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Florida Keys Luxury Vacation Rentals

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    Travellers to Florida Keys are booking January dates now. Secure your vacation rental today, and have the perfect trip.
    231 Matching Rentals in Florida KeysView all 1,545 rentals
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    The Meeting Point - Key West ~ Weekly Rental1 / 54
    (2)Average
    11 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
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    Alligator Reef Compound1 / 99
    (2)Excellent
    10 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 30, 2018
    We stayed for a week the end of June, we rented all four houses which was perfect for our group of 22. We ranged in age from one to 68 and everyone had a blast!The pools are...
    Reviewed May 30, 2018
    We had a great time at Alligator Reef. The house is so well stocked. The view is breathtaking. And there is so much to do we never left the property. We kayaked, swam in the...
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    About this property
    Got a large group that wants to 'get away from it all'? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 10 Bedrooms, 10 Bathrooms, Sleeps 28
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Secure Parking
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy the unique experience of sailing, fishing, snorkeling, scuba diving and paddling aboard an air-conditioned, 47-foot catamaran while sleeping under the stars for a vacation of a lifetime. Our 3 bed / 3 bath sailing catamaran charter boat with your onboard owner-hosts provide gourmet meals, as...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Family Reunion ~ Weekly Rental1 / 53
    (2)Very good
    9 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 17, 2016
    We rented the family reunion for a 50th birthday celebration with family and friends flying in from all over the country. It worked out great! We had 22 people and each person...
    Reviewed June 25, 2015
    Planned well in advance as Key West can be hit or miss with getting the place you want. The garden and pool mesh great for the outside wedding. For me the pool house is the best...
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    About this property
    Thinking about getting your extended family or friends together for a Key West vacation? This one-of-kind gated Key West vacation rental compound, with large private swimming pool in spacious landscaped tropical garden setting, could be the perfect place. Family Reunion Key West vacation rental...
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    Key West, Florida Keys 33040
    Holiday Rental House - 9 Bedrooms, 10 Bathrooms, Sleeps 28
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    Exclusive Oceanfront Estate - Feels Like a Resort1 / 39
    (3)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Hot Tub
    • Washer
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 5, 2015
    Just a wonderful house and the renter's agent was so helpful with making sure everything was working and that we were settled in. the house is phenomenal and the guest house is...
    Reviewed July 5, 2015
    I don't have enough accolades for this property and for the service provided by Larry and Lisa of Keys Vacation Rentals. The home is perfect. Every single detail has been...
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    About this property
    OCEANFRONT and IRMA READY! Extraordinary Oceanfront Estate with Forever Ocean Views. A private resort-like property in an amazing convenient location. 5 bedroom, 4 full 1 half bath home on over an acre of landscaped privacy. All recently Designer Furnished and ready to begin your Luxury Keys...
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    Tavernier, Key Largo 33070
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    7 Bedrooms, 4 Bathrooms, Sleeps 16 Quick View
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    • Wi-Fi
    • Ocean Views
    • Patio
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private and stunning, the Shadow Point peninsula is surrounded by water on three sides and is nestled within a tropical native hammock with garden planters to wander between. We believe it to be the most charming, spectacular and intimate private property in Key Largo With a PRIVATE BEACH, private...
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    Pigeon Key, Florida Keys 33037
    Condo/Apartment - 7 Bedrooms, 4 Bathrooms, Sleeps 16
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    12 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're looking for the perfect location to host your corporate retreat, family reunion, or getaway with friends, consider booking this beautiful 12-bedroom, 11-bathroom bed and breakfast. In addition to standard home comforts, you and your travel companions will enjoy the convenience of a...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 12 Bedrooms, 11 Bathrooms, Sleeps 24
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    Grande Dame Key West - 'The Watson House' ~ Weekly Rental1 / 38
    (10)Very good
    7 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
    • DVD Player
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    • Wi-Fi
    • Grill
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 14, 2017
    From booking to our stay everything was flawless. The house is amazing for large groups and centrally located one block off Duval. The home is beautifully appointed and the...
    Reviewed July 4, 2016
    We had 7 couples and 2 singles for 16 people total. There was plenty of room for everyone. Upon arrival we found the house to be in very good condition, clean, and stocked...
