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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(#516)
4 BR 3 BA Sleeps 8 - 10
We invite you to discover that incredible experience of Déjà vu ... you know, when you enter someplace for the very first time, and instantly you get that sense that you’ve been there before. When I first walked into this house it happened to me. My mind sparked and I felt an instant kinship with the surroundings.
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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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(#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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Key West Bungalows & Cottages |
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Find your own cozy retreat or tropical 'love nest' in a charming Key West cottage. If it's just the 2 of you or a "couple of couples," go for a Key West cottage and relish in the romantic ambiance of vintage style decor with all the modernized comforts of a home. Get a real taste of the original Key West life-style and actually live in an authentic wooden custom built 'turn-of-the-century' abode.
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(#4532)
1BR 1BA Sleeps 4
"Vintage Luxury Cottage" - Just off Upper Duval Street. This is an elegant Cottage with Private Heated Pool. "Best Kept Key West Secret."
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(#508)
2BR 2BA Sleeps 2-6
Everything about "Down Island Digs" adds up to make a precious private garden cottage. Sitting in the mature tropical tree garden in the hidden back yard, you would never know you're just 1/2 block off Duval Street.
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(#1103)
Small Dipping Pool
2BR 2BA - Sleeps 2-6
Ideally situated in the Historic Seaport side of Key West, this one-and-one-half-story Classic Revival shotgun island cottage stands in one of the most charming and interesting Old Town residential neighborhoods.
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(#515)
2 BR 2 BA
Sleeps 4 - 6
This proud 1890's 'cigar maker's cottage' has been newly transformed into a stylish contemporary spa-garden retreat. Captivated by the weirdly wild yet wonderfully elegant Key West life-style, the owner created a fabulous balance of opposites.
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(#1304)
Private Renovated Cottage
1BR + DEN 1BA - Sleeps 2 - 4
Use of Swimming Pool
An artist-owner's delightful design and renovation of a carriage house has created an adorable intimate two-story, one bedroom fantasy island sea-shell cottage.
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(#512)
Private Renovated Cottage
2 BR 1BA - Sleeps 2 - 5
Private Jacuzzi Tub
Welcome to a little piece of hidden paradise you never knew existed. Once you're nestled into this hideaway, you'll never know you're right in the center of Old Town Key West.
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(#506)
Also known as "Flamboyant Tree Cottage"
2BR 1½ (plus Spa) BA Sleeps 2-6
Just steps from Duval Street, this unique Key West cottage has an authentic Caribbean feel, with original wood planked polished floors, vintage hand-hewned beams, bright blue tile and Bahama style wooden window shutters.
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(#1227)
2 BR 2 BA
Private Swimming Pool
Sleeps 4 - 6
Open the front door of this hand crafted Key West cottage and look south toward Havana Cuba and you'll catch a view of the ocean where the full moon rises with a soft salt southern breeze.
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(#1229)
2BR 2 BA (with Jacuzzi Bath Tub) Sleeps 4-6
Beginning Oct. 15, 2012 - This Cottage will have a Private Swimming Pool.
Key West cottage architecture has been "time-tested" in "island life and culture" in this infamous little wooden "cigar maker's" cottage located on famous Duval Street, at the "classier upper-end."
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(#527)
1BR 1BA Sleeps 2
"Deco Vibe" cottage is beautifully set on the perimeter of the historic Key West Grande Dame Estate property. Located on Simonton Street you are just 1 short block from Duval Street.
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(#722)
1 BR 1 BA
Love Nest
Sleeps 1 - 4
Dipping Pool
In all it's delightful charm - our 'Story Book Key West Cottage.' Sweet, petite, romantic, and endearingly askew. Feels like a neighborhood in Green Turtle Cay Bahamas. It’s as if a turn-of-the-century seafaring carpenter picked this spot to live one day, gathered together the heart pine lumber, and went to work.
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(#1004)
1 BR (+Den) 1 BA
'Heads Up' to all of you incurable romantics who are looking for the perfect retreat. This Key West cottage is so story-book worthy that I live in the same neighborhood and even I want to stay in this cottage for a month... at least.
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(#1693)
1BR 1BA Sleeps 1-4
Completely hidden from the street, this recently redecorated historic garden flat provides you with two private entrances off the large gated garden. An private sitting porch outside your front door beckons you to sit in the freshness of the garden and watch for the butterflies.
