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Key West Luxury Holiday Homes

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    AU$1,203 Average
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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    42 Matching Rentals in Key WestView all 282 rentals
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    Price (High to low)
    The Meeting Point - Key West ~ Weekly Rental1 / 54
    (2)Average
    11 Bedrooms, 11 Bathrooms, Sleeps 24 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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    ~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Heated Pool on Duval St!1 / 45
    (3)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 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 15 June 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 4 July 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
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 16
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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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    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 4 weeks ago
    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 31 May 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
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point. The home is just a few blocks away from the Southernmost Beach, night clubs, and popular areas which makes it a perfect spot to vacation as it is a quick walk to everything Key West has to...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    The Caroline House Estate ~ Weekly Rental1 / 35
    (8)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 2 weeks ago
    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 27 June 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Tropical ~ Tranquility ~ Weekly Rental1 / 17
    (7)Very good
    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 21 March 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...
    Reviewed 13 February 2018
    Tropical Tranquility was a great home! There were 4 couples in our group and we had plenty of space. Our 2 golf carts(Sunshine Scooters) fit nicely in the driveway. As we...
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Top Of Duval- 6 Bedroom Penthouse1 / 26
    (14)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 5 days ago
    This was such a perfect place for our group! All the suites are clean and large! The pool area was just perfect! You’re literally right in the middle of all the action of Duval...
    Reviewed 8 April 2018
    The location is perfect -- nearly equidistant from the Atlantic and the Gulf and in the midst of Duval Street restaurants, shops and bars. And, the rooms are great -- attractive...
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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
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    6 Bedrooms, 4 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Balcony
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES consist of four Luxury Vacation Rentals that can be rented together or separately. LOCATED ONE HALF BLOCK FROM DUVAL STREET, this location is perfect for a multi generation family...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 18
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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 19 April 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
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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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 24 October 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 29 March 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 10 Bedrooms, 6 Bathrooms, Sleeps 22
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    ~ CHAVEZ HOUSE ~ World Class Luxury w/ Private Heated Pool & Great Location!1 / 37
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2017
    The Chavez House more than met our expectations. The layout was perfect for our needs with a large room downstairs and two rooms upstairs. The Kitchen was stocked with...
    Reviewed 11 April 2017
    This was my families first stay in Key West. The Chavez house was absolutely beautiful. All modern amenities and the location was close to everything! We didn't need our car...
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    About this property
    The Historic Chavez House on Margaret Street! This 3 bedroom 2 bath two story eyebrow house was Built in 1870 and is in the National Register of Historic Places. Newly renovated and very well appointed! Fine linens, gorgeous furniture, ultra comfortable mattresses, and a cool and calming color...
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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, 4 Bathrooms, Sleeps 8 Quick View
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    • 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    ~ CLOUD 9 ~ Lavish Home In Perfect Location w/ Heated Pool & Private Parking1 / 31
    (16)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Parking
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Everything Key West is right outside the courtyard door! Less than one block from Duvall St. All the best restaurants and bars with great live music are within walking distance...
    Reviewed 31 March 2017
    This place was absolutely perfect! Steps from all the action of Duval and yet, amazingly, you couldn't hear anything but nature when sitting by the pool! The house was...
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    About this property
    The Absolute Best Luxury Private Vacation Rental Home by Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    ~ CHICK-A-PEA COTTAGE ~ Incredible 'Old Town' Home w/ Private Heated Pool!1 / 56
    (3)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    This cottage is located feet away from the southern end of Duval Street. We were steps away from anything we wanted to do. The rented bicycles were a homerun. You didn't need...
    Reviewed 11 April 2017
    Such a wonderful and comfortable home. We were steps away from Duval street but it was so quiet at night. The pool was a great way to relax after a long day of walking and...
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    About this property
    The house is a traditional Key West cottage that has undergone a complete renovation in 2012. The charm and historic features have been retained, while all the luxuries of today have been added. There is a master bedroom, with king bed and full bath, on the first floor. Additionally, there is a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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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 13 February 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 13 May 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Villa Nouveau Key West ~ Weekly Rental1 / 38
    (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 20 September 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Key West Spa Villa ~ Weekly Rental1 / 44
    (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 30 April 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 29 April 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
    Holiday Rental House - 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 22 May 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 18 August 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
    Holiday Rental House - 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 31 August 2017
    Great houses in a perfect location. Everything was very clean and to the highest standard. Easy to book. Highly recommended.
