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Florida Keys House Rentals

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    897 Matching Rentals in Florida KeysView all 1,478 rentals
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    bayfront beach house with sandy beach1 / 15
    (23)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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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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    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Moon Bay A2041 / 33
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 March 2018
    This condo was a perfect location for our vacation. Restaurants, shopping and parks close by. The most beautiful sunsets I have ever seen.
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    About this property
    Want to be close to the Mainland while still being in the Upper Keys? Look no further. This beautifully decorated condo at Moon Bay will not disappoint. The Master bedroom has a spacious King size bed. Guest bedroom has 2 twin beds and there is a bonus room with a trundle bed. Vibrant colors...
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    Tavernier, Key Largo 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    Kid friendly
    Smoking allowed
    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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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 February 2018
    Wow! This property is just perfect for a quick getaway! The backyard was so fun, for our entire family. My kids loved the hot tub, my wife loved the waterfront view and I loved...
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    About this property
    The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (upper unit) island retreat is...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Florida Keys Beach Home Pool Fishing Diving1 / 108
    (30)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Housekeeping Included
    • Air Conditioning
    • Ocean Views
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 days ago
    The facility was good but the beach sucked bad had to leave our rental to find other beaches to swim
    Reviewed 11 February 2018
    Had a great time! Staff was helpful and loved having a laundry room. Still lots of work to be done in Marathon and surrounding keys after the hurricane but don’t let that stop...
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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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    Catherines Tropical Paradise - 3 Bedroom 2 Bath1 / 35
    (7)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Washer
    • Waterfront
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2017
    My husband and I really enjoyed staying in Catherine place for our 31st anniversary. Good fishing in Marathon, and mid way in the keys make it a short drive either direction...
    Reviewed 9 August 2016
    The house was spacious and comfortable. Beaches, restaurants, grocery stores, etc. were all a short drive from the house and easy to get to. The rental is a good value for the...
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    About this property
    Stay at our Marathon Key Vacation Rental House in the heart of the Florida Keys. Vacationers find great tarpon, dolphin, sailfish, and snapper fishing, coral reefs and wrecks for scuba diving. Marathon is situated at the mid-point of the Florida Keys island chain, which is why locals have declared...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Private Heated Pool, New Boat Dock and Ready Enjoyment!1 / 23
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 2017
    Spent our week family vacation here. Fresh, clean and adorable cottage. Although on the smaller side the yard is excellent and larger than most with plenty of shade. Access to...
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    About this property
    Come enjoy the Keys Life in the single best location in all of the Florida Keys. 'Miloh's' has been completely renovated in 2016. Dock your boat in the large deep water canal and cool off in your private pool. Enjoy the built-in underwater bar stools in the pool as you enjoy a cold beverage and...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Blue Bungalow1 / 12
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Wi-Fi
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    The only drawback to this cute place is that it is on the highway. Otherwise it was very nice. It is small as advertised. It has a nice fenced yard for a small dog if needed...
    Reviewed 19 March 2018
    Very nice for 2 people. Had everything we needed. Clean. Great location. We really enjoyed our stay and would book again.
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    About this property
    Come enjoy the Florida Keys! Many local companies offer opportunities to get out on the water. Go diving or snorkeling. Rent a fishing charter. Rent a kayak or stand up paddle board. We are close to the Everglades where you can birdwatch or see an alligator. Take a day trip to the beaches down...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 35
    (21)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 8 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...
    Reviewed 28 February 2018
    This was the best vacation I’ve ever had in Florida! This house is gorgeous and has stunning views from the decks. You feel like your on your very own private vacation. It comes...
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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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    SUMMER SPECIAL! Hurry, couple weeks left!! Kayak, Dock,  Bikes, Pool, 2 Beaches1 / 70
    (11)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Patio
    • Waterfront
    • Grill
    • Wi-Fi
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 July 2017
    Beautiful spot, the canal was cool and great for a boat rental! Dee really thought of everything, the bikes were great to get around and really enjoyed swimming at inch beach...
    Reviewed 19 March 2017
    We had the pleasure of staying the month of January at Key Colony beach in the Florida keys. We stayed at 591 9th Street, a cute house on the canal. We could walk, run or bike...
