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Pet Friendly Holiday Rentals in Florida Keys

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    Travellers to Florida Keys are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    459 Matching Rentals in Florida KeysView all 1 502 rentals
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    Blue Bungalow1 / 12
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort1 / 11
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Tropical Escape1 / 52
    (85)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    Tropical Cottage with Sandy Beach1 / 12
    (48)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Grill
    • Cable/satellite TV
    • Balcony
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2017
    This cottage was everything we were looking for and expected! So relaxing to walk too the dock and watch the stunning Keys sunsets. We loved the decor of the cottage, too! Lots...
    Reviewed 12 August 2017
    We stayed in the pet friendly cottage. It was my husband and I, my 2 college age kids, and our 2 yorkies. Very comfortable 2 bedroom, 2 bath cottage nicely decorated and...
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    About this property
    Cozy cottage with sandy beach located in Key Largo on an acre of tropical waterfront. The children will enjoy playing on the beach with toys provided. Or fish from the 100ft dock with fishing equipment provided. Bring a boat and have FREE dockage. Lounge in the hammock under the palm trees and...
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    33037, Key Largo, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise In Marathon, FL Keys Large Oceanside Home1 / 22
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    33050, Marathon, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 35
    (21)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 April 2018
    Our family has been coming to Marathon for the last 4 years. The Dolphin Oasis house fully exceeded our expectations. The attention to details on this property are second to...
    Reviewed 28 February 2018
    This was the best vacation I’ve ever had in Florida! This house is gorgeous and has stunning views from the decks. You feel like your on your very own private vacation. It comes...
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    About this property
    This 4 bedroom 3 1/2 Bath House has ample sleeping options for every type of family/friend gathering and provides parking for several vehicles. The newly installed heated pool with hot tub measures 40'x 16'. There is a Tiki hut right at pool side for visiting, Canal Side Beach area and Tiki...
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    33050, Marathon, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Comfortable Clean HouseBoat in an amazing location1 / 25
    (4)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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    • Wi-Fi
    • Patio
    • Grill
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 October 2016
    What's not to love? Heidi greeted us with warmth and a smile. She showed us around and provided recommendations for great dinner and SCUBA spots. The house boat was spotless, it...
    Reviewed 3 August 2016
    This is a great little houseboat, clean and comfortable. The owner is kind and responsive. I would highly recommend. There is a little bar and grill at the marina, it closes at...
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    About this property
    Very spacious Houseboat. One bedroom with queen size bed. Very comfortable queen size pull out sleeper sofa, and extendable single sleeper Large closet and lots of storage space. Full bathroom, shower and bath towels, hand towels and washcloths. A fully equipped galley with all the comforts of...
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    33070, Tavernier, Key Largo
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Spacious Top Floor Condo w/ Water View!!1 / 33
    (8)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2016
    This was our second stay at this property. We loved the condo first time around and it was even better for this stay with improvements to the condo and all building works...
    Reviewed 26 October 2014
    Lovely, clean and well furnished condo with great view onto the Gulf. Condo was large with ample room for all six of us with screened verandah ideal for relaxing and watching...
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    About this property
    Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area....
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    33050, Marathon, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxurious 3bd/3bth Villa - Your Keys Escape1 / 30
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Hot Tub
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 March 2018
    For months I had been trying to figure out how my family & I could take a vacation together with kids & grandkids and this house in the Keys was perfect! We all had an...
    Reviewed 27 July 2016
    I stayed in this condo for a week with my 3 children (ages 12, 19, and 20) and a friend and her child (age 20). The condo was located near all that we wanted to explore in...
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    About this property
    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the...
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    33050, Marathon, Florida Keys
    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
    • Parking
    • 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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    Location Information
    33070, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Eagle's Nest1 / 19
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    • Secure Parking
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 March 2018
    My family and I just spent the week down here. The house was perfect for the 3 of us and one dog. This was close to some great restaurants and lots of state parks and activities...
    Reviewed 25 February 2018
    We loved staying at the Eagle's Nest. It was close to so many great restaurants and has a fenced in yard, which made it great for us to bring our dog with us. It even has a...
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    About this property
    This is a two-story typical keys-style home, w/ two bedrooms & two baths. One bathroom is on the ground floor, serving the two bedrooms, & the other is near the living/dining area upstairs. A large sun deck located in front overlooks the marina across the street. At the back of the house facing...
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    33037, Tavernier, Key Largo
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    New Listing Family Friendly1 / 32
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 April 2018
    What a nice stay! Roy’s communication as host was fantastic. Definitely appreciated the extra effort made. For example, we had ordered cribs for delivery since we were traveling...
    Reviewed 18 March 2018
    Wonderful place.we we would stay here again. Very well stocked.nice pool.nice and clean.roy made it easy for us.roy was a very good host.
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    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand...