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    About this property
    Grande Dame Key West – (The Watson House) vacation rental estate is an impeccably detailed 3-story Classic Folk Victorian home with 7 bedrooms and 7 bathrooms. An award winning renovation of this stately Victorian mansion has achieved an impressive balance of timeless charm, classic elegance, and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 7 Bathrooms, Sleeps 16
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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
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    • Private Garden
    • Private Outdoor Pool (Heated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Live your tropical dream at this palatial oceanfront estate. Located near mile marker 89, on Islamorada's Millionaires' Row, this 4 bedroom / 6 bath home comes with just about every convenience you can imagine, as well as some you probably haven't even considered. Enjoy a swim in the pool that...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 10
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    Six dog-friendly homes in a quiet neighborhood w/ private pool & hot tub1 / 25
    (1)Excellent
    12 Bedrooms, 9 Bathrooms, Sleeps 36 Quick View
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    • Hot Tub
    • Patio
    • Washer
    • Cable/satellite TV
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    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 21, 2016
    We rented out the entire Tropical Village compound for our December 2015 destination wedding. While renting all 6 cottages may not be the "norm," it worked out perfect...
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    About this property
    If you're planning your next family friendly group getaway or a large family reunion, this grouping of six separate Key West homes is the perfect spot for everyone to spread out and enjoy some privacy in a quiet residential neighborhood. Featuring street parking, a private pool, hot tub, grilling...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 12 Bedrooms, 9 Bathrooms, Sleeps 36
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    East Sister Rock Island1 / 16
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2017
    I would recommend this rental property any time of the year, great place to be with the family,perfect!
    Reviewed July 13, 2017
    I spend one amazing week at East Sister Rock Island with my family. The sunrise, endless ocean views, the sunset and the incredible views of the stars in the evening. It was...
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    About this property
    Enjoy a private island paradise located at MM50. East Sister Rock Island is 1/4 of a mile off the Atlantic Shores off the City of Marathon in the Florida Keys. On the private island sits a dream come true getaway home with 5000 sq.ft of living area which includes a 2700 sq.ft. covered veranda,...
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    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ocean-Front Caribbean Home.1 / 42
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 2018
    Very much enjoyed our stay. House was beautiful and clean, staff was friendly and helpful. My mother and I loved relaxing in the hot tub and my father and husband very much...
    Reviewed April 24, 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    About this property
    The Royal Palm, South - Ocean Front Home Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Full kitchen with Subzero appliances and Viking stove. Chiseled-rock flooring throughout. Wrap-around verandas. Seamless curved-glass corner windows. High open-beam ceilings. Located on The...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Classic Key West Estate ~ Weekly Rental1 / 30
    (7)Average
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 23, 2018
    We had a group of 13 adults who were able to stay comfortably in this rental property. The house was clean, well stocked and in the perfect location to walk to many of our...
    Reviewed May 30, 2017
    We had this house full, 14 people. Had plenty of space for everyone and privacy when needed. Great location and grocery store right down the street. House was clean, had...
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    About this property
    Featured on HGTV House Hunters on Vacation, the timeless charm of this distinguished Classic Key West Estate vacation rental is at once authentic and magnificent. If you have ever had the opportunity to stroll the residential streets of the Historic Seaport of Old Town of Key West, you have...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Wi-Fi
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    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ultra Luxurious home in Islamorada, Florida Keys. Extravagantly manicured ocean front estate with pool, tennis court, and more. Extremely private. Experience complete relaxation in the heart of Islamorada, near the best restaurants, galleries, bars and breweries. With sandy beach, ocean...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Terrace
    • Air Conditioning
    • Internet Access
    • Balcony
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for the perfect Key West vacation rental to host your family reunion or corporate retreat? Your search stops with Curry House Bed & Breakfast, a nine-bedroom, nine-bathroom getaway with historic charm, modern comforts, a private swimming pool, and room for up to 18 guests. Curry House is...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    Sandy Beach, Direct Ocean, Pool, Dock & Lagoon1 / 34
    (33)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 22, 2018
    This house is amazing!! The view from the second floor is breathtaking but from the third floor window watch, it's spectacular!! The yard is very large with a lagoon, beach and...
    Reviewed July 20, 2018
    We found a little oasis of oceanfront paradise!! With meticulous attention to the lush grounds, this property rivals any luxurious resort.This spacious open concept home...
