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Florida Keys Romantic Vacation Rentals

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    Travelers to Florida Keys are booking February dates now. Secure your vacation rental today, and have the perfect trip.
    125 Matching Rentals in Florida KeysView all 1,537 rentals
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    Florida Keys Sailing on Conch Key. Bayfront 2 BR cottage with 23 foot Sailboat1 / 19
    (18)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Islamorada Waterfront Paradise Getaway!1 / 28
    (31)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    All NEW Interior Oceanfront 5th Floor End Unit, Pool, WiFi, Great Ocean Views!1 / 31
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Waterfront
    • Ocean Views
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 3, 2018
    Simply an amazing condo. Location was perfect, made a great trip AMAZING. Owner was very accessible and friendly. Sunrise and set, along with the full moon views , just...
    Reviewed April 28, 2018
    Totally renevated condo with gorgeous views of ocean It was so nice to stay here! So cozyNice pool area! Co-owners were very friendly and made you feel at “home”Condo...
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    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. And new this year, a sandy beach. For two couples or a family with 2 kids. The two new extra long twin Pillow Top beds in 2nd bedroom convert to a comfy King Bed! Master bedroom has new Simmons Beautyrest Pillow Top...
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    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Balcony
    • DVD Player
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    • Grill
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to gorgeous Marathon, Florida Keys for a romantic getaway or a fun family retreat. For families with young children this Keys Vacation home is located just two blocks away from beautiful Sombrero Beach with a children`s playground, baseball diamond, volleyball net, picnic areas and roped...
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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    DECEMBER 18 THROUGH 26TH AVAILABLE1 / 12
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Washer
    • Ocean Views
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 22, 2018
    Nice unit and pleasant stay. Unit had well equipped kitchen and nicely furnished with a central location to all of the best spots in the Keys.
    Reviewed November 25, 2017
    In the middle of the keys. Good central location. Splash pool nice touch! Can access canal with paddle board.
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    About this property
    HEART OF THE FLORIDA KEYS SPA VILLA OPEN SURVIVED HURRICANE IRMA! Nestled within the charming island of Duck Key Escape to your very own Tropical Paradise in the heart of the Florida Keys. Everything the Keys has to offer is right at your fingertips and all within walking distance. After your...
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    Duck Key, Florida Keys 33050
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key West Florida Beachfront Condo1 / 22
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Air Conditioning
    • Hot Tub
    • Sauna
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 2, 2018
    Mrs Carol thank you for the beautiful place to stay in for a beautiful trip. The views were awesome from the room. The sunsets you can watch from balcony was dream like. Highly...
    Reviewed October 24, 2017
    I went to Key West with four other childhood friends for a 50th celebration! We booked our week five months prior, and of course hurricane Irma ravaged the Island. We...
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    About this property
    WELCOME to our beachside condo in Key West. Our terrace directly overlooks Smather's Beach and is the focal point of our home; watch the sunrise with coffee; watch the kids on the beach and the parasailors fly by; have a private sunset dinner; enjoy a late night drink and watch the cruise ships...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Oceanfront duplex with beautiful beach and dock for boat access! Dogs OK!1 / 37
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Internet Access
    • Waterfront
    • Grill
    • Parking
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 10, 2016
    We had our 2 children with us on this trip. (5years, and 3 years.) The beach was beautiful and the kids had a great time swimming and fishing. The house was perfect. We can not...
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    About this property
    Discover the very best of the Florida Keys in this charming dog-friendly (for an additional fee) rental with a dock and beach! The unique home offers the makings of a romantic getaway or intimate retreat with friends. The rental is three miles from town and a few hundred feet from the Long Key...
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    Long Key, Florida Keys 33001
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Sandy Beach, Direct Ocean, Pool, Dock & Lagoon1 / 34
    (33)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 22, 2018
    This house is amazing!! The view from the second floor is breathtaking but from the third floor window watch, it's spectacular!! The yard is very large with a lagoon, beach and...
    Reviewed July 20, 2018
    We found a little oasis of oceanfront paradise!! With meticulous attention to the lush grounds, this property rivals any luxurious resort.This spacious open concept home...
