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Key West House Rentals

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    164 Matching Rentals in Key WestView all 339 rentals
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 33
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    5 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    Caribbean Cottage ~ Duval Street Key West ~ Weekly Rental1 / 14
    (5)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Washer
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine the quintessential Caribbean island village, its cottages nestled hand-in-hand on charming historic pedestrian streets. As people stroll by, sun kissed from an afternoon of beaching and sight seeing, they'll say hi to one another even if they've never met. This is your neighborhood during...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'In-the-know' travelers who return to Key West to vacation love to choose the more elegant area of Upper Duval St. as their favorite area to stay... and this is exactly where you find Amelia's Hideaway vacation rental. This one-of-a-kind vacation villa is perfectly situated just off Upper Duval,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
    • Air Conditioning
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience what is like to live in Old Town at the desirable Historic Seaport. This beautiful home is filled with amazing furniture, artwork and amenities that give you the tropical, old town feel you seek when visiting Key West. The smallest details have not been missed, high thread count...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Exclusive Key West Beach Front ~ Weekly Rental1 / 21
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
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    • Ocean Views
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    Pet friendly
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    Smoking allowed
    About this property
    Rare, one-of-a kind designer luxury condominium located in an exclusive gated Key West beachfront property. The Exclusive Key West Beachfront vacation rental has breath taking views overlooking the ocean and natural aquatic bird sanctuary. A spacious ocean front balcony provides the perfect setting...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key West Dreamin' ~ Weekly Rental1 / 20
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Dreamin' vacation rental is a private historic home that is beautifully furnished and offers all the amenities of a luxury accommodation situated in a genuine Old Town Key West location. I love to trace our authentic properties to their historic significance and this home has a rich one...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Nautical Dreams1 / 24
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Shared Outdoor Pool (Unheated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NAUTICAL DREAMS (monthly rental): Here's the perfect spot for whatever you desire, parties or peace & quiet in a Florida vacation home Key West. This 2-bedroom 2-bath cottage is located in a small compound of 8 cottages behind its own privacy fence. French doors offer access from each bedroom,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV channels, free current...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The Meeting Point - Key West ~ Weekly Rental1 / 54
    (2)Average
    11 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
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    • Patio
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    • Grill
    • Washer
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    • DVD Player
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 11 Bedrooms, 11 Bathrooms, Sleeps 24
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    Poinciana House1 / 25
    (48)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Cable/satellite TV
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    Kemp House1 / 25
    (19)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
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    • Wi-Fi
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Civil War Era home sits in Key West's most desirable Historic Seaport District, less than a block from the Gulf of Mexico. Did Abraham Lincoln sleep here? Probably not. But anyone staying today in this classic revival valued in the millions will find not only history but every creature comfort...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Family Reunion ~ Weekly Rental1 / 53
    (2)Very good
    9 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 28
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Waterfront
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Hot Tub
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3000 SF, 3BDR, 2.5BATHS, SLEEPS 6 Treat yourself to a dream vacation in our beachfront residence on the private island of Sunset Key, located in the middle of Key West Harbor. Our tastefully designed upscale villa has beautiful ocean views, private pool, and 2 hot tubs for our guests to enjoy. It...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West home with boating and private swimming pool! Lovely, well appointed home, remodeled, granite and stainless appliances, 2 bedrooms, each with ensuite baths, 3 baths, tile and wood floors throughout. Open living and kitchen, living room and master bedroom opens to swimming pool and boating...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Penthouse On Duval ~ Weekly Rental1 / 20
    (11)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    • Balcony
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    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfectly staged in the island's city center, this spectacular downtown Key West rental received a major renovation to become the fabulous Penthouse on Duval. This unique private Caribbean style penthouse is the perfect prescription for some lofty relaxation. Perched just above the fun and frolic...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Classic Key West Estate ~ Weekly Rental1 / 30
    (6)Average
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Grill
    • Patio
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    • DVD Player
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once authentic and magnificent. If you have ever had the opportunity to stroll the residential streets of the Historic Seaport of Old Town of Key West, you have...
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    Key West, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    A Tropical Tradition (Gallup Arms) ~ Weekly Rental1 / 10
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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'...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Leave behind all of your worries and whisk your loved ones off to this two-bedroom, two-and-a-half bathroom home on Sunset Key! This private island home surrounds you with nothing but natural beauty, gorgeous beaches, and high-quality amenities. Your home is nestled on the private island of Sunset...
