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Key West House Rentals

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    157 Matching Rentals in Key WestView all 323 rentals
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    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 23
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access1 / 27
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 21
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Coral Hammock - Comfortable 3 Bedroom Home1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 June 2018
    Thank you so much for the wonderful stay in your home Bob. We will defiantly stay here again if there is availability when we come. Everything from towels, beach towels, sand...
    Reviewed 27 March 2017
    Great times in key west coral hammock is about a fifteen minute drive to duval street. The place is real nice and quiet a lot of space for your whole group. Great trip all...
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Garden
    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come enjoy Island Living at it’s finest, Your own “Little Paradise”. This Two Bedroom Two bath home is nestled on a quiet one way street in The Historic Seaport District. This location is desirable for being walking distance to Duval Street and the proximity to 5 star restaurants, art galleries and...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY1 / 41
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2018
    Best part, it is right off of Duval and close to so many things to do. The beach is 5 minute walk and the community pool is an amazing unused gem. Free bus to lower Duval is...
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    About this property
    Check out the new 'Duval Loop' that ferries you around Old Town for free and is located at the corner of this homes block!!!!Map is included in pictures. Hemmingway House, Lighthouse, Butterfly World, Southern Most Point, Conch Tour Train, Beach, Galleries & Restaurants are all located within a 5...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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 Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 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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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6 This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    We hope you will enjoy this home where Ernest Hemingway and Jimmy Buffet memorabilia welcome you into the abode our first guest affectionately called “The Writer's Retreat'. This two bedroom, one bath condo with bleached grey hardwood flooring throughout is highlighted by a massive 65 inch Plasma...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
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    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Two blocks from the seaport,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 44
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 18 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Casa Del Sol, a Key West Vacation (Truman Annex)1 / 26
    (59)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • DVD Player
    • Washer
    • Grill
    • Internet Access
    • Cable/satellite TV
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 days ago
    Had a wonderful visit to Casa De Sol in the delightful community of Truman Annex.We were within walking distance to all the all the attractions, including the water front...
    Reviewed 5 days ago
    The Casa Del Sol house in Key West was amazing! It is a super cute and comfy house and within walking distance of all the highlights of Key West. Jim and Joanne are wonderful...
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    About this property
    Welcome to Casa Del Sol, a Key West Vacation...your very own luxurious and elegantly appointed 2 bedroom and 2.5 bath townhome with private carport... part of 45 lushly landscaped acres in Truman Annex. As part of President's Walk townhomes in gated Truman Annex, this premier waterfront community...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Make this your Key West Vacation home! Cozy 2 bedroom, 1 bath home set on the back half of a residential lot with new kitchen, bath, and furniture. Privacy provided by the fenced outdoor area, with a shaded porch and furnished gazebo for relaxing. The location is 5 minutes max to anywhere on the...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    HISTORIC KEY WEST  - Conch House - Sleeps 51 / 21
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • Porch
    • Internet Access
    • Washer
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2014
    My husband & I found the Conch House online. The property manager, Craig, met us upon our arrival and was very friendly. Throughout our trip, he was very helpful and very...
    Reviewed 22 June 2014
    This property is so beautiful and peaceful.!! Perfect location, 2 short blocks from Duval, 1 block from Ft. Zach beaches. We stayed in the Conch House , We could not have been...
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    About this property
    OVERVIEW The Conch House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of five (5) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (2) twin...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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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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    • 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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    Key West, Florida Keys 33040
    Holiday Rental House - 10 Bedrooms, 6 Bathrooms, Sleeps 22
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    • Balcony
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional outdoor space on your wrap around porch and large bricked patio to enjoy the tropical breezes. Welcome to your home away from home in Key West. This lovely townhome is located in the exclusive Golf Course community, and allows you to enjoy all that Key West has to offer while staying in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Terrace
    • Wi-Fi
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps away from the large lagoon style pool surrounded w/lush tropical landscape. Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Bring the family to this 3 bed, 2 bath private conch home and enjoy your large private pool and outdoor area as the days pass by. You know the feeling. Rushing to go on vacation, to the airport, driving in traffic, so many people around you doing the same thing, finally in Key West at your home...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Casa Grande1 / 24
    (4)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 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
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Newly remodeled family home with a shared swimming pool and fitness center!1 / 32
    (3)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Balcony
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    • Terrace
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    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2018
    So, lets start by saying the place was clean. BUT, the furniture and rugs were so old and stained. The TV downstairs worked one day then not the next. There are areas on the...
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    About this property
    Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off. Imagine yourself in a secluded, gated community steps from the golf course, minutes from the beach, airport and some of the local's favorite...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sunny View1 / 24
    (2)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Grill
    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2014
    The property was exactly as described and in tiptop shape. Everything was ready for our stay, the house was comfortable and a fair value.Also, the folks from at Home in Key...
    Reviewed 9 February 2011
    We had a wonderful time. The weather was great. The cottage was in the perfect location, very clean and filled with everything we needed. It was better than the condo we had...
