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Florida Keys House Rentals

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    Travellers to Florida Keys are booking March dates now. Secure your holiday home today, and have the perfect trip.
    662 Matching Rentals in Florida KeysView all 1,173 rentals
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    Blue Bungalow1 / 16
    (17)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    4 Bedroom 2 Bath With Ocean View and with hot tub1 / 28
    (8)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 8 w/ 60 Feet of Dockage1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2018
    This rental was simply amazing. The house was emaculant, cleaner than anywhere we have ever stayed. Every detail was laid out for us. The beds were comfortable, the house was...
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    About this property
    Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of Dockage in Marathon, FL, the heart of the Florida Keys. A newly renovated 2 bedroom & 2 bath home that sleeps 8. The boat ramp is 300 yards away and plenty...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Florida Keys Beach Home Pool Fishing Diving1 / 36
    (33)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 November 2018
    The good:Great beach, very clean, machine cleaned during the night Great location in close proximity to good bars, restaurants and cheap bus transportation to the KeysClean...
    Reviewed 15 September 2018
    The place was very nice. Staff were kind and very helpful. Everything was perfect.We had a good time in Marathon.
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    About this property
    2 bedroom 2 bathroom vacation villas on Atlantic Ocean. This is Tropical Island villa, one of the villas located close to the office and tennis court and has a Garden View. It is within less than 1-minute walking distance to the beach, pool overlooking the ocean and Jacuzzi. Heated pool...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    OUTSTANDING Oceanfront House with Pool and Deep water dockage!!1 / 45
    (20)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Washer
    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2017
    You know when you find a great place to stay and don't want to tell anyone because you want to have a beautiful home to stay in. Ya this rental is like that. We didn't want to...
    Reviewed 10 July 2016
    This property is a can't miss ! It has everything including the most refreshing pool I have ever been in (and I have my own back home). Well appointed kitchen, all the outdoor...
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    About this property
    Create a memory that will last a Lifetime! Never on the Rental Market before, this newly renovated Million Dollar House will become your vacation destination year after year. 4 bedrooms, 3 bathrooms, 28 foot Pool, 44 foot patio, 40 foot concrete pier, endless views, and privacy. You can bring your...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Escape to Paradise in a Gated Tropical Bayfront Estate (Free Wifi)1 / 19
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 13 January 2018
    Loved the cottage, we had such a nice time staying here. It's a great Location, near a lot of nice restaurants and there is great snorkeling and kayaking nearby. Had a BBQ every...
    Reviewed 14 June 2017
    The best part about this rental is the bayside snorkeling and the fact that 2 double kayaks are included with the rental. You can kayak across the bay to the mangroves. The best...
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    About this property
    Tucked away on a gated tropical estate, is our 'Island Breeze Cottage'. This cottage is located in the middle of the Estate and steps away from our white sandy beach and those beautiful Gulf of Mexico sunsets !! There is a tiki hut on the beach. And a dock to fish from or go snorkeling right from...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Lovely Key Colony Beach  3/2 SFH, pool, 80' deep water dockage1 / 47
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Patio
    • Grill
    • Internet Access
    • DVD Player
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2018
    We rented this house the week of Christmas 2017. The house is older and could use some updates. The kitchen has some cooking implements, but if you are planning to cook a lot...
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    About this property
    Absolutely charming, warm and inviting home. Single family home on lovely 12th Street in Key Colony Beach with Cabana Club priviledges. Quick access to the ocean or gulf, with 80' of deep water dockage (with step down dock). Bait freezer, fish cleaning table, gas grill, hi speed wireless, 3 TV’s...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Paradise In Marathon, FL Keys Large Oceanside Home1 / 22
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2017
    We enjoyed our stay in this private home right in the heart of Marathon. It is within walking distance of the Cracked Conch restaurant which serves up great local fare and the...
    Reviewed 22 March 2017
    We had a great time staying at this house! Very comfortable for 7 people and the location was nice and convenient - close to supermarkets, restaurants, beach, etc. The owner...
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    About this property
    This house has everything! You can rent 1/2 or the whole house. The top unit has 2bd/ 2bths. Lower spacious unit has 1bd/1bth. Enjoy dinner on breezy upper or lower outdoor patios. This house is more convenient and offers much more than your ordinary 3/3. Each unit is very spacious, sleeps up to...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Sandy Beach, Direct Ocean, Pool, Dock & Lagoon1 / 34
    (33)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2018
    This house is amazing!! The view from the second floor is breathtaking but from the third floor window watch, it's spectacular!! The yard is very large with a lagoon, beach and...