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(#4007)
2BR 2BA Sleeps 4-6
Spa Garden with Swimming Pool
From the outside this adorable Key West garden cottage almost resembles a big toy house. But hidden in the back is an exotic tropical spa garden, complete with swiimming pool and outdoor bathroom.
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(#1317)
Private Pool
2BR 2BA - Sleeps up to 6
Everyone dreams of a sun drenched Caribbean style cottage, like this one, tucked away behind a tall picket privacy fence where flowers drape over the weathered slats. Here you live the authentic Key West lifestyle.
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(#13172)
Upscale Modern Luxury Cottage
2BR 2 BA Sleeps 2 - 4
Private Pool
A designers dream to creatively transform a tropical garden hideaway into an intimate contemporary island retreat was the inspiration of the owner-designer of this upscale modern luxury cottage.
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Key West Town Houses & Condos |
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Sometimes it just doesn't get any better than the carefree convenience of a modern tropical style gated complex. What's not to love about manicured gardens, swimming pools with the added security of gated shared grounds? The interior of each town house and condo has its own unique individual style. Take a look and find the one you love the best. |
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(#316)
3 BR 3 BA
Sleeps 6
Key West sunsets are famous. Holding a perfect perch overlooking the entrance to key West Harbor, this spacious luxury condominium gives you a wonderful balcony to celebrate sunset in private.
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(#1500)
Designer Condominium Overlooking Key West
Ocean Sanctuary
2BR 3BA (One is a Spa Bath)
You can see for miles & miles & miles ... South over the turquoise ocean the White Street Pier stretches out in the near distance. Fresh Caribbean Breeze, great white herons wade in clear shallows below, relaxing on the balcony, southern sunrise, full moon rising ...
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(#6055)
2BR 2BA Sleeps 2 - 4
Just as you're inspired by an island oasis, so is this tropical island garden town home, cleverly hidden in the heart of Old Town Key West.
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(#82634)
2 BR 2 BA
Sleeps 4 - 6
Duval de Dulce vacation condo is what happens when you combine two of the most delicious suites set on top of the 800 block of Duval Street, well away from the bustle of the street below.
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(#2002)
2 Br 2.5 BA
Sleeps 4 - 6
An exclusive island style brownstone perfectly nestled in Key West's most prominent gated waterfront neighborhood known as "Truman Annex."
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(#1311)
3BR 2.5 BA
Sleeps 6
A lush private tropical garden complete with large 40' X 16' swimming pool is the main focus of this unique island setting, and this traditional Key West town-home home is situated at the "pool-side" of the garden.
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(#5005)
2 Br 2.5 BA
Sleeps 4 - 6
A striking tri-level condominium situated in Key West's most historic gated waterfront luxury neighborhood offers a beautiful combination of classic historic charm and refined modern ambience.
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(#827)
4 BR 4 BA + 4 Dens
Sleeps 8 - 12
Swimming Pool
A fabulous foursome of tropical ‘super suites,’ discretely positioned above the center of Duval. Completely hidden from the street below, set-up as a colorful four bedroom condo right downtown, and yet far enough away from the nightlife that you’re perfectly poised to chill.
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(#1310)
3BR 2½BA Sleeps 6-8
The artist-owner of this sun-lit pool-side town-home has created a delightful living space that welcomes you to an authentic tropical life-style in a unique Key West "pool garden compound."
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Key West Suites |
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Find your own special slice of paradise in a Key West suite. If you don't really need your own house... but you definitely don't want to stay in a hotel or condo, then a suite is a great choice. There is nothing "cookie cutter" about our suites. They combine bargain with all the authenticity you could want plus the amenities of a private condo. |
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(#8266)
1 BR 1 BA
Sleeps 2 - 4
Secretly perched above Duval Street Mile Zero Suite is a little luxurious Key West suite with an enviable down-look view of the scene below. Here you have immediate access to Duval Street and a quiet escape from it all.
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(#2091)
2BR 2 BA + Den
2 Kitchens + Private yard w/ Jacuzzi
Sleeps 4 - 6
A nicely situated twosome of ground level suites that has a little bit of something for everyone. Within steps from Key West’s Front Street and famous Mallory Square, the Key West Historic Seaport, and of course Sloppy Joe’s bar, this understated flat is cleverly tucked away from view and provides great privacy for it’s convenient location.