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    About this property
    WARNING: DO NOT WIRE MONEY Casa de Lida large estate with 3 separate buildings on almost an acre of land and is directly on the ocean . It is very private, has large sandy beach, a pool, a large dock and phenomenal views. The Kids will enjoy playing in the sand, and the adults will enjoy...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    Rent a private island with 25ft boat Pure Luxury1 / 69
    (6)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 15, 2014
    This is such a unique property! We loved the privacy, the space, the sea life. The house is very spacious and comfortable. We went there with the idea that we were...
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    About this property
    In the Florida Keys At MM 50 - East Sister Rock Island is a ¼ mile off the Atlantic shore of Marathon. On this private island sits a dream come true getaway home with 5000+ square feet of living area including a 2700 square foot veranda, boat dock (fisherman's dream), helicopter launch pad and many...
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    Marathon, Florida Keys 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    FLORIDA KEYS OASIS # The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 31
    (5)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Ocean Views
    • Patio
    • Private Outdoor Pool (Heated)
    • Waterfront
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 30, 2018
    Despite our rainy week in Islandmorada, Sean helded to make our vacation seemless! We had 10 people staying with us to help celebrate my husbands 50th birthday. The house had...
    Reviewed July 12, 2017
    The property manager was super helpful and walked us through the entire house showing us all the nooks and crannies. I must say I've never had someone take close to 45-an hr to...
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    About this property
    ***7 day minimum rental - notwithstanding anything in the rates page the MINIMUM rental is 7 days ****This custom built 5 bedroom house has been immaculately taken care of and has a proper size elevator and is fully wheel chair accessible. Enjoy your stay in Sereni-key looking out to an endless...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Key West Vacation Rental - The Duval Street Compound1 / 28
    (3)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Internet Access
    • Private Outdoor Pool (Unheated)
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    • Cable/satellite TV
    • DVD Player
    • Hot Tub
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    The Ocean Never Felt So Close!1 / 12
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
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    • Grill
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    • Balcony
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 20, 2018
    We've been renting this duplex for quite a few years and have always found it to be the best value in the Keys and all the amenities you need. It is so convenient to the Cabana...
    Reviewed June 25, 2018
    This truly has been our 'home away from home' for many years and we have never been disappointed. We have even rented both sides to bring the entire family for a wonderful...
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    About this property
    Our side by side full ocean view duplex is 200 feet from the Atlantic Ocean. We are the closest rental to the Cabana Club Beach and Pool, that we give you membership to during your stay. Great for multi family vacations! Rent half for up to 6 people or both sides for up to 12. Both sides have 2...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Top Of Duval- 6 Bedroom Penthouse1 / 26
    (17)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed November 1, 2018
    This has been our favorite place to stay in Key West. Very clean, super convient and had everything we needed.
    Reviewed October 25, 2018
    13 guys rented this house for a long weekend getaway. It was a great location for us. The private pool out back was a nice bonus. The rooms were all well equipped and very...
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    About this property
    Ready to escape to Key West? Make the most of your visit and stay at Top of Duval Vacation Rentals, located in the heart of Key West's Old Town. It's like having your own private hotel. If you are vacationing with family and friends, Top of Duval offers a truly unique layout with six individual...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 16
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    Private Beachfront -Perfect for Families and Events Historic Shadow Point Estate1 / 82
    (20)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 5, 2018
    I was so fortunate to visit Shadow Point for a second time. I just love the feeling of being in such a special place. It is old Florida at its best with all the modern...
    Reviewed April 29, 2018
    First visit to the Keys after Hurricane Irma and return visit to Historic Shadow Point since November 2015. Same group of friends enjoyed much better weather this time around...
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    About this property
    Why would anyone want to rent a house on a canal right next to other houses and no real place to swim when you could rent this private, secluded, stunning place surrounded on 3 sides by water? We have the most charming and spectacular and intimate property in Key Largo for your vacation rental....
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 16
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    5 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Located just off US-1 behind a gated fence awaits a Fantastic Keys Getaway. Little Bay is a private compound situated on a beautiful 1-acre piece of paradise on the Florida Bay. The property has a total of three separate rental units, accommodating a total of 18 people. The Upper Duplex &...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 18
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Secure Parking
    • Wi-Fi
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    • Private Garden
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Two adorable, private cottages right on the Atlantic Ocean. Located in the heart of Islamorada at mile marker 83. This stunning property is truly a tropical paradise with a private, sandy beach and observing pier. Relax at the beach or cool down in the beachside pool. The front home sits...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Historic house w/ private pool & easy beach access - ideal for groups! Dogs OK!1 / 31
    (1)Very good
    7 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
    • Internet Access
    • Balcony
    • Grill
    • Washer
    • Cable/satellite TV
    • Parking
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 26, 2016
    We stayed in one of the units at the property (Banana Split). This is a 1 bedroom / 1 bath apartment on the second floor. It has a full kitchen, small sitting area and two decks...