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 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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    33050, Marathon, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 17
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
    Reviewed 14 July 2016
    This condo was amazing. The service provided was excellent. I loved the location and it was just what i was looking for. Knowing we had a great place to stay made the trip even...
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    About this property
    This quiet four-story condominium building is located just a short walk across the road to the Ocean with a recreational side walk miles long for running, walking, rollerblading and biking to Smaters Beach which is Key West's largest beach. This 2 bedroom, 2 bathroom unit offers all the convenience...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • 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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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Great Summer Rental! 400 4th St. Key Colony Beach1 / 11
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Porch
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 2015
    This is a great little duplex. Nicely equipped kitchen, spacious bedrooms, fabulous patio on the canal, Wi-Fi so I could get my homework turned in, washer and dryer. The area...
    Reviewed 13 July 2015
    Since I waited so long to book this was about all that was available at short notice that accepted pets. PROS: The place was clean and had all the basics; dishware, pots, pans...
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    About this property
    newly renovated 1000 square ft half duplex on canal -two bed two bath- ground level with 32 ft dock space for your boat walking distance to 4 restaurants. Also walking distance to Cabana Club which has a beach and a large pool. Great keys fishing -easy access to atlantic or gulf. -Master bedroom...
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    33051, Key Colony Beach, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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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
    • Grill
    • Washer
    • Air Conditioning
    • Parking
    • Internet Access
    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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    33037, Key Largo, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Manatee Haven1 / 16
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 April 2018
    Good peaceful location, Manatee seen every day that we stayed there, super market within walking distance if you don’t want to drive
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    About this property
    Waterfront Home, 3 bedroom, 2 bath, with it's own dock. Centrally located, walking distance to shopping, bank, KMart, deli, movie, museum, popular beach, dining, fishing and snorkel boats. Boat rentals available. Bike path to public beach. Where sun-kissed bathers enjoy the easy life.......and...
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    33050, Marathon, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3/2 or 6/4 Tropical Parroteyes, Location,Comfort Views!1 / 27
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. You Can Rent One Level a 3/2...
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    33070, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 September 2017
    House was great for us unfortunately Hurricane Irma caused a mandatory evacuation on Wednesday morning. Not sure if there is anything left of the house. Not sure the Trp Advisor...
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    About this property
    This is a fantastic community and is one of the most unique places in the world. The gem clear waters are the home of an almost endless variety of fish and marine life. It has a private 60-foot dock with deep water that will accommodate any size boat. In minutes you can be fishing in either the...
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    Location Information
    33050, Marathon Shores, Marathon
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Conch Key Villas Unit 1, Quiet, Clean with Awesome VIews in Paradise1 / 19
    (13)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
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    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    I could write a novel about this place and most importantly the amazing couple that run it. They make me feel at home everytime I am there. Hurricane Irma brought me to the keys...
    Reviewed 4 March 2018
    I was so lucky to stay two nights at the Conch Key Villas during my bicycle touring trip from Virginia to Florida. I can’t think of a more perfect place to end my trip! The view...
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    About this property
    If Comfort, Fun, Fishing and Views Are on Your List, Stay Here! We have ground level or second floor units. We provide outside table and chairs, and just around the corner the barbecue grill is located to grill up those freshly caught Florida Keys' lobster or our wonderful assortment of Keys'...
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    Location Information
    33050, Conch Key, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of Dockage in Marathon, FL, the heart of the Florida Keys. A newly renovated 2 bedroom & 2 bath home that sleeps 8. The boat ramp is 300 yards away and plenty...
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    Location Information
    33050, Marathon Shores, Marathon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Great Fishing Right Off the Dock!!1 / 22
    (6)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Grill
    • DVD Player
    • Internet Access
    • Waterfront
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 February 2017
    Having the Florida Keys on my bucket list can now get a BIG check mark! I took my family and both small dogs (which go everywhere with us) to the keys and can say that renting...
    Reviewed 20 October 2016
    Here's the scoop!... The fishing off the dock truly is great and just the relaxing atmosphere and access to the channel and ocean are worth it alone. Make sure you have fishing...
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    About this property
    This is one of the best vacation spots in the keys.It's a lovely 4 bedroom/3 bath Duplex on 3rd St. The sleeping arrangement include 1 King, 2 Queens, 2 twins plus sleeper sofa. The living room is spacious. Enjoy fishing on the large 56 foot dock The ocean is just seconds away by boat.There is a...
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    Location Information
    33051, Key Colony Beach, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    ROCK HARBOR CLUB-Endless bay views!!!1 / 9
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Ocean Views
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 March 2016
    I am very pleased with the condo and the property in general. It is in an excellent location in Key largo near many restaurants, stores, a Starbucks, and docks. The property is...
