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Key West Luxury Rentals

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    Travelers to Key West are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    47 Matching Rentals in Key WestView all 318 rentals
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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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Family Reunion ~ Weekly Rental1 / 53
    (2)Very good
    9 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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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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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2017
    From booking to our stay everything was flawless. The house is amazing for large groups and centrally located one block off Duval. The home is beautifully appointed and the...
    Reviewed July 4, 2016
    We had 7 couples and 2 singles for 16 people total. There was plenty of room for everyone. Upon arrival we found the house to be in very good condition, clean, and stocked...
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    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
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 16
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    Classic Key West Estate ~ Weekly Rental1 / 60
    (7)Average
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 23, 2018
    We had a group of 13 adults who were able to stay comfortably in this rental property. The house was clean, well stocked and in the perfect location to walk to many of our...
    Reviewed May 30, 2017
    We had this house full, 14 people. Had plenty of space for everyone and privacy when needed. Great location and grocery store right down the street. House was clean, had...
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    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
    Rental Home - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    Real World MTV House Key West1 / 247
    (49)Very good
    10 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    Amenities & Details
    • Waterfront
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 24, 2017
    This house was really cool rooms were spacious and massive , the master room was so lavish . Jacuzzi in living room was a great feature and the games room . Only downside was it...
    Reviewed March 29, 2017
    What would you expect when you first see this colorful place? Party?Well, you might bring your group here and party all night long. Or you can take them here to have an...
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    About this property
    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis...
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    Key West, Florida Keys 33040
    Rental Home - 10 Bedrooms, 6 Bathrooms, Sleeps 22
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    Key West Vacation Rental - The Duval Street Compound1 / 28
    (3)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    Top Of Duval- 6 Bedroom Penthouse1 / 26
    (17)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This has been our favorite place to stay in Key West. Very clean, super convient and had everything we needed.
    Reviewed 2 weeks ago
    13 guys rented this house for a long weekend getaway. It was a great location for us. The private pool out back was a nice bonus. The rooms were all well equipped and very...
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    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Tropical ~ Tranquility ~ Weekly Rental1 / 17
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 9, 2018
    We were highly impressed with this beautiful secluded home. The plain gray fence hides an oasis. We opened up the french doors in the kitchen over looking the patio & pool...
    Reviewed March 21, 2018
    We arrived at house we opened gate and walked into PARADISE!! We were greeted by Kevin who showed us around and couldn't have been nicer.house is immaculate and the pool will...
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    About this property
    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    The Caroline House Estate ~ Weekly Rental1 / 35
    (9)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
    Reviewed June 6, 2018
    My group had such an easy time booking, checking-in and checking-out of this property. The house plus cottage had ample room for our group of 13 and the location (about a 5...
    Reviewed June 27, 2016
    take your own towels as the very few that are there are tiny and paper thin. the clothes dryer didn,t work at all and took till the end of our stay to get it replaced. the oven...
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    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
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Flower Power House ~ Weekly Rental1 / 29
    (2)Average
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 18, 2016
    This house was a great choice for our group of 3 families traveling together. We each had a separate apartment with its own kitchen and bathroom, but were able to gather for...
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    About this property
    Flower Power House 5 - 6BR (Sleeping Porch) 4BA Sleeps 12+ Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the real Key West than the shiny hotels around town. Kindred to memories we share about ‘the good old days,’ this 1938 wooden house...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Catchin' Moments is a beautiful 82' Hatteras, located in Key West, Florida. She is docked at the best slip in Key West Harbor Marina. Stay fully accommodated with a four bedrooms/bathrooms, huge living area, large kitchen, outside dining area, and upstairs lounge. The marina has a pool with pool...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 24
    (40)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 20, 2018
    This place has everything you could need and want while you stay in Key West. Conveniently located near restaurants, attractions and things to do. Very happy with Seaside Place!
    Reviewed January 24, 2017
    What a great house for our one-week getaway over the New Year holiday! We had a group of 11 people, and we were all comfortably housed inside the well-appointed home. From the...