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    About this property
    Palm trees, sunsets, and the blissful pace of island time will all be yours when you stay at this large historic house on Key West. Featuring a private heated pool, four private parking spaces, and a communal area with plenty of room for everyone, this seven-bedroom, eight-and-a-half bathroom house...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 18
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    The Caroline House Estate ~ Weekly Rental1 / 35
    (9)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Patio
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 6, 2018
    My group had such an easy time booking, checking-in and checking-out of this property. The house plus cottage had ample room for our group of 13 and the location (about a 5...
    Reviewed June 27, 2016
    take your own towels as the very few that are there are tiny and paper thin. the clothes dryer didn,t work at all and took till the end of our stay to get it replaced. the oven...
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    About this property
    This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbean with stunning island-modern that we have seen. An exceptional degree of refinement was reserved for the sophisticated renovation and décor of this circa 1930’s Key West...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Tropical ~ Tranquility ~ Weekly Rental1 / 17
    (8)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Air Conditioning
    • Patio
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    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 9, 2018
    We were highly impressed with this beautiful secluded home. The plain gray fence hides an oasis. We opened up the french doors in the kitchen over looking the patio & pool...
    Reviewed March 21, 2018
    We arrived at house we opened gate and walked into PARADISE!! We were greeted by Kevin who showed us around and couldn't have been nicer.house is immaculate and the pool will...
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    About this property
    Few places exist where you can ride the fine line separating a secluded tranquil luxury villa, and the Heart of Old Town Key West. It may sound like a poetic abstraction, but for this masterful property with 5-Star amenities, the distinction is definitely real. Extraordinarily secluded and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    6 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take the worry out of coordinating housing for your next big family reunion or holiday celebration and reserve this entire Key West property. Consisting of five separate rentals all sharing a large, outdoor gathering area, your very own swimming pool, sundeck, and even a bar, up to 22 people can...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 22
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    Private Island Rental with 19' Boat, Seabird Key1 / 85
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
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    • Waterfront
    • Cable/satellite TV
    • Ocean Views
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 15, 2016
    Seabird Key was absolutely perfect for our family. We were were a party 4 adults, a 2 year old and an infant. The island was well-suited for all. We enjoyed going to the beach...
    Reviewed March 19, 2015
    Wow. Seabird Key is one of a kind. We felt like we were in the swiss family robinson movie. The house's main floor is perched at the same level as the tree canopy. If you...
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    About this property
    Seabird Key is a ten acre private island available for rental by the week featuring an architecturally stunning home with gracious porches and multi level decks; a private, sandy beach and beautiful, tropical gardens throughout. Only 5 minutes offshore by boat, this is the Island that has it...
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    Location Information
    Marathon, Florida Keys 33156
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Waterfront
    • Cable/satellite TV
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    • Grill
    • Hot Tub
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you have your sights set on the ideal spot to spend your next tropical getaway, then jump on the chance to book your stay at this dog-friendly, oceanfront Islamorada home on a one-acre lot. Boasting a private stretch of white sand beach, a private pool, hot tub, and water toys like kayaks and...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 14
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    Incredible Luxury Home with Waterfront!! Paradise1 / 17
    (2)Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • DVD Player
    • Grill
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    • Hot Tub
    • Balcony
    • Central Heating
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed December 5, 2017
    Cannot even express in words how great of an experience my family had! The house is unbelievable, with two apartments downstairs and three bedrooms upstairs. The yard is amazing...
    Reviewed December 5, 2017
    I loved having everyone at one location and with the 3 separate living areas, there was plenty of space! Easy access to a great bike/walking path. Great restaurants just a...
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    About this property
    Lo-Key Estate is truly a luxury Keys home situated on a private 400’ waterfront peninsula with the use of a tropical swimming pool w/waterfall and hot tub(shared w/guest house) There are Ocean Views from the 2 & 3rd floors. Lo-Key is a custom 5 bedroom/5 bath home that opens onto Florida Bay...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 12
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    Bayside Retreat. Pool, Boat and Beach1 / 13
    (4)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • Porch
    • Washer
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 26, 2016
    We rented both of the houses for two weeks in June 2016. The houses were large and the views were great. Although the furnishings were sparse, and the televisions small, the...
