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Florida Keys Luxury Vacation Rentals

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    Travellers to Florida Keys are booking March dates now. Secure your vacation rental today, and have the perfect trip.
    229 Matching Rentals in Florida KeysView all 1,528 rentals
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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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    4 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy a little European elegance combined with Florida Keys Charm at this Lower Matecumbe Key oceanfront property.  The main home has four bedrooms and 4.5 baths.  A separate bungalow contains a king suite with kitchenette, as well as its own patio overlooking the Atlantic.  Spend your vacation...
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    Villa Thenardier1 / 68
    (1)Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 May 2016
    What else can be said about this property? It has everything. Pool – check, beach – check, ocean view – check, a gym, and even your own personal luxury outdoor shower. My...
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    About this property
    Live your tropical dream at this palatial oceanfront estate that is newly available through Freewheeler Vacations. 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...
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    Islamorada, Florida Keys 33070
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    6 Bedrooms, 7 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Hot Tub
    • Grill
    • Washer
    • Ocean Views
    • DVD Player
    • Waterfront
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Grand Estate This luxuriously appointed home is situated amongst an enclave of exquisite homes on the very desirable Coury Drive in Key Colony Beach. This gated home offers supreme peace and privacy overlooking the Atlantic Ocean. The meticulously maintained grounds are homes to many varieties...
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    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 10
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    Exclusive Oceanfront Estate - Feels Like a Resort1 / 50
    (3)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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 5 July 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 5 July 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, 5 Bathrooms, Sleeps 10
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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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    Amenities & Details
    • Cable/satellite TV
    • DVD Player
    • Air Conditioning
    • Wi-Fi
    • Grill
    • Patio
    • Washer
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 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 4 July 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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    Ocean-Front Caribbean Home.1 / 21
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • Washer
    • Balcony
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 April 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 ( recent fraud. NEVER wire us money. Payment for reservations can only be done via the phone, not online or via wire) Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil with nothing compromised this luxurious Caribbean home...
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    Islamorada, Florida Keys 33036
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    ~ MAISONS de LUXE ~ 2 Stunning Homes w/ Private Heated Pool on Duval St!1 / 45
    (2)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Balcony
    • Cable/satellite TV
    • Grill
    • Washer
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed yesterday
    We love Key West and knew we wanted to share the fun here with our friends for our Honeymoon! This beautiful, immaculate space was our home base for a week of fun! Every bedroom...
    Reviewed 11 July 2017
    Recently a group of twelve close friends traveled to Key West for a few days of fun in the sun. Since we live in the Chicago area we wanted a place to stay that could house all...
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    About this property
    Grand Maison and Petite Maison together sleep a total of 12 guests. They boast 6 bedrooms each with its own en suite bathroom. Spacious with plenty of room allowing for large family get-a-ways, reunions, or wedding parties. Great outdoor spaces where friends and family can gather or taking time...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    Classic Key West Estate ~ Weekly Rental1 / 30
    (6)Average
    7 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Air Conditioning
    • Grill
    • Patio
    • Wi-Fi
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 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...
    Reviewed 15 April 2015
    The house was in great condition when we arrived. As described. Had everything we needed and more. Perfect for our group of 12. The location is ideal.
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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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    Family Reunion ~ Weekly Rental1 / 53
    (2)Very good
    9 Bedrooms, 7 Bathrooms, Sleeps 22 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    • Wi-Fi
    • DVD Player
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 February 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 25 June 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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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 9 Bedrooms, 7 Bathrooms, Sleeps 22
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    10 Bedrooms, 10 Bathrooms, Sleeps 28 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    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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    Sandy Beach, Direct Ocean, Pool, Dock & Lagoon1 / 34
    (31)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • 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 9 January 2018
    We were warned that all was not in working order because of the hurricane but inspire of that we found the house to be beautiful and spacious, with the help of 2 xtra mattresses...
    Reviewed 1 April 2016
    We could not have been happier with the house! The grounds are beautiful, and the house was perfect! Everyone had a great time and we all want to vacation at the house again!
