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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.
    456 Matching Rentals in Florida KeysView all 1,494 rentals
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    Tropical Cottage with Sandy Beach1 / 24
    (49)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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    Elegant, Two Bedroom Condo Close to the Ocean1 / 34
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Spacious Top Floor Condo w/ Water View!!1 / 33
    (9)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 2 weeks ago
    The view is far more than just spectacular! The marina below is well maintained and makes sitting on the lanai a dream as there is always activity to watch. As for the unit...
    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...
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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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    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 35
    (21)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 April 2018
    Our family has been coming to Marathon for the last 4 years. The Dolphin Oasis house fully exceeded our expectations. The attention to details on this property are second to...
    Reviewed 28 February 2018
    This was the best vacation I’ve ever had in Florida! This house is gorgeous and has stunning views from the decks. You feel like your on your very own private vacation. It comes...
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    About this property
    This 4 bedroom 3 1/2 Bath House has ample sleeping options for every type of family/friend gathering and provides parking for several vehicles. The newly installed heated pool with hot tub measures 40'x 16'. There is a Tiki hut right at pool side for visiting, Canal Side Beach area and Tiki...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Paradise In Marathon, FL Keys Large Oceanside Home1 / 22
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Private Outdoor Pool (Unheated)
    • Ocean Views
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    • Waterfront
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2017
    We enjoyed our stay in this private home right in the heart of Marathon. It is within walking distance of the Cracked Conch restaurant which serves up great local fare and the...
    Reviewed 23 March 2017
    We had a great time staying at this house! Very comfortable for 7 people and the location was nice and convenient - close to supermarkets, restaurants, beach, etc. The owner...
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    About this property
    This house has everything! You can rent 1/2 or the whole house. The top unit has 2bd/ 2bths. Lower spacious unit has 1bd/1bth. Enjoy dinner on breezy upper or lower outdoor patios. This house is more convenient and offers much more than your ordinary 3/3. Each unit is very spacious, sleeps up to...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    WOW – waterfront, boat lift, private heated pool, walk to beach and shops!1 / 27
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Ocean Views
    • Washer
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 April 2018
    The location is amazing! This duplex is very clean, stocked with anything you would need to cook, play at the pool or go to the beach. We enjoyed the screened in porch and best...
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    About this property
    This is Keys living at its best! Tropical classy, comfy and private – yet easy access to everything you could want. This 2 bedroom, 2 bathroom home on a quiet dead end street with open views and ocean access (with houses only on one side) in the heart of the heart of the Keys comes with all the...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Fabulous 6/4 Tropical Waterfront Pool Home!1 / 27
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. Our beautiful home is Great...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 12
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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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    75130 Overseas Highway1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 August 2017
    We stayed here for a few days and it was amazing. The house is warm and cozy and has all the details you need when away from home. The beachfront is wonderful and can go...
    Reviewed 21 June 2016
    This two bedroom home was the perfect getaway for my husband and me. The cute sea-theme décor added to the cozy ambience. The living room/kitchen are flanked with a queen...
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    About this property
    Great house in Lower Matecumbe (south side of Islamorada) at the 75 mile marker on the bayside. This house has fabulous sunset views in a nice quiet part of town. There is a small beach area in the back with palm trees giving you a little more privacy. A screened in porch with tables and chairs...
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    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    SPECIAL DISCOUNT!  45' Luxury Sailing Yacht and Other Yachts & Boats1 / 19
    (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
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, 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
    • Grill
    • Internet Access
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 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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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    New Listing Family Friendly1 / 32
    (7)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 1 week ago
    Wow! Great space! 3 bedroom 3 bath was enough room for everyone. Big tub in one of the king bedrooms and full kitchen with pots pans and extras. Nice back porch with a grill...
    Reviewed 10 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...
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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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    Islamorada Tropical Canalfront Paradise1 / 13
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Patio
    • Parking
    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 February 2018
    Wow! This property is just perfect for a quick getaway! The backyard was so fun, for our entire family. My kids loved the hot tub, my wife loved the waterfront view and I loved...