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    About this property
    Lovely 1 bed/2 bathroom private home with covered back porch and bricked courtyard within walking distance to Duval Street. Adorable, affordable, and a great location! You bet! Sunny View is the monthly rental Key West perfect escape for a couple or singles looking to get away from it all in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    A Place In Paradise1 / 48
    (23)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Wi-Fi
    • Cable/satellite TV
    • Balcony
    • Parking
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2017
    The townhouse is in the perfect location. Close to everything. The community is very clean and quiet and the pool, albeit small, was great and just around the corner...
    Reviewed 13 November 2013
    I've been going to KW every year for about a decade and have learned that your home base for the week can be the difference between a good trip and a truly great trip. I've...
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    About this property
    Located on Porter Lane of Truman Annex you can find your real PLACE IN PARADISE! A PLACE IN PARADISE - You will experience true Key West living when you stay in this delightful 2 bedroom 2.5 bath Conch-Style townhome in Truman Annex. One of the most desirable locations for vacationers, you will...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West home w/shared pool and just steps from historic Old Town1 / 24
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • DVD Player
    • Grill
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    • Internet Access
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This perfectly positioned rental with access to a shared pool puts you close to everything in Key West, so bring the whole family for a memorable tropical retreat. Situated in the premiere gated community of Truman Annex, this home is just steps from historic Old Town. The Truman Annex offers...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Grill
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a classic Key West vacation at this charming 1BR apartment in a restored 1920's conch house. This prime Old Town location is just a short walk from Duval Street, the historic seaport, beaches, dining, and one-of-a-kind shops. Guests enjoy use of the heated pool. ABOUT THE APARTMENT This...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Coral Garden1 / 23
    (27)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Balcony
    • Grill
    • DVD Player
    • Wi-Fi
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 September 2013
    Our visit to Key West was amazing. At Home in Key West Inc. has the best services they were very informal and personal. At Home made sure we had everything that was needed for...
    Reviewed 16 August 2013
    We were thrilled to see that the home was so well kept and looked exactly like the photographs. I would definitely recommend people staying here especially if you have children...
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    About this property
    For those looking for a cozy little getaway on a budget - Coral Garden is the asnwer! A 2-bedroom 2.5 bath townhome in the private gated community of Coral Hammock, this Key West vacation rental offers the finest accommodations for you and your family. Furnished with comfort in mind with a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Dreaming1 / 24
    (58)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2017
    Nice and quiet with pool. Two bed rooms and two baths. Nice and clean house only draw back, has limited parking since we had 2 cars.
    Reviewed 21 July 2015
    Very Nice! Photos are true to form. Needed a place we could bring our small dog. Perfect distance from Duval. Pool was small but we had only 4-6 max (plus the dog). Grilled a...
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    About this property
    Do not look any further! Your perfect vacation home rental is right here! Offering private pool with lounge chairs and covered outside porch. You can also bring your Fido! A distinctive private Key West vacation home with sparkling pool, Tropical Dreaming is the classic example of the best of...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Verandah1 / 24
    (11)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 December 2012
    We enjoyed everything about our wonderful home in Key West. We felt right at home, great location, we could walk everywhere, short drive to the beach, harbor, and restaurants...
    Reviewed 2 September 2011
    Everything was great about my stay. At Home Key West is great to work with and very easy to get in touch with should an issue arise. The location of this house is great, and...
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    About this property
    Beautifully designed yet comfortable private home that you may never leave, only to go outside to your private pool and secluded space to hang out. Tucked away on historic Frances Street lies your island escape… Verandah is a stunning monthly vacation rental -- two bedroom two bath home with a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Coral Casita1 / 24
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Private Outdoor Pool (Heated)
    • Parking
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 April 2017
    We stayed at Coral Casita for two weeks with our extended family. We were very happy with the rental accommodation from start to finish. The property was very clean and well...
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    About this property
    Ideal for a family vacation or group of friends looking for a rental on a budget. Located very close to some great Key West restaurants this property is a steal! Completely re-designed, re-decorated and ready for your island adventures! When Key West is calling your name and nothing else will...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    LOCATION! Feel like a Local! Spacious Suite steps off Duval St.-Eyebrow Suite1 / 28
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    This was our 2nd time staying with Andrews Inn and Cottages. They are amazing!! The staff is very accommodating, the suites are wonderful, and we can't wait to go back. I highly...
    Reviewed 22 March 2017
    Eyebrow House has a ton of room, lovely front porch and rear patio. The negative for senior citizens is that it has only a queen bed and hideabed which works for kids, not...
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    About this property
    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    President's Walk1 / 24
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Terrace
    • Grill
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 June 2017
    This place was perfect for the three adults and infant. The proximity to the pool, Duval St., and Green Parrot really made this beautiful condo ideal for a long Key West trip...
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    About this property
    Large outside deck invites you to just unwind after a long day of exploring with a good book and a glass of wine or enjoy it with friends grilling your fresh catch PRESIDENT'S WALK: It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Linger Longer1 / 23
    (22)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • DVD Player
    • Balcony
    • Terrace
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2015
    I am a repeat renter and plan to return next year. Walking distance to everything but in a quiet community off Duval.
    Reviewed 27 April 2014
    This was the first trip to Key West for my husband and I, but we traveled with more experienced Key West-ers who booked the rental. We were pleasantly surprised when we arrived...
