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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.
    454 Matching Rentals in Florida KeysView all 1,479 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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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 21
    (6)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 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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    Dolphin Oasis 4bdr/4bth  Pool/hot tub 115' dockage1 / 35
    (21)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Cable/satellite TV
    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 April 2018
    Our family has been coming to Marathon for the last 4 years. The Dolphin Oasis house fully exceeded our expectations. The attention to details on this property are second to...
    Reviewed 28 February 2018
    This was the best vacation I’ve ever had in Florida! This house is gorgeous and has stunning views from the decks. You feel like your on your very own private vacation. It comes...
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    About this property
    This 4 bedroom 3 1/2 Bath House has ample sleeping options for every type of family/friend gathering and provides parking for several vehicles. The newly installed heated pool with hot tub measures 40'x 16'. There is a Tiki hut right at pool side for visiting, Canal Side Beach area and Tiki...
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    33050, Marathon, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Spacious Top Floor Condo w/ Water View!!1 / 33
    (8)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 August 2016
    This was our second stay at this property. We loved the condo first time around and it was even better for this stay with improvements to the condo and all building works...
    Reviewed 27 October 2014
    Lovely, clean and well furnished condo with great view onto the Gulf. Condo was large with ample room for all six of us with screened verandah ideal for relaxing and watching...
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    About this property
    Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area....
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    33050, Marathon, Florida Keys
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    New Listing Family Friendly1 / 32
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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...
    Reviewed 19 March 2018
    Wonderful place.we we would stay here again. Very well stocked.nice pool.nice and clean.roy made it easy for us.roy was a very good host.
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    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand...
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    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort1 / 11
    (1)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Patio
    • Waterfront
    • Grill
    • Washer
    • Central Heating
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Ocean view, on a canal, three lots from open water in Venture Out Resort; a safe, gated community. Park your boat or kayak right outside your front door on the canal, or just relax and enjoy your mosaic picnic table and 4 patio chairs, and Weber charcoal BBQ. Only 7 steps up or down to...
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    33042, Cudjoe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    • Washer
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    In search of tropical views and blissful privacy in the Florida Keys? This beautiful four-bedroom Marathon home provides guests with their very own beach, swimming pool, and dock on serene Florida Bay. And two dogs are welcome, too, for a small nightly fee! Scenically situated on Grassy Key Bay,...
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    33050, Marathon, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Elegant, Two Bedroom Condo Close to the Ocean1 / 17
    (16)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Hot Tub
    • Balcony
    • Washer
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 November 2016
    Overall we were satisfied with our stay at this condo, but there were pros and cons. Pros: The layout was nice, almost like 2 separate hotel rooms joined by a shared kitchen...
    Reviewed 15 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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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Great Summer Rental! 400 4th St. Key Colony Beach1 / 11
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Cable/satellite TV
    • Internet Access
    • DVD Player
    • Porch
    • Washer
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 October 2015
    This is a great little duplex. Nicely equipped kitchen, spacious bedrooms, fabulous patio on the canal, Wi-Fi so I could get my homework turned in, washer and dryer. The area...
    Reviewed 13 July 2015
    Since I waited so long to book this was about all that was available at short notice that accepted pets. PROS: The place was clean and had all the basics; dishware, pots, pans...
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    About this property
    newly renovated 1000 square ft half duplex on canal -two bed two bath- ground level with 32 ft dock space for your boat walking distance to 4 restaurants. Also walking distance to Cabana Club which has a beach and a large pool. Great keys fishing -easy access to atlantic or gulf. -Master bedroom...
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    33051, Key Colony Beach, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Tropical Escape1 / 26
    (85)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    This place is just perfect! Nice and clean, and check in was a breeze! But what I really loved about it is the location! You are in Key West, but you are far enough away from...
    Reviewed 8 July 2017
    Owners were great and very accommodating. The condo is beautiful. Has everything you need. Pool was great to use. We would rent again when we come to key West. We had a great...
