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Florida Keys Villas

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    60 Matching Rentals in Florida KeysView all 1,518 rentals
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    Tropical Retreat With Sandy Beach1 / 16
    (15)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Indigo Reef, 32' dock, Marathon FL1 / 23
    (5)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    FALL SPECIAL STAY 4 NIGHTS GET 5TH NIGHT FREE1 / 12
    (8)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 May 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 18 May 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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    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 26 March 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 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...
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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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    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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    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 8 May 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 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...
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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 14 June 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 19 January 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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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    CORAL LAGOON RESORT NO. 3 WITH DOCK1 / 17
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Ocean Views
    • DVD Player
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2018
    Great house for our family of 5. We stayed for 3 nights following a busy 2 weeks in Disneyland and were able to relax and slow our pace down here. The house was well equipped...
    Reviewed 2 August 2018
    This place was quite lovely & very accommodating. We needed a couple extra towels & a blanket, we contacted the property manager about this & they delivered them...
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    About this property
    No. 1 rated resort in Marathon Completely renovated w/ dock. We will be ready to take reservations for Thanksgiving. 3 bedrooms 1 King, 2 queens and a queen size sleeper. 2.5 bathrooms. Walking distance to Marathon and Key Colony activities. Representing a new concept that offers...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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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    Marathon, Florida Keys 33001
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Patio
    • Washer
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. 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 terrace with barbecue, front porch seating, balcony, and dock....
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 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 (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 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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    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 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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    ***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 27 February 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 27 February 2018
    Our family just returned from our vacation and we can't wait to go back. Latitude Adjustment is a beautiful property, inside and out. We thoroughly enjoyed sitting on the porch...
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    About this property
    Your toes dipping into warm turquoise waters. Lounging contentedly by the pool. Breathing in the magnificent views. Being mesmerized by the gently swaying palms. Strolling along the elegantly sweeping grounds. Immersing yourself in the beautiful designer accommodations. An exciting 3D Virtual...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Gorgeous Spa Villa, Marina in Florida Keys1 / 35
    (19)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Hot Tub
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Loved this apartment. Hawks Cay is such a great property. So many activities for my little one. Wife tried out the spa and she loved it. I was a little bummed that the marina...
    Reviewed 4 weeks ago
    We have been staying at Silvia's beautiful and charming Villa #7027 for a few years now, but this year was extremely special for us. Last year we also stayed at Villa #7027...
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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. Embracing the most alluring qualities of the Florida Keys—beauty, relaxation, and turquoise waters in this luxury villa featured with dock where you can fish...
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    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 3 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. 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, and dock. Boat...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 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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    • 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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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Parking
    • Private Garden
    • Private Outdoor Pool (Heated)
    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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    Key West Vacation Rental - The Duval Street Compound1 / 28
    (3)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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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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    • 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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    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. 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,...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • 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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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • 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....
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 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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    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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    Amenities & Details
    • 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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    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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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 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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    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
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    • 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Terrace
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    • DVD Player
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    • 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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    Duck Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Ocean Views
    • Hot Tub
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    • 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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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    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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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Balcony
    • Waterfront
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    • Central Heating
    • Terrace
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    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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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    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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    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
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • 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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    LITTLE BAY - Cottage1 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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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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    Licensed Manager W/10 Rentals Available - 3/3 Villa - OCEANFRONT BEACH RESORT!1 / 80
    (6)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Wi-Fi
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    • Waterfront
    • Balcony
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 August 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 15 March 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 / 22
    (41)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 29 July 2018
    So glad we stumbled upon this listing! Dave and his son were so welcoming when we arrived, and everything one could need for fishing, kayaking, and paddleboarding, was all...
    Reviewed 7 January 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...
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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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Central Heating
    • Washer
    • Grill
    • Waterfront
    • Terrace
    • DVD Player
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2 Bedroom and 2.5 Bath Villa, in Anglers Reef. 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, back yard patio with barbecue, front porch seating, and balcony. Boat slip can be...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    SUNSHINE PLACE1 / 23
    (12)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We loved this condo in a beautiful location with excellent amenities. Spotlessly clean and very comfortable.
    Reviewed 22 August 2018
    Beautiful property! A piece of paradise in Islamorada. Great service from the Keys Holidays Rentals team. We will come back to this piece of heaven.
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    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, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Waterfront
    • Washer
    • 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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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 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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    Licensed Manager W/10 Rentals Available - 2/2 Suite - #1 KL OCEANFRONT RESORT!1 / 78
    (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 25 May 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 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...
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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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    • Wi-Fi
    • Patio
    • Grill
    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    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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    Licensed Manager W/10 Rentals Available - 3/3.5 Villa - #1 KL OCEANFRONT RESORT1 / 37
    (1)Very good
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Private Garden
    • Secure Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 February 2018
    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
    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 - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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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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