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Holiday Rentals in Florida Keys, FL

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    956 Holiday Rentals in Florida Keys
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    €2,782
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    €139
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    5 of 5 stars (11) Excellent
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    €2,272
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    €1,136
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    About this property
    Welcome to the BEST rental LOCATION in KCB, 1038 W. Ocean Drive, FL Keys 33051! We have EVERY amenity you're looking for! 'KEYS OCEAN DRIVE' is #1 with MOST 5 Star Guest Reviews (68) in the ENTIRE FL Keys! Plus we are #1 with the MOST Guest Reviews (73) in the FL Keys! Plus 99+ Photos on... View all property information
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    5 of 5 stars Reviewed 8 April 2015
    My wife and I stayed here the third week in March this year . This was the first time I have ever rented a house for vacation . I have to say It was a great experience . This home...
    5 of 5 stars Reviewed 9 March 2015
    We just enjoyed our second visit to Key Colony Beach. We stayed at Keys Ocean Drive both times (the month of February 2015 and 2014). This home is immaculately maintained and...
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    €116
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    4.5 of 5 stars (10) Very good
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    Overview Reviews (10)
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    • Waterfront
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    About this property
    Come relax on the tropical island of Duck Key. Our Florida Keys Vacation condo is uniquely designed and decorated to capture that island paradise feel. This one bedroom one bath condo is clean, spacious, and relaxing. Our condo is completely updated, fully furnished, and has all kitchen... View all property information
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    3 of 5 stars Reviewed 14 January 2015
    We spent almost a week in this condo with our 1-year old. It is really ideally located in the Duck Keys in a quiet, gorgeous area, and not too far from services (supermarket...
    5 of 5 stars Reviewed 31 July 2014
    Condo was clean when we came in. We enjoyed our stay at Duck keys. WE were there with our 11 Yrs old daughter, she slept on the hide a bed sofa. Condo was Well furnished, beach...
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    €964
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    1 / 19
    5 of 5 stars (3) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    Overview Reviews (3)
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    About this property
    Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure... View all property information
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    5 of 5 stars Reviewed 13 March 2015
    If your looking for the whole package in one this is the place. View, comfortable, privacy and location. Best place I've stayed in the keys, hands down!
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    €5,564
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    5 of 5 stars (1) Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Suitable for children
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    About this property
    Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. We are located on Lower Matecumbe Key just a few miles south of the hustle and bustle of downtown Islamorada. This is a spacious three bedroom with vaulted ceilings, a... View all property information
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    5 of 5 stars Reviewed 19 November 2014
    We stayed at Captains Cove again for our annual fishing weekend. Cindy, the new owner, has made several updates to the house, deck and dock which enhanced the property since our...
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    4.5 of 5 stars (2) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
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    • Shared Outdoor Pool...
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    • Smoking allowed
    • Suitable for children
    • x
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    About this property
    Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving.... View all property information
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    4 of 5 stars Reviewed 7 March 2015
    We truly enjoyed our stay at the Flats. Tucked away off the beaten track, it was a nice quiet spot with a beautiful waterfront (not an ideal spot for swimming but great for...
    5 of 5 stars Reviewed 23 July 2014
    Our unit was just big enough for the two of us having one bedroom, one bath. Walk out about 15 ft. to the pool and another 20 ft to the water. Beautiful sunsets! Diving nearby...
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    €510
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    About this property
    This is a beautiful new 5 Bedroom, 4 1/2 Bath home in Key Colony Beach. The sleeping arrangements are 4 King bed rooms,1 twin bed room and 2 twin sleeper sofas. Sleeps 10. All bedrooms and Covered porch have wall mounted flat screen TVs. This home has a private pool, 30' boat dock with 80 feet of... View all property information
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    €255
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    1 / 29
    5 of 5 stars (3) Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Overview Reviews (3)
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    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
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    • Suitable for children
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    About this property
    Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling,... View all property information
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    €162
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    1 / 23
    5 of 5 stars (1) Excellent
    Tavernier
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
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    About this property
    Find a “Peace of mind” in this beautiful Tropical Paradise. This two bedroom home is conveniently located at Mile Marker 92 in Historical Tavernier, Florida. It is only 69 miles from Miami International Airport, and the residence will truly captivate your mind and help you relax! Want to... View all property information
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    5 of 5 stars Reviewed 20 August 2014
    10 dagen met veel plezier doorgebracht in de woning Peace in the Keys. Een woning in een grote tuin met mooie palmbomen waar je al snel een "thuisgevoel" krijgt. De woning is...
