Key West Vacation Villas |
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Want to rent your own home for your family or a few couples or friends? Then a vacation villa could be your best choice. Our privately owned houses have "full fledged" interiors, their own swimming pools and sun decks, and many have beautiful tropical gardens. In a Key West villa you'll live in local Key West neighborhood in your own private 'home-away-from-home.' |
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(#3714)
4BR 3.5BA Sleeps 6-10
"In-the-know" travelers who return to Key West love to choose the more elegant area of Upper Duval St. as their favorite area to stay... "Amelia's Hideaway."
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(#223)
3 BR 2 BA
Private Jacuzzi
Bohemian by design, off-beat, and a little bit funky, this old house on Ann Street is authentic to the bone. It’s decidedly charming and very comfortable but not over done. Reminds you that a little bit of ‘Old Key West’ is alive and well.
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(#5222)
4BR 3BA Sleeps 10
A Private Tropical Paradise... is the feeling you get when you enter the pavilion of this extraordinary award winning villa just a half block off Duval St. in Old Town Key West.
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(#209)
4BR 4BA
Sleeps 8-12
The authentic presence and spirit of the Key West Quarter House have much more in common with the real Key West than the shiny new hotels that dot the landscape just 2 blocks away.
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(#1017)
3 BR 2 BA
Sleeps 5-6
Authentic "old-world" charm meets modern tropical luxury in this wonderful historic island home. Built of original glistening heart pine from floor to ceiling, the interior rooms radiate a warm and magical feel.
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(#8248)
4 BR 3.5 BA
Sleeps 8
Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real.
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(#1223)
5 BR 4.5 BA
Exquisitely Key West yet exotically Cuban, this classy compendium of an elegant casa grande plus vintage casita is ideally located in the fascinating Upper South End of Duval Street.
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(#1613)
3-4BR (Den) 2½BA - Sleeps 8
Just Off Upper Duval Street
Private Adjoining Cottages
with Private Pool and Jacuzzi
This one-of-a-kind island villa perfectly blends two charming historic cottages right into a little bit of Old Town Key West island heaven. Your own private tropical resort is the feeling you get when you enter the bricked courtyard.
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(#1224)
3 BR 2.5 BA
Sleeps 8
Displaying the most romantic elements of neoclassicism design this inspired home has a special fairy-tale charm. At long last this splendid 5-Star home of fine distinction and testimony to our Key West - Cuban architectural history lives again!
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(#1228)
4 BR 4 BA Sleeps 8
"Two is definitely better than One!" A rare set of early 1900's "twin-cigar maker's cottages" are both adorable and elegant and a perfect solution for a discerning group who want to lodge together in luxury but require maximum privacy.
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(#1002)
3 - 4 BR (Den) 3 BA
You've just discovered a private Key West house with a beautiful sea view that's next to Key West's Fort Zachary Taylor Beach, and just a few short walking streets from the heart of downtown.
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(#522)
2 BR 2 BA
Private Swimming Pool
Sleeps 4 - 6
This private rental home offers all the luxury amenities. A stroll through this charming Upper Duval neighborhood is to rendezvous with an important part of our island's rich cigar and rum history.
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(#1307)
Large Private Swimming Pool
with Spacious Outdoor Cabana
3BR 2½BA Main house
Sleeps 6
Experience true tropical Key West living in this lush garden oasis home with large swimming pool and garden cabana located just one block from the beach. Easy bike ride to center of Old Town.
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(#1308)
Large Private Swimming Pool
with Spacious Outdoor Cabana
4BR 3½BA Main house plus Studio Cottage
Sleeps 8
(avail. June - November)
During the months of June through November this genuine Key West combo of our "Private Pool Garden Villa" plus a classy private studio cottage that adjoins the property can be your very own get-away.
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(#1306)
5BR 3BA Sleeps 8-10
Originally built in the 1940's, this charming large wooden home has two full stories with deep porches which overlook the garden and pool. A renovation of the home redesigned the floor plan so it can also be utilized as two separate units.
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(#524)
6BR 6BA Sleeps up to 12
The Watson House is a one-of-a-kind 'timeless award-winning Victorian home' in the heart of Old Town Key West. Just half a block from Duval Street you can easily walk everywhere in the island village.
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(#709)
Large Private Swimming Pool
4BR 3 BA Sleeps 8
Tucked away on a huge lot, nearly smack dab in the middle of Old Town Key West, this home is cleverly camouflaged on a very spacious lot in between 2 little lanes that most folks have never even heard of.
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(#412)
3BR 2BA Sleeps 6
Located on the famous Key West Heritage House compound where the island was first settled, this 2-story Caribbean style home is full of authentic charm.
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(#906)
3 BR 3 BA
Sleeps 6
Easy elegance permeates every room of this renovated villa that married a 1940’s bungalow style island house with a next door Caribbean style cottage on two lots in the beautiful Old Town Key West Meadows neighborhood.
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(#812)
4 BR 4 BA Sleeps 8 - 10
This spectacular Key West villa has maintained its historic residential authenticity, while being redesigned as two separate wooden structures joined by a Caribbean-style covered wooden walkway-porch.
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(#318)
2BR 2BA Sleeps 2-4
Private Pool - Off-Street Parking
A celebration of island style is made imminent throughout the interior of the cottage with soft modern tropical furnishings and a beautiful display of tropical artwork by local artists.
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(#5251)
4 BR 3 BA + Library-Office
Neatly situated between a fashionably narrow island street and a hidden lane, this "house-plus-guest-cottage" villa displays a West Indies design that smoothly melds a sophisticated British Colonial gracefulness with a carefree Caribbean flare. The overall effect both warms the heart and tickles the soul with a fanciful-folly-of-charm.
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(#4796)
2BR 2BA Sleeps 6
Spanish-style Private Luxury Villa right in the Heart of Old Town Key West. Originally built in 1938, this fully renovated luxury home is a spectacular show piece and one of the most creative designs in Key West.
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(#6169)
2BR 2BA Sleeps 4
Gentle Retreat in the Key West Meadows. Perfectly Renovated and Immaculate Neighborhood.
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(#1006)
2 BR 2.5 BA
Private Pool
The Island Modern Colonial shows off a classic Key West front porch & white picket fence with capital posts and white railing. Two rockers are set waiting for you to arrive, and the front door is punctuated with an artful brass door-knocker in the shape of a golden frog.
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(#1214)
3BR 2½BA Sleeps 6
Tucked behind a breathtaking tropical garden wall and located along one of Key West's most desirable residential streets, this spectacular home reflects a dynamic blend of contemporary Mediterranean and Caribbean architectural design.
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(#1205)
3BR 3BA + Den - Sleeps 7
Designed by a well known Key West abstract artist and a landscape architect this unique art deco living space is at once daring, serene, and comfortable.
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(#4121)
3BR (+Den) 3½BA - Sleeps 6-7
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.
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(#1207)
3 BR 3 BA - Sleeps 6 - Main House + Pool Cottage
A marriage of traditional Key West ‘conch house’ with island cosmopolitan has found the harmonious sweet spot between casual elegance and laid-back Caribbean.
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