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    About this property
    WARNING: DO NOT WIRE MONEY Casa de Lida large estate with 3 separate buildings on almost an acre of land and is directly on the ocean . It is very private, has large sandy beach, a pool, a large dock and phenomenal views. The Kids will enjoy playing in the sand, and the adults will enjoy...
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    Marathon, Florida Keys 33050
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** This Houseboat is for Adventurous Campers*** Welcome to “The Blue Marlin”! A houseboat that is anchored down in the Gulf of Mexico. Choosing seclusion, and not being 'tied up' to marina life, let this private cabin transport you to your own oasis on the water. Enjoy your vacation on your...
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    ***NEW 3D Tour Indigo Reef Luxury Villa Exquisite 'Latitude Adjustment'! #331 / 43
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Central Heating
    • Balcony
    • Patio
    • Grill
    • Washer
    • Waterfront
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 27, 2018
    Location! Style! View! Decor! If you are thinking about visiting the Keys, and you dont want to stay in a hotel (if so, we recommend the Bayview on Conch Key )this townhome is...
    Reviewed February 26, 2018
    Our family just returned from our vacation and we can't wait to go back. Latitude Adjustment is a beautiful property, inside and out. We thoroughly enjoyed sitting on the porch...
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    About this property
    Your toes dipping into warm turquoise waters. Lounging contentedly by the pool. Breathing in the magnificent views. Being mesmerized by the gently swaying palms. Strolling along the elegantly sweeping grounds. Immersing yourself in the beautiful designer accommodations. An exciting 3D Virtual...
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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Internet Access
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    • Balcony
    • Parking
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    101 Sombrero is a stunning waterfront property that offers you gathering areas to visit with your friends but still allows the opportunity to retreat to your own space with a private bed, bath, and kitchen. Each floor is appointed with colorful decorations as well as comfortable furnishings and...
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    Marathon, Florida Keys 33050
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Luxury Open Water Vacation Home1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Ocean Views
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 20, 2016
    We just returned from a fabulous vacation at this house. It was so relaxing, the views were awesome. We saw so many kinds of birds. It is absolutely a perfect place to enjoy...
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    About this property
    OPEN WATER PRIVATE ESTATE 3 Bedroom 2 Bath, with a large Pool. Sleeps 4 to 6 $250 - $268 Per Night Minimum Stay 1 Nights Enjoy your piece of paradise and the warm tropical air of the Florida Keys in your own 2600 square foot, private open water estate in a quiet relaxing neighborhood....
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    Big Pine Key, Florida Keys 33043
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    CORAL LAGOON RESORT NO. 3 WITH DOCK1 / 17
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Ocean Views
    • DVD Player
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 13, 2018
    Great house for our family of 5. We stayed for 3 nights following a busy 2 weeks in Disneyland and were able to relax and slow our pace down here. The house was well equipped...
    Reviewed August 1, 2018
    This place was quite lovely & very accommodating. We needed a couple extra towels & a blanket, we contacted the property manager about this & they delivered them...
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    About this property
    No. 1 rated resort in Marathon Completely renovated w/ dock. We will be ready to take reservations for Thanksgiving. 3 bedrooms 1 King, 2 queens and a queen size sleeper. 2.5 bathrooms. Walking distance to Marathon and Key Colony activities. Representing a new concept that offers...
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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Private Yard
    • Wi-Fi
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    BOOK NOW and receive DISCOUNT!!! Creating memories is the one thing we will treasure forever! This is a beautiful two story: 3 bedroom home. 2 bedroom, 1 bathroom on top floor, and another 1 bedroom 1 bathroom on bottom floor. The house has one of the most amazing backyards and perfect BBQ space....
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    Islamorada, Florida Keys 33036
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Enjoy the Florida Keys!1 / 33
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Sauna
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Balcony
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 8, 2016
    Very relaxing, friendly environment, with an excellent view of the ocean, we had a great time during our stay.The owner "Tad" was very helpful, whenever we had questions...
    Reviewed February 1, 2016
    The location is in a very good position and permit to visit all the most important site of Keys, Everglades and Miami in a daily tour.The set up of the apartment is complete and...