    Reviewed January 21, 2014
    We needed space for 10 adults who were willing to share beds. This place was perfect. The stacking condos was a good idea and there was enough space in the top condo for...
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    About this property
    Island style, waterfront home with exclusive private white sand beach, A pool and protected dockage. 10 bedrooms, 8 bathrooms should be enough room for any size group.4 Living Rooms, Dining Room, Kitchen all have unsurpassed views of the open water and Sunset. On the first level is the pool. This...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Ocean Front Executive Retreat1 / 52
    (4)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Ocean Views
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 3, 2014
    What can I say that would do this place justice? Privacy with a gated entrance on famed Millionaire's Row in Key Largo. Or Maybe the spectacular views from all over the...
    Reviewed December 30, 2013
    This luxurious double house is ideal for a large family group. The location is convenient, the houses are spacious and well equipped, the pool and spa are very comfortable, and...
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    About this property
    This is considered a monthly rental, please contact for rates, as they vary depending on how many people and how many days are occupied during the month.... Minutes from the mainland and an hour from Miami Airport...This giant estate with 2 separate residences come with a contemporary...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 13
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    10 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • Secure Parking
    • Wi-Fi
    • Private Garden
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the heart of Key Largo, our property consists of a pair of 5 bedroom, 4 bath homes. Located directly on Florida Bay in Sunset Cove Key Largo, you will experience the best sunsets in the area. Bring your boats or watercraft and keep them at our 140ft dock. Local kayak and bicycle...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 10 Bedrooms, 8 Bathrooms, Sleeps 20
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    82754 Overseas Highway1 / 29
    (4)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
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    Pet friendly
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    Smoking allowed
    Reviewed June 7, 2017
    We have been staying in the keys for 5 years in a row & this was the best rental property we found. We are 4 guys (over 50) who want to go fishing and relax and this property...
    Reviewed May 9, 2017
    Our family (three generations) wanted a place in Islamorada with 5 bedrooms. We rented the Osprey Bay Villa for a week and it was a perfect fit. The bay side location provided...
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    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    75731 Overseas Highway1 / 32
    (13)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Islamorada is the Spiritual Center of the Keys, the Sportfishing Capital of the World, and home to the largest fleet of charter boats in the Keys. Fish deep water or the back bay. Snorkeling and SCUBA sites abound. Restaurants, art galleries, and other shopping are plentiful in Islamorada....
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    Location Information
    Matecumbe Key, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Private Garden
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    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand NEW tennis court installed 2018! Situated right on the Atlantic Ocean in The Heart of Islamorada! Panoramic views of the water from almost every room, the main house has 3 bed/3baths. Guest cottage has 1bd/1ba. Nestled amongst lush tropical gardens and gated for total privacy. Take a morning...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Flower Power House ~ Weekly Rental1 / 29
    (2)Average
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 18, 2016
    This house was a great choice for our group of 3 families traveling together. We each had a separate apartment with its own kitchen and bathroom, but were able to gather for...
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    About this property
    Flower Power House 5 - 6BR (Sleeping Porch) 4BA Sleeps 12+ Boho beautiful, the free-spirited presence of the Key West Flower Power House has much more in common with the real Key West than the shiny hotels around town. Kindred to memories we share about ‘the good old days,’ this 1938 wooden house...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is the Perfect getaway for large groups!  You can rent from 1 to 4 homes depending on the size of your group. The Pelican and Egret homes will offer you 2 homes, 5 bedrooms, and one pool.  The Pelican is a 3 bedroom 2 bath ocean front pool home which will sleep up to 8 people.  (Sofa...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Housekeeping Included
    • Ocean Views
    • Waterfront
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Catchin' Moments is a beautiful 82' Hatteras, located in Key West, Florida. She is docked at the best slip in Key West Harbor Marina. Stay fully accommodated with a four bedrooms/bathrooms, huge living area, large kitchen, outside dining area, and upstairs lounge. The marina has a pool with pool...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Real World MTV House Key West1 / 247
    (49)Very good
    10 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Waterfront
    • Hot Tub
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed October 24, 2017
    This house was really cool rooms were spacious and massive , the master room was so lavish . Jacuzzi in living room was a great feature and the games room . Only downside was it...