    Reviewed 20 July 2018
    We found a little oasis of oceanfront paradise!! With meticulous attention to the lush grounds, this property rivals any luxurious resort.This spacious open concept home...
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    About this property
    WARNING: DO NOT WIRE MONEY Casa de Lida large estate with 3 separate buildings on almost an acre of land and is directly on the ocean . It is very private, has large sandy beach, a pool, a large dock and phenomenal views. The Kids will enjoy playing in the sand, and the adults will enjoy...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Bayside home with dock!1 / 29
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Air Conditioning
    • Washer
    • Grill
    • Cable/satellite TV
    • Wi-Fi
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 2016
    The house was pretty much like I expected, nothing fancy but it had everything we needed for the most part. One of the pros was the location. It was on the end of a canal and...
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    About this property
    Paradise point! This is a newly renovated (Spring 2014) home in a private gated community. Located at mile marker 106 on the bayside in Key Largo, this home is an ideal location for those looking to enjoy life on the water in the Florida keys. The home is situated for convenient access to...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    75130 Overseas Highway1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    We stayed here for a few days and it was amazing. The house is warm and cozy and has all the details you need when away from home. The beachfront is wonderful and can go...
    Reviewed 21 June 2016
    This two bedroom home was the perfect getaway for my husband and me. The cute sea-theme décor added to the cozy ambience. The living room/kitchen are flanked with a queen...
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    About this property
    Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs...
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront 2 Bedroom/ 2 Bathroom House located directly on the Gulf of Mexico !! This 2 Acre Estate is it's own private compound with a total of only 3 houses that are spread out throughout the property. Life doesn't get any better than looking out at the Gulf of Mexico from the Kitchen and...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Villa Sombrero, Marathon1 / 48
    (1)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 January 2019
    Easy access to fishing areas, Boat worked fine.Plenty of space for everyone.Large family group from Syracuse NY, Seattle Wa, and Kissimmee Florida.Had a great...
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    About this property
    Villa Sombrero is an exclusive and private waterfront destination in the heart of the fabulous Florida Keys located in Marathon. This unique retreat is perfectly positioned overlooking a natural preserve on a serene protected deep waterway; providing the discriminating yachtsman or sport fisherman...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Sip your coffee looking out to a tropical sunrise1 / 46
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Washer
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Air Conditioning
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 December 2018
    This home was perfect! It was our first time to the Keys and we couldn't have picked a better spot! This location was perfect and this home was spectacular!!! We wanted for...
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    About this property
    Picture yourself on a tropical island, half-asleep in a poolside lounge chair of your own private home, with sun-kissed skies and the sparkling blue Atlantic Ocean nearby. Feel your body succumb to the tropcial breeze as it gently cascades over you, draining your stresses away! It is not a...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    75731 Overseas Highway1 / 32
    (13)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada....
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    BUCCANEER'S DEN - 20Ft. of Waterfront w/ Dock1 / 26
    (13)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • Patio
    • Waterfront
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2017
    Cozy marina setting on a canal. Great seating area beside the docks where we watched boaters and paddle boarders. Great pool. Easy drive into Key Largo to enjoy great...
    Reviewed 17 May 2016
    Nestor was so helpful with instructions as we expected to arrive late. The unit is fully equipped with 2 a/c units and very quiet but only 10 mins from Key Largo. Had breakfast...
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    About this property
    IF YOU ARE BRINGING A BOAT LET US KNOW PRIOR TO BOOKING 20 FT. MAX. INCLUDING OUTDRIVE. COMMUNITY HAS SMALL BOAT RAMP, PLEASE DISCUSS BOAT SIZE IN ADVANCE PRIOR TO MAKING A BOOKING THERE ARE SIZE LIMITATIONS AT THE DOCK AND AT THE RAMP. WE CANNOT GUARANTEE SUITABILITY IF THIS IS NOT DONE IN...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • DVD Player
    • Waterfront
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy all the Keys have to offer in this quiet neighborhood location, 3 BR/2BA gulf front home! This home will offer you the perfect vacation with your family and friends. The “Gulfview Escape” is minutes away from Sombrero Beach or a little further, Bahia Honda State Park, both are Keys gems that...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 35
    (22)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2018
    This was our second stay at this beautiful rental that feels like you have your own resort. All the amenities are perfect and the owners couldn't be more accommodating. Highly...