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    About this property
    The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (upper unit) island retreat is...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    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 5 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 4 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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    Tavernier, Key Largo 33070
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 5
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    Blue Bungalow1 / 13
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 26 May 2018
    The only drawback to this cute place is that it is on the highway. Otherwise it was very nice. It is small as advertised. It has a nice fenced yard for a small dog if needed...
    Reviewed 19 March 2018
    Very nice for 2 people. Had everything we needed. Clean. Great location. We really enjoyed our stay and would book again.
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    About this property
    Come enjoy the Florida Keys! Many local companies offer opportunities to get out on the water. Go diving or snorkeling. Rent a fishing charter. Rent a kayak or stand up paddle board. We are close to the Everglades where you can birdwatch or see an alligator. Take a day trip to the beaches down...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • DVD Player
    • Waterfront
    • Hot Tub
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a spacious, canal water front, open layout, 2 bedrooms, 2 baths, ground level home that can accommodate up to 6 guests with plenty of room to spare. It is a short walk from multiple restaurants, bars, waterfront parks, and the Cabana Club. We are located on the ocean side, however you will...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant Beach Home With Dockage1 / 24
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Grill
    • Washer
    • Air Conditioning
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 April 2017
    They home was great. It had everything you could ask for. The people that we met at the home very friendly. We had a great stay and I will come again. I high recommend this home.
    Reviewed 19 September 2016
    We stayed here Aug 8-12 with my parents, brother and sister. Not only was the home perfect, but the location was great with several food places in walking distance. We walked...
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    About this property
    Elegant home with many unique, architectural features, located on a family-owned waterfront piece of property, with 3 other rental cottages, sandy beach, and small marina. This lovely house, 'Tropicasa', has everything needed for a large group - full kitchen with granite countertops, stainless...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of Dockage in Marathon, FL, the heart of the Florida Keys. A newly renovated 2 bedroom & 2 bath home that sleeps 8. The boat ramp is 300 yards away and plenty...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    BEST LOCATION & PRICE! King Suite w/ Jacuzzi steps off Duval St.-Mango Hideaway1 / 12
    (8)Very good
    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 27 June 2018
    I have been traveling to Key West for years and sometimes several times a year. Accordingly, I have stayed in all kinds of hotels and guest houses. We had been planning a trip...
    Reviewed 7 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...
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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
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    New 4 bedroom,4bath in Beautiful Key Colony Beach1 / 21
    (5)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 May 2017
    The house was everything it was advertised to be, very clean and comfortable. Key Colony is a beautiful place to stay and Toni is one of the easiest home owners I have ever had...
    Reviewed 27 March 2017
    Location and home layout was great, however rental needs some TLC: mattresses were old or cheap - very uncomfortable, pool was dirty (pool on other side of duplex was clean to...
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    About this property
    New 4 bedroom, 4 Bath duplex. This beautiful new home has a private pool, a dock- 2 10 by 30 decks on the channel. The dock is 37 1/2 ft. There are 2 refrigerators, bait freezer, fish cleaning table, 2 bicycles. All bedrooms have flatscreen TV's. The family room also has a queen sofa bed. 3 of the...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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 28 September 2014
    Arrived September 15th to this amazing villa, everything we could want for our family, 3 couples & 3 young adults (late teens) beautiful clean & spacious, kitchen had...
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    About this property
    This is a beautiful new 4 bedroom, 3 bath home in fablulous Key Colony Beach. The sleeping arrangements are 3 King bedrooms,1 bedroom with twins and a sleeper sofa in the living room. Sleeps 8-10. All bedrooms and screened porch have wall mounted flat screened TVs. The home has a private pool, boat...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
    • Air Conditioning
    • Wi-Fi
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Confortable and spacious, 2 bedrooms 1 baths. Home is in a residential fishing village. Full house is actually a 3/2, split master suite. Rental increase $35 per night for the full 3/2. Trailer parks in the neighborhood, like most of the Florida Keys, but the home is not a trailer. The housekeeper...
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    Pigeon Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Luxury Open Water Vacation Home1 / 114
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Ocean Views
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 November 2016
    We just returned from a fabulous vacation at this house. It was so relaxing, the views were awesome. We saw so many kinds of birds. It is absolutely a perfect place to enjoy...
