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Key West House Rentals

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    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    4.5 of 5 stars (7) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    4.5 of 5 stars (13) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Built in the 1990's, The Du Pont House is a two story hideaway on a quiet lane. Completely gated and fenced, your private pool is surrounded by tropical plants ablaze with color. French doors in the living room and bedroom open to your private courtyard and outdoor shower. The second bedroom and... View all property information
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    Key West, Florida Keys 33040
    1 / 28
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 32
    5 of 5 stars (1) Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 | Quick View
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    While you won’t need a treasure map to find this exclusive resort-style estate, you’ll know you’ve discovered a rare island gem from the moment you walk through the private gates. Hidden by white picket fences and mature tropical landscaping, this spacious Seaport Treasure Estate is cleverly... View all property information
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    Key West, Florida Keys
    1 / 50
    3.5 of 5 stars (2) Average
    11 Bedrooms, 11 Bathrooms, Sleeps 24 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 11
    5 of 5 stars (4) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Open the front door of the hand crafted Havana Moon Key West cottage located on Upper Duval Street, step from the porch, and look south toward Havana Cuba and... Mmmm... You'll catch a view of the ocean where the full moon rises with a soft salt southern breeze. Originally built in the late 1800's... View all property information
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    Key West, Florida Keys 33040
    1 / 40
    4 of 5 stars (20) Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    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, writing desk and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, and a/c.. The upstairs... View all property information
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    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    To say this townhouse condominium is worth the amassed treasure of Blackbeard, one of the most notorious and wealthy pirates in seafaring history, is a major understatement. The 1950's era art deco Steamplant at water's edge has been quintessentially transformed into Old Town Key West's most... View all property information
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    Key West, Florida Keys 33040
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    1 / 29
    5 of 5 stars (38) Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer.... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (20) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around... View all property information
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    Key West, Florida Keys
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    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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    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    Caribbean Dreams is an inviting space, decorated in rich wood and cane furnishings, perfect for your Key West vacation! Just a few steps up from the garden entry path, "Caribbean Dreams" offers a calm and cozy atmosphere. Enjoy the ultra comfy queen sized bed, free wifi, and daily housekeeping.... View all property information
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    Key West, Florida Keys 33040
    1 / 24
    5 of 5 stars (1) Excellent
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    The Bougainvillea is located just steps from our heated pool and adjacent to the Hibiscus Room. Both share a large semi-private deck, which has access to the front yard and the pool area. This arrangement is perfect for couples traveling together: plenty of common space and plenty of privacy. The... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 stars (7) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Everything about this historic Key West tropical gem 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 in Old Town Key West. It is indeed rare to find a cottage property... View all property information
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    Key West, Florida Keys 33040
    1 / 17
    4 of 5 stars (1) Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 20
    3 of 5 stars (8) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 21
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    CONCH WIND - Stop searching, Conch Wind is the property you have been hunting for! This two story Conch Style townhome located in Old Town Key West is nestled in a quiet, secure compound and has everything you have been looking for in a vacation rental home. Plenty of space, beautifully furnished... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 15
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Outdoor Dining Area
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    THE MARTHA SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! 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... View all property information
    Location Information
    Key West, Florida Keys 33040
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    1 / 54
    4 of 5 stars (1) Very good
    7 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    About this property
    All together this home has 7 separate bedrooms, each with it’s own bathroom and a ½ bath downstairs in the main house, 2 full kitchens, a BBQ grill and shared courtyard with a plunge pool. The historic downtown property also has 4 off street parking spaces right outside the gated courtyard on... View all property information
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    Key West, Florida Keys 33040
    1 / 31
    5 of 5 stars (4) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Book this property at or call our office to avoid unnecessary 3rd party service fees! Alexandria's Secret is a private retreat in the historic district of Key West. With impeccable location and amenities, this three bedroom home is a Key West favorite for its secluded ambiance.This serene... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (9) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Terrace
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    • Waterfront
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    About this property
    Stay on our fabulous 3 bedroom houseboat and you'll have a vacation that will challenge your imagination! This spacious vacation rental on the water comfortably sleeps up to 8 guests and is completely air-conditioned and heated to keep you comfortable even on the hottest days! Your full kitchen... View all property information
    Location Information
    Key West, Florida Keys 33140
    1 / 25
    5 of 5 stars (5) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    About this property
    The name Hermitage invokes the sense of secluded residence or private retreat that aptly describes this inspiring four-bedroom, four-bath home in the heart of Old Town Key West. You'll know the minute you walk through the front door that an artist with considerable flair has decorated Hermitage... View all property information
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    Key West, Florida Keys
    1 / 16
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 33
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Located on a quiet street in the Meadows of Key West; a tranquil residential neighborhood located just behind the Key West Historical district. This home offers you a two bedroom one bathroom main house with a separate one bedroom cottage with a full bathroom. The private pool and outdoor deck area... View all property information
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    Key West, Florida Keys 33040
    1 / 46
    5 of 5 stars (1) Excellent
    11 Bedrooms, 9 Bathrooms, Sleeps 32 | Quick View
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    About this property
