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Key West Vacation Rentals

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    All 915 Rentals in Key West
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    Twice as Nice ~ Weekly Rental1 / 17
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Tropical Dreaming1 / 24
    (57)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Duval Square Courtyard Condo is just steps from the action1 / 23
    (26)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Balcony
    • Satellite TV
    • Patio
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    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Tucked away in an inviting compound you'll find a blissful retreat called Namaste; a tranquil and relaxing one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Patio
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Grill
    • Satellite TV
    • Air Conditioning
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    Ann Street Gardens1 / 25
    (53)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Penthouse On Duval ~ Weekly Rental1 / 20
    (10)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
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    • Balcony
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    • DVD Player
    Suitability
    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Amelia Home1 / 24
    (54)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    • Parking
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    AMELIA HOME - A 2 bedroom 2.5 bath private home with sparkling private pool that is only four blocks from the Atlantic Ocean and one block from all the Duval Street entertainment is the Amelia Home. This is the Key West Florida vacation home rental you have been seeking, tucked away in one of the...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Admiral's Lane1 / 24
    (21)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    As part of the Truman Annex, this stately four-bedroom, three-bath home on Admiral's Lane is tucked away in the beauty and privacy of thick tropical foliage. The Annex neighborhood, named for President Harry Truman who wintered at The Little White House just blocks away, is Old Town's premiere...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beach Club #103 - Unique oceanfront living with breathtaking views1 / 38
    (18)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Balcony
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential building that sits directly on the water. The breathtaking view can be seen as soon as you enter the unit. This spacious 2 bedroom unit features a large oceanfront balcony accessed...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Hermitage South1 / 25
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Patio
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Poinciana Place Garden: First Floor, Hot Tub, Walk to Beach & Downtown!1 / 24
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Balcony
    • Air Conditioning
    • Hot Tub
    • Grill
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    • Washer
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Poinciana Place Vacation Rentals are located on a tiny lane in Old Town Key West. This two story duplex is one block to Duval Street and central to all that Key West has to offer. There are two one bedroom vacation rental units in this home. The Garden at Poinciana Place is a cozy and...
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    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Henry's Piece Of Paradise On The Ocean In Key West1 / 5
    (34)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Hot Tub
    • Sauna
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Waterfront
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Vacation Rentals 2 Bed 2 Bath Condos On The Ocean with ocean and partial ocean views - rent weekly or nightly. To see both my condos on my website with active availability calendars and virtual tours - Scroll down to "About the owner" and in that box click on the "See more" button -...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Pelican Landing Aruba Retreat1 / 21
    (38)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Casablanca: Perfect Getaway for 2, Soak up the Sun! Private Pool & Parking1 / 34
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Satellite TV
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca is the perfect get-a-way vacation rental for two! Key West Casablanca is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Air Conditioning
    • DVD Player
    • Parking
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I must confess, there’s something about walking along an exotic tropical pool-garden path that sends me to an instant state of calm. Palm fronds gently dancing in the breeze, orchids hanging in the trees, manicured gardens, a pristine swimming pool set with comfortable lounge chairs. This is what...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • 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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    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Lavender Jungle1 / 24
    (25)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
    • DVD Player
    • Grill
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    LAVENDER JUNGLE - Beautiful 2 bedroom 1 bath downstairs Shipyard condo for rent Key West located in Truman Annex, this home has a renovated kitchen and upgraded bathroom. For those who don't want to climb stairs, this property is on the first floor and has a large brick patio and grill. Master...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Balcony
    • Internet Access
    • DVD Player
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM RENTAL .... NO PETS ACCEPTED Break away from it all at Escape on Fleming. This comfortable and fresh two bedroom one bathroom apartment is located in the heart of Old Town. Conveniently located near charming Old Town restaurants such as Azur and Cafe Sole, yet off the beaten path,...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Key West Casa1 / 24
    (25)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Satellite TV
    • Terrace
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one of only a few 3 bedroom 2 bath condos in the Shipyard complex. This great rental property is located in the prestigous Truman Annex community just 2 blocks to famous Duval Street and walking distance to shopping,...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Louisa House: A comfortable four bedroom vacation hideaway1 / 27
    (41)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great location, just half a block off Duval Street, walking distance to restaurants, the Atlantic beaches and the Southernmost Point. Casually decorated in soft pine and white, wicker furnishings and sofa sleeper in living room, this four bedroom, three and a half bath home provides a comfortable...