    Reviewed 7 April 2018
    Our family has been coming to Marathon for the last 4 years. The Dolphin Oasis house fully exceeded our expectations. The attention to details on this property are second to...
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    About this property
    This 4 bedroom 3 1/2 Bath House has ample sleeping options for every type of family/friend gathering and provides parking for several vehicles. The newly installed heated pool with hot tub measures 40'x 16'. There is a Tiki hut right at pool side for visiting, Canal Side Beach area and Tiki...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    bayfront beach house with sandy beach1 / 15
    (28)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 January 2019
    We're a family of five adults who arrived on Dec 30th for four nights. The place is so beautiful and so comfortable that we did not feel like leaving to explore the area. The...
    Reviewed 2 January 2019
    House and property were very nice. Nice location. Would not hesitate to book again. Only complaint is we had to leave so soon !
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    About this property
    Spacious Key Largo bayfront home with sandy beach in tropical garden on one acre with spectacular bay views and sunsets. Relax on the large porch with ceiling fans. Sunbathe on the beach or enjoy water activities using the kayaks, fishing tackle FREE. Children will enjoy the beach and toys...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Straight shot to the Atlantic Ocean!1 / 46
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2018
    House was beautiful, all amenities perfect, highly recommend it. We definitely consider renting again.
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    About this property
    Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most memorable vacation you will ever experience. Very stylish, newly built, modern home of 2700 square...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    76004 Overseas Highway1 / 23
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 December 2018
    It was perfect- ideal location on the waterfront in Islamorada which is easily the best part of the Keys. Close to Robbie’s and Bud N Mary’s for all the activities....scuba...
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    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  This home sits directly on the bay and has 2 bedroom 2 bath upstairs and has a 2 bedroom 1 bathroom apartment.  The home is located at mile marker 76.   Near...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Gated Bayfront Paradise, Caribbean Cottage in a Tropical Oasis (Free Wifi)1 / 18
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    The Cottage is located in a Gated Estate on the Gulf of Mexico in the Florida Keys for watching those beautiful Keys Sunsets !!! 'Tiki Palm Cottage' has it's own private Tiki hut for relaxing with a cool beverage or just for reading a favorite novel. Walk in through double French doors to a large...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    132 Columbus Drive1 / 18
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 11 January 2014
    Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
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    About this property
    Beautifully renovated home sits right on the ocean. With panoramic ocean views from every room in the house, you'll never want to leave. This 2 bedroom, 2 bath home has a great back porch, large yard, and shaded carport/ sitting area. Located in Lower Matecumbe, this house is close to downtown...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Private Home, with Beach Access, Best Value in the Keys1 / 68
    (85)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Washer
    • Balcony
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2018
    We stayed for a birthday/anniversary celebration with friends and loved the property. Close to everything, especially the great restaurants and the private beach/park area...
    Reviewed 14 July 2018
    This home has everything you need for a stay in the Keys - well equipped kitchen, large assortment of games, Netflix, Amazon Prime, comfy beds, good location, plus access to a...
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    About this property
    Most Rated Key Largo Rental on TripAdvisor and FlipKey, Rated 'Excellent' by Flip Key and Trip Advisor Guests! You will truly enjoy this Key Largo vacation home! Our home is rented for a minimum period of 28 nights, per Monroe County Code. The home is yours to enjoy for the whole month for less...
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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, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Balcony
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to gorgeous Marathon, Florida Keys for a romantic getaway or a fun family retreat. For families with young children this Keys Vacation home is located just two blocks away from beautiful Sombrero Beach with a children`s playground, baseball diamond, volleyball net, picnic areas and roped...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    **Winter Promo** Luxurious Key Largo Family Home with Pool & Large Dock1 / 24
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2016
    Loved this house! It was beautifully decorated, spacious, comfortable and immaculate. The kitchen was great for eating meals in, but there were also plenty of really fun...
    Reviewed 27 October 2015
    We always go down to the Keys as a family in the summers and spend about a month there. In all my years of spending my summers down in the Keys, I do not think I have ever...
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    About this property
    This luxurious waterfront home is located on mile marker 106, on the ocean side of northern Key Largo (The Sport Fishing Capital of the World). Superb quality, beauty, and location, this house has it all! Everything you need is right here waiting. If you prefer the outdoors, you can catch some...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Duck Key Paradise1 / 30
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
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    • Hot Tub
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 October 2018
    Incredibly peaceful location. We could actually see the stars at night. We had a group of 8 and the accommodations were great and spacious for so many adults. Outdoor living...