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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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    Amenities & Details
    • Patio
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Waterfront
    • Internet Access
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 July 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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    12 Bedrooms, 11 Bathrooms, Sleeps 24 Quick View
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    • Internet Access
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 12 Bedrooms, 11 Bathrooms, Sleeps 24
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    DREAMING ON DUVAL- Luxury 5 Bed & Private Pool- As seen on HGTV House Hunters1 / 38
    (20)Excellent
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Hot Tub
    • Grill
    • Patio
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 25 May 2015
    My girlfriends and I stayed here for my bachelorette weekend in Key West. Hands down, this was the BEST trip I've had with the girls, and it was due in large part to us choosing...
    Reviewed 13 December 2014
    We had our five year vow renewal on the Jolly Rover in Key West and invited our closest friends and family to join us at Dreaming on Duval. Everyone was stunned with how...
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    About this property
    Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    Families and Weddings Historic Shadow Point Estate1 / 82
    (17)Excellent
    6 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    Amenities & Details
    • Patio
    • Cable/satellite TV
    • Washer
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2017
    We had a wonderful week at Shadow Point- there is something for everyone at this property. We had 13 familymembers ages ranging from 12 to 80 years old. The location of the...
    Reviewed 17 June 2017
    Our family rented Shadow Point for a week in June. We invited our four children, their spouse/ boyfriends, and our two young grandchildren. The houses and property make you...
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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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    3 Bedrooms, 4 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Washer
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Laidback and lovely Situated right by the water, Mahogany Bay is both splendid and soothing. You enter into an open-plan living area, which has white walls, stone floors and wide windows. In one corner is the kitchen – full of glossy wood and marble, with a breakfast bar and a dining table. The...
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    Location Information
    Tavernier, Key Largo 33037
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 7
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    Twelve Bedrooms! Up to 30 peoplePools-Docks-Kayaks1 / 31
    (2)Excellent
    12 Bedrooms, 8 Bathrooms, Sleeps 30 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    • Waterfront
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 September 2014
    Watch the sunset after your busy day on the water. The pool is refreshing and all you need is a libation! We have stayed MANY places in the Keys and this one is THE best...
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    About this property
    WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This rental offers a great option for multi-family vacationing by providing three 4-bedroom homes side-by-side. This gives you 3 kitchens, 3 pools, 3 deep water docks, 3 gas grills, parking for 8 vehicles and 6 kayaks! These properties are non-smoking and...
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    Location Information
    Marathon, Florida Keys 33050
    Holiday Rental House - 12 Bedrooms, 8 Bathrooms, Sleeps 30
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    12 Bedrooms, 9 Bathrooms, Sleeps 36 Quick View
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    • Hot Tub
    • Patio
    • Washer
    • Cable/satellite TV
    • Air Conditioning
    • Internet Access
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you're planning your next 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. Featuring street parking, a private pool, hot tub, grilling stations, and room for up to 36 guests, this is the...
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    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 12 Bedrooms, 9 Bathrooms, Sleeps 36
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    The Caroline House Estate ~ Weekly Rental1 / 35
    (7)Very good
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • 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 27 June 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...
    Reviewed 22 June 2016
    The Caroline House was absolutely amazing! We just loved the layout of the house -- so many areas to comfortably gather. What a wonderful kitchen -- also great for getting...
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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
    (7)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Patio
    • Washer
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Grill
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    Tropical Tranquility was a great home! There were 4 couples in our group and we had plenty of space. Our 2 golf carts(Sunshine Scooters) fit nicely in the driveway. As we...
    Reviewed 26 June 2017
    We recently returned from a one week stay at Tropical Tranquility. This was an amazing Key West find! It's close to Duval St and we walked or biked to almost all activities...
