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Key West Apartments, FL

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$2,563
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1 / 8
1 Bedroom, 1 Bathroom, Sleeps 2
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$3,588
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1 Bedroom, 1 Bathroom, Sleeps 2
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1 Bedroom, 1 Bathroom, Sleeps 4
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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About this property
Monthly rental. Key West private home right on the water - family owned for three generations (former home to WWII war hero Admiral Edward McCarthy, the former mayor of Key West (Mayor Alan Cleare), and the former District Attorney (Alan B. Cleare)). Just a few doors down from Jimmy Buffet's... View all property information
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$3,844
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1 / 34
2 Bedrooms, 1 Bathroom, Sleeps 4
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About this property
28 NIGHT MINIMUM STAY REQUIREMENT - ANGELFISH COTTAGE 2 Bedroom 1 Bath Historic Conch House on a quiet Lane in Historic Old Town Key West This monthly vacation home is located in the heart of Historic Old Town Key West Florida on a very private, quiet lane. Restaurants and bars, marinas and... View all property information
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$3,204
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1 / 34
Studio, 1 Bathroom, Sleeps 2
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About this property
Beautifully Renovated First Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street.... View all property information
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$288
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1 / 28
2 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
DUVAL SEA TURTLE - This townhome has two bedrooms and two and one half baths and a balcony off the master bedroom and another off the living room. The entire property has been decorated using art from the local galleries and artists. The theme is 'Key West' from scenes around the area including... View all property information
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1 / 42
5 Bedrooms, 6 Bathrooms, Sleeps 12
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About this property
Perfectly positioned on Sunset Key, ‘the islands island,’ the Ultimate Key West Beach House ~ Sunset Key VIP, is within 500 yards off-shore of the ‘main island’ of Key West. A splendid view gazing toward Mallory Dock and the famous sunset celebration, this one-of-a-kind waterfront property offers a... View all property information
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$641
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1 / 23
3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Gym
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About this property
2-Story Private Home in Coral Hammock, 3 Bedrooms, 3 Baths (Sleeps 6-8) Available Weekly This home has been whimsically decorated, with furnishings that reflect the laid-back, funky island life style of Key West. Located in the gated community of Coral Hammock, you will be just down the street... View all property information
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1 / 17
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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About this property
My home is in a quiet neighborhood, and just minutes away from all that Key West has to offer. Come relax and enjoy life on the island. Just a few moments walk to Smathers Beach, Higgs Beach, and close to local restaurants. With 3 bedrooms, 2 baths, a beautifully manicured front yard, pool,... View all property information
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1 / 14
1 Bedroom, 1 Bathroom, Sleeps 3
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  • Suitable for children
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About this property
THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses... View all property information
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1 / 9
2 Bedrooms, 3 Bathrooms, Sleeps 4
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About this property
Hidden from view at the end of a little lane that intersects with downtown Duval Street, this Starlight Siesta vacation rental encompasses the rear half of the Key West penthouse property known as Penthouse On Duval. Perfectly staged in the island's city center, this spectacular downtown Key West... View all property information
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$436
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1 / 37
2 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Key West vacation you have been seeking. Tucked away in one of the most interesting neighborhoods in the historic... View all property information
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$2,307
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1 / 11
2 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as 'Truman Annex', this striking tri-level historic building has all the architectural allure of a 19th century urban brownstone with an unparalleled modern Caribbean... View all property information
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$7,048
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1 / 13
3 Bedrooms, 2 Bathrooms, Sleeps 6
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About this property
Key West has long been loved for its playful spirit, forever attracting all genres of fun-loving artists, musicians, and writers. In recognition for the island’s historical humor, we have fondly named this beautiful upscale home, On Hemingway’s Rounds. Paying tongue-in-cheek homage to Papa’s... View all property information
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$4,229
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1 / 15
3 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
Key West sunsets are famous, and so remarkably spectacular that each-and-every-day of the year, hundreds of people gather at the Mallory Square dock in Key West to celebrate the days end. As the sun slowly 'sinks into the sea', the Key West Sunset Celebration festivities rev up, and every island... View all property information
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$6,728
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1 / 17
3 Bedrooms, 3 Bathrooms, Sleeps 6