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer....
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Harbor Walk Hideaways1 / 44
    (20)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 2016
    Our party of eight absolutely LOVED this place. Location was to die for and price could not be beat! Just steps from Sloppy Joes, The Green Room and Lagerheads Beach Bar just...
    Reviewed October 25, 2015
    My husband and I, and three other couples came to Key West for a friend's wedding. After much research, I am so thankful to have come across Harbor Walk Hideaways. The grounds...
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    About this property
    Very private gated compound sleeping eight guests right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing...
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    Location Information
    Key West, Florida Keys 33040
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 13, 2018
    The home was just as described. The location made for easy walking to any of the local attractions. There are several restaurants and cafes within a few blocks. The french cafe...
    Reviewed May 12, 2016
    This property was truly more than we expected. The home was lovely, but our expectations were exceed by the outside living space. The pool is perfect for 8-12 people. There is...
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    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Twice as Nice ~ Weekly Rental1 / 17
    (4)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Air Conditioning
    • Patio
    • Cable/satellite TV
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 31, 2017
    Great houses in a perfect location. Everything was very clean and to the highest standard. Easy to book. Highly recommended.
    Reviewed October 27, 2016
    We rented. Other cottages for a family vacation. Both units were better than expected for all that we wanted to do. The rooms were spacious, the pool area was private and...
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    About this property
    In this case... 'Two is definitely better than One'! A rare set of early 1900's 'twin-cigar maker's cottages' perched on the southern end of famous Duval Street. The Twice As Nice vacation rental is at once adorable and elegant and a perfect solution for a discerning group who want to lodge...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Villa Nouveau Key West ~ Weekly Rental1 / 19
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 20, 2015
    We loved Villa Nouveau! It's a really well-done small 4 bedroom cottage. Bedrooms are small but nice. King beds in 3 rooms and doubles in the 4th, all very comfortable. Each...
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    About this property
    Sometimes a Key West cottage that at first glance appears predictable from the outside, is full of abundant surprises when you walk inside. Villa Nouveau Key West vacation rental has an interesting story that attests to this truth. Once a prosaic 'shot-gun' style cottage, a modern redesign has...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Key West Spa Villa ~ Weekly Rental1 / 22
    (7)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 29, 2014
    The house we rent was absolutely beautiful, the pictures do not do it justice. The house was extremely clean, the pool and hot tub area were wonderful. The little extras such...
    Reviewed April 29, 2014
    If you're looking for an amazing place to stay, this house is for you! In walking distance to everything. The house was clean and comfortable, the pictures don't do it justice...
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    About this property
    This proud 1890's 'cigar maker's cottage, just off Duval Street, has been lovingly transformed into a stylish 4 bedroom, 4 bathroom spa villa. Captivated by the uninhibited yet wonderfully elegant Key West island life-style, the designer created a fabulous balance of opposites. Opposites attract...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Pavilion Villa ~ Weekly Rental1 / 20
    (8)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Washer
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 21, 2016
    Stayed with friends and family place need work. A/C in bathroom terrible, none. Kitchen, family room in main house never stayed cool. it says 3 baths 1 is outside beside the...
    Reviewed August 17, 2015
    When we arrived the main house smelled very musty. I immediately cranked the AC units down to 73 to get some of the air dried out. The King bedroom never lost the musty smell...
