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....
Bonair Suite
Orchid Suite
Key West Florida
Suites
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
...
Orchid Suite
Family House
Key West Florida
Home
2 Bedrooms
1.5 Baths
Sleeps 6
Over $250 Per Night
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...
Family House
Esperanza Suite
Key West Florida
Suites
1 Bedrooms
2 Baths
Sleeps 4
$100 to $250 Per Night
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...
Esperanza Suite
Oceania Suite
Key West Florida
Suites
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
...
Oceania Suite
A Key Escape
Key West Florida
Home
3 Bedrooms
2.5 Baths
Sleeps 8
Over $250 Per Night
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...
A Key Escape
Casa Key West
Key West Florida
Condo
3 Bedrooms
2 Baths
Sleeps 8
Over $250 Per Night
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...
Casa Key West
Fishtail Hideaway
Key West Florida
Home
1 Bedrooms
2 Baths
Sleeps 4
$100 to $250 Per Night
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 ...
Fishtail Hideaway
The Casa de Mango
Key West Florida
Condo
2 Bedrooms
2.5 Baths
Sleeps 6
Over $250 Per Night
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...
The Casa de Mango
Mermaids Cove
Key West Florida
Home
4 Bedrooms
4 Baths
Sleeps 10
Over $250 Per Night
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 ...
Mermaids Cove
Garden House
Key West Florida
Home
2 Bedrooms
2 Baths
Sleeps 6
Over $250 Per Night
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 ...
Garden House
The Bahama Breeze
Key West Florida
Condo
2 Bedrooms
1 Baths
Sleeps 4
Over $250 Per Night
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...
The Bahama Breeze
Poolside Suite
Key West Florida
Duplex
2 Bedrooms
1 Baths
Sleeps 4
Over $250 Per Night
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...
Poolside Suite
Windward Isle
Key West Florida
Home
2 Bedrooms
1 Baths
Sleeps 6
Over $250 Per Night
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...
Windward Isle
Island Oasis
Key West Florida
Home
2 Bedrooms
2.5 Baths
Sleeps 6
Over $250 Per Night
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...
Island Oasis
Casa Serendipity
Key West Florida
Home
3 Bedrooms
2 Baths
Sleeps 6
Over $250 Per Night
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...
Casa Serendipity
Amelia House
Key West Florida
Home
3 Bedrooms
2 Baths
Sleeps 8
Over $250 Per Night
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...
Amelia House
Hemingway's View
Key West Florida
Home
3 Bedrooms
2 Baths
Sleeps 8
Over $250 Per Night
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...
Hemingway's View
Havana Hideaway
Key West Florida
Condo
2 Bedrooms
2.5 Baths
Sleeps 6
Over $250 Per Night
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...
Havana Hideaway
Howe Street Hideaway
Key West Florida
Home
2 Bedrooms
2 Baths
Sleeps 6
$100 to $250 Per Night
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 ...
Howe Street Hideaway
Helen's Hideaway
Key West Florida
Home
2 Bedrooms
2 Baths
Sleeps 6
Over $250 Per Night
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...
Helen's Hideaway
Heron Hideaway
Key West Florida
Condo
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
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...
Heron Hideaway
The Tropical Retreat
Key West Florida
Home
3 Bedrooms
3.5 Baths
Sleeps 8
Over $250 Per Night
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...
The Tropical Retreat
Casa Maria
Key West Florida
Condo
2 Bedrooms
2.5 Baths
Sleeps 6
Over $250 Per Night
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...
Casa Maria
Casa 625
Key West Florida
Home
2 Bedrooms
2 Baths
Sleeps 6
$100 to $250 Per Night
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 ...
Casa 625
Ospreys Nest
Key West Florida
Condo
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
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...
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...
The DuPont House
The Villa Azul
Key West Florida
Home
3 Bedrooms
3 Baths
Sleeps 6
Over $250 Per Night
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...
The Villa Azul
Artist Retreat
Key West Florida
Home
3 Bedrooms
2 Baths
Sleeps 6
Over $250 Per Night
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 ...
Artist Retreat
The Casa Blanca
Key West Florida
Home
2 Bedrooms
3.5 Baths
Sleeps 6
$100 to $250 Per Night
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...
The Casa Blanca
Pinder House
Key West Florida
Home
2 Bedrooms
2 Baths
Sleeps 1
$100 to $250 Per Night
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...
Pinder House
Palm Isle
Key West Florida
Condo
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
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...
Palm Isle
Cigar Makers Cottage
Key West Florida
Home
2 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
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...
Cigar Makers Cottage
Providence Suite
Key West Florida
Suites
1 Bedrooms
1 Baths
Sleeps 6
$100 to $250 Per Night
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...
Providence Suite
Key Lime Cottage
Key West Florida
Townhouse
1 Bedrooms
1 Baths
Sleeps 2
$100 to $250 Per Night
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...
Key Lime Cottage
Duval Square Penthouse
Key West Florida
Condo
2 Bedrooms
2.5 Baths
Sleeps 6
Over $250 Per Night
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...
Duval Square Penthouse
Mel Fisher Suite
Key West Florida
Suites
3 Bedrooms
2 Baths
Sleeps 8
Over $250 Per Night
...
Mel Fisher Suite
Almost Southernmost
Key West Florida
Home
2 Bedrooms
1 Baths
Sleeps 6
Over $250 Per Night
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...
Almost Southernmost
Southernmost Retreat
Key West Florida
Condo
2 Bedrooms
1 Baths
Sleeps 6
$100 to $250 Per Night
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...
Southernmost Retreat
Leeward Isle
Key West Florida
Home
2 Bedrooms
1 Baths
Sleeps 4
Over $250 Per Night
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...
Leeward Isle
Caribbean Suite
Key West Florida
Suites
1 Bedrooms
1.5 Baths
Sleeps 4
$100 to $250 Per Night
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, ...
Caribbean Suite
Bermuda Suite
Key West Florida
Suites
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
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...
Bermuda Suite
Little Havana Suite
Key West Florida
Suites
1 Bedrooms
1.5 Baths
Sleeps 4
$100 to $250 Per Night
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...
Little Havana Suite
Andros Suite
Key West Florida
Suites
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
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...
Andros Suite
Abaco Suite
Key West Florida
Home
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
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...
Abaco Suite
Conch Casa
Key West Florida
Home
2 Bedrooms
1 Baths
Sleeps 6
$100 to $250 Per Night
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...
Conch Casa
Sunset Suite
Key West Florida
Suites
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
...
Sunset Suite
Verde Suite
Key West Florida
Suites
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
...
Verde Suite
Heathers Villa
Key West Florida
Home
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
...
Heathers Villa
Audubon House
Key West Florida
Home
1 Bedrooms
2 Baths
Sleeps 4
$100 to $250 Per Night
...
Audubon House
Jasmine Suite
Key West Florida
Suites
1 Bedrooms
1 Baths
Sleeps 4
$100 to $250 Per Night
...
Jasmine Suite
Fleming-O
Key West Florida
Home
2 Bedrooms
1 Baths
Sleeps 6
$100 to $250 Per Night
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 ...
Fleming-O
Key West Hideaway
Key West Florida
Home
4 Bedrooms
4 Baths
Sleeps 10
Over $250 Per Night
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...