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    About this property
    SPECIAL Summer rate is $1300 per week for 4 guests (guest 5 and 6 are $10 per person per day) excluding lobster weeks which are $1700. (Lobster week of Aug 04 just opened plus 06/23 and 07/28) Totally remodeled 2/2 home on the water! 2019 Winter rates are $5600 per month for Jan Feb Mar, or $1500...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Escape to Paradise in a Gated Tropical Bayfront Estate (Free Wifi)1 / 38
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 14 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 15 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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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This beautiful home overlooking the Atlantic Ocean is part of the Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes, is located right in the center of the Lower Keys. Key West is only 16 miles in one direction and Marathon 25 miles in the other. This 1200...
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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Florida Keys Fishing & Diving, waterfront Home heated pool, deep dock, parking1 / 43
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Patio
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 bedroom and 5 full bathrooms private gated home, heated pool, Tiki hut, deep 135ft boat dock, fish cleaning station, bait freezer, gourmet kitchen, 2 full size refrigerator and freezers. Sleeps 10, covered parking for 4 cars. Awesome sunset views over Bonefish Bay, veranda, 3 hammocks, plenty of...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether an avid adventurer or a family seeking to relax and enjoy the expansive view, Sunset Catch is the place for you. These three bedrooms, two bath home has a private pool (with heat available for an additional charge) and sit on the Gulf of Mexico sporting incredible views. The large bedrooms,...
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    Grassy Key, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    132 Columbus Drive1 / 18
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 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
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Key West Oasis - Private Pool, Separate Cottage - Great for Couples & Families1 / 23
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 February 2018
    The Oasis is truly a bit of heaven on earth! We have been visiting Key West for a number of years and could not imagine staying anywhere else.This rental is fully equipped, in a...
    Reviewed 27 January 2018
    Recently spent 10 days at KWO. This property is superb and reflects a pride of ownership. KWO clearly exceeded the already impressive presentation on the website. Paula and...
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    About this property
    Key West Oasis is a private two bedroom/two bath rental house ideally located in Charming Old Town, Key West, Florida, close to Duval street, great restaurants, bars and the beach. This 1906 'cigar maker's cottage' has been newly renovated into a stylish Key West retreat. The house features an open...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Paradise In Marathon, FL Keys Large Oceanside Home1 / 22
    (6)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 28 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 23 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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    4 Bedroom 2 Bath With Ocean View and with hot tub1 / 56
    (4)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Hot Tub
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Ocean Views
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 April 2018
    Don was very friendly and accommodating. Had a great time and would definitely return again. My whole group was very satisfied with the price of the house and there were no...
    Reviewed 13 August 2017
    My friends and I come down to The Keys every August for Lobster Season and to fish. Some in the group have been coming for over 20 years. This was honestly one of the nicest...
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    About this property
    The 'Mermaid House' sits directly on the ocean with the unobstructed views, gorgeous sunrises and some of the best boating access in the Marathon area. House offers 4 Queen Bedrooms and 2 full bathrooms. 3 bedrooms and a bathroom are located on the ground level. Upstairs is the Queen Master bedroom...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Oceanfront Anglers Reef Islamorada Florida Keys1 / 14
    (3)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    • Patio
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2018
    This home is in a gated community in the heart of Islamorada. The site is beautiful, and seemed to have suffered no damage from Hurricane Irma. There are two artificial...
    Reviewed 25 August 2017
    Very well appointed and comfortable house, conveniently located to local amenities in Islamorada. It was like a home from home with easy to use washing machine, dryer and...
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    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    ONLY AVAIL: April 10-28 for 6; 2BR/2BA/INCH BEACH/30' Dock; NO CC POOL or pets!1 / 92
    (94)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • Washer
    • Waterfront
    • Wi-Fi
    • Housekeeping Included
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2017
    This was the third time we've rented this house and as usual it was great. They updated some of the outdated furniture, which was a nice surprise. I can never say enough nice...
    Reviewed 19 May 2017
    Seriously, if you are looking for a place in the Keys you can stop looking now. I don't know how any place could beat this one. The house has EVERYTHING you could possibly need...
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    About this property
    Welcome to 'KEYS OCEAN DRIVE', the BEST rental LOCATION in KCB!!! 2018: • April 7 -28 available ONLY! We are closing on the sale after 4/28th! • 7 night 'licensing' minimum, flexible check in & check out dates, ASK! We are located ocean side with quick & convenient boating access to gulf side...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant Beach Home With Dockage1 / 48
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 April 2017
    They home was great. It had everything you could ask for. The people that we met at the home very friendly. We had a great stay and I will come again. I high recommend this home.
