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Florida Keys Villas

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    Travellers to Florida Keys are booking March dates now. Secure your holiday rental today, and have the perfect trip.
    61 Matching Rentals in Florida KeysView all 1,525 rentals
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    Serenity Waterfront-Dock, View, Tiki Hut, spa/hot1 / 22
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    CORAL LAGOON RESORT NO. 3 WITH DOCK1 / 17
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Florida Keys Beautiful 2B 2B Townhouse1 / 18
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
    • Wi-Fi
    • Grill
    • Waterfront
    • Cable/satellite TV
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In the heart of tropical key largo, Port Largo Villas has an atmosphere of a 5 star resort with its own sandy beach and within walking distance to Marina Del Mar (305.451.4107 call Dock Master to reserve slip). For the water enthusiasts, it doesn't get any better for sportfishing, diving,...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LUXURY KEYS HOME IN PARADISE-106 ANGLERS REEF1 / 25
    (1)Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Waterfront
    • Grill
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    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 November 2016
    Everything we expected and more!! Condo very well maintained. Very adequately supplied with everything you need during your stay. Wonderful!! Thank you Susie and Matt for...
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    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Waterfront luxury Villa (51) with sunset views and boat slip1 / 22
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2017
    Unit 51 faces the water and Indigo Reef is very well maintained. Unit had porches up and down but bring bug spray. Complex is on flight path for Marathon Airport so small...
    Reviewed 7 October 2015
    Had a lovely couple of weeks in this villa,could not fault anything everyone very friendly including owners who were also very helpful would definitely stay again if visiting...
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Luxurious 3bd/3bth Villa - Your Keys Escape1 / 30
    (8)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 July 2016
    I stayed in this condo for a week with my 3 children (ages 12, 19, and 20) and a friend and her child (age 20). The condo was located near all that we wanted to explore in...
    Reviewed 24 November 2014
    Really enjoyed this home, clean,secure, owner answered all questions in a timely fashion. Highly recommended!
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    About this property
    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Indigo Reef, 32' dock, Marathon FL1 / 10
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Internet Access
    • Washer
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 August 2016
    Repeat customer. This is premiere property for location, views, amenities and well rounded stays. Property is well maintained and serviced, facilities for boating, fishing...
    Reviewed 13 August 2015
    it was just a great place , we just loved it there , the location to all , the pool and marina was just great , and the sunsets with a drink were just wonderful.
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    About this property
    Luxurious direct bayfront townhome with dock, upgraded unit. best location in the 50's overlooking large green yard and open bay with slip in front. 3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat, beautiful pool, mins to ocean through vaca cut. 1 king, 1...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Washer
    • Waterfront
    • Cable/satellite TV
    • Internet Access
    • Patio
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fully renovated Spa Villa with 2 bedrooms and 2.5 Bathrooms. The Villa has new furniture, stainless steel appliances, flat screen TV's and new wood floors. Come and relax in the accommodations our Villa has to offer.The Villa has an open room concept with the Kitchen open to the Living Room which...
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    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront luxury Villa (34) with sunset views and boat slip1 / 12
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    Great location beautiful grounds wonderful condo everything you need is there will definitely be renting this condo again this was our 2nd year and we are already planning to...
    Reviewed 10 November 2016
    Excellent stay we will definitely be back! Excellent community. Unit was well stocked and very clean! We had a great time!
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    TROPICAL RETREAT IN THE HEART OF KEYS ( OPEN FOR RENTAL SURVIVED HURRICANE IRMA1 / 12
    (6)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 25 November 2017
    In the middle of the keys. Good central location. Splash pool nice touch! Can access canal with paddle board.
    Reviewed 27 August 2017
    In 1996 we were married by my father-in-law on his boat outside the Duck Key marina, and spent our honeymoon and celebration at Hawks Cay Resort. Amazing experience for a small...
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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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quiet Open Water On Wild Life Sanctuary1 / 20
    (5)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    • Grill
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 December 2017
    We spend a 6 days in this well kept place close to a state park. It is best suited for a couple, although it has two beedrooms and can keep 4. Despite all the damage that the...
    Reviewed 16 January 2017
    Having stayed in most of the Keys over the years. We (Wife,son, and brother in law from England) found Jerry's rental just as advertised. You are right on the water. Enjoyed...
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    About this property
    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your living room sofa, only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these...
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    Location Information
    Marathon, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Studio has a King-size bed as well as a pull out futon in the living room. We can accommodate 2 adults and 1 child under12. This Villa is literally 10’ from the water and has a combined living and dining area. The Villa has a kitchen equipped with microwave, coffee maker, toaster,...