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    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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    33040, Key West, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    Blue Bungalow1 / 26
    (13)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    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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    33037, Key Largo, Florida Keys
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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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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    33051, Key Colony Beach, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3/2 or 6/4 Tropical Parroteyes, Location,Comfort Views!1 / 54
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
    • Waterfront
    • DVD Player
    • Ocean Views
    • Hot Tub
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 June 2017
    We are one of two couples who each have rented a level for the past six winter seasons and we are so looking forward to returning in 2018. The location is perfect-within one...
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    About this property
    Beautifully Decorated, Fully Furnish and Equipped Vacation Pool Home, Located in a Quiet and Safe Residential Area in Islamorada, Florida Keys. Video of house and area available upon request. It consists of Two Levels, Each Separate Level Has 3 Bedrooms/2 Bathrooms. You Can Rent One Level a 3/2...
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    33070, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Great Fishing Right Off the Dock!!1 / 22
    (6)Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Grill
    • DVD Player
    • Internet Access
    • Waterfront
    • Washer
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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 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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    33051, Key Colony Beach, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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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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    33050, Marathon, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Welcome Aboard!  Relax, unwind, enjoy the water! in key west1 / 50
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 6
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    Luxury Open Water Vacation Home1 / 19
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Ocean Views
    • Washer
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    33043, Big Pine Key, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean Side Villa  in Exclusive Key Largo Community1 / 15
    (1)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Shared Indoor Pool
    • Internet Access
    • Air Conditioning
    • Patio
    • Waterfront
    • Washer
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 March 2015
    Very comfortable home but not with very young children-glass table tops and white carpeting.Easy walking distance to pools and other amenities. Some distance from Key Largo and...
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    About this property
    213 Andros Road Welcome to the Ocean Reef Club! 213 Andros Road is a 1950's cinder block 3 bedroom 2 bath home in the elegant and exclusive Ocean Reef Club in Key Largo. 213 Andros is a 5 minute walk from the club's central facilities which include the main restaurant, gift shop, pool, tennis (14...
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    33037, Key Largo, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful Single Family Home in Key Colony Beach!1 / 22
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 September 2014
    Arrived September 15th to this amazing villa, everything we could want for our family, 3 couples & 3 young adults (late teens) beautiful clean & spacious, kitchen had...
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    About this property
    This is a beautiful new 4 bedroom, 3 bath home in fablulous Key Colony Beach. The sleeping arrangements are 3 King bedrooms,1 bedroom with twins and a sleeper sofa in the living room. Sleeps 8-10. All bedrooms and screened porch have wall mounted flat screened TVs. The home has a private pool, boat...
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    33051, Key Colony Beach, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    SPECIAL DISCOUNT!  45' Luxury Sailing Yacht and Other Yachts & Boats1 / 17
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Balcony
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 March 2018
    Husband and I enjoyed our recent five-day stay on The Lion’s Paw - a new and unique experience for us compared to the typical lodging options we normally choose. It was really...
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    About this property
    This yacht is very spacious and bright with windows surrounding it making views of the ocean amazing. The marina and its grounds are meticulous and located in the middle of a turquoise paradise with amazing water clarity. Your stay will include free access to the marina's private pool,...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Elegant Beach Home With Dockage1 / 24
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 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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    Location Information
    33037, Key Largo, Florida Keys
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Manatee Haven1 / 8
    (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
    33050, Marathon, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Balcony
    • Washer
    • Grill
    • Cable/satellite TV
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    • DVD Player
    • 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
    33050, Marathon, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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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
    • Wi-Fi
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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 24 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
    33040, Key West, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    75130 Overseas Highway1 / 19
    (5)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    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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    Location Information
    33036, Matecumbe Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    **Summer Promo** Amazing views from this Oceanside Home near Pennekamp, dining a1 / 24
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
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    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 25 March 2015
    Great House! Big enough for extended family. I really enjoyed the dock and the view of the water. Clean and neat.