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    About this property
    Rock Harbor Club, gated community, Key Largo's best kept secret with a rare private beach is located on 10 acres of Bayfront property and is one of the most quiet and beautifully landscaped complexes in the Upper Keys. Ensuite master bedroom, with king bed, and endless bay views.... sleeps 2 and...
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    Location Information
    33037, Key Largo, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Hot Tub
    • Washer
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Tavernier family vacation home is like 'home away from home'. Property is fenced. Nicely decorated and tiled throughout our home is very well kept and clean only four homes from open Bay access with clear water canal and direct ocean access via Tavernier Creek. Master bedroom features queen...
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    Location Information
    33070, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 12
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    BEST LOCATION & PRICE! King Suite w/ Jacuzzi steps off Duval St.-Mango Hideaway1 / 18
    (7)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2018
    Just off Duval St. this cottage is efficient and offers all the basics for a relaxing stay. We had everything we needed - being self sufficient. No frills were offered nor...
    Reviewed 14 February 2018
    My husband and I were mostly thrilled with Mango Hideaway. The king suite was quaint but well-appointed. The location is just one block from the action of Duval St. and we...
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    About this property
    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,800...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 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)
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    • Waterfront
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    • Cable/satellite TV
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    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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    33051, Key Colony Beach, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Oceanfront House1 / 50
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Private Garden
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    • Private Outdoor Pool (Heated)
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2018
    What a find in renting this home. It’s one of the nicest we have stayed in since coming to the Keys. From the owner’s, to the manager, to the pool guy, to the grounds’ keeper...
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    About this property
    This luxurious, but cozy and comfortable, three-story home, overlooks the blue Atlantic, punctuated by small tropical islands, the most prominent of which is Looe Key reef, a popular diving/snorkeling area. (There is an island, located a few miles out directly in front of the home, was formerly...
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    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    **Summer Promo** Ocean Front Keys Home with Private Beach - Great for Kite Surfi1 / 25
    (2)Average
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Had a wonderful time beach just out front and did a lot "beaching". Close to a nice supermarket and rental places. Will definitely be back! Thanks for a great get away!
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    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** Beautiful four bedroom, Ocean Front home with...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (4)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2018
    Great location!!! They supplied many extras beach chairs and beach towels. Loved that they had bikes right at the condo. We would definitely book this condo again
    Reviewed 22 June 2017
    Great place to stay. Wonderful amenities! Would highly recommend. Location is great for beach, Mallory square and Duval Street.
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table and...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (3)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 January 2018
    Yes there was..DO NOT RENT FROM ITRIP/PHOENIX RENTALS.They were totally dishonest with me. They did not tell me that there was major construction going on in the building I...
    Reviewed 2 February 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
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    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium...
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    Location Information
    FL 33036, Islamorada, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Washer
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    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Sombrero is an exclusive and private waterfront destination in the heart of the fabulous Florida Keys located in Marathon. This unique retreat is perfectly positioned overlooking a natural preserve on a serene protected deep waterway; providing the discriminating yachtsman or sport fisherman...
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    33050, Marathon, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Cable/satellite TV
    • Housekeeping Included
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large...
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    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Summer Promo** Amazing views from this Oceanside Home near Pennekamp, dining a1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
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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
    33070, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful Bayside View1 / 39
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2018
    My family just LOVED this house. The backyard is amazing with a beautiful view and plenty of space for boat-dockage. My family had fun paddle boarding, kayaking, and...
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    About this property
    Bayside View is truly an amazing Florida Keys home, with great Bay views from all floors! Bayside View is a 3 bedroom/3 bath home that is directly on the Florida Bay. This location satisfies all of your fishing & water sport desires. The home is completely renovated and absolutely gorgeous. The...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In search of tropical views and blissful privacy in the Florida Keys? This beautiful four-bedroom Marathon home provides guests with their very own beach, swimming pool, and dock on serene Florida Bay. And two dogs are welcome, too, for a small nightly fee! Scenically situated on Grassy Key Bay,...
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    Location Information
    33050, Marathon, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    SPECIAL DISCOUNT!  45' Luxury Sailing Yacht and Other Yachts & Boats1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Balcony
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2018
    Husband and I enjoyed our recent five-day stay on The Lion’s Paw - a new and unique experience for us compared to the typical lodging options we normally choose. It was really...
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    About this property
    This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise with amazing water clarity. Your stay will include free access to the marina's private pool,...
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    Location Information
    33040, Key West, Florida Keys
    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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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront unit with a 23 ft Center Console boat. The boat is docked outside your unit for your exclusive use during your stay. We are conveniently located for either bayside or ocean access. There is a dive shop and bait shop in the complex. The unit is 2 bedrooms and has wifi, cable tv,...
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    Location Information
    33037, Key Largo, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Laid Back and Waterfront (Monthly Rental)1 / 7
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
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    • Waterfront
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 August 2016
    My family and I stayed for a month. We had a great time would definitely rent again. Owner was very accommadting. The neighborhood was quiet and neighbors were very friendly.
