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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.
    469 Matching Rentals in Florida KeysView all 1,501 rentals
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    Comfortable Clean HouseBoat in an amazing location1 / 32
    (4)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 5 Quick View
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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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    Beautiful Beachfront Home w/Heated Pool+45' Dock1 / 82
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    4BR Waterfront Retreat-Tiki-Jacuzzi-Dock1 / 12
    (1)Very good
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Grill
    Suitability
    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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    Marathon Shores, Marathon 33050
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    Luxurious 3bd/3bth Villa - Your Keys Escape1 / 30
    (8)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 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...
    Reviewed 23 November 2014
    Really enjoyed this home, clean,secure, owner answered all questions in a timely fashion. Highly recommended!
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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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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    **Ready After Irma** 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 property has been inspected after hurricane Irma, is in good standing and is gladly accepting reservations at this time. We look forward to having you stay with us! *** Owner is highly motivated to rent! Contact us for discounts *** This luxurious waterfront home is located on mile marker 106,...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    New 4 bedroom,4bath in Beautiful Key Colony Beach1 / 21
    (5)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2017
    The house was everything it was advertised to be, very clean and comfortable. Key Colony is a beautiful place to stay and Toni is one of the easiest home owners I have ever had...
    Reviewed 26 March 2017
    Location and home layout was great, however rental needs some TLC: mattresses were old or cheap - very uncomfortable, pool was dirty (pool on other side of duplex was clean to...
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    About this property
    New 4 bedroom, 4 Bath duplex. This beautiful new home has a private pool, a dock- 2 10 by 30 decks on the channel. The dock is 37 1/2 ft. There are 2 refrigerators, bait freezer, fish cleaning table, 2 bicycles. All bedrooms have flatscreen TV's. The family room also has a queen sofa bed. 3 of the...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spacious Top Floor Condo w/ Water View!!1 / 17
    (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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    Marathon, Florida Keys 33050
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 14
    (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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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    TARPON FLATS INN AND MARINA1 / 6
    (6)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Washer
    • Housekeeping Included
    • Shared Outdoor Pool (Unheated)
    • Waterfront
    • DVD Player
    • Ocean Views
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 February 2017
    My husband and I reserved a suite on the ground floor which was both convenient and lovely. The Inn was a quiet oasis minutes from Pennekamp state park and was just what we were...
    Reviewed 5 June 2015
    one of the nicest place&staff i have ever rented hope to go back soon and visit gilda & crew DANNY&SHIRLEY TRY IT YOU WILL LIKE IT DANNY
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    About this property
    Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving....
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Key Colony Beach, Florida Keys 33051
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Conch Key Villas, Quiet, Clean with Awesome VIews in Paradise(# 1)1 / 19
    (9)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Patio
    • Washer
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 May 2017
    If you are looking for a layed back peaceful vacation this is the place for you. The owners Stewart and Katie were awesome! The sunsets are beautiful and the villas are well...
    Reviewed 16 April 2017
    This vacation place is the perfect get away for someone going to the Keys for the first time or 50th. Location is great! Just a short drive and you're in Key Largo or Key West...
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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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    Conch Key, Florida Keys 33050
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (2)Excellent
    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 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...
    Reviewed 5 January 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and...
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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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    Islamorada, Florida Keys FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Quaint KeyLargoCottage, 1 bedroom,sleeps 4 comfy1 / 40
    (25)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Porch
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Washer
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    This cottage is just as advertised. Just spent 4th of July week here and our stay was perfect. This cottage is conveniently located to Islamorada and Marathon we traveled all...
    Reviewed 11 December 2016
    We stayed 5 days/4 nights in early December. Two adults and a 40lb dog, plenty of room and the place had everything we could possibly need: tidy bathroom with full-size...
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    About this property
    Quaint cottage located on mile marker 100. Key Largo is known as the 'Dive Capital of the World.' John Pennekamp Coral Reef State Park has two beaches, and a replica of a shipwreck in the water which is great for snorkeling. We are located only a few blocks from the Marina where you can go fishing,...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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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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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Waterfront
    • Central Heating
    • Balcony
    • DVD Player
    • Patio
    • Housekeeping Included
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Welcome Aboard the 'Manatee' as we say here at Mangrove Marina, located in the northern end of Islamorada in Tavernier at Mile Marker 91.7 on the Bay side in a protected tranquil oasis cove of the beautiful Florida Keys. Our houseboats are a boat lovers dream with all the comforts of home,...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 4 Bedrooms, 1 Bathroom, Sleeps 8
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    Mango Hideaway-King Suite just steps off Duval St1 / 18
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • Private Garden
    • Wi-Fi
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    My husband and I stayed here for our wedding anniversary. Very cute and private little place. Perfect for couples. We would definitely come back again and recommend it to others...
    Reviewed 6 May 2017
    The Mango Hideaway is a nice spot in the middle of Old Town. Walking distance to everything. Private patio and entry off of the side street are a plus. Great location and a...
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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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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    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
    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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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    New Listing Family Friendly1 / 64
    (4)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • DVD Player
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    • Patio
    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 August 2017
    Awesome condo. Perfectly placed near to the hustle and bustle of Key West yet far enough to be tranquil. Roy's condo has all the amenities of my home. Great kitchen, plenty of...
