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Florida Keys House Rentals

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    Travellers to Florida Keys are booking February dates now. Secure your holiday rental today, and have the perfect trip.
    961 Matching Rentals in Florida KeysView all 1,545 rentals
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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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    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Blue Bungalow1 / 16
    (15)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    4 Bedroom 2 Bath With Ocean View and with hot tub1 / 56
    (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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    75731 Overseas Highway1 / 32
    (13)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada....
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    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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    Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access1 / 27
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Waterfront
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 March 2017
    Perfect stay for all of us. The kitchen was perfect for our meals. We all slept very comfortable and we enjoyed the decorating that has been done. We enjoyed all the different...
    Reviewed 12 January 2017
    Very cool and unique lodging. Not luxury but very nice and clean. Great communication with host. Very friendly. Great decks/outdoor spaces on boat.
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    About this property
    The M/V Coconuts is a completely unique home with 360 degree water views. It also happens to be an exceedingly rare 50-foot Florida Bay Coaster Trawler permanently docked at the Key West Harbour Yacht Club, featuring a restaurant, infinity pool and a private beach! This is more than a boat. It...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    FL Keys Waterfront Pool Home 2 Bedrooms Sleeps 6 w/ 60 Feet of Dockage1 / 26
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 September 2018
    This rental was simply amazing. The house was emaculant, cleaner than anywhere we have ever stayed. Every detail was laid out for us. The beds were comfortable, the house was...
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    About this property
    Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of Dockage in Marathon, FL, the heart of the Florida Keys. A newly renovated 2 bedroom & 2 bath home that sleeps 6. The boat ramp is 300 yards away and plenty...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    76004 Overseas Highway1 / 46
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Enjoy spectacular sunsets while drinking margaritas on the observation deck of this stunning home nestled back behind swaying palm trees.  This home sits directly on the bay and has 2 bedroom 2 bath upstairs and has a 2 bedroom 1 bathroom apartment.  The home is located at mile marker 76.   Near...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Paradise In Marathon, FL Keys Large Oceanside Home1 / 22
    (7)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
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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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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Duck Key Paradise1 / 30
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Washer
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 October 2018
    Incredibly peaceful location. We could actually see the stars at night. We had a group of 8 and the accommodations were great and spacious for so many adults. Outdoor living...
    Reviewed 22 September 2018
    House was perfect and spacious for my family vacation. Beautiful pool and jacuzzi over looking the water. Kitchen is fully stocked for cooking if needed. Close to restaurants...
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    About this property
    Canal Front property. This fabulous home is a 3 bedroom 2 bath located in the sought after area of Duck Key. Minimum stay is flexible. The home is updated and ready for your adventure of a life time. Upstairs you will find 2 bedrooms and 1 bathroom. The kitchen, dining room, and living room are...
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    Duck Key, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    • Air Conditioning
    Suitability
    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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    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    132 Columbus Drive1 / 18
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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
    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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    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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    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 May 2018
    Despite our rainy week in Islandmorada, Sean helded to make our vacation seemless! We had 10 people staying with us to help celebrate my husbands 50th birthday. The house had...
    Reviewed 13 July 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
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    About this property
    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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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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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    75130 Overseas Highway1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Pet friendly
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    Reviewed 13 August 2017
    We stayed here for a few days and it was amazing. The house is warm and cozy and has all the details you need when away from home. The beachfront is wonderful and can go...
    Reviewed 21 June 2016
    This two bedroom home was the perfect getaway for my husband and me. The cute sea-theme décor added to the cozy ambience. The living room/kitchen are flanked with a queen...
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    About this property
    Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs...
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Secure Parking
    Suitability
    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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    Straight shot to the Atlantic Ocean!1 / 46
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Patio
    • Waterfront
    • Washer
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 March 2018
    House was beautiful, all amenities perfect, highly recommend it. We definitely consider renting again.