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About this property
Tucked behind a breathtaking tropical garden wall this spectacular Mediterranean Caribbean vacation rental home reflects a dynamic blend of contemporary Mediterranean with Caribbean architectural design. Located along one of Key West's most desirable residential streets this 'Casa el Paradiso' most... View all property information
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$732
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1 / 21
3 Bedrooms, 4 Bathrooms, Sleeps 8
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  • Suitable for children
  • x
  • x
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About this property
EASY LIVIN' -- The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located in the historic Old Town neighborhood, in walking distance of anything you'll want to do during your visit. The formal entrance... View all property information
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$513
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1 / 9
3 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Suitable for children
  • x
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About this property
Nestled in one of Key West's original gated 'mini-compounds,' the Tropical Tradition vacation rental is a spacious 1990's three-story Key West town home providing an island living experience in a traditional tropical style - both inside and out. A lush tropical garden complete with large 40' X 16'... View all property information
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$231
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1 / 22
2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this home offers the finest accommodations for you and your family. Furnished with comfort in mind with a fully equipped kitchen for preparing your fresh catch or a quick breakfast to start your day of... View all property information
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$9,611
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1 / 23
3 Bedrooms, 3 Bathrooms, Sleeps 8
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About this property
'Who says you can't have your cake and eat it too?' Well here's the proof you can ... and it's To the Nines -Key West vacation rental. When you rent this totally unique vacation rental, you will have the 'best of both worlds' ... a penthouse and a pool courtyard villa, all wrapped up into one! I've... View all property information
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From
$769
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1 / 15
4 Bedrooms, 3 Bathrooms, Sleeps 8
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About this property
This one-of-a-kind Fantasy Resort Villa vacation rental perfectly blends two charming historic cottages right into a little bit of island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard of this extraordinary property just off Upper Duval St. in... View all property information
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From
$1,730
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1 / 40
9 Bedrooms, 7 Bathrooms, Sleeps 22
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  • Elder access
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About this property
Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental... View all property information
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From
$2,819
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1 / 21
3 Bedrooms, 2 Bathrooms, Sleeps 8
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  • Hot Tub
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  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Elder access
About this property
Waterfront Condominium with 3 bedrooms, 2 bathrooms, sleeps 6 Imagine waking up every morning to the sun rising over the azure blue Atlantic Ocean. That's what you will experience with this beautifully furnished three bedroom condo right on the ocean at Oceanside Marina. With direct views of the... View all property information
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$7,112
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1 / 9
2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Elder access
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About this property
If you have ever had the fortune to wander the historic streets and lanes of Key West's famous seaport neighborhood then you know how time seems to stand still. Yet right in the heart of Key West's bustling seaport this blissfully ideal cottage-style house offers all the amenities one could desire... View all property information
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From
$7,689
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1 / 16
3 Bedrooms, 3 Bathrooms, Sleeps 7
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About this property
Live in the lap of luxury in this stunningly renovated Key West classic 'Eyebrow House.' An esteemed Key West renovation builder assembled a creative team of elite woodworkers, masons, local craftspeople, and an internationally known traveling artist / sailor to execute his plans to create this... View all property information
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$218
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1 / 4
1 Bedroom, 1 Bathroom, Sleeps 2
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  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Elder access
  • x
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About this property
This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away from Duval Street. This unit is only minutes from attractions like the Southernmost Point, Hemingway House, Mallory Square, and the Historic Seaport. This... View all property information
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$5,895
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1 / 7
2 Bedrooms, 2 Bathrooms, Sleeps 4
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About this property
This gentle Governor's Retreat in the Key West Meadows is an immaculate luxury vacation rental cottage ideal for a quiet couple or single person with discerning taste. The property is the perfect Key West setting for rest, relaxation, and rejuvenation. It is ideal for the person of distinction who... View all property information
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$3,172
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1 / 47
11 Bedrooms, 11 Bathrooms, Sleeps 24