    Tropical Village is comprised of 6 separate vacation rentals properties that can also be rented separately. Located at 706 and 708 South St - near The Southernmost Point - this nightly group unit is the perfect getaway spot for large groups of friends and family. COTTAGE @ TROPICAL VILLAGE:... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    5 of 5 stars (2) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    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. Extraordinarily secluded and... View all property information
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    Key West, Florida Keys 33040
    1 / 25
    4.5 of 5 stars (20) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has... View all property information
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    Key West, Florida Keys
    1 / 24
    5 of 5 stars (4) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Part of TROPICAL VILLAGE Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4 of 5 stars (4) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Key West, Florida Keys 33040
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    This is an amazing summer rental. Available during June and part of July only for either long weekends or by the week. Stunning location within the old town of Key West, over two levels, full kitchen, bbq, 2 bedrooms, shared pool. (Only between 4 houses) It just doesn't get better than this This... View all property information
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    Key West, Florida Keys 33040
    1 / 22
    4.5 of 5 stars (7) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    You know that incredible experience of Déjà vu? When you enter someplace for the very first time, and instantly you get that sense that you’ve been there before? When I first visited this vacation rental house, it happened to me. My mind sparked, the place seemed wonderfully familiar, and I felt an... View all property information
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    Key West, Florida Keys 33040
    1 / 35
    4.5 of 5 stars (2) Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    ***Both bathrooms and kitchen completely renovated as of September, 2015*** 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... View all property information
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    Key West, Florida Keys 33040
    1 / 15
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    THE BESS SUITE Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! 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 - Recently... View all property information
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    Key West, Florida Keys 33040
    1 / 30
    5 of 5 stars (11) Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    The Absolute Best Luxury Private Weekly Vacation Rental Home on Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** Nestled in tropical, flowering gardens, the Providence Suite is perfectly located, 1/2 block from Duval Street Downstairs is the living room with Queen sleeper sofa, dining room and fully equipped kitchen.... View all property information
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    Key West, Florida Keys 33040
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    It is a pleasure to present the recently renovated Room Nine! It used to be a good room, now it's a great room! Comfortable and very peaceful, this room was originally opened up to make use of a portion of the attic space. Note that the ceiling is sloped in two directions and some taller guests... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    4.5 of 5 stars (2) Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    Located in one of Key West's most striking gated waterfront luxury neighborhoods, Foundry on the Waterfront vacation rental provides a unique opportunity to enjoy a modern condominium, constructed within an important piece of historic American architecture. Situated along the gateway waterfront to... View all property information
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    Key West, Florida Keys 33040
    1 / 26
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    This gem is located at the end of a hidden lane, just off Simonton Street, behind The Gardens Hotel. Helen's Hideaway is a step back in time to Key West during its slumbering past. Built by David Wolkowski, who built many of Key West's premier resorts, including the Pier House, this paradise... View all property information
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    Key West, Florida Keys 33040
    1 / 4
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Nestled behind hisbiscus and stands of bamboo Lone Palm welcomes you to a tropical oasis in the heart of Old Town. Located just a block off Duval at the corner of Truman & Simonton in Windward Park a gated community consisting of 13 privately owned homes around a sparkling 20 x 60 ft. pool; a... View all property information
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    Key West, Florida Keys 33040
    1 / 34
    4.5 of 5 stars (12) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    The kitchen is fully equipped with a glass top stove, refrigerator with ice-maker, microwave and everything needed for cooking a gourmet meal or just heating leftovers! French doors open from the kitchen and breakfast bar onto a private deck with a large 4 person private hot tub, table and chairs,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 Bedrooms, 3 Bathrooms, Sleeps 18 | Quick View
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    • Internet Access
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    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** a passport tucked away off of mile marker 15. While relaxing in the 20x12 free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Around the back of the... View all property information
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    Key West, Florida Keys
    1 / 26
    3 of 5 stars (1) Average
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
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    • Balcony
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    • Terrace
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    • x
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    KEY WEST FOUND - A striking 2 bedroom, 2.5 bath townhome located in the historic brick Foundry building within the Truman Annex. This 3 story townhome is decorated in a whimsical Key West style with new living room furniture including the sleeper sofa. The first floor features open and airy... View all property information
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    Key West, Florida Keys 33040
    1 / 10
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • x
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    Cleverly hidden from view at the end of a narrow island urban 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... View all property information
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    Key West, Florida Keys 33040
    1 / 37
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 23
    3 of 5 stars (1) Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    Originally built in 1938, Amanda's Dream Suites vacation rental is a charming large wooden home offering two full stories with deep porches which overlook the garden and pool. An exterior stair case on one end of the building join the first and second floor. A renovation of the home in the early... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 41
    5 of 5 stars (52) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    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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    Key West, Florida Keys 33040
    1 / 22
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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
    Location Information
    Key West, Florida Keys 33040
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Wi-Fi
    • DVD Player
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    • Ocean Views
    • Satellite TV
    • Hot Tub
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    • x
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    3 bedrooms, 2 full bathrooms, sleeps 6<BR><BR>Boat in, boat out. Inspired by Balinese design this private waterfront retreat has deep-water access and is the ultimate base for the ocean enthusiast. Choose to escape, relax and meditate by the waterfall or head out for a day of adventure on the high... View all property information
    Location Information
    Key West, Florida Keys 33040