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    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Waterfront luxury Villa (60) with sunset views and boat slip1 / 42
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2016
    Really there is not one bad or negative thing to say about this place. Everything you need is there for you. Indigo Reef is centrally located to just about everything in the...
    Reviewed 20 December 2016
    house marina the central place i recommend it.spend a good holiday.with children or single couples special all.
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Marathon, Florida Keys 33050
    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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    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
    View all property information
    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Waterfront luxury Villa (43) with sunset views and boat slip1 / 16
    (25)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2017
    My family of 6, 2 couples and 2 ten-year olds stayed in unit #43 for a week. The townhouse was perfect. Everyone had their own space and there was a huge living room for...
    Reviewed 4 April 2017
    Our family had a wonderful stay at indigo reef. It's a lovely place with great sunset views, and Marathon is a good location for exploring the Keys. We liked it so much we...
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Balcony
    • Waterfront
    • Grill
    • Central Heating
    • Terrace
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'SOMBRERO HEAVEN' ~ Brand New, Designer Decorated and Perfectly Appointed 4-Bedroom (1 King, 3 Queens, Pull Out Couch), 3-Bath. Private Pool Villa with Neighborhood Ocean Front beach and Second Story Screened Balcony that Over Looks Private Pool and Canal! Everything you need for the perfect keys...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • DVD Player
    • Patio
    • Ocean Views
    • Washer
    • Central Heating
    • Housekeeping Included
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Complete paradise on the Gulf of Mexico!! This townhome has two full bedrooms and two full bathrooms upstairs with a half bath downstairs. Fully furnished with quality furniture with a kitchen fully stocked with crate and barrel items. All linens and towels are there so just bring your clothes...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Waterfront luxury Villa (59) with sunset views and boat slip1 / 16
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2018
    We thoroughly enjoyed our time here! The house was extremely clean and well appointed. All the necessities we needed for a long weekend were provided, and all we needed to do...
    Reviewed 4 August 2014
    The accommodations were excellent. The docking was safe and convenient to the Gulf. There was plenty to do on the property. Beds were comfortable. Linens were fresh and the...
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Quiet Open Water Retreat On Nature Preserve1 / 25
    (6)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Internet Access
    • Air Conditioning
    • Outdoor Dining Area
    • Grill
    • Washer
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 August 2015
    Jerry, the property owner, is an ABSOLUTE dream to work with. He answered all of my questions including recommending restaurants that served vegetarian options. He even meets...
    Reviewed 30 June 2015
    My wife and I decided to return to The Keys this summer and we decided to return to this place. I honestly have nothing bad to say about this place. Jerry is a gracious host who...
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    About this property
    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your private deck only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these environmentally...
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    Location Information
    Marathon, Florida Keys 33001
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront luxury Villa (54) with sunset views and boat slip1 / 12
    (7)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Parking
    • Terrace
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Heated)
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 January 2017
    Each summer our family attempts to find that perfect spot in the Keys for our family of 5. We have stayed many places, Ocean Reef Club, Hawks Cay, Tranquility Bay...each had...
    Reviewed 29 February 2016
    My family (2 adults and 3 children, 18, 14, & 12) stayed at this beautiful property Christmas week. It was wonderful. The community is amazing. The location is mid-way...
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Waterfront luxury Villa (29) with sunset views and boat slip1 / 15
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    ***NEW 3D Tour Indigo Reef Luxury Villa Exquisite 'Latitude Adjustment'! #331 / 42
    (2)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 4 weeks ago
    Latitude Adjustment @ Indigo Reef in Marathon Florida is a remarkable place. In preparation of our arrival, the property managers were a delight to work with. Upon our arrival...
    Reviewed 16 December 2017
    We booked Latitude Adjustment for an early December diving trip to the Keys. Initially, we were a bit concerned as this was a new rental and as such, did not have any reviews...
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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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Waterfront luxury Villa (30) with sunset views and boat slip1 / 17
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2016
    This townhouse was the perfect place to bring 5 friends for an awesome fishing vacation. The place is spacious, has great views and is close to plenty of great fishing spots...
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    About this property
    This spacious three bedroom, two and a half bath Villa will make you feel right at home.  Each bedroom has it's own television, with a 60” flat screen TV in the living room. The Villa has direct sunset views looking out to the Gulf of Mexico, which can be enjoyed from the porch or upper balcony....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Balcony
    • Internet Access
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relax in this peaceful, open-water, bird and wildlife sanctuary with private views of the State Park. From your patio look-out, only 9 feet from water's edge, you can watch fish swim and birds fly, or if you prefer, you may simply sit and enjoy the ebb and flow of the tide. In these environmentally...