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About this property
The Meeting Point – Key West is by-far the most spacious and classically elegant vacation rental property on the island. Situated in the heart of Old Town, there is nothing else like it. If you’re looking for luxury and plenty of room, The Meeting Point is the grandest vacation rental in Key West,... View all property information
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From
$896
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1 / 8
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Studio, 1 Bathroom, Sleeps 2
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  • Waterfront
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  • Suitable for children
  • x
  • x
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About this property
Hyatt Sunset Harbour Residence Club. Studio room. Location, Location, Location. Room is equal to a hotel room . Available June 14th through June 21st only. Great resort in a great old town location. Room has a king size bed, microwave, coffee maker, and mini refrigerator. No balcony. Beautiful... View all property information
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$320
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1 / 18
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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About this property
Incredible resort during the 'peakest' of peak seasons in Key West, Florida. This extraordinary resort is not right in the heart of the Duval Street area, and it therefore offers the best of both worlds to visitors. Since it's within a short car or cab or scooter or bike ride from the Old Town... View all property information
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From
$384
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1 / 7
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
This stunning 2 bedroom/2 bath suite can accommodate up to 6 guests. Whether you want the hustle and bustle of Key West or just want to kick back and relax, this resort has it all. View all property information
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From
$370
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1 / 11
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1 Bedroom, 1 Bathroom, Sleeps 4
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About this property
Tropical oasis in the heart of key west. Historic landmark 1 block from duval street. Walk to the pier for sunset celebrations, artists, musicians and entertainment. Surrounded by restaurants and shops and key wests popular theatre. Mel fishers museum is just down the street. Enjoy bicycles,... View all property information
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From
$256
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1 / 23
1 Bedroom, 1 Bathroom, Sleeps 6
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  • x
  • ?
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About this property
Have you ever wondered what it would be like to live on a boat? Well now you can try out the liveaboard experience on board Capt Andy, a 43 ft fishing boat in Key West! This is the perfect rental for a group of boat loving friends looking for a budget friendly rental in Key West. Featuring a full... View all property information
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$1,922
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1 / 6
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2 Bedrooms, 1 Bathroom, Sleeps 6
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  • Suitable for children
  • x
  • ?
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  • Elder access
  • x
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About this property
Experience a world full of lush and fragrant gardens on a Caribbean Estate tucked away in the heart of Old Town, Key West. Stay in a 2 bedroom unit in a restored historic wrecker's home and wander through the extensive gardens as time transcends you to an era long ago. You can relax and indulge... View all property information
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$769
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1 / 24
2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Smoking allowed
  • Suitable for children
  • x
  • ?
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  • Elder access
  • x
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About this property
2 bedrooms, 1 Bath, 1 Outdoor Shower and Pavillion, Tropical Garden (sleeps 4-6). Open the gate and stroll through the lush gardens of this beautiful two bedroom, one bath home, built in 1953 and entirely renovated. In addition to the updated kitchen and bath, there's a screen porch, a covered... View all property information
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From
$15,378
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1 / 22
5 Bedrooms, 4 Bathrooms, Sleeps 12
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About this property
Classic romantic 1800’s Key West architecture has inspired a superbly executed renovation of this extraordinary historic Victorian estate. Displaying a perfected cosmopolitan flair, the owner / designer has artfully intertwined a look-back into architectural history with a sophisticated... View all property information
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From
$3,844
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1 / 23
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1 Bedroom, 1 Bathroom, Sleeps 4
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About this property
***Due to licensing restrictions, this home requires a minimum stay of 28 nights*** This inviting HGTV Featured Home (Bang for Your Buck, 2010) surrounds you with luxury, comfort and history. Originally a Cuban Cigar Maker’s Cottage (circa 1920’s), this vacation home has been updated with no... View all property information
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From
$1,856
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1 / 24
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11 Bedrooms, 9 Bathrooms, Sleeps 32
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About this property
Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. COTTAGE @ TROPICAL VILLAGE POOLSIDE @ TROPICAL VILLAGE SOUTHERN CROSS @ TROPICAL VILLAGE TOON HALL @ TROPICAL VILLAGE RETREAT @ TROPICAL VILLAGE HIDEAWAY @ TROPICAL VILLAGE... View all property information
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$952
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3 Bedrooms, 4 Bathrooms, Sleeps 6
