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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.
    921 Matching Rentals in Florida KeysView all 1,496 rentals
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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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    Florida Keys Beach Home Pool Fishing Diving1 / 36
    (32)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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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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    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
    (1)Excellent
    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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    bayfront beach house with sandy beach1 / 15
    (24)Very good
    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 3 weeks ago
    The house had plenty of room and plenty of beds. Kitchen was well stocked with everything you could need to cook a meal. Charcoal grill is available also. There were a lot of...
    Reviewed 19 May 2018
    Was perfect cottage for multi family/multi generation stay. Location very convenient and so handy to have sandy beach right out the back door.
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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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    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedroom 2 Bath With Ocean View and with hot tub1 / 28
    (7)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 29 July 2018
    The house was better than the pictures! Excellent location on the water close to vaca cut for access to gulf or Atlantic side. Plenty of room for 10 people! Everything in the...
    Reviewed 15 July 2018
    Great stay at the mermaid house for a week. Rented a boat at Capt Pips went snorkeling and scuba diving at Sombrero reef. Bahia Honda state park is a mess from hurricane main...
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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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    Blue Bungalow1 / 15
    (14)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Such a perfect and quaint little bungalow to hide away from the hum drum of every day. The owners are so kind and attentive to every detail. Happily tucked away from the hustle...
    Reviewed 26 May 2018
    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...
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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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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Luxury Open Water Vacation Home1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Ocean Views
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 November 2016
    We just returned from a fabulous vacation at this house. It was so relaxing, the views were awesome. We saw so many kinds of birds. It is absolutely a perfect place to enjoy...
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    About this property
    OPEN WATER PRIVATE ESTATE 3 Bedroom 2 Bath, with a large Pool. Sleeps 4 to 6 $250 - $268 Per Night Minimum Stay 1 Nights Enjoy your piece of paradise and the warm tropical air of the Florida Keys in your own 2600 square foot, private open water estate in a quiet relaxing neighborhood....
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    Big Pine Key, Florida Keys 33043
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    500 Ocean - Tropical Florida Keys Vacation Home1 / 35
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • DVD Player
    • Waterfront
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 May 2018
    We had a wonderful Jimmy Buffet Christmas at 500 Ocean. Coconut Chuck set us up with a fantastic place, right on the water, right in the middle of everything we wanted to do. We...
    Reviewed 17 May 2018
    We have stayed at 500 Ocean for 3 months every year for the past 8 years and we love it!! Comfortable, clean, fully stocked, great location! The owners have left no stone...
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    About this property
    500 Ocean is truly a great value and sells out quickly. We provide luxury level setting in a Coconut Palm Paradise for a great fishing, diving or relaxing family value vacation in Marathon Key Florida. This place is really a Coconut Palm paradise, it is like living in a Palm Tree house 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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    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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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    WOW – waterfront, boat lift, private heated pool, walk to beach and shops!1 / 54
    (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 25 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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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 21
    (9)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Private Garden
    • Wi-Fi
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2018
    This home is beautifully decorated and modern. It has everything you need to make your stay comfortable. Very modern. Nice pool right out back. Close to downtown. Tucked...
    Reviewed 20 July 2018
    My husband & 3 teenagers had a wonderful vacation. This lovely home surpassed our expectations! We enjoyed the pool every day, usually late afternoon and in the evenings - it...
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    About this property
    Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis. Includes washer and dryer. This is a beautiful Key West home in old town. All amenities included. Dogs are...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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 6 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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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    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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    Mediterranean styling, oceanview, pool, dockage, hot tub1 / 51
    (1)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Patio
    • Cable/satellite TV
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2018
    The house was very nice, clean, had the amenities we needed traveling with 2 small babies. Kitchen well appointed, 4 large bedrooms, beds were comfortable, enough space for...