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    About this property
    VILLAGE OF ISLAMORADA REQUIRES MINIMUM OF 29 NIGHT STAY Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on...
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    Tavernier, Key Largo 33070
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Keys Spectacular Gulf of Mexico Views1 / 25
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 14, 2018
    On the Gulf but so close to the Atlantic, location is key when spending so much time on the water and this place has it. After changing spots each summer we stopped after...
    Reviewed March 9, 2018
    We stayed here February 24-March 3, 2018. Great location, great accommodations, unbeatable views, lots of water wildlife right at the dock, great fishing from the dock. There...
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    About this property
    Newer waterfront Keys home with wide open view of the Gulf of Mexico. 3 Bedroom 3 bath, half-duplex home with private pool, dock with great amenities - perfect for three couples or a family. Great location that's walk-able to the 7-Mile bridge and some of Marathon's best restaurants and bars....
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    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Atlantis House Master Suite1 / 22
    (24)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Hot Tub
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The Atlantis House and owners Steve and Kayla are wonderful! Located just steps from one of the few beaches on the island and away from Duval Street , the master suite is a...
    Reviewed December 29, 2017
    We stayed two nights in the Master suite. (Our second time at the Atlantis House)It was another beautiful experience- everything was prepared with special care from the Turkish...
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    About this property
    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
    • Ocean Views
    • Parking
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Grill
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Key West condo is legally listed as a one-bedroom. However it could easily accommodate two couples, or a family of 4, with privacy. The first floor includes a full kitchen, full bath, dining area, TV area with a sofa, and a Murphy Bed. The second floor (a lock-out unit) includes a 'closet...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Quiet oasis in Old Town Key West that offers a beautiful shared pool and off street parking. Here is your dream come true. Centrally located on one of Old Town's most popular streets, nestled in a tranquil corner of a sought-after gated compound with lushly landscaped walkways leading to the...
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    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 27, 2018
    The Oasis is truly a bit of heaven on earth! We have been visiting Key West for a number of years and could not imagine staying anywhere else.This rental is fully equipped, in a...
    Reviewed January 26, 2018
    Recently spent 10 days at KWO. This property is superb and reflects a pride of ownership. KWO clearly exceeded the already impressive presentation on the website. Paula and...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Elegant Beach Home With Dockage1 / 24
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 3, 2017
    They home was great. It had everything you could ask for. The people that we met at the home very friendly. We had a great stay and I will come again. I high recommend this home.
    Reviewed September 19, 2016
    We stayed here Aug 8-12 with my parents, brother and sister. Not only was the home perfect, but the location was great with several food places in walking distance. We walked...
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    About this property
    Elegant home with many unique, architectural features, located on a family-owned waterfront piece of property, with 3 other rental cottages, sandy beach, and small marina. This lovely house, 'Tropicasa', has everything needed for a large group - full kitchen with granite countertops, stainless...
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Waterfront! Key Largo, Terrific 1/1 Apt on 2nd Floor, Pet Friendly, Sleeps 41 / 16
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Terrace
    • Cable/satellite TV
    • Waterfront
    • Balcony
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 20, 2018
    We had a great time. The apartment was as described, very clean. The bed was comfortable and the linens towels etc were excellent. The apartment is located close to shopping...
    Reviewed March 23, 2017
    Terrific pet friendly one bedroom apartment in Key Largo. Super cosy and beautifully appointed apartment very conveniently located for the beach and snorkelling/diving trips at...
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    About this property
    Welcome to 'Largo Lookout'! This fabulous 2nd floor, waterfront apartment is ideal for singles, couples, or a small family. Largo Lookout is a pet friendly vacation rental that offers guests the opportunity to travel with their well-behaved pets. We require a reasonable, non-refundable pet fee...
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    Location Information
    Key Largo, Florida Keys 33037
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Mariners will find this 3BR/3BA home the perfect retreat after a day on the water. Dock your boat nearby at one of the many spots available for rent, and then stroll back to the house to rest and recharge. You’ll feel on top of the world as you gaze over the clear waters of Florida Bay from the...