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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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    Key Colony Beach Oceanfront Rental Experience1 / 21
    (3)Very good
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Washer
    • Patio
    • Waterfront
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 January 2017
    Wonderful house. Loved the poop, hot tub an dock. We enjoyed the local restaurants, beach club and par three golf course. Larry and Lisa were very helpful and easy to work with.
    Reviewed 30 March 2016
    We enjoyed our stay so much! Larry was extremely responsive before and during our stay. The house was very clean, beautifully decorated and worked nicely for 3 couples, each of...
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    About this property
    Beautiful Direct Oceanfront rental home in Key Colony Beach. Updated 5 bedroom, 3 bath home with Pool and Hot Tub. Open Living space with spectacular views from the living room, dining room and kitchen as well as two bedrooms with direct ocean views. Brand new large Flat Screen TV's thru-out the...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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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 26 August 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 21 January 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 / 49
    (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 3 August 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 30 December 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
    *** CHRISTMAS HOLIDAYS ARE AVAILABLE*** Contact ASAP for details! This is 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...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 13
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    Top Of Duval- 6 Bedroom Penthouse1 / 27
    (13)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Internet Access
    • Washer
    • Grill
    • Air Conditioning
    • Parking
    • Private Outdoor Pool (Heated)
    • Outdoor Dining Area
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    The Top of Duval is amazing....great location, clean, fully stocked! June was excellent to work with
    Reviewed 25 October 2017
    We rented all six rooms and loved every minute of it. Perfect for walking Duval Street and close enough for anything else you want to do. So nice having your own pool to...
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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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    10 Bedrooms, 8 Bathrooms, Sleeps 20 Quick View
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    • Cable/satellite TV
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    • 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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    East Sister Rock Island1 / 12
    (2)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Balcony
    • Grill
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 July 2017
    I would recommend this rental property any time of the year, great place to be with the family,perfect!
    Reviewed 13 July 2017
    I spend one amazing week at East Sister Rock Island with my family. The sunrise, endless ocean views, the sunset and the incredible views of the stars in the evening. It was...
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    About this property
    Enjoy a private island paradise located at MM50. East Sister Rock Island is 1/4 of a mile off the Atlantic Shores off the City of Marathon in the Florida Keys. On the private island sits a dream come true getaway home with 5000 sq.ft of living area which includes a 2700 sq.ft. covered veranda,...
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    Location Information
    Marathon Shores, Marathon 33050
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
    • Washer
    • Hot Tub
    • Balcony
    • Central Heating
    • Patio
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 December 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 5 December 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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    6 Bedrooms, 4 Bathrooms, Sleeps 15 Quick View
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    • Air Conditioning
    • Terrace
    • Cable/satellite TV
    • Balcony
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    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Steps from Duval Street, the Lighthouse, the Hemingway Home, shops, restaurants, and galleries! THE TRUMAN SUITES consist of four Luxury Vacation Rentals that can be rented together or separately. LOCATED ONE HALF BLOCK FROM DUVAL STREET, this location is perfect for a multi generation family...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 15
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    Private Island Rental with 19' Boat, Seabird Key1 / 51
    (11)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • DVD Player
    • Waterfront
    • Cable/satellite TV
    • Ocean Views
    • Grill
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 January 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 19 March 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 12 Quick View
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    • Private Outdoor Pool (Heated)
    • DVD Player
    • Grill
    • Cable/satellite TV
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Welcome to Murphy’s Paradise, a one acre private gated beachfront estate in the heart of Islamorada, Florida. This home features a private beach, 5 bedrooms, 3 ½ baths, family room, living room, game rooms, pool and bar. This home can comfortably accommodate 10-12 people with room to spare....
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    Location Information
    Islamorada, Florida Keys 33036
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    FLORIDA KEYS OASIS - The Corona commercial-welcome ****7 DAY MINIMUM RENTAL****1 / 64
    (4)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 12 July 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...
    Reviewed 12 February 2017
    On our recent family trip to the keys, we were lucky enough to find this amazing home. We stayed for one week and wish we had stayed a month!The house is 6 stars and the hosts...