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    About this property
    We help make the most of your vacation by providing Free Admission to some of the area's top attractions each and every day! Create exciting memories, have more fun, and truly experience your destination! ***Free Fun Rules and Restrictions Apply *** *** Owner is highly motivated to rent! Contact...
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    Location Information
    33070, Tavernier, Key Largo
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    BEST LOCATION & PRICE! King Suite w/ Jacuzzi steps off Duval St.-Mango Hideaway1 / 18
    (8)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
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    • Private Garden
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    • Hot Tub
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    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 6 April 2018
    Just off Duval St. this cottage is efficient and offers all the basics for a relaxing stay. We had everything we needed - being self sufficient. No frills were offered nor...
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    About this property
    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as...
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    Location Information
    33040, Key West, Florida Keys
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    LITTLE BAY - Upper Duplex1 / 25
    (3)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    At this gorgeous Sugarloaf Key vacation home, you'll have five spacious bedrooms (including two master suites)! Enjoy beautiful Gulf views set over three acres, offering privacy for a memorable Florida escape. It's even dog-friendly! Just 18 miles from Key West, this location offers easy access to...
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    Location Information
    33042, Sugarloaf Key, Florida Keys
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
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    • Cable/satellite TV
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    • Grill
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    MINIMUM STAY: 28 DAYS Flamingo Cottage is an adorable 3 bedroom stilt home nestled among tropical foliage. There are two bedrooms and one bath on the main living level of this home plus a private studio type apartment with a private bath on the ground level. This home has a cozy cottage like...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our beautiful, private home is located in a private, small subdivision with about 25 homes all on the open water, Gulf view. Its's a lovely home with 1 bedroom downstairs with a half bath and 2 large bedrooms upstairs with 2 full bathrooms. The master upstairs has a balcony with an exquisite view...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
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    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
    33040, Stock Island, Florida Keys
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Terrace
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 1 Month *****SUMMER SPECIAL ***** RECEIVE A $100 VISA GIFT CARD FOR ALL BOOKINGS BETWEEN JULY 1, 2018 AND AUGUST 31, 2018. RESERVATION MUST BE MADE BY JULY 31, 2018. . Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home!...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Patio
    • Ocean Views
    • Air Conditioning
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    • Private Outdoor Pool (Heated)
    • Waterfront
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discover the Ease of Booking a FL Keys Vacation...Welcome to Sachs' Sea Shack…Bayside Deep Waterfront Pool Vacation Home with 60 feet of Dockage in Marathon, FL, the heart of the Florida Keys. A newly renovated 2 bedroom & 2 bath home that sleeps 8. The boat ramp is 300 yards away and plenty...
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    Location Information
    33050, Marathon Shores, Marathon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Luxurious 3bd/3bth Villa - Your Keys Escape1 / 60
    (9)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
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    • 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 27 July 2016
    I stayed in this condo for a week with my 3 children (ages 12, 19, and 20) and a friend and her child (age 20). The condo was located near all that we wanted to explore in...
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    About this property
    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the...
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    Location Information
    33050, Marathon, Florida Keys
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Deep canal Bring your yacht. Very private bedrooms on both sides. very large balcony looking at the water view. close to retaurants, beach,Public, Kmart,Windixie, CVS, WellsFargo, UPS, Homedepot, West Marine & Wallgreen walking distance. Beach 10 minutes walking. Safe area. 5 bicycls their,...
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    Location Information
    33050, Grassy Key, Marathon
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 9
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Balcony
    • Patio
    • Internet Access
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 1 MONTH * SUMMER SPECIAL $200 DISCOUNT FOR ALL RESERVATIONS MADE BY MAY 15, 2018 FOR BOOKINGS BETWEEN MAY 1, 2018 AND AUGUST 31, 2018 This is a gorgeous 3 bedroom townhouse in a private upscale ocean front condominium community! Super convenient to the mainland. Everything...
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    Location Information
    33037, Key Largo, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
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    Pet friendly
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    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
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Private Garden
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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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    Location Information
    33050, Pigeon Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, 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
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    • Waterfront
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 February 2018
    Wow! This property is just perfect for a quick getaway! The backyard was so fun, for our entire family. My kids loved the hot tub, my wife loved the waterfront view and I loved...
