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Florida Keys Villas

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    Travellers to Florida Keys are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    64 Matching Rentals in Florida KeysView all 1,233 rentals
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    Tropical Retreat With Sandy Beach1 / 16
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 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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    Indigo Reef, 32' dock, Marathon FL1 / 10
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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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 December 26, 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 December 19, 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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    April 9th-14th Available1 / 12
    (7)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
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Serenity Waterfront-Dock, View, Tiki Hut, spa/hot1 / 66
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 6, 2016
    Wonderful vacation nice, relaxing. I would definitely return. Charlie was very informative on where to go to eat. Locals were very nice too.
    Reviewed October 16, 2015
    What a great little spot! Was quiet and very peaceful. Clean and cozy! Had everything we needed. Will be back to Stay again soon! :)
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    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas...
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    Islamorada, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Waterfront luxury Villa (51) with sunset views and boat slip1 / 23
    (9)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 May 8, 2018
    The villa was fantastic for our family vacation! Clean, spacious and comfortable. The views from the numerous balconies were breathtaking! We will definitely be back!
    Reviewed March 12, 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...
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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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    Waterfront luxury Villa (43) with sunset views and boat slip1 / 17
    (25)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Wi-Fi
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 2, 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 April 3, 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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    Waterfront luxury Villa (59) with sunset views and boat slip1 / 17
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Grill
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 15, 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 August 4, 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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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    No dockage allowed. Florida Keys. Beautiful condo. Short walk to the beach area.1 / 18
    (7)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Washer
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2016
    This was our first trip to Florida, it was agreed that we would leave Orlando and the parks for a few years as our children are still quite young (4 and 1). We did extensive...
    Reviewed January 18, 2016
    We had very nice time staying in Ana's townhouse in Islamorada. It is nicely decorated, well equipped, comfortable and spotlessly clean. There is more than enough room for a...
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    About this property
    Our unit is a short walk to the beach and dock... No view of the ocean from our unit. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a private beach 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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    Waterfront luxury Villa (34) with sunset views and boat slip1 / 14
    (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 January 16, 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 November 9, 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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    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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    Luxurious 3bd/3bth Villa - Your Keys Escape1 / 30
    (9)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 March 25, 2018
    For months I had been trying to figure out how my family & I could take a vacation together with kids & grandkids and this house in the Keys was perfect! We all had an...
    Reviewed July 27, 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...
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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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    Waterfront luxury Villa (54) with sunset views and boat slip1 / 13
    (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 January 12, 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 February 28, 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 (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 January 24, 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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    A quiet spot in paradise close to fishing with dockage included (#4)1 / 13
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 28, 2018
    Best view in the Keys! Extremely clean and spacious! Owners very attentive and friendly! Had the most relaxing holiday weekend! Recommend without a doubt and will be back!
    Reviewed May 17, 2018
    Awesome spot, Owners gracious and very helpful with local attractions.Would love to book for next year.
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    About this property
    This second floor 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 situated facing due West right on the water and has a combined living and dining area. The Villa has a kitchen equipped with microwave, coffee...
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    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Washer
    • Waterfront
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Anglers Reef Villa Resort 2 Bedroom and 2.5 Bath Villa, in Anglers Reef with Boat Slip. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 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
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 9, 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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    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 December 17, 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 January 15, 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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    Marathon, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    ***NEW 3D Tour Indigo Reef Luxury Villa Exquisite 'Latitude Adjustment'! #331 / 42
    (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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Waterfront luxury Villa (29) with sunset views and boat slip1 / 16
    (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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    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 July 2, 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 November 5, 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, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Patio
    • Ocean Views
    • Cable/satellite TV
    • Grill
    • Washer
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef with Boat Slip. An upscale gated community with resort living in the Florida Keys. Everything you need for your vacation is here,: gorgeous private beach, heated resort style pool, private back yard patio with barbecue, front porch seating, balcony,...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 29, 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 May 28, 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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    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 August 9, 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 June 30, 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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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
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    • 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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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
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    • Ocean Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spacious and charming villa featuring 3 bedrooms, 2.5 baths and 1600 sq/ft of living space at one of the Florida Keys most prestigious resorts, Indigo Reef. Magnificent views from the villa with a 31 foot dock and accommodations for up to 8. Step out of your Luxurious Master Suite and step into...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Gorgeous Spa Villa, Marina in Florida Keys1 / 90
    (14)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Hot Tub
    • Patio
    • Air Conditioning
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    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 10, 2017
    Everything was great, but the spa didn't work. My wife and I enjoyed the visit the rental was centrally located
    Reviewed March 20, 2017
    Location was great if you want to explore all the Keys. Great dock to sit out back to fish or just relax and look at the water. Everything was just as stated. Perfect for our...
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    About this property
    Preferred Style and Furnishings are in this beautiful Spa Villa! Tucked along a deep harbor, with direct boat access to the Atlantic Ocean (boat slips available from Hawks Cay Marina). Embracing the most alluring qualities of the Florida Keys—beauty, relaxation, and turquoise waters in this luxury...
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Hot Tub
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    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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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • Washer
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    • Hot Tub
    • Grill
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Stay at the hammocks right on the water in beautiful Marathon Fl. The 2 bedroom villa has a king size bed in the master bedroom and 2 twins in the guest bedroom . Also a pull out sofa bed. includes 2 full size bathrooms and a full size fully equipped kitchen. A balcony and DVD player. On sight...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Conch Key Villas Unit 2 Spectacular open water views!1 / 16
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Grill
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 14, 2018
    We had a wonderful week stay at the Conch Key Villas. I would highly recommend Conch Key Villas to anyone and everyone. The owners Stewart and Katie are absolutely fantastic...