    Reviewed 7 March 2017
    The townhouse on Stock Island (Key West) met all of our needs. It was clean, roomy and convenient. Having 3 full baths was a real plus for 6 women. The pool was delightful...
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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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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Washer
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    • Grill
    • 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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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Washer
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    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    The Eagle's Nest1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Private Garden
    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2017
    This house was plenty for the 4 of us and our 2 dogs. We loved that the yard was fenced off and didn't have to worry about our dog getting out. House was close to water. There...
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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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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 2 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
    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Washer
    • Cable/satellite TV
    • DVD Player
    • Ocean Views
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    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 June 2017
    Great place to stay. Wonderful amenities! Would highly recommend. Location is great for beach, Mallory square and Duval Street.
    Reviewed 18 June 2017
    We had such an awesome time in Key West, and it all started with our accommodations at Tiki Beach Too! The Shipyard complex where the condo is located is in the perfect place...
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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
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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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
    Waterfront Vacation Pool Home 2 Bedroom & 2 Baths Sleeps 8 w/ 60 Feet of Dockage We survived Hurricane Irma and these pictures were taken after the storm. Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Waterfront two Bedroom Paradise Villa with Pool WF 1a1 / 24
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Private Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2017
    Took me a while to write this reviewOh!!!still missingWe loved this pkace , the cleanness, the privacy , the confort and. ..the LadiesThank yu so much. For this placeWe had a...
    Reviewed 28 June 2017
    I have walked into a spotless most beautiful rental property I have stayed in. Everything you want to do from dinning, boat rentals and kayaking is so close from home. You...
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    About this property
    Charming doesn't even begin to describe this modern, tastefully appointed waterfront 2 bedroom 2 bathroom house. Plush bedding, upgraded kitchen and bath, and a breezy terrace perfect for bbq's and relaxing. This home features a private pool, and dock and direct canal access to the open water....
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    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Eyebrow Suite-1 BR/1BA steps off Duval St.1 / 24
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
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    • DVD Player
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    This was our 2nd time staying with Andrews Inn and Cottages. They are amazing!! The staff is very accommodating, the suites are wonderful, and we can't wait to go back. I highly...
    Reviewed 22 March 2017
    Eyebrow House has a ton of room, lovely front porch and rear patio. The negative for senior citizens is that it has only a queen bed and hideabed which works for kids, not...
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    About this property
    The Eyebrow House 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...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This neat oceanfront home is located directly on the Atlantic and is available Sat to Sat. This ideal location is near MM 51.7 at the end of 84th street Oceanside Marathon 33050. This Ocean front home is completely tiled and has central air. The 3 bedrooms have TVs with a 2 full bathroom. There is...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Keys Cove Getaway 2BR 2BT1 / 10
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Secure Parking
    • Grill
    • Private Garden
    • Ocean Views
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 July 2017
    What can I say? I will definitely rent this place again. It's located in a convenient place and most of all it's quiet and clean. The owner is a nice honest lady too.
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    About this property
    Looking to vacation in the beautiful keys? Our spaceous 950sq ft. Home is conveniently located close to many of the things the keys has to offer! After enjoying a fun filled, sun soaked day come home kick back and relax at our little piece of paradise. Our beautifully decorated beach theamed home...
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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    'SANDY BEACH' Key Largo,Fl. Luxury Vacation Rental1 / 31
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2014
    This place is truly amazing! The beach is clean and the good sand extends out into the water. The amenities are endless in the house. Kids loved the pool as it gave them a...
    Reviewed 15 March 2014
    My family of 7 including 2 babies just had a wonderful week at Sandy Beach. The house is perfect for a groupwith large quiet bedrooms. The outdoor kitchen and beautiful private...
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    About this property
    Welcome to 'SANDY BEACH' in Key Largo, Fl. Enjoy amazing sunsets from your own private white sandy beach and swaying palm trees that leads you into the warm ocean blue waters of the Florida Bay. This gated 1 acre 3/3 pool home has been updated and beautifully decorated. It can sleep 8 to 10...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    East Sister Rock Island1 / 12
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    I would recommend this rental property any time of the year, great place to be with the family,perfect!
    Reviewed 13 July 2017
    I spend one amazing week at East Sister Rock Island with my family. The sunrise, endless ocean views, the sunset and the incredible views of the stars in the evening. It was...
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    About this property
    Enjoy a private island paradise located at MM50. East Sister Rock Island is 1/4 of a mile off the Atlantic Shores off the City of Marathon in the Florida Keys. On the private island sits a dream come true getaway home with 5000 sq.ft of living area which includes a 2700 sq.ft. covered veranda,...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 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
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    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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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Up dated open home, 2 queen size beds in each room and 2 bath, sleeps 6 confortable with all the comfort of home, warmth and beauty you can desire. WI-FI, cable, complete kitchen with a BBQ on the deck area. Enjoy the peace and tranquility that the Keys life brings you. Water front property,...