    Reviewed 21 September 2018
    House was perfect and spacious for my family vacation. Beautiful pool and jacuzzi over looking the water. Kitchen is fully stocked for cooking if needed. Close to restaurants...
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    About this property
    Canal Front property. This fabulous home is a 3 bedroom 2 bath located in the sought after area of Duck Key. The home is updated and ready for your adventure of a life time. Upstairs you will find 2 bedrooms and 1 bathroom. The kitchen, dining room, and living room are upstairs. Off the dining room...
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    Duck Key, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    **Winter Promo**  Amazing views from this Oceanside Home near Pennekamp, dining1 / 25
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2016
    Here is the bottom line..after about a week of our two month rental we had already rented this home for next year. The location is awesome and fishing off the dock was...
    Reviewed 25 March 2015
    Great House! Big enough for extended family. I really enjoyed the dock and the view of the water. Clean and neat.
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
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    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With quick, easy access to the Gulf and Atlantic Ocean, this home is perfect for fishing, snorkeling, boating and just laying by the pool! This three-bedroom, three-bath home, which sleeps eight, has a 60-foot dock with ample room for your boat. It is only one house away from the mouth of a...
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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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    • Cable/satellite TV
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    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Owner motivated to book March 2019–contact us with all offers!! Welcome to your...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 40 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to enjoy the party atmosphere of Key West! Dock your boat out back, sip on your favorite drink under the...
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    Location Information
    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi.  The Bay Harbour Complex comes complete with two tennis courts, weight room, pool, your own dedicated boat slip, a fish...
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    Location Information
    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Fabulous 6 Bedrooms /4 Bathrooms Tropical Waterfront Pool Home!1 / 15
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Our beautiful home is Great...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Reel Paradise - Big Pine Key1 / 17
    (10)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
    • Waterfront
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    Very nice house.Everything is kept immaculate.The house is very roomy and well stocked.The grounds are beautiful.There is a nice spot to relax or cookout by the canal.The owner...
    Reviewed 6 August 2015
    This is a great place to enjoy the lower keys. Extremely clean and well appointed. We stay there as often as we can. I can't wait to go back.
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    About this property
    REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in a spacious third bedroom, 3 baths, large kitchen, dining room, family room, sitting area, large...
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    Location Information
    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    quick access to gulf and fishing! 35 ft. dock, bait freezer, canal front1 / 66
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 January 2018
    We had a wonderful stay. There were a few bumps in the road upon arrival but quickly attended to by management. Would love to come back to visit.
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    About this property
    Looking for a nice clean and updated place in the Keys? This home will NOT disappoint. Superbly renovated, ground level house. The kitchen has been updated with stone tile counters. Bathrooms are marble and tile. Full kitchen with stove and fridge, dishwasher, pots and pans and microwave. All...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Parking
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Welcome to our newly renovated, little slice...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    'Gulfside Grouper', Waterfront-Ground floor, 60' Dockage, Pool/Hot Tub, Pets OK1 / 43
    (6)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 November 2018
    Beautiful house on Marathon Key. It was our own private resort. The one level house has easy access to all the amenities it has to offer. We enjoyed the unique beautiful...
    Reviewed 13 October 2018
    Grouper has all the amenities you could need in a vacation rental. Large open concept home, screen porch, fire pit, patio chess/checkers, corn hole. Poolside tiki hut. The beach...
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    About this property
    Brand New Vacation Rental completely remodeled in 2018 and Available for rental in November 2018 Ground Floor Home 'NO STAIRS' we love that the house located on a Quiet street 4 houses in from the gorgeous Gulf of Mexico and minutes from the Ocean Side and Sombrero Reef via VACA cut or under 7...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    March 30 - April 6, OWNER’S SPECIAL, $3300, Nature’s Finest Address, private1 / 19
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Ocean Views
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Great mid marathon location with beautiful view of the ocean from the pool! The hosts were very accomodating and friendly. Loaded with balconies, seating, and a great set up...
    Reviewed 10 July 2018
    Our family, stayed in this beautiful home for a week over the fourth of July holiday and had a fantastic time. The home is amazing, it comes equipt with everything your family...