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(#8263)
1 BR 1 BA
Sleeps 2 - 4
Nicely situated above Duval Street, yet tucked back away from the bustle, this pretty one bedroom suite plus den offers the ideal retreat from the action. Decorated in beautiful layers of palm tree greens against contrasting dark stained bamboo furniture and wood floors, the Palm Tree Suite ~ On Top of Duval has a nice touch of elegance.
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(#8262)
1 BR 1 BA
Sleeps 2 - 4
This imaginative suite wears a perfect palette of paradise ...vibrant and beautiful, inspired color surrounds you when you open the door of The Paradise Suite ~ On Top of Duval Street. Color me paradise, color me happy … it’s impossible not to smile when you open the door.
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(#8264)
1 BR 1 BA
Sleeps 2 - 4
In honor of a world famous Key West desert that’s an international icon, we’re delighted to present Suite Key Lime Pie ~ On Top of Duval. Brilliantly done up in bright key-lime green and creamy yellow, dark stained bamboo floors makes a chocolaty contrast. A decidedly delicious downtown escape in Key West.
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(#8265)
1 BR 1 BA
Sleeps 2 - 4
Classy and comfy, Suite Cuban Club is situated in a renovated 1950’s building between a tiny little lane off the front entrance, and Duval Street off the back. Here you have a view and instant access to Duval Street below and at the same time a beautiful retreat from the bustle.
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(#8261)
1 BR 1 BA
Sleeps 2 - 4
If you’re dreaming about discovering the tropical beauty, the mysterious lore, and the famous attractions of Key West, Suite Key West vacation rental offers a perfect retreat right downtown Old Town. On an island of contracts, color saturation meets sophistication from the moment you walk in the door of this suite.
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(#209D)
1 BR 1 BA
The Crow’s Nest Suite vacation rental, is secretly perched on the 2nd floor where you’ll enjoy plenty of privacy and a ‘bird’s eye view.’
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(#209A)
1 BR 1 BA
Located just steps from famous Key West Front Street and Mallory Square and around the corner from Sloppy Joe’s Bar.
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(#209B)
1 BR 1 BA
Sleeps 2 - 4
Just steps from Duval this vacation rental is about 100 yards from all the action, it's completely hidden from the street... so nobody knows it's there!
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(#209C)
1 BR 1 BA
Ideally situated on tiny Ann Street, where the Key West downtown Old Town and Historic Seaport neighborhoods meet. A command view of famous Greene Street from the front porch, literally around the corner from Sloppy Joe”s on Duval Street.
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(#7181)
2 BR 2.5 BA
Perched just above the fun and frolic of Duval Street you're sure to capture the "island beat" that stirs this tiny tropical island of Key West, Florida. Close to Mallory Square and the beach.
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(#425A)
2BR 1BA Sleeps 2-4
"Topsail Suite" is a spacious 2 bedroom, 1 bathroom hideaway that encompasses the entire second floor of our Classic Revival Key West Bahamian Estate.
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(#7182)
2 BR 2.5 BA
Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major upscale just completed in June, 2009. Close to Mallory Square and the beach.
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(#425B)
1BR 1BA Sleeps 2-4
Situated in the heart of the Key West Historic Seaport District, the "Green Turtle Suite" offers a sun filled spacious accommodation on the first-floor front of the Key West Bahamian Estate.
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(#425C)
2BR 2BA Sleeps 2-6
Completely hidden from the street, "Abaco Suite" encompasses the back two-thirds of the first floor of our Classic Revival Key West Bahamian Estate.
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(#525A)
Exquisite Victorian Suite
Vacation Rental
With Pool Garden, trickling waterfall, and Jacuzzi
(Entire first floor of the Grande Dame Estate)
2 BR 2 BA Sleeps 2-4
If you are looking for something spectacular and unique, we invite you to celebrate the era of romance in this beautiful and lavishly styled Victorian suite.
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(#525B)
Balcony Terrace Suites
Vacation Rental
With Pool, Garden, and Historic Home Views
(located in the Grande Dame Estate property)
4BR 4BA - Sleeps 6-8
Situated in the heart of Old Town Key West on historic Simonton Street, this spectacular suite property encompasses the entire 2nd and 3rd floors of the large Victorian home in the Grande Dame Estate property.
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(#1306A)
2BR 1BA Sleeps 4
Tree Tops Suite provides approximately 750 square feet of living space offering an open floor plan joining the beamed ceiling living room and galley kitchen.
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(#1306B)
Garden Suite
Vacation Rental
3BR 2BA - Sleeps 6
Garden Suite offers over 1200 square feet of living space and features a large living room with cathedral ceilings.