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    About this property
    OPEN WATER PRIVATE ESTATE 3 Bedroom 2 Bath, with a large Pool. Sleeps 4 to 6 $250 - $268 Per Night Minimum Stay 1 Nights Enjoy your piece of paradise and the warm tropical air of the Florida Keys in your own 2600 square foot, private open water estate in a quiet relaxing neighborhood....
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    Location Information
    Big Pine Key, Florida Keys 33043
    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
    Summerland Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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
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    • 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
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (2)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    Loved Jen and Mitch! Very welcoming! Made everything very comfortable and relaxing! Thier friends and neighbors are very nice and welcoming too! We enjoyed a cookout, a...
    Reviewed 13 April 2018
    My husband and I enjoyed a 3 day stay on the Fat and Sassy. The owners are welcoming and helpful with any questions or recommendations you it need. The marina is perfect, with a...
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    About this property
    Join us in Key West where we are docked at a beautiful Marina. Enjoy all the comforts of home and the added beauty of the Ocean. There are pools and a Waterfront Bar & Grill for your enjoyment. We will be Aboard in the private owner’s suite to make sure your stay is hassle free and exciting....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Bayside View1 / 39
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 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
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Great Fishing Right Off the Dock!!1 / 44
    (6)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Grill
    • DVD Player
    • Internet Access
    • Waterfront
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 February 2017
    Having the Florida Keys on my bucket list can now get a BIG check mark! I took my family and both small dogs (which go everywhere with us) to the keys and can say that renting...
    Reviewed 21 October 2016
    Here's the scoop!... The fishing off the dock truly is great and just the relaxing atmosphere and access to the channel and ocean are worth it alone. Make sure you have fishing...
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    About this property
    This is one of the best vacation spots in the keys.It's a lovely 4 bedroom/3 bath Duplex on 3rd St. The sleeping arrangement include 1 King, 2 Queens, 2 twins plus sleeper sofa. The living room is spacious. Enjoy fishing on the large 56 foot dock The ocean is just seconds away by boat.There is a...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    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 3 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 22 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
    Marathon, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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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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    Location Information
    Key Largo, Florida Keys 33037
    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
    • Washer
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    • Internet Access
    • 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Tropical Blue Adventure Waterfront at Venture Out1 / 29
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
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    • Ocean Views
    • Children's Pool
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Comfortable and charming, this newer stilt home has everything you could want for a vacation for just the two of you, a few friends, or the whole family! Fantastic waterfront open canal views. Located on a 60' wide canal, you can bring your powerboat, jet ski, kayak, or what have you, and dock...
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    Location Information
    Cudjoe Key, Florida Keys 33042
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MILE ZERO STUDIO (monthly rental): Here's a cozy spot for 1-2 people who are looking for comfort and convenience. Large studio has queen bed and sofa in the living space, full bath, and kitchenette that includes a microwave, dorm refrigerator and full size oven. Ample storage space in kitchen to...
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    Location Information
    Stock Island, Florida Keys 33040
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Cute, comfortable home in Lower Matecumbe, Mile Marker 76.5, Oceanside. Wake up to the sun and water each morning from either bedroom at our charming stilt house. Take time to relax with all the conveniences of home with a full kitchen, washer/dryer and living area that opens up onto a large...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Summer Promo** Amazing views from this Oceanside Home near Pennekamp, dining a1 / 25
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
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    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2016
    Here is the bottom line..after about a week of our two month rental we had already rented this home for next year. The location is awesome and fishing off the dock was...
    Reviewed 26 March 2015
    Great House! Big enough for extended family. I really enjoyed the dock and the view of the water. Clean and neat.
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    House, 4 Bedrooms + Convertible bed(s), 3 baths, (Sleeps 8-10) This is one of the best vacation spots in the area. It's an immaculate 4 bed/2.5 bath two Story on 3rd St. Sleeps 8-10 (King, King, Queen, 2 Twins and sleeper sofa) .All bedrooms have flat screen TVs. The living area is tremendously...
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    Location Information
    Key Colony Beach, Florida Keys 33037
    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
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Wi-Fi
    • Air Conditioning
    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 23 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
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 bedrooms at Ocean Harbour Apartment, Islamorada, Florida Keys.1 / 41
    (4)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 3 weeks ago
    I was having trouble booking my reservation online (technicality), and had to call in for help. One of the girls there was able to help me quickly, booked me & took my payment...