    Reviewed March 29, 2017
    What would you expect when you first see this colorful place? Party?Well, you might bring your group here and party all night long. Or you can take them here to have an...
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    About this property
    THIS ISN'T JUST A HOUSE, THIS IS YOUR OWN PRIVATE MINI RESORT IN KEY WEST, FLORIDA. THIS IS THE PROPERTY USED BY MTV TO FILM THE 2006 REAL WORLD KEY WEST. 500 FEET OF OCEANFRONT, 8 to 10 BEDROOMS are available (sleeps up to 20) , 5 1/2 baths, 11 plasma TVs, pool table (and Ping Pong), tennis...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 10 Bedrooms, 6 Bathrooms, Sleeps 22
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    Southern Diversion Marathon see our spring special1 / 67
    (2)Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    • Air Conditioning
    • Internet Access
    • Washer
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 3, 2016
    While still glowing from my daughter's wedding this past Sat., I am compelled to share with others just how perfect this property really is for a wedding venue or family reunion...
    Reviewed April 10, 2015
    We recently stayed at Southern Diversion Two during our March break. We traveled with our extended family, my brother and his family, my sister and her family and my mother. 13...
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    About this property
    Southern Diversion Two is an exclusive private gated estate located in Marathon in the Florida Keys. This sprawling 2 acre private estate is located directly on the gulf of Mexico featuring 300 feet of open water to capture the most breathtaking sunset views. There is deep water dockage and a...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 8 Bedrooms, 5 Bathrooms, Sleeps 20
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    7 Bedrooms, 9 Bathrooms, Sleeps 14 Quick View
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    • Hot Tub
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New House in the Heart of the Florida Keys. Enjoy Paradise in this modern house that has every ones need in mind. 7 Room with 8.5 Bathrooms, fully equipped kitchen, Jacuzzi, pool, dockage for boats and more more much! The space Total of 7 Room with: 3 King beds 2 Queen beds 1 Full bed 2...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 7 Bedrooms, 9 Bathrooms, Sleeps 14
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    Seaside Place Key West FL 5 Bedroom House 4 Baths1 / 24
    (40)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Patio
    • Washer
    • DVD Player
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 20, 2018
    This place has everything you could need and want while you stay in Key West. Conveniently located near restaurants, attractions and things to do. Very happy with Seaside Place!
    Reviewed January 24, 2017
    What a great house for our one-week getaway over the New Year holiday! We had a group of 11 people, and we were all comfortably housed inside the well-appointed home. From the...
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    About this property
    Seaside Place is located half a block from our main street, Duval Street. We are across the Street from a public beach, and down the street from the Southernmost Point of the US. We have parking for you to leave your car in the drive and walk to all the main activities that Key West has to offer....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Harbor Walk Hideaways1 / 22
    (20)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Porch
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 11, 2016
    Our party of eight absolutely LOVED this place. Location was to die for and price could not be beat! Just steps from Sloppy Joes, The Green Room and Lagerheads Beach Bar just...
    Reviewed October 25, 2015
    My husband and I, and three other couples came to Key West for a friend's wedding. After much research, I am so thankful to have come across Harbor Walk Hideaways. The grounds...
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    About this property
    Very private gated compound sleeping eight guests right in the heart of Key West's Old Town. Enjoy the beat of Key West's nightlife, the romance of sunset at Mallory Square, or the excitement of deep sea fishing or water sports all less than a two-minute walk from our tropical paradise. Standing...
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    Location Information
    Key West, Florida Keys 33040
    Private Room - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    8 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Hot Tub
    • Air Conditioning
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    • Patio
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    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Spend your Key West vacation in style here at this high-end house with a private hot tub! There's plenty of room for everybody in this house's eight bedrooms, and you're steps away from the ocean. Key West's most popular attractions surround this home - walk down to Mallory Square a few blocks...
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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 8 Bedrooms, 7 Bathrooms, Sleeps 24
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    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Hot Tub
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    • Patio
    • Waterfront
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Perfect for your next group getaway to the sun-soaked Florida Keys, book these canal-front Key Colony Beach condos together and let the adventures begin! Amenities include a private pool, quick access to the ocean, and enough space for up to 13 guests (12 adults maximum, please). Encompassing...
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    Location Information
    Key Colony Beach, Florida Keys 33050
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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