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    About this property
    Gorgeous, 4 bedroom, 4 full bath home, plus 1/2 bath, located on exclusive Tingler Island and near Sombrero Beach! This 3297 square feet tri- level floor plan provides space and privacy for visitors, while the softly lit pool area create a wonderful atmosphere for entertaining and relaxation....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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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    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
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    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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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    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
    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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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Vaca Cove - Open Water, Protected Dockage and Great Pool, Jan, Feb Specials!!!1 / 22
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
    • Waterfront
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 January 2018
    Impressed by the location and condition of the property. Property manager was very attentive to our needs. Great Aquarium within walking distance. Two great restaurants you can...
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    About this property
    Vaca Cove is an exclusive compound with Bonefish Bay Views, a fantastic pool and beach area for the kids (and adults) to play i!. Brand new 4 bedroom homes with 3 baths, and deep water dockage. The pool and beach area is breathtaking, with palm trees and a large tiki hut framed by sea and sky....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    • Grill
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 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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    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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    Islamorada Waterfront Paradise Getaway!1 / 28
    (31)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Ocean Views
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2017
    We spent a wonderful, spirit rejuvenating MONTH with Ewa and Peter at their beautiful home by a lagoon in Lower Matecumbe Key. At first we bustled about, kayaking from the dock...
    Reviewed 1 March 2016
    We had a delightful stay in this lovely property - by the water and with hammocks and a very peaceful setting. The room was well equipped and the owner were very helpful.
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    About this property
    Please contact us for all of our rates for different length of stays! For shorter stays...make sure you have a minimum of 28 days entered in your contact form! This is a very popular rental, so ask about your preferred dates early! This best Islamorada waterfront location, has quick easy access...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    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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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    ISLAMORADA Waterfront GREEN IVIS PARADISE Min 28 Ngts. Max 10 ppl. 26% Disc >1mo1 / 17
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Balcony
    • Ocean Views
    • Grill
    • Washer
    • Waterfront
    • Central Heating
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2018
    We had. Great time. Can't wait to come back. The house was impeccable and the host gave us great customer service. Amazing time in the water. Great canal!
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    About this property
    Relax in this peaceful keys home with wide canal with easy access to ocean & bay. Located in one of the best neighborhoods in the keys!! You will enjoy a morning stroll, jogging or a bike ride around this picturesque neighborhood. We have plenty of room for your boat and all your toys. Bring or...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 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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    Private Heated Pool, New Boat Dock and Ready Enjoyment!1 / 46
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    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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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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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
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 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 18 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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    Beautiful Beachfront Home w/Heated Pool+45' Dock1 / 42
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 July 2018
    We enjoyed a relaxing week in Marathon at this beautiful house. It was well appointed and any and all of our needs were met immediately. Everything was as expected. The dock...
    Reviewed 17 April 2018
    This property is in great shape. It is everything advertised. The owners are great to work with. If hurricane Irma did any damage, its no longer evident here. Our family...
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    About this property
    Beautiful Beachfront home located directly across the street from famous Sombrero Beach. Sombrero Beach is surely one of the stand-out beaches in the Florida Keys. This gorgeous beach has something for everyone. Kayaks, boating, fishing & biking all easily available for great fun in the sun. You...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    132 Columbus Drive1 / 18
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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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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    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 26 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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    Casa Havana1 / 24
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 January 2018
    Location is the best. Casa Havana is 1/2 block off of Duval and 3 blocks from everything in Key West. Deck is great for drink and a cigar in the afternoon and having it own...
    Reviewed 23 February 2016
    Casa Havana is a beautiful rental home with a premier location. It is very close to all of the action on Duval Street, yet far enough to sit on the patio and relax. My group...
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    About this property
    The Space Fully renewed, beautiful colors and large spaces. The affordable luxury in downtown Key West. Two blocks from the Ocean, two minutes walk to watch the beautiful Key West Sunset. Guest Access You take over the full house, deck, balcony, large living-room, kitchen, garden and the best...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tropical Blue Adventure Waterfront at Venture Out1 / 29
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Hot Tub
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    • Ocean Views
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable and charming, this newer stilt home has everything you could want for a vacation for just the two of you, a few friends, or the whole family! Fantastic waterfront open canal views. Located on a 60' wide canal, you can bring your powerboat, jet ski, kayak, or what have you, and dock...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Confortable and spacious, 2 bedrooms 1 baths. Home is in a residential fishing village. Full house is actually a 3/2, split master suite. Rental increase $35 per night for the full 3/2. Trailer parks in the neighborhood, like most of the Florida Keys, but the home is not a trailer. The housekeeper...