    Reviewed 9 April 2014
    I rent a house in Key Largo every year, and this canal side paradise is the best I've ever had. The house is spacious, comfortable and clean. The location is convenient to the...
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    About this property
    Minimum rental is 30 days. Our 2/2 modern comfortable house has plenty of dock space (over 100 ft.) and is very close to our community boat ramp. Do you like back-country (shallow water and remote) or deep sea fishing, scuba diving or snorkeling, sailing, nature-watching, canoeing or just...
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    Location Information
    33037, Key Largo, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean Side Villa  in Exclusive Key Largo Community1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Internet Access
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2015
    Very comfortable home but not with very young children-glass table tops and white carpeting.Easy walking distance to pools and other amenities. Some distance from Key Largo and...
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    About this property
    213 Andros Road Welcome to the Ocean Reef Club! 213 Andros Road is a 1950's cinder block 3 bedroom 2 bath home in the elegant and exclusive Ocean Reef Club in Key Largo. 213 Andros is a 5 minute walk from the club's central facilities which include the main restaurant, gift shop, pool, tennis (14...
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    Location Information
    33037, Key Largo, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Paradise By The Bay1 / 27
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Hot Tub
    • Ocean Views
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 May 2017
    Place was great. Pool, jacuzzi, outdoor bar/kitchen. Was very relaxing. Being on the water was convenient for your boat. Really no complaints. Everything u want if your a...
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    About this property
    Come bring your boat and leave your worries at home. And enjoy our little Paradise By The Bay. This is a beautiful mobile home,3 bedrooms 2.5 bath with spacious living room and a flat smart screen TV and comfortable furniture. The master bedroom has a Quinn size bed with half a bathroom a flat...
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    33037, Key Largo, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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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
    • Waterfront
    • Private Outdoor Pool (Heated)
    • DVD Player
    • 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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    33051, Key Colony Beach, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Tropical Private Island w/Houseboat, Boat & Kayaks1 / 31
    (4)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Outdoor Dining Area
    • Private Garden
    • Grill
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 January 2012
    Renting the houseboat was a unique experience. I was concerned about the logistics of our stay, but we were well instructed on the workings of the houseboat and island, and felt...
    Reviewed 21 February 2011
    If you like semi rustic conditions and loads of privacy, this is the spot! We booked this rental for a week in February for our first "getaway from it all" vacation...
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    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own tropical island in a quiet cove of protected mangroves in the Gulf of Mexico. You stay on a 2 bedroom houseboat that is docked on the island. You have your own 17 foot boat for the entire week! HOW MANY PEOPLE CAN...
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    Location Information
    33050, Marathon, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterfront Cottage with boat1 / 10
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Grill
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    • Air Conditioning
    • Cable/satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 January 2015
    Wonderful location for paddle boarding. Saw manatees every day. Not to far from shopping, restaurants and local businesses for boat rentals or snorkeling. The house has clean...
    Reviewed 30 December 2014
    We rented this property for a family Christmas vacation. We had a great time.Pros:Lots of screened in outdoor space including a dining set.Plenty of parkingDock and...
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    About this property
    Keysey home with direct access to the bay or ocean from the dock. Centrally located to stores, restaurants and all that Key Largo has to offer. We are located 2 miles from Pennekamp Park and 4 miles from the Jacobs Aquatic Center. Enjoy the Manatees swimming at the dock or fish and snorkel at the...
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    Location Information
    33037, Key Largo, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
    33042, Summerland Key, Lower Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    A quiet spot in paradise close to fishing with dockage included (#4)1 / 13
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Best view in the Keys! Extremely clean and spacious! Owners very attentive and friendly! Had the most relaxing holiday weekend! Recommend without a doubt and will be back!
    Reviewed 17 May 2018
    Awesome spot, Owners gracious and very helpful with local attractions.Would love to book for next year.
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    About this property
    This second floor Studio has a King-size bed as well as a pull out futon in the living room. We can accommodate 2 adults and 1 child under12. This Villa is situated facing due West right on the water and has a combined living and dining area. The Villa has a kitchen equipped with microwave, coffee...
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    Location Information
    33050, Conch Key, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
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    • Balcony
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    YOUR PRIVATE GETAWAY IN KEY WEST, FLORIDA.  This beautifully historic 2 bedroom 2 bath home is conveniently located in Old Town Key West, FL. Just a short walk from everything you could dream of, for your island vacation. Just 5 blocks from the famous Duval Street. Two blocks from the seaport,...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in Key Largo at mile marker 95, oceanside, this pool home will really seal the deal. This home has been remodeled, and offering stunning Atlantic views, the home is ideal for a family seeking a combination of camaraderie and privacy. Divided into separate units on its two floors,...
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    Location Information
    33036, Key Largo, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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