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Key West House Rentals

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    Travellers to Key West are booking January dates now. Secure your holiday rental today, and have the perfect trip.
    155 Matching Rentals in Key WestView all 319 rentals
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Duval On The Square1 / 21
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Our beautiful Key West home is located in the quiet charming neighborhood called the Meadows. We are within walking distance to most of the activities offered in historic Key West. There are fabulous restaurants, beaches and water sports only minutes away. The famous Hemingway House and the Truman...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – on a private island surrounded by sparkling turquoise waters and balmy breezes. How...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    A Place In Paradise1 / 24
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE! You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will spend your vacation...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes. Welcome to your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy all that Key West has to offer while staying in...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Shared Outdoor Pool (Unheated)
    • Private Garden
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 3 Bedroom, 2 1/2 bath Key West Home just steps to Duval. Nice Pool and Jacuzzi. Living Room, Dining Room, Kitchen, Family Room 1/2 bath on First Floor. 3 Bedrooms 2 baths on second floor. 30 Day Rental
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Key Lime Pie1 / 22
    (7)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private cottage that has all the amenities you would require for your stay, private pool, outdoor space for lounging, grill and dining. One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town. Refurbished with updated kitchen cabinets,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Flagler Station1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying. This one is a priceless gem in a true established residential neighborhood in midtown Key West! Flagler Station was recently remodeled, refurbished and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Washer
    • Waterfront
    • Grill
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy some of the great back country fishing the Lower Keys has to offer! Welcome to Bonefish Lodge, an upscale, tastefully furnished, 2 bedroom, 2 bathroom duplex on Big Coppitt Key. This home is located on a deep canal just minutes from Snipe Point and the gulf, or out front to the Atlantic...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    The Hemingway1 / 25
    (27)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Parking
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The location does not get better than this! Short bike ride to the beach and walking distance to most restaurants and shops! A beautiful 2 bedroom 2 bath Florida Keys rental home located in the private, gated community of Truman Annex. An ideal location only 2 blocks from famous Duval Street...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Perfect Pineapple1 / 24
    (8)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Smoking allowed
    About this property
    Sit along side your private pool for morning coffee or your evening glass of wine. Long considered a sign of hospitality, the pineapple is now widely recognized as sign of Welcome and Friendship.....and so we welcome you to the Perfect Pineapple. On the corner of Southard and Margaret streets...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    HISTORIC KEY WEST - Turtle House - Sleeps 61 / 24
    (3)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Porch
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OVERVIEW The Turtle House is a 100+ year old recently completely renovated historic house. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open living environment - (1) queen bed, (1) full bed, (2) queen sleeper sofas. The house can be described...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Amelia Home1 / 24
    (55)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Wi-Fi
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    • DVD Player
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    After a long day cool off in the private pool, enjoy cold Margarita on the covered porch and cook up some fresh catch on the grill! Welcome to your dream vacation 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...
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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 6 Quick View
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    • Terrace
    • Balcony
    • DVD Player
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer! Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma Streets in Truman Annex, a most...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Poinciana House1 / 75
    (51)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Would you enjoy truly modern luxury within walking distance to Key West's best restaurants, clubs, and art galleries? If so, this is the vacation house for you! We are set within Key West's Historic District, a block from famous Duval Street, 2 1/2 blocks from the Hemingway House, 7 blocks 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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    Royal Palm1 / 25
    (4)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    There's no better way to experience 'Island Time'-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this two-bedroom, three-story brick townhouse...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    Leeward Isle Key West Retreat1 / 24
    (35)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Terrace
    • Balcony
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With an elegant design Leeward Isle Key West Retreat offers a small but luxurious retreat. Dwell in the possibility! From the moment you park in the private parking lot for this Key West vacation condo you know you are someplace special. A small gated and secured compound with only 13...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Breezy Bungalow1 / 24
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Terrace
    • Parking
    • Balcony
    • DVD Player
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a nice home in Truman Annex community? Breezy Bungalow is the answer for you! When a name says it all you know you have made the perfect choice for your Key West island escape. Bright and colorful with plenty of windows, balconies and French doors open to allow sunshine and seaside...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Brand New! Ohana Paradise At Historic Seaport ,Old Town, Key West. Private Home.1 / 42
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Wi-Fi
    • Terrace
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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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Tropical Dreaming1 / 24
    (59)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Washer
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido! A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Grande Dame Key West - 'The Watson House' ~ Weekly Rental1 / 38
    (10)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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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
    Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 16
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Grill
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    • Wi-Fi
    • Patio
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    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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Duval Sea Turtle1 / 24
    (49)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    • Washer
    • DVD Player
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Duval Square, rooftop community which is just off Duval Street, easy walking distance to it all! You do not even need a car! 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 Key West rental...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Easy Livin'1 / 24
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Terrace
    • Cable/satellite TV
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Heated)
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cozy, but upscale, this charming vacation rental with a private pool and great outside space is guaranteed to make you feel right at home. The name says it all! This lovely private home with pool is located in a secluded cul-de-sac in Truman Annex. Truman Annex is a gated community located...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Balcony
    • Terrace
    • Grill
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect view from your screened porch to watch golfers play the first hole on the Rees Jones designed Key West Golf Course. Imagine yourself living with the vibrant golf course greens in your backyard and cool tropical breezes wafting your way. Coral Breeze has that and more. Two bedrooms share...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    The Dolphin House1 / 23
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wonderful for larger groups or family get togethers, The Dolphin House offers a roomy vacation home in one of Key West's most desirable locations, Truman Annex. Twice the comfort and twice the amenities - located in the exclusive Truman Annex. The Dolphin House Key West Vacation Rental is...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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 luxury house 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. You'll be situated only six blocks from the beach for fun in the sun anytime you want it, and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Classic Two Story Old Town Key West 'Pink Conch House'. Furnished ,close to the Historic Seaport,Walking Distance to Duval Street and all the action. The first floor has a living room, 2 bedrooms, 2 full baths, kitchen and dinning area.French doors open to the rear bricked courtyard with private...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Ecco Domani1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool. Ecco Domani means 'Here Tomorrow' which is where you'll want to be when you see what you're missing. A beautiful 3 story home with private pool, off...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Villa Deja vu Key West ~ Weekly Rental1 / 36
    (8)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Alluring Porches1 / 24
    (17)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
    • Terrace
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully decorated and spacious home in the community of Truman Annex is awaiting for you! A beautiful 2 bedroom 3 bath townhome with an additional den, is the tranquil escape you have been looking for. Wonderfully decorated with Key West charm and unique art work, stunning orchids surround...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Duval Penthouse1 / 24
    (25)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Location, location, location! Practically overlooking famous Duval Street from large upstairs deck! A large luxury vacation rental in Key West located in downtown Key West. This property has it all, fabulous location, beautifully furnished and plenty of space to accommodate your friends and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is 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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    Wind Swept1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Screened porches up and down for you to enjoy the the extra living space in this lovely townhome. Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. This lovely 2 bedroom 1.5 bath...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Havana Moon ~ Weekly Rental1 / 22
    (6)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 33
    (9)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Balcony
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both beginning and ending your journey at the same time. But when you rent this Heavenly Hideout at Rainbow’s End, you’re spot on, and you can do exactly that. This tropically...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    La Prive1 / 25
    (24)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Central Heating
    • Washer
    • Balcony
    • Patio
    • Waterfront
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property can only be rented by the month. This estate has it all waterfront, luxury,pool,jacuzzi and dockage for your boat with over 3,800 sf of living space and 13,600 square feet of lush landscaped grounds. This private residence gives you the space and comfort one needs to relax and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Classic Key West Estate ~ Weekly Rental1 / 30
    (7)Average
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Valhalla1 / 50
    (55)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Washer
    Suitability
    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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Just as you're inspired by an island oasis, so is this tropical Island Oasis Garden Home vacation rental. Cleverly hidden in the heart of Old Town Key West, this small private gated oasis uses a traditional Key West style architecture of tin roofs, wooden planking, sash windows, and charming front...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    HISTORIC KEY WEST  - Main House - Sleeps 101 / 47
    (4)Average
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Grill
    • Balcony
    • Washer
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    OVERVIEW The Main House is a (2) story 100+ year old, recently completely renovated Conch house. The design of this property lends itself perfectly to small gatherings of families and friends. The house can comfortably accommodate a maximum of ten (10) guests - (1) queen bed, (1) full bed, (1)...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    The Meadows House1 / 19
    (23)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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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    Bahamian Reed1 / 24
    (1)Average
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Balcony
    • Parking
    • Wi-Fi
    • DVD Player
    • Terrace
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Look No Further!! Bahamian Reed is a vacation rental home that you will come back to again and again 2 bedroom 1.5 bathroom townhome located in Truman Annex in Old Town Key West. Conveniently located near all the reasons you came to Key West: Fort Zachary Taylor State Park , Duval Street...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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