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    About this property
    Just imagine stepping out of the rental and stepping right into the pool! Just relax and enjoy your vacation! LINGER LONGER -- Enjoy a carefree vacation in this beautifully decorated, 2 bedroom 1.5 bath home rental Florida Keys, located in the President's Walk of Truman Annex. Master bedroom...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Quilted Giraffe1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 December 2017
    Charming historic home, comfy beach cottage feel. GREAT LOCATION, beautiful pool area great for dining under the stars or a relaxing day in the sun. If your lucky you might get...
    Reviewed 7 June 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is...
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    About this property
    Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part of Old Town...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BOWE CONCH HOUSE (monthly rental): The Bowe Conch House has evolved within the Thomas family, Conchs, born and raised in Key West, for more than 4 generations. Prior to buying the house in the 1930's for $2,500, George and Ethel Bowe-Thomas lived across the street paying $3.00 per month for rent!...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Casa1 / 24
    (26)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Terrace
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 August 2017
    We just recently returned from our stay in Key West Casa. This condo has everything you need. We did not use the bikes because we did not know how to unlock them, but we never...
    Reviewed 12 June 2016
    We stayed in Key West Casa and absolutely loved that property. It is a 3 bedroom, 2 bath with a porch, back patio, balcony. The kitchen is fully equipped, one of the best we've...
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    About this property
    This spacious 3 bedroom apartment is located in Shipyard of Truman Annex, one of the most desirable Key West communities, close to Blue Heaven and Santiago's Bodega, one of Key West most popular restaurants. KEY WEST CASA – Beautiful and spacious Shipyard condo Key West, Key West Casa is one 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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    Flagler Station1 / 25
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With family in mind this lovely 3 bed, 2 bath private home has plenty to offer with a private outdoor space and pool to spend your days enjoying. This one is a priceless gem in a true established residential neighborhood in midtown Key West! Flagler Station was recently remodeled, refurbished and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Parking
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully restored private cottage located in Old Town Key West. Have you been dreaming of living like a local in Key West? Your dream can come true. Green Orchid offers a true Conch Cottage experience on a narrow lane in one of the last historic Old Town neighborhoods. Situated on a lane that...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Cayo Hueso Sunshine1 / 23
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Parking
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Terrace
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    French doors leading from your kitchen to this homes beautiful outdoor space with porches, deck and private pool. Awaken your senses with tropical breezes, turquoise waters and Key West Sunshine in this brand new 2-bedroom, den, 3-bath home. A secluded location yet the best of both worlds allows...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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 20 June 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 24 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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    HISTORIC KEY WEST -  Cigar House - Sleeps 41 / 27
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Porch
    • Washer
    • Grill
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    We have stayed here 2 or 3 times. It is small, but there are just 2 of us and our dog. Works for us! Very cute and cozy. Washer & dryer. Compound is quiet and...
    Reviewed 13 August 2016
    The Cigar House has one the best location you can expect in Key West, close to Fort Zachary, Hemingway's House or Duval St. and all its attractions.This lovely house is full of...
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    About this property
    OVERVIEW The Cigar House is a 100+ year old Cigarmaker's house. The house is recently renovated, charming, spacious, secluded and private. The house can comfortably accommodate a maximum of four (4) guests, who are comfortable sharing an open sociable living environment - (1) queen bed, (1) queen...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Bahama House1 / 24
    (27)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Balcony
    • Parking
    • Cable/satellite TV
    • DVD Player
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 May 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 13 April 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Wind Swept1 / 24
    (2)Average
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Grill
    • Terrace
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Balcony
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 December 2013
    The house was great Loved being on the golf course very quite area great pool Security was very nice and helpful The staff: At home was great Libby is the best
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    About this property
    Screened porches up and down for you to enjoy the the extra living space in this lovely townhome. Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. This lovely 2 bedroom 1.5 bath...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Secure Parking
    • Private Garden
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Sea View Cottage is a 2 bedroom, 1 bath home built within feet of the Atlantic Ocean with 180 degree ocean views. The property is a 5 acre gated private estate located within the Florida Keys National Wildlife Refuge. Fishing and diving just steps outside your door. Then at night, Key West...
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    Location Information
    Key West, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ecco Domani1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Terrace
    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully designed and decorated this private home has the gourmet kitchen with French doors that lead to your private outdoor space and pool. Ecco Domani means 'Here Tomorrow' which is where you'll want to be when you see what you're missing. A beautiful 3 story home with private pool, off...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Imagine the ultimate Key West dream home that feels like a faraway oasis - where you can watch crowning tropical sunsets from a private rooftop deck. Someplace truly extraordinary, elegant yet also comfortable – on a private island surrounded by sparkling turquoise waters and balmy breezes. How...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 3 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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Balcony
    • DVD Player
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful 2 bedroom, 2.5 bath vacation rental. Enjoy the convenient proximity to most events Key West has to offer! CAPTAINS WHEEL: Take control of your vacation, be the master of your fate. Captains Wheel will not disappoint. Situated on the corner of Southard and Emma Streets in Truman...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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