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    Location Information
    Marathon, Florida Keys 33001
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
    • Parking
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    **Property undamaged by hurricane Irma, perfect for relief workers and service crews!!!** There is no better option for your next Florida retreat than this fantastic Marathon vacation rental townhouse on Pirate's Playground at Hawks Cay community. Boasting 2-bedrooms, 2-bathrooms and...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Tropical Retreat With Sandy Beach1 / 16
    (13)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    • Internet Access
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 November 2017
    We just finished a week at Alamar on the Bay and couldn't have been happier there. The cottage was just as described, one bedroom with a queen bed and attached bath and one...
    Reviewed 24 August 2017
    This was absolutely perfect for our 3 teens, husband, and I. The location was the best. We slept and relaxed well. I would visit the very same place next time.
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    About this property
    Tropical villa surrounded by lush tropical foliage. Villa with patio overlooking the open water, with sandy beach is great for a family vacation. Two bedroom, two bath, ground level home, one queensize bed in master and two twin beds along with a queensize sleeper sofa in the livingroom. The...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Patio
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area...
    Reviewed 5 November 2012
    We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach...
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    About this property
    Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Waterfront
    • Washer
    • DVD Player
    • Internet Access
    • Balcony
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Escape to this 2BR/1.5BA waterfront Duck Key villa boasting two balconies overlooking the aquamarine ocean with breathtaking sunset views. Your two-story end unit features nautical-inspired design elements paired with lots of natural light and privacy. Easily access nearby...
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    LITTLE BAY - Cottage1 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2016
    Stayed in the cottage, 5 of us in total. Gorgeous cottage inside and out, set on a fabulous site with beautiful trees, shrubs, birds, green grass, stone paths, lots of parking...
    Reviewed 29 May 2013
    The pictures really don't do this place justice, there are so many comforts that it feels more like a home. It is in a great location and since it is gated, it was safe enough...
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    About this property
    Minimum Rental: 7 Days 'Little Bay's Cottage' is one of three rental units on this property. The cottage is a ground level dwelling separate from two duplex units. It offers a unique floor plan with the main living area in the center of the house with kitchen, dining area, sitting area and a...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    SUNSHINE PLACE1 / 23
    (7)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We were thoroughly satisfied with the sunshine house and staff. We will continue to return when we can.
    Reviewed 14 May 2016
    Having been acquainted with the area and having been, physically, all 'round the property, occasionally, but never in it - it was a shocking and wonderful surprise that this...
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    About this property
    Minimum Rental: 7 Days 'Sunshine Place' is setup perfectly for privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Private Garden
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Live your tropical dream at this palatial oceanfront estate. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about every convenience you can imagine, as well as some you probably haven't even considered. Enjoy a swim in the pool that...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    This 3 story condo had plenty of space for the four of us. The beds were great, sturdy and comfortable as was the living room furniture. We had a driveway to park the car, and...
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    About this property
    An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largos newest oceanfront gated destination, with some of the most...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 7 Days Little Bay's Lower Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Front 3 bedroom 3 Bath Villa1 / 14
    (2)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 April 2017
    Literally on the beach...which was fantastic! Also, one of the few places we were able to obtain less than a week rental.We were 2 families and the place was larger than I...
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    About this property
    ALL of our villas overlook the ocean, and the beach is just steps away! 3 Bedroom, 3 Bath villa directly on the beach with 2200 square feet of oceanfront living. Gorgeous views of the ocean from the living room, dining & kitchen, and master bedroom! When you step into the main living level, your...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Central Heating
    • DVD Player
    • Patio
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful spacious 2 bedroom villa with 2 full bathrooms and a fully equipped kitchen. Has a balcony and in room safe. Heated outside pool with tikki bar. on sight laundry facilities and elevator. BBQ grills . boating, canoe / kayaks and wave runner etc. Internet access and fitness room. Lots of...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    OPEN Endless Bay Views...  Villa on Private Beach and Dock in Islamorada1 / 34
    (27)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Waterfront
    • Air Conditioning
    • Washer
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    Every part of our experience with this rental was beyond exceptional. The owners were always quick to respond prior to our arrival with any questions that we had. Our flight was...
    Reviewed 15 January 2017
    I was looking for somewhere where we could celebrate big birthdays and a once in a lifetime holiday. We have just returned and I did not want to leave, the Garden Villa was...
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    About this property
    Centrally located at MM 75.5 in beautiful Islamorad, you are only minutes from boat ramps , great restaurants, beaches, shopping, fishing, diving, snorkeling, bike riding, etc. We provide bikes, kayaks and you can snorkel right from our dock. There are some resident iguanas in our mangroves and...