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    Location Information
    Marathon, Florida Keys 33050
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    President's Walk1 / 24
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Terrace
    • Grill
    • Wi-Fi
    • Balcony
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Hot Tub
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 4, 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 It wasn't that long ago that President Truman took casual walks in this same location; now it's your turn. President's Walk exudes...
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Sep 3-Dec 1 Open! EZ Ocean Access*Boat Slip*Roof Top Deck*Hot Tub*28 nt min1 / 44
    (2)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Hot Tub
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 22, 2015
    In our first trip to the Florida Keys, we stayed at this home. It is a very nice home, located close to everything. Great kitchen - it was nice to be able to comfortably cook...
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    About this property
    Fabulous, like-new, waterfront vacation home located in the Heart of Key Largo! You'll love the convenient location, the boat slip, and the peek-a-boo ocean view from the fabulous roof top deck! This stunning vacation home is ideal for vacationers planning to enjoy either land or sea activities or...
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes, is located right in the center of the Lower Keys. Key West is only 16 miles in one direction and Marathon 25 miles in the other. This 1200...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    You Should Have Seen the One That Got Away!1 / 33
    (24)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2018
    Husband and I enjoyed our week stay at this nice duplex in KCB. House was perfect for the two of us but also has a extra bedroom with bunk beds and a single bed. House came with...
    Reviewed July 24, 2017
    the listing you should have seen the one that got away, is just as advertised + more. the owners have left more than the average rental for the necessities for a rental...
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    About this property
    We are pleased to announce that our little piece of paradise came through with flying colors in the aftermath of Hurricane Irma! If you are interested in staying prior to December 23, please email or call us. Our home has been offered, free of charge, to house folks in the area as they are...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    100' Private Beach Front Ocean Front Estate1 / 42
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 15, 2018
    INCREDIBLE HOME ON THE BEACH!This beachfront home offered more amenities than any other home we have rented for vacation. Complete game room as well as kayaks and paddle...
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    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 5 bedrooms, 3 ½ baths, family room, living room, game rooms, pool and bar. This home can comfortably accommodate 10-12 people with room to spare....
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    Location Information
    Islamorada, Florida Keys 33036
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this gorgeous Sugarloaf Key vacation home, you'll have five spacious bedrooms (including two master suites)! Enjoy beautiful Gulf views set over three acres, offering privacy for a memorable Florida escape. It's even dog-friendly! Just 18 miles from Key West, this location offers easy access to...
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    Location Information
    Sugarloaf Key, Florida Keys 33042
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    About this property
    NEWTON'S NEST (Monthly Rental) Newtons Nest (Monthly Rental) A quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence. A 1 bedroom condo that has been lovingly restored to showcase beautiful Dade County Pine walls,...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Terrace
    • Balcony
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Modern Keys Living with Bay Views! New from top to bottom!!! Newly remodeled and beautifully decorated 1st floor corner unit with a private entrance. Enjoy the mix of vintage and new furniture and the most comfortable sofas, beds, linens and more! This home is equipped with everything...
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    Location Information
    Islamorada, Florida Keys 33070
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relish in emerald canal views at this lovely 4BR/3BA Key Colony Beach home, complete with a spacious waterside deck and sparkling private pool. New wood-grain ceramic tiles line every room, with fun mermaid accents greeting you at every turn. Bring your boat along or rent one nearby to make use...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
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    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV channels, free current...
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    Location Information
    Key West, Florida Keys 33042
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    >1 / 27
    (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 March 13, 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 August 18, 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
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV channels, free current...
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    Location Information
    Key West, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    • Private Yard
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sea Vista Estate Stay in a beautifully appointed villa or cottage located directly on the Atlantic Ocean. Only a 15 minute drive to Key West's history, restaurants and nightlife, this tropical retreat known as Sea Vista, is as serene as a private island. Enjoy full use of direct TV...
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    Location Information
    Key West, Florida Keys 33042
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Paradise Oceanfront Home with Pool1 / 24
    (10)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 16, 2017
    Our family of four loved everything about this property - the location, the kayaks and bikes that are provided, Cudjoe Bay (which is just steps from the deck), the view! So...