    Reviewed 28 October 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Terrace
    • Hot Tub
    • DVD Player
    • Washer
    • Balcony
    • Housekeeping Included
    • Waterfront
    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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    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 32
    (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 4 days ago
    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 25 January 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
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Harbor Walk Hideaways1 / 22
    (20)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 March 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 26 October 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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    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 7 March 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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    Truman House1 / 40
    (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 14 February 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 13 December 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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    ~ SOUTHARD COMFORT ~ Breathtaking Home w/ Pvt Pool, Parking & Quiet Location1 / 28
    (13)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2017
    This home's Decor and comfort was amazing. Quite neighborhood with many Fun things close by. Our Daughter was married in the Living room in front of the open doors to the pool...
    Reviewed 6 August 2016
    This was the perfect place for my friends and I to spend vacation. House is super clean. Very private. Close enough to walk to duval but far away from the craziness when you go...
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    About this property
    “Southard Comfort” is true Island living in downtown Historic Old Town Key West. Two story, 3 bedroom, 2.5 bath plus outdoor shower Nancy & Carl welcome you to their Key West vacation home! This established rental is a dazzling property, and we are committed to continuing its reputation of...
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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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    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
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    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
    About this property
    DISCOUNTED RATES for Open Dates this SUMMER! 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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Heavenly Hideout at Rainbow's End ~ Weekly Rental1 / 33
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Patio
    • Balcony
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 October 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...
    Reviewed 21 February 2017
    If you want to immerse yourself in true Key West charm .. This is a perfect place for you. From the front porch through the front door you enter a world that is rich in Key...
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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
    Holiday Rental House - 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 18 July 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 28 December 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Private Garden
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 rental homes within 5 private gated acres of scenic beauty in the heart of the Florida Keys. Located within the keys wildlife preserve, Sea View Estate is just a 15 minute drive to the shopping and nightlife of Key West and just minutes to some of the finest restaurants the Florida Keys has to...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Admiral's Lane1 / 20
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 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 14 June 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
    DISCOUNTED RATES for Open Dates this SUMMER! 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...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Casa Havana1 / 24
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 January 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 23 February 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
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Penthouse On Duval ~ Weekly Rental1 / 20
    (11)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Parking
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 March 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 26 October 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
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Sauna
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Waterfront
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MAR Y Sol is a Beautiful 3 Bedroom Two and a half Bath ocean-front condominium at 1800 Atlantic. Enjoy the balmy breezes from your 60 foot private wrap around balcony with a fabulous view of the Atlantic ocean. Mar Y Sol has renovated kitchen and bathrooms. Mar y Sol is in high demand so during...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Kemp House1 / 25
    (19)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 18 April 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...
    Reviewed 21 March 2018
    Well maintained. Maybe a pruning of the pool area; however the flowers are terrific. A parking spot would add to this value property. Parked at a lot on southward/William for...
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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
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Expansive group escape w/shared pool & five separate villas 1/2 block from Duval1 / 41
    (1)Excellent
    5 Bedrooms, 7 Bathrooms, Sleeps 20 Quick View
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    • Grill
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 February 2015
    I stayed here with a group of friends and we reserved all five of the villas for 14 people. Each villa had one bedroom and most had one and a half bath with a small kitchen that...
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    About this property
    This family-friendly Key West home features five separate villas grouped together, a shared pool, and a location that puts you close to all of the action. Notice: This is in a residential area, Quiet Hours are 10:00pm- 8:00am Located on Center Street, this home is just a mile from the Key West...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 7 Bathrooms, Sleeps 20
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    ~ POTTERS COTTAGE ~ Perfect Key West Home, Private Pool, 1 block to Duval St1 / 37
    (19)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    The pictures are entirely accurate, this place is adorable and perfect for two couples. The two bathrooms was a deal sealer for us. It's near the main drag and we love, love...
    Reviewed 18 September 2016
    We stayed at the Potter's Cottage and thoroughly enjoyed our experience. The property was in fantastic condition - fully modern with generally high quality finishes. One full...
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    About this property
    Historic Old Town Location - Private Pool - Just Steps from World Famous Duval Street, The Ernest Hemingway Home, The Southernmost Point, and Southernmost Beach! Experience hotel-like 5-star luxury but with the exclusive privacy of this adorable Key West home. Potter’s Cottage is located in the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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