    Reviewed 19 September 2016
    We stayed here Aug 8-12 with my parents, brother and sister. Not only was the home perfect, but the location was great with several food places in walking distance. We walked...
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    About this property
    Elegant home with many unique, architectural features, located on a family-owned waterfront piece of property, with 3 other rental cottages, sandy beach, and small marina. This lovely house, 'Tropicasa', has everything needed for a large group - full kitchen with granite countertops, stainless...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    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
    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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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    PARKING,2bd/2bth,20yrd TO DUVAL,FREE OLD TOWN SHUTTLE,MAJOR ATTRACTIONS NEARBY1 / 41
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Patio
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2018
    Best part, it is right off of Duval and close to so many things to do. The beach is 5 minute walk and the community pool is an amazing unused gem. Free bus to lower Duval is...
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    About this property
    Check out the new 'Duval Loop' that ferries you around Old Town for free and is located at the corner of this homes block!!!!Map is included in pictures. Hemmingway House, Lighthouse, Butterfly World, Southern Most Point, Conch Tour Train, Beach, Galleries & Restaurants are all located within a 5...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Marathon Vacation Rental - Beautiful Private Home, Pool, Billiard Table1 / 37
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Balcony
    • Private Outdoor Pool (Heated)
    • Washer
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 November 2017
    Boocked this property for weeks and it has been a great experience. This is well located in Marathon and Keys overall. Will definately book this place again when time comes.
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    About this property
    Welcome to Marathon Vacation Rental, located in Marathon, FL - the Heart of the Florida Keys. This is a private single-family home, so during your stay, these amenities are provided exclusively for you and your guests. Enjoy the Afternoon from our Private Pool, relax, sit and read a nice book on...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Florida Keys Splendor at Hammer Point1 / 24
    (14)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Patio
    • Grill
    • Wi-Fi
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    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 April 2016
    I would recommend staying here it was a very comfortable home in a great location close to everything sunsets were beautiful and (5) manatees came to visit twice a day right off...
    Reviewed 19 December 2015
    We stayed here for three nights in December. Migdy is the best. Manatees visited us at the dock. All conveniences of home are here.Nice restaurants in the area, but the house...
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    About this property
    If you want peace and quiet and disconnect from the daily stresses of life, this is the place to be! Come enjoy all that the Florida Keys has to offer in this 'home away from home' Your reservation includes so many amenities! Great for a well-deserved get-away or Mini-vacation! Located in the...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    WOW – waterfront, boat lift, private heated pool, walk to beach and shops!1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2018
    The location is amazing! This duplex is very clean, stocked with anything you would need to cook, play at the pool or go to the beach. We enjoyed the screened in porch and best...
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    About this property
    This is Keys living at its best! Tropical classy, comfy and private – yet easy access to everything you could want. This 2 bedroom, 2 bathroom home on a quiet dead end street with open views and ocean access (with houses only on one side) in the heart of the heart of the Keys comes with all the...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Last week available summer 2018,   July 28 - August 4,  $1000 discount available1 / 11
    (1)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
    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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    This townhome at Executive Bay will sure make your home away from home!  This unit has been completely renovated and decorated beautifully.  This  2 bedrooms and 3 bathrooms has a (1) King Bed, (1) Queen Bed and  there is a bonus room off the Master that has 2 twin beds. Executive Bay Club is a...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Available JAN 1-27 and last two weeks of March 2018.TROPICAL KEYS PARADISE1 / 24
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Grill
    • DVD Player
    • Washer
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 January 2017
    Just got back from staying there for a week on my honeymoon, and it was so relaxing and perfect! It was EXTREMELY clean when we arrived, which made us feel relaxed from the...
    Reviewed 25 February 2016
    We have been renting this unit from Maria since 2004 and go 2x a year for 2 weeks at a timeWe love the neighborhood and the overall clean and tropical feel of this house. It...
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    About this property
    Half duplex located in prestigious Key Colony Beach. Tropical decor throughout. Located on a 100ft. wide canal and a great patio in the back. You are within walking distance to the 'Cabana Club' , a private beach club with a heated pool, beach, bar, restaurant and game room. Access to the club...