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    €3,988
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    5 of 5 stars (1) Excellent
    Marathon
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    Overview Reviews (1)
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • Elder access
    • x
    About this property
    Great Heron House Ocean Front - Estate Luxury in ever detail and design with spectacular ocean views throughout. Private pool and spa. Spacious 5 bedroom 5.5 bath sleeps up to 10 guests. Sister property to the Grand Mangrove. Both accommodations reflect a meticulous attention to detail. Granite... View all property information
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    €278
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    • Air Conditioning
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    • Gym
    • Safe
    • Satellite TV
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    • Smoking allowed
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    About this property
    This remodeled 2 bedroom 2 bath condo is directly on the Atlantic Ocean with ground access via a spiral staircase. Stunning views from the Master bedroom and balcony. Wake up to the sunrise and enjoy your leisurely day on the boat, at the nearby sand bar, or lounge in the zero entry pool. There... View all property information
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    5 of 5 stars Reviewed 6 January 2012
    My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never...
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    €218
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    1 / 24
    5 of 5 stars (1) Excellent
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Overview Reviews (1)
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    • Air Conditioning
    • Dishwasher
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    • Private Fishing...
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    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
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    About this property
    Dock you boat or jet skis behind this nicely decorated 2 bedroom 2 bathroom(sleeps up to six people) on a deep water canal just a stone's throw from the open water of the Atlantic Ocean. On-site amenities include an 80 foot heated swimming pool, seperate pool for the kiddies, jacuzzi, marina, boat... View all property information
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    5 of 5 stars Reviewed 25 October 2014
    Awesome Cudjoe Key get a way. Good sized personal dock behind the house for my boat and great Atlantic Ocean access, was in deep water in about 10-15 minutes. Good fishing off the...
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    €872
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    1 / 15
    5 of 5 stars (2) Excellent
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
    Overview Reviews (2)
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    • Grill
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    About this property
    Minimum Rental: 7 Nights SATURDAY to SATURDAY Calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomenal fishing is... View all property information
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    5 of 5 stars Reviewed 30 April 2014
    The place was clean and felt like home. A little noisy from a running pump and the exit gate got stuck closed, no outside deck or water view. But all in all it was great, I would...
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    €129
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    1 / 10
    5 of 5 stars (4) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
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    About this property
    This 2 bedroom 2 bath ground level home with a glassed in Florida room, is on a boating canal with only 1/4 mile to open water. In five minutes at idle speed you have immediate access to the Atlantic or the Gulf of Mexico via Bogie Channel. The Canal has 50 feet of concrete seawall with bumpers... View all property information
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    5 of 5 stars Reviewed 3 January 2015
    We rented this home for the week following our destination wedding in Key West, FL. It's in a very quiet neighborhood which we really appreciated after the craziness of KW. The...
    5 of 5 stars Reviewed 17 September 2014
    This was my 4th year staying at Capt Ron's rental on Big Pine Key. We come down every year for a week of fishing. The house is clean, well stocked with items needed for cooking...
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    €219
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    • x
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    • x
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    About this property
    3 bedroom, 2 full bathroom, 1 outdoor shower, Sleeps 8 This three bedroom home boasts of many special features and offers a perfect location. The unit can sleep 6-8 . Laying at the corner of Dolphin Marina and Little Palm Island you'll vacation in one of Key's finest neighborhoods. A 60 second... View all property information
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    5 of 5 stars Reviewed 8 August 2014
    This home is clean, very comfortable and well equipped. It has a charming island decor that really lends to the atmosphere and everything is well planned. You can enjoy a drink...
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    1 / 41
    4.5 of 5 stars (2) Very good
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Air Conditioning
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    • Private Fishing...
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    • Pets allowed
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    • Suitable for children
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    About this property
    Beautiful 3 story 3 bedroom 2 baths home. Locate in key largo at MM 101 is on a canal which opens up to beautiful Tarpon Basin Bay with access to the Atlantic Ocean. Minutes from beautiful Penny Camp National Underwater Park. Close to local shopping, fine restaurants or just swimming with the... View all property information
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    4 of 5 stars Reviewed 25 February 2015
    Overall our three week stay here was very pleasant. The outisde lower level of the house had a very nice patio and seating area where you can entertain while cooking food on the...
    5 of 5 stars Reviewed 20 August 2014
    We enjoy staying at this place. Very big place, very clean. I got my deposit back. I will visit again
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    €209
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    5 of 5 stars (1) Excellent
    Long Key
    4 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Beautiful canal front, clean, home located on ocean side in Long Key. MM 68. 4 bedrooms 3 baths total: 3 bedroom, 2 bath upstairs, 1 bedroom/bath (studio) downstairs. Great fishing and diving moments away. This is our family's vacation hideaway. Never rented prior to December 2012. Direct TV w HBO,... View all property information
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    5 of 5 stars Reviewed 14 June 2014
    Currently staying here and couldn't be happier. Comfortably sleeping 9 people in our party (4 adults, 4 kids/teens and a baby). The kitchen is stocked very well. Gorgeous view of...