    Reviewed 20 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...
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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
    Islamorada, Florida Keys FL 33036
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • DVD Player
    • 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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    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
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    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 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
    Key Largo, Florida Keys 33037
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Cable/satellite TV
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Patio
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Exclusive Key Colony Beach home with heated pool and dock, just off of mile marker 53. Enjoy some of the Keys' best fishing. Shopping, groceries and dining are just a short drive away, or venture off to Key West, which is 53 miles south. Or soak up the sun at the sandy beach with tiki hut and...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Patio
    • Cable/satellite TV
    • Balcony
    • Terrace
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 July 2013
    We have rented the upper duplex of Little Bay in April for the last few years. it is a beautiful property in a perfect setting. The grounds are kept immaculately and the area...
    Reviewed 5 November 2012
    We found Little Bay after our previously planned accomodation had been damaged in a fire so Andi & Katy at Keys Holiday Rentals literally saved us from camping on the beach...
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    About this property
    Minimum Rental: 7 Days Little Bay's Upper Duplex is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    LAST MINUTE DISCOUNT! 48' Sailing Yacht. Other Yachts & Boats Available!1 / 31
    (29)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 May 2018
    The best AirBnB experience I’ve had! This yacht was a dream come true! I imagined everything I wanted for my bachelor party and medical school graduation and found it on this...
    Reviewed 25 April 2018
    Such a cool, unique experience! Anyone can go to Key West... But staying on a boat like this really sets the trip apart. Everything in this listing is spot-on. Here is a pretty...
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    About this property
    Ocean view yacht with beautiful sunsets and sunrises. Underwater windows in the forward cabins makes this yacht unbelievable. Located in the finest most elegant first class marinas giving you full access to its restaurant and private pool during your stay. The marina is located close to...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Manatee Haven1 / 24
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    3 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Parking
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a very spacious 2,352 sf canal front house accommodating up to 12 guess. It is fully furnish with all brand new high end furniture. The house is located on the ocean side in Downtown Key Largo on MM 100. It’s 5-15 minutes away from all the restaurants, bars and cafes. It is also 5-15...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Air Conditioning
    • Waterfront
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    • Grill
    • Ocean Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This 3 BR, 2 BA home offers so many special features all in one perfect location! Situated around the corner from Dolphin Marina, a quick 60 second trip down the canal puts you directly to open water offering access to both the Gulf and Ocean. The canal has a depth of 8-10 ft which can accommodate...
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    Location Information
    Little Torch Key, Lower Keys 33042
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    Cozy Couple Getaway! or Great Family Home1 / 15
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Internet Access
    • Private Garden
    • Washer
    • DVD Player
    • Patio
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    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 May 2016
    My spouse and I are caregivers to a 3 yr old boy who was abandoned by his mother. The stressful situation was reason enough for us to get away for a few days. We selected this...
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    About this property
    Great 2/1 house. Completely renovated. Full kitchen with new stainless steel appliances: Microwave, Range/Oven, Dishwasher, Refrigerator. Central A/C & Heat. Master bedroom has queen size bed and a 32' flat screen tv. Second bedroom has a full size bed and a twin size trundle (full sleeps 2 and...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Houseboat Trawler MV Coconuts: Once in a Lifetime Vacation With Pool Access1 / 162
    (18)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Patio
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Balcony
    • Waterfront
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 March 2017
    Perfect stay for all of us. The kitchen was perfect for our meals. We all slept very comfortable and we enjoyed the decorating that has been done. We enjoyed all the different...
    Reviewed 12 January 2017
    Very cool and unique lodging. Not luxury but very nice and clean. Great communication with host. Very friendly. Great decks/outdoor spaces on boat.
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    About this property
    The M/V Coconuts is a completely unique home with 360 degree water views. It also happens to be an exceedingly rare 50-foot Florida Bay Coaster Trawler permanently docked at the Key West Harbour Yacht Club, featuring a restaurant, infinity pool and a private beach! This is more than a boat. It...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 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 26 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 28 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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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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