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    Location Information
    Key Colony Beach, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Summer Promo** Amazing views from this Oceanside Home near Pennekamp, dining a1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
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    • Patio
    • Air Conditioning
    Suitability
    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 26 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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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    THE PERFECT GETAWAY1 / 14
    (6)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2016
    My husband and I searched for six weeks to find the perfect house for our vacation with another couple, and kept coming back to this one. All four of us were looking for a...
    Reviewed 10 April 2016
    We thoroughly enjoyed staying at the Perfect Getaway. My family and I had enough space to sleep, relax and enjoy meals together. The pool was a great addition to the property...
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    About this property
    This four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. It is situated in a clean, upscale neighborhood of all waterfront homes. The house is equipped with all the comforts of home. It is modernly furnished. Upstairs there are...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Secure Parking
    • Grill
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    • Cable/satellite TV
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Tranquility Cottage, a beautifully appointed, well maintained, and updated 2BR/2B half-duplex on 7th Street in Key Colony Beach. Located on the widest canal in Key Colony Beach and opposite Sadowski Causeway you will be in walking distance of local restaurants, Sunset Beach, Fishing and...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Great Fishing Right Off the Dock!!1 / 22
    (6)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Grill
    • DVD Player
    • Internet Access
    • Waterfront
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    Having the Florida Keys on my bucket list can now get a BIG check mark! I took my family and both small dogs (which go everywhere with us) to the keys and can say that renting...
    Reviewed 21 October 2016
    Here's the scoop!... The fishing off the dock truly is great and just the relaxing atmosphere and access to the channel and ocean are worth it alone. Make sure you have fishing...
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    About this property
    This is one of the best vacation spots in the keys.It's a lovely 4 bedroom/3 bath Duplex on 3rd St. The sleeping arrangement include 1 King, 2 Queens, 2 twins plus sleeper sofa. The living room is spacious. Enjoy fishing on the large 56 foot dock The ocean is just seconds away by boat.There is a...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Terrace
    • Grill
    • DVD Player
    • Washer
    • Balcony
    • Ocean Views
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is Paradise! Spectacular water view takes your breath away. Our private beach makes you want to stick your toes in the white sand or let your mind drift away as you lay in one of our hammocks and listen to the ocean breeze. This oceanfront residence has a large, sparkling swimming pool and an...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    3/2 or 6/4 Tropical Parroteyes, Location,Comfort Views!1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • 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. You Can Rent One Level a 3/2...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    LOOKOUT POINT - Wide Open Views, Beach & 30ft Dock1 / 27
    (17)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Air Conditioning
    • Cable/satellite TV
    • Parking
    • Waterfront
    • Internet Access
    • Grill
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 October 2017
    This is a very cute place in a quiet neighborhood and good for a couples retreat! It is comfortable, neat, clean and a great price! It has beautiful sunrise views and is right...
    Reviewed 10 November 2016
    I can't recommend this property enough. My wife and I absolutely loved our stay at Lookout Point. Nestor was great to deal with, and very responsive to all questions and...
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    About this property
    Enjoy your Own Private Secluded Retreat, Lookout Point....One Bedroom, 40ft. Park Trailer, W/ Three Pull-Outs, One Full Bath W/Additional Convertible Beds. Ocean Wide-Open Views, Key Largo, Florida LOOKOUT POINT is a One (1) Bedroom Convertible to two (2) Bedrooms, 40 FT. Park...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Coral Hammock - Comfortable 3 Bedroom Home1 / 15
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Grill
    • Terrace
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Thank you so much for the wonderful stay in your home Bob. We will defiantly stay here again if there is availability when we come. Everything from towels, beach towels, sand...
    Reviewed 28 March 2017
    Great times in key west coral hammock is about a fifteen minute drive to duval street. The place is real nice and quiet a lot of space for your whole group. Great trip all...
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    About this property
    This beautiful home in Key West has recently been updated with new furnishings. It has over 1400 sf of living space. On the upper level there are two good sized bedrooms (one has a king size bed, the other has two twin size beds) each with their own bathroom. There is a bedroom on the main...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    New 4 bedroom,4bath in Beautiful Key Colony Beach1 / 21
    (5)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2017
    The house was everything it was advertised to be, very clean and comfortable. Key Colony is a beautiful place to stay and Toni is one of the easiest home owners I have ever had...
    Reviewed 27 March 2017
    Location and home layout was great, however rental needs some TLC: mattresses were old or cheap - very uncomfortable, pool was dirty (pool on other side of duplex was clean to...