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Hot Tub
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3 Bedrooms, 3 Bathrooms, Sleeps 6 MINIMUM STAY REQUIRED - NOT A SHORT TERM RENTAL - PLEASE CONTACT US FOR SPECIFIC DATES, AVAILABILITY AND RATES. Every time we stay, we never want to leave. 3 story bayside villa with its own beach. Great location. Views of both the Bay and the Ocean. Three good...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Wi-Fi
    • Ocean Views
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa (Half Duplex), three bedrooms / two bathrooms plus a loft and a crow's nest area with great views. Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. There is approximately 50' of deep-water dockage with access to...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hammocks at Marathon is the Florida Keys at its best. Just off the only All-American road in Florida, The Florida Keys Overseas Highway, the entrance road envelops you in lush tropical foliage and Caribbean music greets you at the door. The glass-enclosed lobby is impressive with its 30-foot...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Laidback and lovely Situated right by the water, Mahogany Bay is both splendid and soothing. You enter into an open-plan living area, which has white walls, stone floors and wide windows. In one corner is the kitchen – full of glossy wood and marble, with a breakfast bar and a dining table. The...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    Licensed 2/2 Villa in Key Largo's Most Upscale Oceanfront Resort - Secured WiFi!1 / 38
    (6)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Parking
    • Internet Access
    • Hot Tub
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 September 2016
    We stayed here the first week of September and found the location conveniently located, well maintained and great value. Our 10 yr old daughter loved the oasis pool. We would...
    Reviewed 19 March 2013
    We were very pleased with our stay in this villa. Mariners Club is nicely landscaped, had wonderful pool, nice hot tub, and was a very safe area. It was a good location for Key...
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    About this property
    An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largo's newest oceanfront gated destination, with no other private...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Southern Diversion Estate Key Largo fall Special open for business post irma1 / 33
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 17 Quick View
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    • Grill
    • Internet Access
    • Cable/satellite TV
    • Porch
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 February 2016
    My family & I stayed here from January 27 thru February 3rd. I had my wedding here on January 30th. This estate was absolute perfection! The Keys is a "mixed bag&quot...
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    About this property
    Southern Diversion Estate Key Largo - Brand New private gated 1 acre estate on the ocean with private beach, tiki hut , tropical private pool and deepwater dockage. There is 105ft of deepwater dockage. Docks provide up to 100amp service and water. There is a deepwater channel right to the dock...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 17
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Sauna
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    AVAILABLE FEBRUARY 5-12, 2018 SLEEPS 6 Charming vacation destination that will give you a lifetime of good memories. Idyllic combination of clear, azure waters,bright Florida sun, some of the best salt water fishing anywhere. Clean and comfortable, dozens of restaurants. Have a drink at the Tiki...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Key Largo Ocean Front Villa with Incredible views1 / 16
    (27)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Cable/satellite TV
    • DVD Player
    • Patio
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2017
    We had a great time in the property. It isn't fancy, could be updated, but we enjoyed every moment. We arrived late in the evening and Norman was there waiting for us. On...
    Reviewed 10 October 2016
    First off Norman the owner met us at the condo for check in and then he showed us around the entire area and pointed out the good spots and where to snorkel and swim which were...
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    About this property
    2 bedroom, 2 bathroom Ocean Front Villa in Key Largo sleeps up to 6. It was completely renovated in 2013. It has dockage for boats up to 50 feet. This Villa is 20 feet from the Ocean and has a private beach 50 feet from the patio. We provide a golf cart, Kayaks, fishing equipment, tennis...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come to Paradise and Enjoy it with Comfort! Located on Mile Marker 87 in Islamorada ( Fishing Capital of the World ), part of the Wonderful Florida Keys. Executive Bay Club is a Private Gated Community with 24 Hr Security, Heated Pool and Club House, Tennis Courts, Private Beach, Fishing off your...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • DVD Player
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset Villas, located on a small quaint island called Conch Key (mile marker 63 - between Marathon and Islamorada), offers quality, affordable 1-bedroom and 2-bedroom OPEN WATERFRONT vacation rentals. The one bedroom (700 square feet) has a King size bed as well as a pull-out futon. The two...
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    Location Information
    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • DVD Player
    • Balcony
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Sunset Villas, located on a small quaint island called Conch Key (mile marker 63 - between Marathon and Islamorada), offers quality, affordable 1-bedroom and 2-bedroom OPEN WATERFRONT vacation rentals. Each one or two bedroom villa includes complimentary deep-water dockage (park your boat right in...
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    Location Information
    Conch Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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