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  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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  • x
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  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Bring more luminescence into your next vacation with evening after evening of incomparable Key West sunsets viewed from the third-floor deck of this spectacular private home. Called The Water's Edge because of its location at the edge of the Gulf of Mexico, this lovely and comfortable... View all property information
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5 Bedrooms, 4 Bathrooms, Sleeps 12
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  • Air Conditioning
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  • Hot Tub
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  • Satellite TV
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  • Suitable for children
  • x
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  • Wheelchair access
  • Elder access
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About this property
Abbey Road - Gated Compound, Sleeps up to 12! Lennon's Lodge (Sleeps 6 with 8 person hot tub), McCartney's Manor (Sleeps 2 with 2 person hot tub), Starr's Suite (Sleeps 2 with 2 person hot tub) and Harrison's Hideaway (Sleeps 2 with 2 person hot tub) and will accommodate up to 12 persons for... View all property information
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1 Bedroom, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
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  • Ocean Views
  • Safe
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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About this property
This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
  • Balcony
  • Dryer
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Safe
  • Satellite TV
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
The Hyatt Windward Pointe is the most luxurious accommodation in Key West. One king bedroom suite with ocean views, queen bedroom and sleep sofa (accommodates 6), Full kitchen, balcony with ocean views, W/D in unit, TV in every room, large pool and hot tub, volleyball court, amazing landscaping.... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Gym
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  • Satellite TV
  • Sauna
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
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About this property
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Playa Royale is located on South Roosevelt Blvd., directly across from Key West's largest beach (Smathers) on the Atlantic Ocean. You can choose to join in activities held in the club house overlooking the... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
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  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
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  • Wheelchair access
  • Elder access
  • ?
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About this property
***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Salt Pond Hideaway is located right off of South Roosevelt Blvd. in the oceanfront Salt Ponds Condominium Complex. It offers a neighborly and relaxing atmosphere with the ocean breezes of the Atlantic... View all property information
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$3,973
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3 Bedrooms, 2 Bathrooms, Sleeps 6
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  • Air Conditioning
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  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
FIRST BREATH: 3-bedroom 2-bath Conch home with pool in Old Town. Fenced and landscaped for the ultimate privacy. Back gate opens onto Elgin Lane.2 bedrooms upstairs, 1 with queen and 1 with twins, share the full bath. Downstairs is the 3rd bedroom with king bed and bath ensuite. Well-stocked... View all property information
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2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
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  • Shared Outdoor Pool...
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  • Pets allowed
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  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
HIDDEN TREASURE (monthly rental): Comfortable open floor plan includes living, dining and kitchen. Master bedroom with queen bed and private bath can be reached from poolside as well. Guest bedroom with queen bed, and flatscreen TV.Just painted and furnished with loving care and kitchen is... View all property information
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$186
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • Smoking allowed
  • Suitable for children
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  • Wheelchair access
  • Elder access
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About this property
OSPREY: Studio cottage located in The Colony Suites, a compound nestled in Old Town Key West. Osprey offers all the amenities for two who want a larger space than a hotel room. Sunny and bright, sitting area, queen size bed, full bathroom and kitchenette. French doors open to a private... View all property information
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1 Bedroom, 1 Bathroom, Sleeps 2
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  • Elder access
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About this property
CITY CAY: City Cay is our 1-bedroom 1-bath upstairs condo in Truman Annex that has been lovingly renovated and furnished in a sleek modern style. Stay connected in the living room with high-end electronics including HDTV, WIFI and an over-the-top stereo system. Relax on the covered back balcony... View all property information
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2 Bedrooms, 3 Bathrooms, Sleeps 6
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  • Wheelchair access
  • Elder access
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About this property
SPA ON DUVAL: 2 story, 2 bedroom 2.5 bath townhome located in Duval Square. Private jacuzzi on its porch that makes relaxing on the spacious deck at the end of a fun filled day the perfect spot. Upstairs the master bedroom has a king size bed and private balcony; the guest bedroom has queen bed... View all property information
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