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    About this property
    A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a half-block off Duval St. in Old Town Key West. I first visited this private home when it was featured on the prestigious Garden Home Tour of Key West which opens a few select...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    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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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Hot Tub
    • Waterfront
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A spacious, airy 3-bedroom, 3-bathroom penthouse at The Galleon Resort & Marina in the Old Historic Seaport in Key West. Available from Saturday March 31 to April 7, 2018. Weekly Rental Only. The first level of the penthouse has a full kitchen and wet bar, with a washing machine and dryer. There...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    The Water's Edge1 / 25
    (2)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 6, 2017
    The house was gorgeous, and the sunset view from the balcony lived up to expectations... Short walk to Duval Street... Totally recommended
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    About this property
    Three bedroom, four bathroom private home with heated pool stocked with massage water jets and special colored lighting. Breathtaking sunsets can be seen from third floor deck overlooking the Ocean. High definition plasma TV and surround stereo throughout the home. High Speed internet and faxing...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    The Mermaid's Garden1 / 24
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Air Conditioning
    • Patio
    • Washer
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 12, 2018
    The Mermaid Garden is close to all of Key West's attractions yet nestled in a quiet historical location. The house has plenty of room, the kitchen has everything you might need...
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    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, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Grill
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for a stunning four-bedroom, three-bath vacation retreat with its own private pool, you've found it at Island Style. Located in Truman Annex, Key West's signature gated community, this home has it all: 2,000 square feet in a compact two-story format, porches and balconies, deck...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Truman House1 / 20
    (20)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 13, 2018
    The house made the vacation very enjoyable. It is in a perfect location, we walked everywhere and no walk was too far from anywhere we wanted to go. The house was cozy and...
    Reviewed December 12, 2017
    This was a awesome 4 bed / 3 bath home. It had everything you would need and then some with a rental. The location was good, the private pool was a plus and there was plenty of...
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    About this property
    The Keys have some of the most charming, top-rated vacation residences in the world. Truman House, a 1920's Conch home with four spacious bedrooms, three full baths, a dazzling pool, and ample amenities easily qualifies for the list. And as an added perk, this classic pet-friendly home is located...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 66
    (9)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • Balcony
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    The accommodations were very nice. Mattresses in every room could definitely use some updating, everyone in our party agreed all the beds were hard and you could feel the...
    Reviewed October 23, 2017
    We (8 adults) stayed at Heavenly Hideout at Rainbow's End in Oct 2017. Due to hurricane Irma we were concerned for the residents of the Keys as well as the property and honestly...
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    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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
    Reviewed July 17, 2017
    Great house, pool is awesome, location is perfect right next to grocery store and 1/2 block off Duval. Very quaint inside and out!
    Reviewed December 28, 2014
    We stayed here for a week over Christmas with 4 adult kids and had the best time ever. The accommodations were great for 6 of us and we couldn't ask for a better location...
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    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
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Patio
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This genuine Key West combo of our Private Pool Garden Villa plus a classy private studio cottage that adjoins the property next door, can be your very own get-away for a week or more. When rented together, we call the property the Lazy Iguana. Off-the-beaten path of most tourist homes and...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Private Yard
    • 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
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This amazing penthouse condo has one of the best view in Key West. Located in historic Mills Place in the main part of Truman Annex, you have the views of the Gulf and ships that pass by the windows as they arrive and leave port. The apartment has four exposures and three of them with balconies....
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Ocean Views
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you have had your fill of hotels and the street scenes of downtown Key West and you don't want to spend another minute on a boat loaded with people but do want to get out on the water, then S/V Tortuga may be the perfect solution for you. Tortuga Sailing Adventures offers a unique, totally...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Admiral's Lane1 / 20
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 17, 2018
    Nice house in a great location. 2 blocks from Duval Street, but quiet at night. Adequate pots and pans for cooking in. Nice bedrooms and bathrooms. Front porch and living room...
    Reviewed June 13, 2017
    We booked a family trip to Key West to celebrate a few wedding anniversaries. Since there was 8 of us, we opted to rent a condo and we were NOT disappointed! This place on...
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    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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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Casa Grande1 / 24
    (5)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    5 couples, one house, and we could not have asked for more. Everyone had their own space and tons of space to share. The pool was amazing, the house was clean. Everyone loved...
    Reviewed May 6, 2015
    This was our second year at Casa Grande and I recommend highly if you're a group of 8-12 people. Beautiful location near 1100 block of Duval. Nice large pool in backyard...
