The Webster Dictionary dates windward back to 1549; defined as, the side or direction from which the wind is blowing. Our Windward Isle is to landlubbers what windward gusts are to sea captains: a mea...
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Island Oasis

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  2.5 Baths
  •  Sleeps 6
  • Over $250 Per Night
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Island Oasis at 613 Amelia St., is located one block from the celebrated sights and sounds of world famous Duval Street. It is close to the world-class restaurants, shops, art galleries and nightclubs...
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Casa Serendipity

Key West Florida

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  •  Home
  •  3 Bedrooms
  •  2 Baths
  •  Sleeps 6
  • Over $250 Per Night
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World-class comfort, lush tropical surroundings and unmatched privacy characterize this deluxe, spacious, two story historic home located across from the famous Key West Cemetery in Key West\'s finest...
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Amelia House

Key West Florida

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  •  Home
  •  3 Bedrooms
  •  2 Baths
  •  Sleeps 8
  • Over $250 Per Night
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Just 3 short blocks from the main guest house, the Amelia House is a recently renovated, painted and decorated 3 bedroom, 2 bath private house located at 505 Amelia Street, (3 houses from world-famous...
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Hemingway's View

Key West Florida

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  •  Home
  •  3 Bedrooms
  •  2 Baths
  •  Sleeps 8
  • Over $250 Per Night
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Located directly behind the world famous Hemingway House grounds, just 2 houses off celebrated Duval Street on quiet, intimate Whalton Lane is this charming private home. One block from Center Cour...

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Havana Hideaway

Key West Florida

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  •  Condo
  •  2 Bedrooms
  •  2.5 Baths
  •  Sleeps 6
  • Over $250 Per Night
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Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), Havana Hideaway is a second story paradise just steps...
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Howe Street Hideaway

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  2 Baths
  •  Sleeps 6
  • $100 to $250 Per Night
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Howe St. Hideaway is located in a traditional old town Key West neighborhood with the feel of a classic line. The neighborhood is complete with conch style homes, little lanes, corner gardens and yes ...
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Helen's Hideaway

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  2 Baths
  •  Sleeps 6
  • Over $250 Per Night
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This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David W...

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Heron Hideaway

Key West Florida

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  •  Condo
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, t...
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The Tropical Retreat

Key West Florida

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  •  Home
  •  3 Bedrooms
  •  3.5 Baths
  •  Sleeps 8
  • Over $250 Per Night
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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. Down...
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Casa Maria

Key West Florida

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  •  Condo
  •  2 Bedrooms
  •  2.5 Baths
  •  Sleeps 6
  • Over $250 Per Night
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Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Maria is a second story paradise just steps from the sights, soun...
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Casa 625

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  2 Baths
  •  Sleeps 6
  • $100 to $250 Per Night
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625 Elizabeth Street..Casa 625 is an address and house of distinction! Finely detailed with unparalled amenities, this is the perfect vacation home for the discriminating guest who wants to enjoy Key ...
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Ospreys Nest

Key West Florida

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  •  Condo
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Historic homes dating to the late 1880s, t...
The DuPont House

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  2 Baths
  •  Sleeps 6
  • Over $250 Per Night
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Stroll out your front gate to DuPont Lane, turn right and you are on Duval Street! This hidden gem will surprise and delight you with wonderful details and total privacy. You even have your own pri...

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The Villa Azul

Key West Florida

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  •  Home
  •  3 Bedrooms
  •  3 Baths
  •  Sleeps 6
  • Over $250 Per Night
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You will certainly enjoy this wonderful historic home with recent renovations, perfectly placed pool, separate cottage and plenty of outdoor living space located at 1116 Curry Lane. This home is situa...
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Artist Retreat

Key West Florida

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  •  Home
  •  3 Bedrooms
  •  2 Baths
  •  Sleeps 6
  • Over $250 Per Night
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You will certainly enjoy this wonderful artist\'s home with recent renovations, perfectly placed pool, and plenty of outdoor living space located at 325 Catherine Street. This home is situated in the ...
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The Casa Blanca

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  3.5 Baths
  •  Sleeps 6
  • $100 to $250 Per Night
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Casa Blanca is your perfect paradise home located a short walk to both Higgs Beach and Smathers Beach. This bi-level duplex is located in a quiet neighborhood and offers off street parking for 2 vehic...
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Pinder House

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  2 Baths
  •  Sleeps 1
  • $100 to $250 Per Night
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Located at 516 Elizabeth Street, the Pinder House is an address and house of distinction! Previously owned by Theopolis Pinder of the historic Pinder Family, whose roots go back to the 1850\'s, this h...
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Palm Isle

Key West Florida

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  •  Condo
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Luxury and fine details define these units on White Street, the heart of the art district and just six blocks from Duval Street and the Historic Seaport. Stroll out your door and enjoy cafe con lec...