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    About this property
    New 4 bedroom, 4 Bath duplex. This beautiful new home has a private pool, a dock- 2 10 by 30 decks on the channel. The dock is 37 1/2 ft. There are 2 refrigerators, bait freezer, fish cleaning table, 2 bicycles. All bedrooms have flatscreen TV's. The family room also has a queen sofa bed. 3 of the...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Oceanfront House1 / 50
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Garden
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    What a find in renting this home. It’s one of the nicest we have stayed in since coming to the Keys. From the owner’s, to the manager, to the pool guy, to the grounds’ keeper...
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    About this property
    This luxurious, but cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands, the most prominent of which is Looe Key reef, a popular diving/snorkeling area. (There is an island, located a few miles out directly in front of the home, was formerly...
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    Location Information
    Summerland Key, Lower Keys 33042
    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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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'The Beach Fixes Everything'. That's the sign that greets visitors as they enter the living room of this newest Freewheeler Vacations home. But while the beach certainly is nice, an awesome vista doesn't hurt either. Located on a narrow residential peninsula in Lower Matecumbe Key, the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Waterfront Paradise with a heated pool and full dock in Marathon key, Florida1 / 18
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Patio
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2018
    We stayed at this property from 3/24 - 3/31..Property is beautiful and clean. Highly recommend this to anyone looking to stay in Marathon. If you have a boat, this is definitely...
    Reviewed 30 April 2016
    Spent my 20th anniversary/birthday with my wife and childhood friend and his wife. The house and location was everything we hoped it would be. Rented a boat and parked it at...
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    About this property
    BOOT KEY RETREAT === OPEN WATER VIEWS SHORT EASY ACCESS TO OCEAN or Bay with Lobster, Dolphin, Wahoo, Sailfish, Amber-jack, Grouper, Snapper and Tarpon all close by. FISHERMEN, DIVERS and FAMILIES---This is the place you are looking for! This-port-of call is located at the base of...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    75130 Overseas Highway1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    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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    Location Information
    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Key Colony Beach Griffins' Getaway1 / 27
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Washer
    • Waterfront
    • Terrace
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 June 2017
    The minute we walked in the door,mew felt comfortable, the house was bright and cheery, and very clean. Lucille did a great job decorating and provided a very comfortable home...
    Reviewed 20 June 2017
    The place was clean, comfortable, and had everything we needed for a wonderful time. We were in constant communication with the owner who obviously takes great pride in the...
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    About this property
    Key Colony Beach Canal Front Property. Nnew deep water boat dock (37.5 ft) directly at your back door with a fish cleaning table, water and power on dock. bait freezer 5 min. boat ride through the 100' wide canal leads toVaca Cut and the Atlantic Ocean and quick access to the Gulf of Mexico...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Sandy Beach, Direct Ocean, Pool, Dock & Lagoon1 / 34
    (31)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 10 January 2018
    We were warned that all was not in working order because of the hurricane but inspire of that we found the house to be beautiful and spacious, with the help of 2 xtra mattresses...
    Reviewed 2 April 2016
    We could not have been happier with the house! The grounds are beautiful, and the house was perfect! Everyone had a great time and we all want to vacation at the house again!
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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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    ~ CASABLANCA ~ Gorgeous Cottage w/ Private Pool, Parking, & Tons of Sun!1 / 29
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Washer
    • Grill
    • Private Outdoor Pool (Heated)
    • Parking
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2018
    First of all the unit it fabulous. Clean as a whistle and has everything you need to make a great stay. The bed was big and comfortable and the kitchen was well equipped. The...
    Reviewed 31 March 2017
    Nice to have a separate living room with a desk for relaxing in the evenings. Wi-Fi was fine - didn't watch TV. Spent a good part of every day outside, by the lovely private...
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    About this property
    Casablanca is the perfect get-a-way vacation rental for those seeking a good time, but would like to stay a safe distance from all the Duval Street craziness!! Casablanca is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    BUCCANEER'S DEN - 20Ft. of Waterfront w/ Dock1 / 26
    (12)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 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 18 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
    Enjoy your Own Private Secluded Retreat, BUCCANEER'S DEN is a Fleetwood, 39 Ft.; Two (2) Bedroom Unit, Two (2) Queen Size Beds in the Bedrooms, with One (1) Full Bathroom. Both, Beds Queen Size. The Color decor is Light Tones. Fully stocked. The Property is on the Water with 20 Ft. of of Dock...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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