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    About this property
    Perfect for an extended family or group of friends, this property offers great amenities including private pool, and close proximity to many Key West attractions! 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...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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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
    Reviewed July 11, 2014
    This property is lovely. With the large main house and several small cottages,it would be great for family reunions. The pool, jacuzzis and landscaping are all beautifully...
    Reviewed November 28, 2011
    I rented The Main House at Bahama Gardens for a family vacation of about 10 days over Thanksgiving. There were 5 of us, myself, my husband, two adult sons and one son's...
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    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
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Casa Havana1 / 24
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Yard
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 2018
    Location is the best. Casa Havana is 1/2 block off of Duval and 3 blocks from everything in Key West. Deck is great for drink and a cigar in the afternoon and having it own...
    Reviewed February 23, 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group...
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Penthouse On Duval ~ Weekly Rental1 / 40
    (11)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Parking
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 1, 2018
    For quick access to Duval St. this is the perfect location. Not exactly for you if you're looking for peace and quiet, as you are right in the middle of all the action. When...
    Reviewed October 26, 2016
    A group of friends and I came down for my bachelor party and couldn't have asked for a better set up. The place is massive, more than enough room for everybody to get either a...
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    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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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Kemp House1 / 25
    (20)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 7, 2018
    Lovely property within walking distance to all of Key West. Beautiful quiet pool and guest house. Main house has 2 BR with twin beds and queen bed. Guest house has full bed. On...
    Reviewed April 17, 2018
    Beautiful historical house transports you back in time. Loved the second floor back porch for reading and relaxing overlooking the pool.Close to great restaurants and the...
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    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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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Dolphin House1 / 23
    (3)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 29, 2014
    The location is perfect for those that want a perfect mix of quiet but close to the action on Duval. The décor was beautiful, pool and outdoors perfect. Great area for grilling...
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    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
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Seaport Treasure Estate ~ Monthly Rental1 / 68
    (1)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Ocean Views
    • DVD Player
    • Patio
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 8, 2016
    My husband and i were celebrating our 50th wedding anniversary and chose this property because we were looking for the ideal location to entertain our friends and family...
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    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
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • 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
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Duval Penthouse1 / 24
    (25)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Private Outdoor Pool (Heated)
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 11, 2018
    Great time! Will stay there again! People that can't sleep with noise shouldn't have the master bedroom, but it didn't bother us. We enjoyed having the bar next door for the...
    Reviewed February 18, 2015
    Love the Duval Penthouse; our second year staying there. Fantastic location, clean, well taken care of. Only one thing I would change... the mattress in the Master bedroom is...
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    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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Bahama House1 / 24
    (27)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 15, 2017
    Bahama House was a wonderful choice for a family gathering and week-long vacation in Key West. Its location in a quiet, short street, a block back from Duval Street, provided us...
    Reviewed April 13, 2015
    We spent Spring Break at the Bahama House and it was perfect for our group. We had 4 adults and 4 teens. Bedrooms were ideal, especially the upstairs room which could fit all...
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    About this property
    Luxury rental with all the amenities you can ask for, Bahama House might just be right right vacation rental for you! Location, Location, Location! Totally gorgeous, this spacious house rental Key West is conveniently located on a quiet street in the heart of Old Town Key West around the corner...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 3 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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    Amenities & Details
    • 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
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    Amenities & Details
    • Cable/satellite TV
    • Washer
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 21, 2016
    Just looking at the pictures of the home as I write the review makes me wish I was still there. Stayed with VHKW for the 2nd time at this property and it was just perfect. The...
    Reviewed June 21, 2016
    Love this place, it has a great outdoor space and relaxing living room. Gas grill for cook-out was great. Great location close to our favorite restaurant El Siboney!
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    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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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Waterfront
    • Patio
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Southern Crosser is the latest luxuriously designed cruising catamaran from world renowned French boat builder Fountaine Pajot. ​Following her initial voyage from France to Ft. Lauderdale for commissioning, she was delivered to her new Key West home in January 2018. This brand new vessel is 40 feet...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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