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    Pigeon Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental is 28 Days to a single family or party (no subleases allowed). Special 11% off Sept - mid Dec 2018 rates on availabile dates.$143/night. All pictures are post IRMA.Simply Breathtaking VIEWS of the sunset over the ocean like this right from this home and from the deck. 2 Bedroom 2...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New House in the Heart of the Florida Keys. Enjoy Paradise in this modern house that has every ones need in mind. 7 Room with 8.5 Bathrooms, fully equipped kitchen, Jacuzzi, pool, dockage for boats and more more much! The space Total of 7 Room with: 3 King beds 2 Queen beds 1 Full bed 2...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    Private Island Rental with 19' Boat, Seabird Key1 / 62
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 2016
    Seabird Key was absolutely perfect for our family. We were were a party 4 adults, a 2 year old and an infant. The island was well-suited for all. We enjoyed going to the beach...
    Reviewed 19 March 2015
    Wow. Seabird Key is one of a kind. We felt like we were in the swiss family robinson movie. The house's main floor is perched at the same level as the tree canopy. If you...
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    About this property
    Seabird Key is a ten acre private island available for rental by the week featuring an architecturally stunning home with gracious porches and multi level decks; a private, sandy beach and beautiful, tropical gardens throughout. Only 5 minutes offshore by boat, this is the Island that has it...
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    Location Information
    Marathon, Florida Keys 33156
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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 26 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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    **Fall Promo** Amazing views from this Oceanside Home near Pennekamp, dining and1 / 25
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 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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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Elegant Beach Home With Dockage1 / 24
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 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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    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 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
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    • Private Garden
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beautiful Single Family Home in Key Colony Beach!1 / 22
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
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    • Private Outdoor Pool (Heated)
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    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 September 2014
    Arrived September 15th to this amazing villa, everything we could want for our family, 3 couples & 3 young adults (late teens) beautiful clean & spacious, kitchen had...
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    About this property
    This is a beautiful new 4 bedroom, 3 bath home in fablulous Key Colony Beach. The sleeping arrangements are 3 King bedrooms,1 bedroom with twins and a sleeper sofa in the living room. Sleeps 8-10. All bedrooms and screened porch have wall mounted flat screened TVs. The home has a private pool, boat...
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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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    Fabulous 6/4 Tropical Waterfront Pool Home!1 / 27
    (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)
    • 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. Our beautiful home is Great...
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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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    Private Beachfront Paradise1 / 45
    (12)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Sauna
    • Waterfront
    • Hot Tub
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 November 2016
    The friends we haven't seen in over 25-years since high school, decided to reunite in Islamorada, FL. The moment we set foot on this property, we knew we were in for a great...
    Reviewed 24 August 2016
    We just got back from a week in this beautiful house. We traveled with extended family and 2 young children- everyone loved it. We did rent a boat to go snorkeling and fishing...
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    About this property
    Village of Islamorada VR-110 Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen....
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    FALL LOWEST RATE EVER,  $275/night + cleaning & tax, A PRIVATE TROPICAL PARADISE1 / 19
    (2)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 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
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    • 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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    Downtown Nassau Oasis 1 Bedroom Townhouse steps to Duval1 / 22
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Terrace
    • Balcony
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2015
    My (adult) daughter and I drove down to Key West for 4 days/nights - I had only been there once; she had never been there. We are from the midwest - it was hard to choose a...
    Reviewed 18 August 2014
    This small townhouse was absolutely the most convenient thing we could have asked for in Key West. 1/2 block off Duval Street at Truman. We literally parked the car and walked...
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    About this property
    Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower. Downstairs in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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