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    About this property
    The moment you step in the back yard, you'll know vacation has begun. . . time stands still as the laid-back island lifestyle takes over...Totally remodeled, canal-front home, quiet and in the nicest of neighborhoods (Plantation Key Colony). The 2 bed/2 bath stilted (upper unit) island retreat is...
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    Location Information
    33070, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect getaway! Enjoy big boat access on a 62 ft wide, flow through canal, complete with 80 ft of concrete seawall dock and an outdoor shower. Only a 3-5 minute ride to open ocean. New washer/dryer Pet Friendly Situated on a lot & a third, this 4bd/2ba home offers room to lay and play in...
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    Location Information
    33042, Summerland Key, Lower Keys
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    LITTLE BAY - Lower Duplex1 / 23
    (4)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Minimum Rental: 7 Days Little Bay's Lower 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. The units are available for rent by the week, or month. Each unit sleeps...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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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
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    • 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 22 June 2017
    Great place to stay. Wonderful amenities! Would highly recommend. Location is great for beach, Mallory square and Duval Street.
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    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table and...
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    Location Information
    33040, Key West, Florida Keys
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    About this property
    This is a very spacious and very well-maintained 4 bedroom, 3 bathroom home toward the mouth of the canal on a quiet street in Plantation Key (Tavernier). You and your group will enjoy stunning views from the main level, master suite, & rooftop sundeck. There is approximately 20ft concrete dockage....
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,800...
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    Location Information
    33036, Islamorada, Florida Keys
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    ROCK HARBOR CLUB-Endless bay views!!!1 / 9
    (3)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • 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
    33037, Key Largo, Florida Keys
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Gorgeous Spa Villa, Marina in Florida Keys1 / 30
    (14)Very good
    2 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Waterfront
    • Hot Tub
    • Patio
    • Air Conditioning
    • Cable/satellite TV
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    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 May 2017
    Everything was great, but the spa didn't work. My wife and I enjoyed the visit the rental was centrally located
    Reviewed 21 March 2017
    Location was great if you want to explore all the Keys. Great dock to sit out back to fish or just relax and look at the water. Everything was just as stated. Perfect for our...
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    About this property
    Preferred Style and Furnishings are in this beautiful Spa Villa! Tucked along a deep harbor, with direct boat access to the Atlantic Ocean (boat slips available from Hawks Cay Marina). Embracing the most alluring qualities of the Florida Keys—beauty, relaxation, and turquoise waters in this luxury...
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    Location Information
    33050, Duck Key, Florida Keys
    Holiday Rental House - 2 Bedrooms, 3 Bathrooms, Sleeps 6
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    Tropical Keys Home - Gulf View, 40' Dock, Kayak1 / 16
    (9)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Wi-Fi
    • Grill
    • Waterfront
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    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 February 2015
    We enjoyed our stay. Nice location and view. The place was clean and as the pictures showed. Plenty of amenities in the kitchen for what we needed. The 2nd bathroom and bedroom...
    Reviewed 21 July 2014
    We enjoyed our stay so much that next time we are in the Keys I would love to stay in this house again. The views from the house are excellent. My kids had a great time on the...
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    About this property
    Lush Tropical Lagoon half duplex home with view of the Gulf of Mexico and incredible sunsets. Recently renovated octagonal shaped home with wide open water views from every window. Newly furnished comfortable interior with all the amenities you'd expect. Brick pavers surround lush landscaping and...
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    Location Information
    33050, Marathon, Florida Keys
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Waterfront unit with a 23 ft Center Console boat. The boat is docked outside your unit for your exclusive use during your stay. We are conveniently located for either bayside or ocean access. There is a dive shop and bait shop in the complex. The unit is 2 bedrooms and has wifi, cable tv,...
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    Location Information
    33037, Key Largo, Florida Keys
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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