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    About this property
    Wake up in your own sunrise paradise! Have coffee while sitting under your gazebo by the pool. This custom built, fully air conditioned, vacation home has all the amenities to make this the most memorable vacation you will ever experience. Very stylish, newly built, modern home of 2700 square...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • DVD Player
    • Waterfront
    • Hot Tub
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy all the Keys have to offer in this quiet neighborhood location, 3 BR/2BA gulf front home! This home will offer you the perfect vacation with your family and friends. The “Gulfview Escape” is minutes away from Sombrero Beach or a little further, Bahia Honda State Park, both are Keys gems that...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Vacation Mode Key Largo Retreat1 / 36
    (11)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Patio
    • Balcony
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 March 2017
    My family and I had an absolutely amazing time! Our rental was perfect,and the owner even left us a key lime pie in fridge. Thank you
    Reviewed 27 February 2017
    The home is exactly as described. Very very nice. A real pleasure to stay here.The location in the Keys is perfect...close to civilization...close to crazy Key West.Lots to...
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    About this property
    Newly remodeled 1,200 + square footage home in the Bayhaven Community. This house has a master bedroom very tastefully decorated as well as a second bedroom with full/twin bunk bed, and a queen sleeper sofa in the living room. Open layout allows you to cook, eat and relax while spending quality...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Casa Havana1 / 24
    (3)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Internet Access
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    • Private Garden
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 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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    4 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    • Air Conditioning
    • DVD Player
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Washer
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful and completely remodeled home only 4 houses from open ocean on the Atlantic side of Marathon. This cozy home features 4 bedrooms, 3 bathrooms with lots of natural light and open floor plan style living room and kitchen and stainless steel appliances. Two of the bedrooms are MASTER SUITES...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 11
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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 6 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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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 15 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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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    76300 Overseas Highway1 / 25
    (10)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 31 July 2018
    Islamorada! Lower Matecumbe! Paradise! This older, ideally located, and well maintained property is a jewel. Since my dad first introduced me to Islamorada 45 years ago, I've...
    Reviewed 2 April 2016
    Three of us stayed for a week in March 2016. Unfortunately two more friends had to pull out due to illness, so we had a surplus of rooms. The house is not the most modern of...
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    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. Near the house is the small Anne's Beach. There are nature trails,...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Florida Keys Beach Home Pool Fishing Diving1 / 36
    (33)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • DVD Player
    • Wi-Fi
    • Hot Tub
    • Ocean Views
    • Air Conditioning
    • Cable/satellite TV
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    The good:Great beach, very clean, machine cleaned during the night Great location in close proximity to good bars, restaurants and cheap bus transportation to the KeysClean...
    Reviewed 15 September 2018
    The place was very nice. Staff were kind and very helpful. Everything was perfect.We had a good time in Marathon.
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    About this property
    2 bedroom 2 bathroom vacation villas on Atlantic Ocean. This is Tropical Island villa, one of the villas located close to the office and tennis court and has a Garden View. It is within less than 1-minute walking distance to the beach, pool overlooking the ocean and Jacuzzi. Heated pool...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 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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    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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    About this property
    The Cottage is located in a Gated Estate on the Gulf of Mexico in the Florida Keys for watching those beautiful Keys Sunsets !!! 'Tiki Palm Cottage' has it's own private Tiki hut for relaxing with a cool beverage or just for reading a favorite novel. Walk in through double French doors to a large...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Balcony
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    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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    BUCCANEER'S DEN - 20Ft. of Waterfront w/ Dock1 / 26
    (13)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 2 Quick View
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    • Cable/satellite TV
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    • 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
    IF YOU ARE BRINGING A BOAT LET US KNOW PRIOR TO BOOKING 20 FT. MAX. INCLUDING OUTDRIVE. COMMUNITY HAS SMALL BOAT RAMP, PLEASE DISCUSS BOAT SIZE IN ADVANCE PRIOR TO MAKING A BOOKING THERE ARE SIZE LIMITATIONS AT THE DOCK AND AT THE RAMP. WE CANNOT GUARANTEE SUITABILITY IF THIS IS NOT DONE IN...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 2
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    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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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
    • Washer
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    • 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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    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
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    • 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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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    OUTSTANDING Oceanfront House with Pool and Deep water dockage!!1 / 45
    (20)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Washer
    • Wi-Fi
    • DVD Player
    • Ocean Views
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 February 2017
    You know when you find a great place to stay and don't want to tell anyone because you want to have a beautiful home to stay in. Ya this rental is like that. We didn't want to...
    Reviewed 10 July 2016
    This property is a can't miss ! It has everything including the most refreshing pool I have ever been in (and I have my own back home). Well appointed kitchen, all the outdoor...