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    About this property
    We live onsite and do our best to make sure you enjoy your a relaxing vacation. Welcome to Conch Key Villas! We are located in the heart of the Florida Keys. Conch Key is a quiet island where relaxing is a way of life. When you first walk through our entrance gate you know you made a great...
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    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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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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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
    • Waterfront
    • Washer
    • DVD Player
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    PROPERTY OVERVIEW Escape to this 2BR/1.5BA waterfront Duck Key villa boasting breathtaking aquamarine ocean and sunset views from a private patio and balcony. Your two-story end unit features nautical-inspired design elements paired with lots of natural light and privacy. Pick up a local...
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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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
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    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 17, 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 January 15, 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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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Village at Hawks cay1 / 20
    (2)Average
    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
    Reviewed March 28, 2018
    Because of all the hurricane damage from Irma last fall, we weren't sure what to expect, however, we absolutely loved this condo and the area. It seemed brand new; all new...
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    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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    Location Information
    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    SUNSHINE PLACE1 / 23
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
    • Grill
    • Internet Access
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Comfortable bed, sofa not so comfy. Clean and well decorated. Boat dock very close to house. Nearby boat ramp usable during high tide. Gated driveway for added security. Nice...
    Reviewed April 2, 2018
    My husband and I have been visiting Islamorada for the past 5 years. This year we stayed at Sunshine Place for the month of March. Loved it! Great views! Private yet close to...
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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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    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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    Key Largo Ocean Front Villa with Dock and 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 January 15, 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 October 9, 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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    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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    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
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    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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    Keys Kottage / Bayside1 / 3
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
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    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 13, 2018
    Islamorada is our place. It's the perfect combination of activities: relaxation, shopping, restaurants, fishing, boating, etc.. We have been coming to the Keys for about 10...
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    About this property
    Keys Kottage Villa is located in beautiful Islamorada, Florida Keys. We are on mile marker 82. Private Marina access and trailer parking available to guests. Bring your boat and or pet. We can accommodate up to 26 ft. vessels. This is a Fisherman's dream for a week of fishing. Please call for...
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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, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A convenient hideaway for your Key West and Lower Keys adventures, this two-bedroom condo is tucked into a quiet complex near shopping, bars, live music, beaches, and Mallory Square. Cozy, fully-appointed rooms include everything you'll need for your Key West vacation but your own clothes. With...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Southern Diversion Estate Key Largo fall Special open for business post irma1 / 26
    (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 February 7, 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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    Licensed Manager W/10 Rentals Available - 4/3.5 Villa - #1 KL OCEANFRONT RESORT1 / 94
    (9)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Hot Tub
    • Washer
    • Air Conditioning
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We stayed in a large four bedroom 2 story unit, close to all the activities, fishing, scuba, snorkeling, and great restaurants. It is in a private, secure area with a couple...
    Reviewed December 27, 2016
    This was a dream come true! My husband, my 74 yr old mom w/ dementia, our 2 sons, and a son's girlfriend... 6 total. We had the time of our life! The home was very...
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    About this property
    This is just 1 of 10 different Licensed Key Largo Vacation Rentals that I manager for you to choose from. So if your dates are not available for this unit, email me your requested dates and I will let you know which other units I have available. An island paradise situated in the heart of Key...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Licensed Manager W/10 Rentals Available - 2/2 Suite - #1 KL OCEANFRONT RESORT!1 / 39
    (7)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 May 25, 2018
    There are many comparable rentals in the area, but management makes all the difference. The unit was clean, spacious and well-stocked. Fernando was very helpful and made the...
    Reviewed September 7, 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...
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    About this property
    This is just 1 of 10 different Licensed Key Largo Vacation Rentals that I manager for you to choose from. So if your dates are not available for this unit, email me your requested dates and I will let you know which other units I have available. An island paradise situated in the heart of Key...
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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 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come visit old town Key West for the Sunset Celebration on Mallory Square while enjoying entertainment, dining and shopping along Duvall Street...This historical city has much to see & do...Water sports of every kind...Swimming, boating, fishing and much more...or...Just relax at your resort around...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Licensed Manager W/10 Rentals Available - 3/3 Villa - OCEANFRONT BEACH RESORT!1 / 40
    (6)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Balcony
    • Air Conditioning
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 2015
    Although we travel to The Keys on a pretty regular basis, this was the first time we opted to stay in Key Largo. The whole complex is well maintained. Some aspects of the...
    Reviewed March 14, 2015
    Beautiful location. Salt water lagoon for swimming and feeding fish located at the back door and outside the screened in porches. Two heated pools, one located steps away from...
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    About this property
    This is just 1 of 10 different Licensed Key Largo Vacation Rentals that I manager for you to choose from. So if your dates are not available for this unit, email me your requested dates and I will let you know which other units I have available. If you want to experience the true meaning of a Key...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    the private & secluded Peninsular house off Grassy Key harbor.1 / 36
    (36)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 6, 2018
    Just got home to freezing northern Wisconsin from a week at this wonderful home with my husband and 5 adult or adult-size children. Convenient and private location between Key...
    Reviewed November 21, 2017
    The Peninsular house in Grassy Key .....What Can I say other than perfect. It has the most beautiful setting , looking out every morning hearing the water was so tranquil and...
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    About this property
    An attractive house with heated pool/spa plus new Hot Tub for 6/7 persons, boat dock & beach, in a unique tucked away, completely private location. The Peninsularhouse only rents Sat to Sat. check-in at 3pm, check-out at 10am the following Sat. 8 Kayaks on site,doubles & singles inc.catamaran...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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