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Condos and house rentals in Key West, FL

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$378
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1 / 29
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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1 Bedroom, 1 Bathroom, Sleeps 4
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About this property
The Truman Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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About this property
28 NIGHT MINIMUM STAY REQUIREMENT - BANANA DREAM Banana Dream offers you an exceptional opportunity to enjoy Key West at its best! This is a charming 2 bedroom / 2 bath - first floor condominium. It is furnished with all of the comforts you would expect from a vacation home in paradise. Enjoy... View all property information
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$418
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1 / 29
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3 Bedrooms, 4 Bathrooms, Sleeps 8
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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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1 Bedroom, 1 Bathroom, Sleeps 4
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About this property
Part of the Nightly Group PALM GARDENS 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 leche and the best Cuban Sandwiches at Sandy's Cafe, pulled pork... View all property information
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Suitable for children
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About this property
This immaculately clean and comfortable air conditioned suite features beautiful vaulted ceilings and pastel colored walls as well as a top of the line flat screen TV and stereo. The living room has tropical furniture and a w/ Queen Sleeper Sofa. Efficiency kitchen is fully equipped for cooking w/... View all property information
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1 / 27
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Satellite TV
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  • Suitable for children
  • x
  • ?
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  • Elder access
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About this property
Southernmost Retreat 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. The perfect place to listen to your favorite music while... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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About this property
BAHAMIAN REED: 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West: Fort Zachary Taylor State Park , Duval Street shops, galleries, bars and restaurants, and Sunset Celebration. Gourmet kitchen,... View all property information
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
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  • Gym
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Elder access
  • ?
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About this property
Part of the Nightly Group PALM GARDENS 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, the tropical paradise has just undergone a complete... View all property information
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1 / 28
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Studio, 1 Bathroom, Sleeps 2
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  • Satellite TV
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  • Pets allowed
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  • Suitable for children
  • x
  • ?
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  • Elder access
  • ?
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About this property
The Mallory Suite is nestled at the rear of the Simonton Court complex. The efficiency studio features a fully-equipped kitchen, flatscreen TV with cable, free wireless internet, and private patio furniture to relax on. The bathroom has a custom tiled shower with glass door and vanity. Take... View all property information
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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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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1 / 31
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Smoking allowed
  • Suitable for children
  • x
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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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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Washer
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
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  • Elder access
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About this property
SEE 'RATES' FOR SPECIAL OFFER OVERVIEW The Cigar House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of four (4) guests, who are comfortable sharing an open sociable living... View all property information
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1 / 20
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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$268
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Located in Duval Square (between Duval Street and Simonton Street), where fine dining abounds (Square One and Origami Sushi Bar), Casa Caribe is a second story paradise just steps from the sights, sounds and excitement of world-famous Duval Street. Lush and tropical gardens surround this... View all property information
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1 / 23
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2 Bedrooms, 3 Bathrooms, Sleeps 7
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  • Air Conditioning
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  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Elder access
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About this property
Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town.... View all property information
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$200
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1 / 31
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2 Bedrooms, 1 Bathroom, Sleeps 4
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  • Air Conditioning
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  • Grill
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
***Due to licensing restrictions, this property requires a minimum stay of 7 nights.*** Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million... View all property information
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 5
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  • Water Views
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  • Pets allowed
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  • Suitable for children
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  • Wheelchair access
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About this property
TRUMAN'S HIDEAWAY: It's hard to say which is more impressive, the view of Florida Bay from your private deck or living in front of Truman's Little White House. This lovely condo in the exclusive Harbour Place condominium complex in Truman Annex offers all the comforts of home and more. Spacious... View all property information
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$178
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1 / 24
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Studio, 1 Bathroom, Sleeps 2
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  • Air Conditioning
  • Grill
  • Gym
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  • Internet Access
  • Shared Outdoor Pool...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
Part of 4 exclusive units at Abbey Road, renovated January, 2010, this suite is at 918-920 Center Street. Featuring a king pillow-top bed and marble floors, the state-of-the-art kitchen includes granite counter top, a 2 burner cook top, dishwasher, under counter refrigerator, microwave and soft... View all property information
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1 / 24
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Studio, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Grill
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  • Satellite TV
  • Shared Outdoor Pool...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Papa's Hideaway is a historic Key West Inn with all the charm of Hemingway's day and the convenience of being just one block off Duval street. The perfect mix of location, atmosphere and value. Feel your tensions release as you soak up the warm tropical sun. Listen to the trade winds rustling... View all property information
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$308
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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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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$188
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1 / 27
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
Part of the Nightly Group PALM GARDENS Flamingo Hideaway is a spacious unit. Historic homes dating to the late 1880s, this tropical paradise has just undergone a complete restoration with exceptional attention to details. The original Dade County pine walls have been saved to create that... View all property information
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$1,255
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2 Bedrooms, 2 Bathrooms, Sleeps 5
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  • Suitable for children
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About this property