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    About this property
    This two-story, ocean-front Florida Keys home is the ideal locale for busy executives, families, retirees and vacationers alike. Developers thoughtfully considered every last detail when designing and constructing this architectural masterpiece - from its breathtaking, scenic ocean views to its...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Family vacation rental, kayak, pool, 50” dock1 / 36
    (2)Average
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 April 2017
    I was a bit worried because of the other review but I'm glad I took the risk. This home is amazing. It is absolutely beautiful. Being from Miami and having stayed at every run...
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    About this property
    Luxury property Designer decorations in a modern-tropical and very cozy style with a friendly and relaxing We are located 45 minutes from the city of Miami that in turn can enjoy mall and night club, and around has broad line of restaurants, and tourist attractions such as fishing, surfing, diving,...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely waterfront home is located on mile marker 29, on the ocean side of Big Pine Key. Just 30 minutes from Key West, this hidden gem offers quiet relaxation, while still close enough to enjoy the party atmosphere of Key West! Dock your boat out back, sip on your favorite drink and grill your...
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    Location Information
    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    **Winter Promo**  Family Friendly Executive Bay Townhome with Beach & Pool1 / 29
    (10)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Balcony
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 September 2015
    We attended with my wife and adult daughters and this apartment had everything we could wish for.The facilities were ideal for our needs and the booking process was simple.Due...
    Reviewed 13 September 2015
    The condo is very nice and spacious for 5 persons. The place is clean and supplies are adequate. Location is good. Swimming pool is big and nice. Able to do a little fishing...
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Washer
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    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    *** Owner is highly motivated to rent! Contact us to inquire about your stay *** Live like a local at this private oasis on mile marker 103 in the Keys. Enjoy your private pool and private beach, or soak up the rays on your own sandy sun deck, while overlooking the vast ocean views. John Pennekamp...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Balcony
    • Private Outdoor Pool (Unheated)
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    • Washer
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Relaxation at its best awaits you in our beautiful, Keys townhome on mile marker 87. Executive Bay Club is located in Islamorada, the Sports Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a heated swimming pool, a clubhouse, a private beach...
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    76300 Overseas Highway1 / 25
    (11)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Reviewed 31 July 2018
    Islamorada! Lower Matecumbe! Paradise! This older, ideally located, and well maintained property is a jewel. Since my dad first introduced me to Islamorada 45 years ago, I've...
    Reviewed 1 April 2016
    Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
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    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. Near the house is the small Anne's Beach. There are nature trails,...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    PIRATE'S COVE - Ocean Front W/ 30Ft Dock Key Largo1 / 25
    (10)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
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    • Waterfront
    • Internet Access
    • Air Conditioning
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2018
    I can't say enough about this fantastic place! The owner (Nestor Loredo) has excellent communication and was easily reached and ready to answer questions. I received detailed...
    Reviewed 27 May 2016
    Stayed here for 2 weeks and we couldn't have asked for a better location for peace and quiet. The accommodation was just beautiful and everything you needed to make our stay...
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    About this property
    IF YOU ARE BRINGING A BOAT LET US KNOW PRIOR TO BOOKING 20 FT. MAX. INCLUDING OUTDRIVE. COMMUNITY HAS SMALL BOAT RAMP, PLEASE DISCUSS BOAT SIZE IN ADVANCE PRIOR TO MAKING A BOOKING THERE ARE SIZE LIMITATIONS AT THE DOCK AND AT THE RAMP. WE CANNOT GUARANTEE SUITABILITY IF THIS IS NOT DONE IN...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Internet Access
    • Grill
    • Cable/satellite TV
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    3/2 open air SFH ready for you to spend your vacation! 30 foot dock can easily handle your boat with quick access to Vaca Cut to head out to the bay or to the Atlantic. Dive, snorkel and fish within minutes. King bed in master with full bath, full size bed in second bedroom and 2 twins in the...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Patio
    • Washer
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most memorable vacation you will ever experience. Very stylish, newly built, modern home of 2700 square...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Ocean Views
    • Washer
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    • Wi-Fi
    • Hot Tub
    • Air Conditioning
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    NEW PROPERTY ON THE MARKET! Don t miss the chance to be one of the first to enjoy this piece of paradise. Welcome to Mariner’s Club, a luxury RESORT-STYLE compound within the premises of a small, private, gated community with Security 24/7. Everything inside the community is walking distance to...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    **Winter Promo**  Ocean Front Keys Home with Private Beach - Great for Kite Surf1 / 25
    (2)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Balcony
    • Grill
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    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Beautiful four bedroom, Ocean Front home with...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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