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    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    Minimum Rental: 1 Month Charming vacation home located in the beautiful neighborhood of Port Antigua. You will love this home! There is a wonderful open concept floor plan with 3 nicely proportioned bedrooms. Sliding doors open from the dining area into the sunroom overlooking the canal.... View all property information
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    €264
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    About this property
    Situated on at natural Key's sandy sunning beach a scant few feet from the water's edge looking out to the Atlantic Ocean you'll find three of the most enchanting 'honeymoon-type' Cottages in the Florida Keys. Made from Dade County Pine with vaulted beam ceilings these beach bungalows offer... View all property information
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    5 of 5 stars Reviewed 17 April 2014
    awesome place to stay for lots of relaxation!!! My kids loved it. The place was very clean, nice breakfast. The pool was very clean and warm. the water was perfect.
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    5 of 5 stars (2) Excellent
    Islamorada
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Shared Outdoor Pool...
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    About this property
    BEAUTIFUL NEWLY REMODELED 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUTOME KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR REFRIGERATOR, DISHWASHER,... View all property information
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    5 of 5 stars Reviewed 24 February 2015
    The place was beautifully decorated and in excellent condition. From the patio you had an excellent ocean view that was a short walk to a small beach. My teens has a blast and...
    5 of 5 stars Reviewed 24 February 2015
    When we first contacted the owner regarding the rental, she responded immediately and was very nice and helpful. The unit was impeccable when we arrived and the location in the...
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    4.5 of 5 stars (4) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Ocean Views
    • Private Fishing...
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    About this property
    This is a brand new furnished vacation rental on the point with the best sunset views. . This home has 2 bedrooms and 1 and a 1/2 bath. It has a 700 sq ft addition of kitchen and family room with direct views of the sunset. New leather furniture and two bedroom sets just added. The home has a Sharp... View all property information
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    €510
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    • Pets allowed
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    About this property
    Key Largo, the first and northernmost of the Florida Keys, is an hour's drive from South Florida's two major airports, and a world away. Home to tropical hardwoods, winding creeks, two state parks, a national park and a portion of a national marine sanctuary, Key Largo boasts some of the most... View all property information
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    5 of 5 stars Reviewed 17 March 2015
    We rented this home for an extended weekend and had an amazing time. The whole house was very well kept. Kitchen was fully stocked and the property is right by a grocery store so...
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    €1,762
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    5 of 5 stars (1) Excellent
    Islamorada
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Balcony
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    • Gym
    • Hot Tub
    • Satellite TV
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    About this property
    Minimum Rental: 1 Month Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed... View all property information
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    5 of 5 stars (5) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    About this property
    A quite, private, waterfront residence in the lower Florida Keys, the American Caribbean. Decorated in Nautical and Tropical décor. Undeveloped property on one side and across the canal. On a boating canal with dockage for your boat, Free launching at the nearby marina and space for your boat... View all property information
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    5 of 5 stars Reviewed 10 February 2014
    Booked this house for a week in early December of 2013. Captain Ron met us for checkin and went over the property with us. Everything was in great condition; very clean, and in...
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    €185
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    5 of 5 stars (6) Excellent
    Matecumbe Key
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
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    • Waterfront
    • Water Views
    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    **We do not use the optional calendar feature on this listing. ** This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not receive a reply, please contact me again! Email me for additional pictures of this wonderful... View all property information
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    5 of 5 stars Reviewed 14 April 2015
    Our break in Islamorada was over the Christmas holiday and very much needed. Unlike the cold snowy seasons we are accustomed to, we were able to fish off the dock, go boating...
    5 of 5 stars Reviewed 14 April 2015
    So many beautiful things to say about this property. The back yard is beautiful with a chiki hut, dock for your boat, bbq, kayak and bicycles. We spent the evenings relaxing in...
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    4.5 of 5 stars (6) Very good
    Big Pine Key
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Internet Access
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    • x
    About this property
    Want to visit the Florida Keys without the high price tag of Key West? Here is a great option for you. We have a tropical hidden guest house on our property in Big Pine Key to provide the perfect relaxing vacation that you need. *Please read below the disclaimer to understand you will be living... View all property information
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    5 of 5 stars Reviewed 22 January 2015
    This is a great little "guest house". Nice location. There is a small hot water tank. I would recommend getting in the shower with the shower head on the floor of the shower...
    5 of 5 stars Reviewed 16 December 2014
    This perfect little retreat is nestled in a tropical garden away from the hustle and bustle of Key West, yet close enough to spend plenty of time there if you wish. The book they...