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Cigar Makers Cottage

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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This delightful Cigar Makers cottage at 1008 Whitehead was built in the 1880\'s. There was once a Cigar Factory across the street on Truman Ave. It\'s history also includes the previous owner, David K...
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Providence Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 6
  • $100 to $250 Per Night
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Nestled in tropical, flowering gardens, the Providence Suite is perfectly located, 1/2 block from Duval Street Providence Suite is a bi-level suite with an upstairs bedroom featuring 2 queen pillow...
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Key Lime Cottage

Key West Florida

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  •  Townhouse
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 2
  • $100 to $250 Per Night
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308 Margaret Street - #5 - is a unique get-a-way for the couple who wants to enjoy a ½ block walk (or maybe a crawl) to Key West\'s Historic Seaport with it\'s fine fishing, restaurants and activities...
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Duval Square Penthouse

Key West Florida

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  •  Condo
  •  2 Bedrooms
  •  2.5 Baths
  •  Sleeps 6
  • Over $250 Per Night
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Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One, Origami Sushi Bar and NY Pasta Garden), Duval Square Penthouse is a second story paradise jus...
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Mel Fisher Suite

Key West Florida

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  •  Suites
  •  3 Bedrooms
  •  2 Baths
  •  Sleeps 8
  • Over $250 Per Night
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Almost Southernmost

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 6
  • Over $250 Per Night
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415 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 is a pe...
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Southernmost Retreat

Key West Florida

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  •  Condo
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 6
  • $100 to $250 Per Night
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1124 Duval Street, across from La-Te-Da and between 2 art galleries, you\'ll find this delightfully newly renovated spacious two bedroom suite welcoming you with amenities usually not found at this pr...
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Leeward Isle

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • Over $250 Per Night
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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 com...
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Caribbean Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1.5 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Caribbean Suite. Work on your tan, which will make you the envy of all your friends at home, ...
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Bermuda Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Bermuda Suite. Enjoy a margarita while listening to songbirds or work on your tan in one of o...
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Little Havana Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1.5 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Little Havana Suite (completely renovated in 2003), 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...
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Andros Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Andros Suite. Enjoy a margarita while listening to songbirds or work on your tan in one of ou...
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Abaco Suite

Key West Florida

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  •  Home
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Nestled in extensive tropical and flowering gardens, complete with aviaries with singing cockatiels is the Abaco Suite. Enjoy a margarita while listening to songbirds or work on your tan in one of our...
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Conch Casa

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 6
  • $100 to $250 Per Night
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Conch Casa is a cigar maker\'s cottage circa 1884 that sits in a historic residential neighborhood half a block from Duval Street. This romantic hideaway is the quintessential conch cottage - both rem...
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Sunset Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Verde Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Heathers Villa

Key West Florida

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  •  Home
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Audubon House

Key West Florida

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  •  Home
  •  1 Bedrooms
  •  2 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Jasmine Suite

Key West Florida

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  •  Suites
  •  1 Bedrooms
  •  1 Baths
  •  Sleeps 4
  • $100 to $250 Per Night
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Fleming-O

Key West Florida

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  •  Home
  •  2 Bedrooms
  •  1 Baths
  •  Sleeps 6
  • $100 to $250 Per Night
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This beautifully restored Conch Cottage is in the heart of old town Key West on Fleming Street. You are at once greeted at this charming cottage with a white pickett fence, soft landscaped front yard ...
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Key West Hideaway

Key West Florida

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  •  Home
  •  4 Bedrooms
  •  4 Baths
  •  Sleeps 10
  • Over $250 Per Night
View Key West Hideaway

Built in the 1880\'s and located just steps from Duval Street, this large historic building includes a great room with vaulted ceilings encompassing the living room and full kitchen with island for ca...
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