    Reviewed July 19, 2016
    I had originally reserved a larger house a few streets down from this one. That was when there was going to be a much larger group. However, due to the fact that some friends...
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    About this property
    Paradise found, this house has it all, beach, dipping pool, screened in porch, kayaks, bikes, floating dock and amazing views. This has been a popular honeymoon and anniversary celebration home for over 15 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Coral Garden1 / 23
    (28)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 September 12, 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 August 16, 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
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Cute, updated Key West home w/ private pool - close to Duval Street, dogs ok!1 / 25
    (17)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 27, 2017
    My friends and I have traveled to Key West for the past three years and we always rent through KWVR. Each year we have rented a different property however this property is...
    Reviewed August 18, 2016
    Stayed here with friends. The setup was perfect for our needs - one couple and two singles. My bed was very comfortable. The only thing missing in my room was a mirror! The...
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    About this property
    Bring the whole family together for a reunion or holiday celebration at this spacious, Key West home located just a block from the non-stop fun of Duval Street. This rental, with space for up to 10 guests, features an enclosed yard, private pool, furnished patio, and off-street parking for two...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    City Cay1 / 22
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Washer
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Air Conditioning
    • Wi-Fi
    • Parking
    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 2017
    We stayed for a week at City Cay. The location could not have been any better. The condo was supper clean and well maintained. We would definitely stay here again! It is a one...
    Reviewed August 1, 2016
    We loved City Cay. It was a small condo with one king bed, a futon and a small kitchen, but it was exactly what we needed. The bed was super comfortable. The bathroom was...
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    About this property
    Recently renovated, modern and cozy upstairs apartment with a large balcony overlooking the neighborhood Looking for a cozy, quiet spot for just the two of you with all the modern conveniences of home? This lovely Truman Annex Condo is the place! City Cay is our 1-bedroom 1-bath upper level...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Unwind for a week in this Florida Keys canal-side duplex, which offers a newly added 30-foot dock and fish cleaning station for the angler in the family, and access to the Cabana Club's pool and beach for those who'd rather catch rays instead of fish. A stay in this home includes complimentary...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    101 Sombrero is a stunning waterfront property that offers you gathering areas to visit with your friends but still allows the opportunity to retreat to your own space with a private bed, bath, and kitchen. Each floor is appointed with colorful decorations as well as comfortable furnishings and...
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    Location Information
    Marathon, Florida Keys 33050
    Condo/Apartment - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unique 1 bedroom, 2 bath cottage is about to become your home away from home! Step in to a tranquil community on a quiet lane, only blocks to Duval Street and discover BOAT HOUSE! This spacious cottage with a large private covered deck, just perfect for enjoying an afternoon cocktail or a...
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    Location Information
    Stock Island, Florida Keys 33040
    Rental Home - 1 Bedroom, 2 Bathrooms, Sleeps 2
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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
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
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    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Location Information
    Key West, Florida Keys 33040
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Wi-Fi
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    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Main House, a fully furnished 2-bedroom split-level house facing the bay. Features include private patio and barbecue, two dining areas and a large living room. The masters bedroom located at the top of the stairs contains 2 queen size, large closet, and an adjoining bathroom. The neighboring...
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    Location Information
    Key Largo, Florida Keys 33037
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Centrally Located Waterfront House Sleeps 12 Large Dock1 / 20
    (2)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Private Yard
    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    This is my home away from home. It's a great location to relax but not too far from everything. I look forward to renting this in the future for my next family trip and bring...
    Reviewed July 24, 2018
    I cannot say enough about this place! 2 couples with kids had the best time this past week at The Escape to Marathon. It was our first time down in Marathon Florida and we were...
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    About this property
    Escape to Marathon in this large 5 bedroom 3 bath waterfront home in the heart of Marathon Florida. This clean home is bright and spacious with a large open living space perfect multiple couples or large families. This unique Florida Keys home has two finished levels so the family/group can spend...
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    Location Information
    Marathon Shores, Marathon 33050
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space. A quintessential cigar makers shotgun style house built circa in 1890s. Located in one of the most desirable historic neighborhoods of Key West – The Meadows with tree-lined...
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    Location Information
    Stock Island, Florida Keys 33040
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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