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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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    Bloom'n Paradise1 / 24
    (3)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • DVD Player
    • Cable/satellite TV
    • Terrace
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 May 2017
    The photos do not impart the beauty of this property. It is perfectly appointed and convenient to Mallory Square and all of Old Town Key West. Jeff is a wonderful host and the...
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    BLOOM'N PARADISE - Relax in luxury in this beautiful Truman Annex private vacation home for rent in the Florida Keys. This property features three bedrooms and three bathrooms in the main house plus a pool house with one bedroom one bath. On Admiral’s Lane in the Truman Annex community, this...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Flower Power House ~ Weekly Rental1 / 58
    (3)Average
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 April 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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    'SANDY BEACH' Key Largo,Fl. Luxury Vacation Rental1 / 31
    (3)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Waterfront
    • Patio
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 June 2014
    This place is truly amazing! The beach is clean and the good sand extends out into the water. The amenities are endless in the house. Kids loved the pool as it gave them a...
    Reviewed 15 March 2014
    My family of 7 including 2 babies just had a wonderful week at Sandy Beach. The house is perfect for a groupwith large quiet bedrooms. The outdoor kitchen and beautiful private...
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    About this property
    Welcome to 'SANDY BEACH' in Key Largo, Fl. Enjoy amazing sunsets from your own private white sandy beach and swaying palm trees that leads you into the warm ocean blue waters of the Florida Bay. This gated 1 acre 3/3 pool home has been updated and beautifully decorated. It can sleep 8 to 10...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Real World MTV House Key West1 / 247
    (51)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 24 October 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 29 March 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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    6 Bedrooms, 6 Bathrooms, Sleeps 22 Quick View
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    • Grill
    • Parking
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    • Patio
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    • Washer
    • Internet Access
    Suitability
    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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    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, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Grill
    • Cable/satellite TV
    • Washer
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point. The home is just a few blocks away from the Southernmost Beach, night clubs, and popular areas which makes it a perfect spot to vacation as it is a quick walk to everything Key West has to...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    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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    • Internet Access
    • Shared Outdoor Pool (Unheated)
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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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    Southern Diversion Marathon see our spring special1 / 24
    (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 3 January 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 10 April 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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    75731 Overseas Highway1 / 32
    (13)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
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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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    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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    ~ CLOUD 9 ~ Lavish Home In Perfect Location w/ Heated Pool & Private Parking1 / 27
    (16)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Parking
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    • Grill
    • Private Outdoor Pool (Heated)
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    • Washer
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 April 2017
    Everything Key West is right outside the courtyard door! Less than one block from Duvall St. All the best restaurants and bars with great live music are within walking distance...
    Reviewed 30 March 2017
    This place was absolutely perfect! Steps from all the action of Duval and yet, amazingly, you couldn't hear anything but nature when sitting by the pool! The house was...
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    About this property
    The Absolute Best Luxury Private Vacation Rental Home on Duval Street In Old Town Just a half block off Duval you’ll find your secret paradise awaiting you at Cloud 9. When you pass through the whimsical custom wrought iron gate decorated with palm fronds and a welcoming gecko, you’ll find...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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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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    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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    Location Information
    Sugarloaf Key, Florida Keys 33040
    Holiday Rental House - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    Villa Tropicale: A lush, secluded estate in the Casa Marina District1 / 34
    (15)Very good
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Grill
    • Cable/satellite TV
    • Patio
    • Balcony
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2013
    After reading great reviews about the Villa Tropicale, we rented this property for six nights last month. We were traveling with a group of eight and wanted a large home where...
    Reviewed 27 January 2013
    This was not our first stay at Villa Tropicale and we certainly intend to come back. When we first opened the gate of the property a few years ago, we were delighted to discover...
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    About this property
    Tropical seclusion best describes this oasis in the Casa Marina District. Enter the splendor of this large estate through a private gate; stroll down brick pathways and wander by the cottage until you reach the two story main home. The gardens are lush and abundant featuring various species of...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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