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    Location Information
    Key West, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Havana Moon ~ Weekly Rental1 / 11
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Blackbeard's Treasure - MONTHLY Rental (30 night min.)1 / 21
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Balcony
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    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discretely built back off the street to quietly overlook an historic tropical garden, this Elegant Key West Tree House, encompasses the entire 2nd floor of a beautifully renovated 1930’s building. Perched among mature tropical trees, the 1200 square foot 2nd floor flat is situated on a quiet road...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Tree House Old Town 2 Bedroom MONTHLY Rental1 / 16
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
    • Air Conditioning
    • Porch
    • Outdoor Dining Area
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    On an island full of resplendent Victorian architecture, the trend toward minimalist design has made its mark. This 2-story tropical luxury home is a ubiquitous example of this, an ingenious melding of classic Old Town Key West architecture with contemporary pared-down design. Created by connecting...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    On Hemingway's Rounds ~ Monthly Rental1 / 14
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
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    • Patio
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sand dollar is a 3 bedroom, 2 bath home built within feet of the Atlantic Ocean with 180 degree ocean views. The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge. Fishing and diving just steps outside your door. Then at night, Key West is...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    When I went to preview this townhome called Cabana Boheme, I was intrigued by the name. And so it was fitting to its nom de plume, that I drive the 10 blocks in our hand-painted conch cruiser truck, transformed into rolling art by local mural artist Rick Worth. Key West is like that, as much a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Seaport Treasure Estate ~ Monthly Rental1 / 34
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Air Conditioning
    • Washer
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    • Ocean Views
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    Hemingway's Library – MONTHLY Rental1 / 20
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Patio
    • Private Outdoor Pool (Heated)
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    • Grill
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This sensational vacation home provides three bedrooms, two and a half baths, pool, and a downtown location yet manages to create a serene, get-away-from-it-all feel. Called Hemingway's Library, the residence maintains the mystique of the island's most famous author by way of books, pictures, and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
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    • Patio
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Without a doubt, this vacation-defining residence will become as much a part of your holiday memories as the island of Key West itself. Its two-story classic Conch architecture, centrally located in Old Town, includes two spacious master bedrooms, two full en-suite baths, one half bath, a large...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Butterfly Garden ~ Monthly Rental1 / 10
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Private Garden
    • Cable/satellite TV
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    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely hidden from the street, this recently redecorated garden flat provides you with two private entrances off a large gated manicured garden. Your own private expansive covered bricked front porch spans the width of the garden right out the front door and leads to a beautiful meditation...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Waterfront
    • Hot Tub
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Children's Pool
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Hot Tub
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Foundry on the Waterfront ~ Weekly Rental1 / 10
    (2)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Porch
    • Patio
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Washer
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Treat yourself, your family and friends to a grand Key West home ideal for an extended stay on the island. This wonderful home, which has recently been completely renovated, boasts 4 bedrooms, 3-1/2 bathrooms, a new modern kitchen, a living room, a dining room, an office nook, a 270 degree wrap...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Starlight Siesta ~ Weekly Rental1 / 10
    (1)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New 1,500 sq. ft. townhouse with 2 large bedrooms with king beds, 3 full bathrooms plus covered deeded parking for your car. Fully equipped kitchen. Sleeps up to 6 comfortably as the downstairs living room has a queen sleeper and full bath. Luxury furnishings and appliances throughout make this...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BOWE CONCH HOUSE (monthly rental): The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations. Prior to buying the house in the 1930's for $2,500, George and Ethel Bowe-Thomas lived across the street paying $3.00 per month for rent!...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
    • Private Garden
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Vista Estate Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Patio
    • Grill
    • Washer
    • DVD Player
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this cozy and chic Key West cottage your home away from home for your next Florida vacation, and revel in a private pool, deck, and covered back porch, as well as close proximity to the beach. And the real bonus: you can bring your favorite canine friend along, too. You'll be situated only...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Caroline House Estate ~ Weekly Rental1 / 35
    (7)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Private Garden
    • Patio
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Strikingly set in the oft-missed Key West mid-town neighborhood, we find Island Elegance, making a classical curbside statement with its craftsman-colonial architecture, lush mature tropical landscaping, and white picket fencing. Built in 2005, the design of this home incorporates the timeless...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Meadows House1 / 19
    (22)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants the Florida Keys has to...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Hot Tub
    • Patio
    • Balcony
    • DVD Player
    • Terrace
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ***Due to licensing restrictions, this property requires a minimum stay of 28 nights.*** 2 Bedrooms with king size beds, 2 Bathrooms, and a third guest room/office/ with gym equipment. Charming 2 story conch house on a quiet street in Old Town, right between Duval and Higgs Beach! Easy access to...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Wabi Sabi ~ Weekly Rental1 / 31
    (3)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Undeniably adorable, Key West Wabi Sabi vacation rental is a celebration of authentic Key West cottage style island living. Built in 1930, the front of the historic wooden plank house is held to vintage form with loads of original details, complete with welcoming front porch and saw-tooth tin roof....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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