PARROT PERCH: Great location and great value for a great vacation. Parrot Perch is an upstairs 2 bedroom 2 bath condo with a balcony from the living room offering a view of the neighborhood and BBQ grill. The best priced 2 bedroom 2 bath condo in Truman Annex with a queen bed and bathroom... View all property information
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4 Bedrooms, 2 Bathrooms, Sleeps 12
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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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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$268
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • x
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About this property
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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$398
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • x
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About this property
The BAHAMA HOUSE located at 508 Amelia Street is a historic Bahamian-style Conch Cottage. It is a perfect example of turn-of-the-century island architecture. This adorable two bedroom cottage, each with queen bed and TV (the master has a large flat screen), two full baths and queen sleeper-sofa is... View all property information
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$408
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Elder access
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About this property
Part of Southern Palms COCONUT PALM (formerly Island Oasis). Take a lot of history and a lot of charm - mix it with a great location and you have the perfect Key West hideaway. A vacation rental home built and operated in the late 1800's as the city's hack concession and stables, has been... View all property information
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$265
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
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  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
LEEWARD ISLE KEY WEST RETREAT: Small gated compound with only 13 properties, this townhome community is quiet and private right in the heart of Old Town. 2-bedroom 2-bath townhome remodeled from top to bottom. Decorated with Key West flair, this is truly a unique property. Flatscreen TVs,... View all property information
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$188
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Studio, 1 Bathroom, Sleeps 2
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  • Suitable for children
  • x
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About this property
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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  • Suitable for children
  • x
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About this property
Part of TROPICAL VILLAGE Tropical Hideaway - Lush gardens surround this lovingly restored two-story vacation house. This downstairs rental cottage has one bedroom with full bath and features a living room with queen sleeper-sofa, cable TV, DVD, stereo with CD player, and wireless internet. The... View all property information
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Air Conditioning
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  • Gym
  • Hot Tub
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  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
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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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
Part of the Nightly Group PALM GARDENS Historic homes dating to the late 1880s, the tropical paradise has just undergone a complete restoration with exceptional attention to details. Osprey's Nest is an upstairs spacious unit at 905 White Street. The original Dade County pine walls have... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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About this property
LAKEVIEW: 2 bedroom 1.5 bath townhome in the gated Key West Golf Club community. Lushly landscaped lanes meander throughout the grounds and one of two community pools is across the street from your front door.This 2-story home has both bedrooms and full bath upstairs with kitchen/living... View all property information
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1 Bedroom, 1 Bathroom, Sleeps 4
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  • Air Conditioning
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  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Elder access
  • ?
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About this property
Overlooking the gardens and lily pond, the entrance to this spacious unit is through a totally enclosed private decked courtyard with a 4-person spa, table and chairs. Inside this spacious unit you will find a living room with cathedral ceilings, 56” TV, A/C, stereo, queen sleeper sofa and fabulous... View all property information
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Studio, 1 Bathroom, Sleeps 2
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  • Air Conditioning
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  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder 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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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Elder access
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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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4 Bedrooms, 4 Bathrooms, Sleeps 10
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
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  • Elder access
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About this property
Two Queen bedrooms upstairs (each with a private bath) and two Queen bedrooms downstairs (each with a private bath) gives sleeping privacy and convenience for up to 8. Each bedroom has flat screen TVs, air-conditioning and ceiling fan. The two upstairs bedrooms have showers, the two downstairs... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Water Views
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  • Suitable for children
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  • Elder access
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About this property
A ZEN OCEAN GARDEN: The perfect 2 bedroom 2 bath Ocean View condo. Enjoy the ocean breezes while unwinding on your private balcony in this tasteful retreat, decorated for your comfort and relaxation. Located on the Atlantic Ocean with views from the living room and both bedroom; every room has... View all property information
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
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  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
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About this property
AUDUBON'S LIVING ROOM HAS JUST BEEN REFURBISHED WITH NEW FURNITURE INCLUDING NEW CHAIRS AND A NEW QUEEN SLEEPER SOFA! The Audubon House is an historic free-standing one bedroom cottage featuring all the comforts of home, and more! The spacious, beautifully furnished great room features a... View all property information
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Hot Tub
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  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit opens to the living room,... View all property information
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
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$238
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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About this property
UPDATE: New King-sized bed w/ pillow top mattress installed June 2015 Outside the front of the complex are the tennis courts. If you choose to stay inside the complex you can enjoy the lush landscape on the inside of the courtyard. Just a short stroll takes you to the relaxing hot tub and then... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
WIND SWEPT: Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States.This lovely 2 bedroom 1.5 bath townhome is freshly painted and newly furnished. Enter the open and airy living space... View all property information
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3 Bedrooms, 3 Bathrooms, Sleeps 8
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  • Private Outdoor...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Elder access
  • ?
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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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Studio, 1 Bathroom, Sleeps 2
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  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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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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Studio, 1 Bathroom, Sleeps 2
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  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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5 Bedrooms, 4 Bathrooms, Sleeps 16
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  • Air Conditioning
  • Balcony
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
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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2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
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  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
CONCH CONDO -- 2-bedroom 2-bath upstairs condo features fully equipped kitchen, custom furniture, plasma TVs and home theatre in living room, plasma TVs in both bedrooms, and plenty of closet space. French doors in the living room open to a large balcony. Master bedroom has queen bed, guest... View all property information
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