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    Big Pine Key, Florida Keys 33043
    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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    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exclusive Key Colony Beach home with pool and dock, just off of mile marker 53. Enjoy some of the Keys' best fishing. Shopping and dining is just a short drive, or venture off to Key West, which is only an hour away. SLEEPING ARRANGEMENTS (Sleeps 10) Master Bedroom: - King Size Bed - TV - Full, In...
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    Key Colony Beach, Florida Keys 33051
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Dog-friendly family home on deepwater canal, close to beaches!1 / 47
    (1)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Grill
    • DVD Player
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nearby beach access, a private dock, and tropical views are a few great amenities at this three-bedroom, three-bathroom, pet-friendly Marathon vacation rental with space for up to eight guests! Located in a quiet neighborhood on a deepwater canal, this home is within five miles of Sombrero Beach...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
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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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    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    The Studio has a King-size bed as well as a pull out futon in the living room. This Villa is literally 10’ from the water and has a combined living and dining area. The Villa has a kitchen equipped with microwave, coffee maker, toaster, refrigerator/freezer, stove/oven, dishes, utensils, cookware,...
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    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Join us on a 57' Luxury Motor Yacht at Faro Blanco Resort and Yacht Club. Enjoying all the comforts of home and the added beauty of the bay off Marathon Key. The yacht is equipped with 4 staterooms, 3 of which are available. We will be on board to make sure your stay is hassle free and exciting....
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Ocean Views
    • Air Conditioning
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    • Waterfront
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    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated keys cottage. Classic and charming design with modern amenities. This is a concrete home on the ground level, not a trailer or mobile home. Master suite with bath on ground floor. Two bedrooms upstairs with balcony overlooking Buttonwood Sound. Lots of room for the whole...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Neat, clean and perfect for a family vacation. This 2 bedroom, 2 bathroom home sits on a wide, deepwater canal Comfortable beds and furniture. Plenty of parking and room for a boat trailer onsite Optional access to a pool at the Glunz Ocean beach club $12 per person per day Outside Covered...
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    Key Colony Beach, Florida Keys 33051
    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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    • DVD Player
    • Grill
    • Patio
    • Washer
    • Central Heating
    • Balcony
    • Waterfront
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Welcome Aboard the 'Starfish' as we say here at Mangrove Marina. Home of the Houseboat Resort We are in Tavernier Florida which is just south of Key largo and north of Islamorada (I-La-Mah-Ra-Da) We are on the Bayside in a protective tranquil Cove of the beautiful Florida Keys. This Houseboat is a...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Beautiful Single Family Home in Key Colony Beach!1 / 22
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • 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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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Greece At The Keys1 / 13
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    My place is water front, located near John Pennekamp state park which offers boat, snorkeling and scuba tours. You’ll love my place because of the views and lovely location, This house is perfect for couples, business travelers, and families (with kids). If you choose to bring your own boat, jet...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 3 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 3 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
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Waterfront
    • Ocean Views
    • Balcony
    • Grill
    • Terrace
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    'Welcome Aboard the 'Conch Shell' as we say here at Mangrove Marina. Home of the Houseboat Resort We are in Tavernier Florida which is south of Key largo and north of Islamorada (I-La-Mah-Ra-Da) We are on the Bayside in a protective tranquil Cove of the beautiful Florida Keys. Our 'Aqua Lodges'...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Terrace
    • Ocean Views
    • Grill
    • Balcony
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    • Patio
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Casa Cayo!, a Magnificent Florida Keys Home With a Bay View, Located in Islamorada at Mile Marker 88.5 in the Exclusive Gated Community of Futura Yacht Club. Casa Cayo Has Been Completely Updated Throughout and Includes Many Luxury Features to Make Your Stay Relaxing and Enjoyable. This...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Waterfront
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    Pet friendly
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    Smoking allowed
    About this property
    This is a WEEKLY RENTAL! Welcome to Sunset Bay, where you’ll experience the most glorious sunsets! Located on tranquil Big Torch Key, Sunset Bay is situated on the open water of Niles Channel, Gulf side. This home is an outdoor lover’s delight! Situated on a large parcel with a long grassy...
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    Location Information
    Ramrod Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Dog-friendly half-duplex w/ 30-ft dock - access to shared pool & beach1 / 30
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Patio
    • Cable/satellite TV
    • Waterfront
    • Washer
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    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 July 2017
    GREAT PLACE! Boat parking out back door. Relaxation at its best. Bicycle paths through community. Beach, pool, bars. Fully furnished kitchen, beach and bath towels, clean linens...
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    About this property
    For a luxurious paradise retreat, look no further than this dog-friendly home in Key Colony Beach. With a 30-foot dock and access to The Cabana Club with a shared pool, beach, and more, it's the ultimate getaway! Located in Key Colony Beach, this duplex home is on a canal that leads out to the...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
    • Terrace
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Gulf View Home us available Sat to Sat. and is located at 11030 1st Ave in a unique key of Marathon. Its location is perfect to enjoy the beach or for boating and fishing. The deep 75 foot dock can moor 2 boats and is close to Vaca Cut so you to fish or dive the Atlantic Ocean or Bay. Or you...
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    Location Information
    Marathon, Florida Keys 33051
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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