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    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Internet Access
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    The Mermaid's Garden1 / 25
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Satellite TV
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Even if you're an experienced vacationer, The Mermaid's Garden will hold you in its thrall. As the name promises, the chaperone of this four bedroom, 3 full, 2 half bath Truman Annex estate is a life-sized brass mermaid sculpture installed in a garden bursting with tropical ferns and palms. A few...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    28 DAY MINIMUM RENTAL Thompson's Court is the quintessential south Florida home: a sprawling, peach-colored, ranch-style design with large doors and windows that let in the natural sunshine. The large living area is decorated in charming vintage wallpaper and bright, tropical colors. To the left...
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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    • 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
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Artist Garden1 / 24
    (27)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Satellite TV
    • Grill
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ARTIST GARDEN -- A bright and breezy 2 bedroom 2.5 bath private Key West house rental located in the prestigious Admiral's Lane neighborhood of the Truman Annex. This property is in the ideal location, walking distance to all Old Town Key West has to offer along with the beautiful beach at Fort...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Valhalla1 / 25
    (51)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Luxury 2 Bedroom with Full Kitchen - Sleeps 5 - Walk to the Beach & Nightlife1 / 25
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    THE HARRY 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 suite...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    A Touch of Bermuda in Key West1 / 19
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEWS BULLETIN. JUST HAD A BLOCK OF WEEKS OPEN UP FOR THE WEEKS OF AUGUST 19 TO OCTOBER 21 IN MY OTHER CONDO FIVE DOORS DOWN FROM MY COTTAGE THAT WILL ACCOMMODATE UP TO 4 PEOPLE SO I WILL DO RIGHT BY YOU WITH THE RATE IF THIS PROPERTY IS BOOKED. Now onto my vacation cottage.. Envision yourself...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
    • Patio
    • Balcony
    • Wi-Fi
    • Grill
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the Old Town Meadows neighborhood of Key West, this spacious two-story, two-bedroom historic home has access to excellent amenities and will be a highlight of your relaxing vacation to Key West. Recently renovated with luxurious furnishings, "Casa Bianca 1411" captures the peace and...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 4
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    Artist Cottage in Truman Annex1 / 21
    (12)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Air Conditioning
    • Waterfront
    • Patio
    • Grill
    • Satellite TV
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Truman Annex Best Location in Town!! 2 Bedroom 1 Bath ground floor Shipyard Condo. This beautiful condo sits on a private quiet walking lane and is just a 5 minute walk to downtown where you will find Key West's famous bars and shopping. Also a 10 minute walk to Ft. Zachary Taylor, our beautiful...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Grill
    • Satellite TV
    • Air Conditioning
    Suitability
    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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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sunset Celebration1 / 22
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Parking
    • Balcony
    • Satellite TV
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    SUNSET CELEBRATION: 2 bedroom 1 bath Shipyard condo located in Truman Annex. New floors, fresh paint, all new furnishings, artwork, linens and towels. Be one of the first to stay in this totally updated vacation home. Master bedroom has queen bed and guest bedroom 2 twins on either side of the...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    BMW Fantasy - 2 Bedroom Condo with a Shared Pool1 / 14
    (35)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Roomy condo in the heart of Old Town. Fully equipped kitchen, washer, dryer, microwave, dishwasher, central AC and TV. Large, shared pool. Below are shops, cafes and a health club offering daily memberships. Secured parking for one car. Three blocks to the nearest beach. Families are welcomed...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key West Found1 / 24
    (31)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Satellite TV
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    KEY WEST FOUND – A striking Key West FL home for rent, this 2 bedroom, 2.5 bath townhome is 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...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Shared Outdoor Pool (Unheated)
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    • Wi-Fi
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious, tranquil Old Town Key West home. Two bedrooms, 2.5 bathrooms, sleeps up to 7. NOTE: On this page, TripAdvisor might be showing the summer price. The price changes seasonally. We are booking **monthly** renters for September, 2017. Also looking for 30-day renters starting April 15,...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Hemingway's Library – MONTHLY Rental1 / 20