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    About this property
    Create a memory that will last a Lifetime! Never on the Rental Market before, this newly renovated Million Dollar House will become your vacation destination year after year. 4 bedrooms, 3 bathrooms, 28 foot Pool, 44 foot patio, 40 foot concrete pier, endless views, and privacy. You can bring your...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 35
    (22)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 October 2018
    This was our second stay at this beautiful rental that feels like you have your own resort. All the amenities are perfect and the owners couldn't be more accommodating. Highly...
    Reviewed 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...
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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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    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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    Location Information
    Grassy Key, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • Patio
    • Washer
    • Internet Access
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    With quick, easy access to the Gulf and Atlantic Ocean, this home is perfect for fishing, snorkeling, boating and just laying by the pool! This three-bedroom, three-bath home, which sleeps eight, has a 60-foot dock with ample room for your boat. It is only one house away from the mouth of a...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
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    • 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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    Location Information
    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    **Winter Promo** Luxurious Key Largo Family Home with Pool & Large Dock1 / 24
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Grill
    • DVD Player
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 May 2016
    Loved this house! It was beautifully decorated, spacious, comfortable and immaculate. The kitchen was great for eating meals in, but there were also plenty of really fun...
    Reviewed 27 October 2015
    We always go down to the Keys as a family in the summers and spend about a month there. In all my years of spending my summers down in the Keys, I do not think I have ever...
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    About this property
    This luxurious waterfront home is located on mile marker 106, on the ocean side of northern Key Largo (The Sport Fishing Capital of the World). Superb quality, beauty, and location, this house has it all! Everything you need is right here waiting. If you prefer the outdoors, you can catch some...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Sandy Beach, Direct Ocean, Pool, Dock & Lagoon1 / 34
    (33)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2018
    This house is amazing!! The view from the second floor is breathtaking but from the third floor window watch, it's spectacular!! The yard is very large with a lagoon, beach and...
    Reviewed 21 July 2018
    We found a little oasis of oceanfront paradise!! With meticulous attention to the lush grounds, this property rivals any luxurious resort.This spacious open concept home...
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    About this property
    WARNING: DO NOT WIRE MONEY Casa de Lida large estate with 3 separate buildings on almost an acre of land and is directly on the ocean . It is very private, has large sandy beach, a pool, a large dock and phenomenal views. The Kids will enjoy playing in the sand, and the adults will enjoy...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Paradise n Summerland Key Cove1 / 20
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Washer
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 March 2016
    Whatever I'd hoped for, this vacation home has without question, surpassed any and all expectations! Excellent location; in a quiet and beautiful strip. Loved relaxing on the...
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    About this property
    Amazing canal front 3 bed 2 bath open concept house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see lobsters, crabs and other sea...
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    Location Information
    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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 25 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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    **Winter Promo**  Amazing views from this Oceanside Home near Pennekamp, dining1 / 25
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
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    • 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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    137 LeSerra Lane1 / 31
    (7)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    Reviewed 26 March 2015
    We had a terrific time at 137 Lessara this February. The wildlife (birds, fish, manatee) viewing was incredible, the weather great, and the house was fantastic- especially the...
    Reviewed 5 June 2014
    This house had more than enough of everything needed away from home.The decks on both floors were great for relaxing,visiting, grilling and tanning.Plenty of space our three...
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    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in  Lower Matecumbe (South part of Islamorada). This home is the second one in on a point  and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee  maker, toaster, and blender. There are...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    bayfront beach house with sandy beach1 / 15
    (25)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Grill
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    • Waterfront
    • Balcony
    • Cable/satellite TV
    • Internet Access
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Amazing stay. More than accommodating. Came down for my brothers wedding which was right down the road. Which made it easy for traveling. The home had everything you needed From...
    Reviewed 30 August 2018
    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...
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    About this property
    Spacious Key Largo bayfront home with sandy beach in tropical garden on one acre with spectacular bay views and sunsets. Relax on the large porch with ceiling fans. Sunbathe on the beach or enjoy water activities using the kayaks, fishing tackle FREE. Children will enjoy the beach and toys...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful modern luxury unit with 3 bedrooms and 2 full bathrooms, along with a half guest-bath! Plasma TV, VCR and DVD player in the living room. This unit does have Wi-Fi.  The Bay Harbour Complex comes complete with two tennis courts, weight room, pool, your own dedicated boat slip, a fish...
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    Location Information
    Long Key, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    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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