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Key West Compounds |
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Looking for the perfect place for a larger group to get together for a family reunion or special occasion with friends? Key West compounds give you fantastic opportunities to gather, reconnect, and "chill out" with plenty of room to spread out and relax. With multiple adjoining dwellings there's ample bedrooms, bathrooms, and multiple kitchens. It's literally like renting your own little private family resort complete with tropical gardens and private swimming pools. |
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(#5730)
6BR 5BA Sleeps 14
An Award Winning Villa and Caribbean Style Cottage side-by-side just 3.5 Blocks from Mallory Square.
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(#2616)
12BR 8 Full BA and 2½BA Sleeps 22 - 28
This is a perfect spacious Key West rental for your family reunion vacation. Why not gather in a three home complex, plus private cottage, grand garden, and large swimming pool - all your own!
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Key West Penthouses |
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Want to be 'in the scene' with a 'birds eye view'? Choose the lifestyle of penthouse chic right in the heart of Old Town Key West. Step out your front door and you're in the village fun. When your senses are sated with all the sites, your own penthouse gives you the private retreat you want. Key West penthouses are unique and luxurious, and literally... "over the top." |
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(#715)
3 BR 3 BA - Sleeps 6 - 8
One-of-a-kind privately owned villa-plus- penthouse; Enviable view of Duval Street from private roof-top deck; Premier Down-town Old Town Key West location. If you rent this property, you will have a penthouse and a villa combined into one... and you'll be in the most requested downtown Duval Street location.
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(#826)
6 suite Penthouse
5+(Den) BR 6 BA
Private Pool
Who says you can’t have it all? Top of Duval ~ Incognito vacation rental is an outrageously colorful 2nd floor 6-suite penthouse property with a great down-look view of Duval Street on one side, and a serene private resort style swimming pool on the other. Fast and fun or laid back and lazy, whatever experience you’re into you can stage it here.
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(#718)
4 BR 4 BA + 2 powder rooms
Perfectly staged on Duval Street Key West, this gorgeous downtown Key West rental received a major upscale renovation to become the premium "Penthouse On Duval." Close to Mallory Square and the beach.
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Key West Estates |
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The Victorian mansions of Key West are famous world-wide. Choose one of these estates and you'll live in classic luxury in the timeless charm of a custom "turn of the century" home, built when families were large and they needed lots of room. Experience "first hand" a piece of exclusive architectural history built by the landed gentry of Key West. But don't let the time honored architecture dissuade you. The beautifully renovated interiors will give you all the modern comforts you want, with all the grace and style you desire. And in the back yard you'll find your own private swimming pool. |
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(#618)
5 BR - 3 BR Classic Victorian House plus 2 BR Caribbean Bungalow
Sleeps 10 - 12
An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West Victorian house plus Caribbean bungalow cottage. Displaying a perfected tropical style the architect and designer artfully intertwined a romantic look-back into architectural history with a superior eclectic cosmopolitan island charm.
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(#525)
Amazing Luxury Mansion Estate
7BR 7BA Sleeps up to 16
This award winning renovation of a Key West mansion is by far one the rarest private estate Key West rentals offered as a single-family vacation home available by the week. Steps from Duval Street.
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(#428)
7 BR 5 BA - Sleeps 10 - 14
Classic Key West Estate" is a meticulously maintained grand wooden estate home available as a weekly Key West vacation rental. It is located on Fleming Street in the Historic Seaport Key West neighborhood.
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(#2541)
7BR 6.5BA
Sleeps 14-16
2 Heated Swimming Pools
Beginning October 15, 2012 - This Property will Provide 3 Private Swimming Pools.
A gorgeous collection of 3 historic residences combines a grand neo-classic home and 2 delightful cottages to create your own private estate. Right on Duval Street, this property is available as a weekly Key West rental.
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(#425)
5+BR 4BA Sleeps 12-14
2 Heated Swimming Pools:
1 large pool, 1 plunge (cocktail) pool
This Grand Marshall is a beautiful representation Key West - Bahamian architecture. Built as a 19th century single family, a refit restored the original exterior of the house and modernized the interior to become three spacious vacation rental suites.
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(#6167)
7 BR 9 BA ~ 6 Private Suites
An extraordinary Victorian Estate in the Historic Seaport Key West neighborhood with 7 bedrooms, 9 baths, and 6 kitchens. This private Key West rental has all the up-scale amenities that you can possibly want.
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