    (2)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    Suitability
    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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    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Ginger Whole House1 / 23
    (50)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    KEY WEST GINGER HOUSE - An absolute jewel of a Key West vacation home a few doors from Duval Street, named for the breathtaking ginger plants blooming in our tropical paradise. Key West Ginger House is a historic home built in 1933, the epitome of what you have in mind when you are thinking about...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing Eleuthera Retreat1 / 23
    (27)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
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    • Shared Outdoor Pool (Unheated)
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    • Terrace
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Palms1 / 23
    (29)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Satellite TV
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    • Terrace
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    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 PALMS: Located 4 Palm trees from the ocean, this seaside 2 bedroom 2 bath condominium will provide the much needed escape to tranquility you need. Let ocean breezes gently lull you to sleep and summer sunshine wake you in the morning from balconies that wrap around the condo allowing access from...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing Harbor Island Retreat1 / 23
    (30)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Garden1 / 23
    (27)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Grill
    • Satellite TV
    • Terrace
    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CORAL GARDEN: A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this Key West vacation rental 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...
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    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Pelican Landing Antigua Retreat1 / 23
    (27)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Terrace
    • Satellite TV
    • Balcony
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tee by the Sea - Luxury 2/3 condo - 7 Bikes FREE1 / 30
    (67)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very nice luxury 2 bedroom / 2 1/2 bath condo of 1100 sq. ft. less than 1/2 mile outside of Key West in very well maintained gated community, including huge heated pool, clubhouse with fitness center. Sleeps up to 6 with a queen bed in each room and a queen sleeper/sofa in LR. We are 4 miles...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    • Washer
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    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Grande1 / 24
    (4)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CASA GRANDE: You hear all the time about grand homes tucked away in little private corners of Key West; this is one of them. Located on a quaint lane just steps from Duval Street with room to park 2 vehicles off-street -- a bonus in Old Town where parking is worth its weight in gold. Casa Grande...
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    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    737 The Place, a  Monthly Rental Old Town Key West1 / 15
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveler has booked this property
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    • DVD Player
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    • Outdoor Dining Area
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Reasonable rates, best for couples and small families, Key West, Private, gated property in Historic Old Town Key West. Fishermen will love smoker grille for their catch. Newly refurbished, tropical furnishings, private deck. Large kitchen with full range and oven, microwave, and toaster oven....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Papaya Place1 / 24
    (30)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Wi-Fi
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    • Satellite TV
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PAPAYA PLACE pops with color! This great 2 bedroom 2 bath waterfront Key West rental condo at 1800 Atlantic Condominiums offers you a wonderful relaxing garden view overlooking the nature preserve. Enjoy the peace and quiet of the tucked away balconies, far from the reaches of the world, allowing...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Suite1 / 23
    (15)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Private Outdoor Pool (Heated)
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    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    CORAL SUITE: A 2-bedroom, 3 bath townhome in the private gated community of Coral Hammock sleeps 6 comfortably. This Key West vacation rental offers the finest accommodations for you, your family and pet within walking distance of some favorite local restaurants, a liquor store and drugstore. the...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Parking
    • Internet Access
    • Air Conditioning
    • Washer
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    • Grill
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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