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    4.5 of 5 stars (9) Very good
    Matecumbe Key
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Dishwasher
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    • Hot Tub
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    • Private Outdoor...
    • Safe
    • Sauna
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
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    • Elder access
    About this property
    Beautiful two story home ......four bedroom three baths.....on your private white sandy Beachfront property with large pool facing the ocean. First floor is independent with a very large one bedroom, bar with wine cooler full bath, living, dinning and new kitchen. The covered patio is huge at... View all property information
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    5 of 5 stars Reviewed 20 January 2015
    I don`t know what place the last reviewer stayed at? It wasn`t here! This house was spectacular from the moment we arrived! The house and grounds were immaculate and clean, no...
    1 of 5 stars Reviewed 2 January 2015
    We arrived at the rental property excited to begin our vacation. Unfortunately we found numerous problems with the property which prevented us from staying at the residence. We...
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    4 of 5 stars (2) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    Overview Reviews (2)
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    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY: 7 NIGHTS. This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens and fresh paint add... View all property information
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    4 of 5 stars Reviewed 6 February 2015
    We booked last minute and were pleasantly surprised to find a roomy, cheerful, well-maintained condo waiting for us when we arrived. The kitchen was well-equipped, and the view...
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    5 of 5 stars (8) Excellent
    Big Pine Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in a spacious third bedroom, 3 baths, large kitchen, dining room, family room, sitting area, large... View all property information
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    5 of 5 stars Reviewed 18 February 2015
    The first thing that stood out was how clean this place is. Everything is spotless and well organized. A binder was provided with menus, helpful hints about the community and...
    5 of 5 stars Reviewed 8 May 2014
    We had a great experience. The owner is extremely friendly and accommodating. The property is excellent. Cannot wait to go back!
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    5 of 5 stars (1) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    5 of 5 stars Reviewed 17 November 2014
    my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located. they would definitely stay...
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    5 of 5 stars (8) Excellent
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Private Fishing...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • x
    • ?
    About this property
    Villa Los-Montes Beautiful Summer Gate away, Paradise in the Keys. All Sales & Florida Taxes are Included on Pricing quote. We have NO hidden fees or additional taxes. Rates quoted are all inclusive, except standard $175.00 Cleaning Fee and PDP Fee. There being no damages, the security deposit... View all property information
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    5 of 5 stars Reviewed 18 February 2015
    Stayed here for two weeks with another couple and we all enjoyed ourselves very much. The house is a very pleasant place and was ideal for 2 couples. Enjoyed sitting on the...
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    4 of 5 stars (6) Very good
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Overview Reviews (6)
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas... View all property information
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    5 of 5 stars Reviewed 30 March 2015
    Cozy, clean, nicely appointed apartment with a gorgeous canal to the bay right outside the door. The owners are warm, friendly, and have thought of every convenience. Wonderful...
    5 of 5 stars Reviewed 29 March 2015
    This was exactly what we were looking for. Pam and Charlie are wonderful hosts. Charlie gave us some insider tracks on fresh seafood and favorite local restaurants. The rental...
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. It is an upstairs unit with 2 bedrooms and 1 Bathroom with 1 queen, 2... View all property information
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    5 of 5 stars Reviewed 25 June 2013
    Stayed at the Shipyard 253 and had a wonderful time. Very nicely decorated, comfortable and a great location - just 2 blocks from Duval St. I would stay there again!
    5 of 5 stars Reviewed 31 May 2013
    Great central location. Walking distance to most things of interest. Liked the fact it's a Gated community with assigned parking place. Not beach front, but that wasn't important...
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Elder access
    • ?
    About this property
    This beautifully refurbished 4th floor condo has great marina and ocean views from the living room, master bedroom & balcony! Gorgeous wood floors throughout and new furnishings lend an elegant atmosphere with lots of comfort in mind. Master bedroom has a king-sized bed, while guest bedroom has 2... View all property information
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    5 of 5 stars Reviewed 25 January 2015
    My husband and I stayed in 401 Kawama Towers in November. We had a wonderful time. The views are even better than the pictures show and the unit was spotless which are both...
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    4.5 of 5 stars (8) Very good
    Key Largo
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Overview Reviews (8)
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Ping Pong Table
    • Sauna
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Updated and comfortable 2 bedroom, 1 and 1/2 bath condominium in Moon Bay Resort in beautiful Key Largo, Florida. Pool, tennis court, marina with boat slips and clubhouse are just some off the amenities. This property has a sunset view of Blackwater Sound from the balcony which also overlooks the... View all property information
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    5 of 5 stars Reviewed 14 August 2014
    We stayed here with our children and had a great time. The condo is older--one of the natives said it was one of the oldest on Key Largo--but you couldn't tell it. The property...
    5 of 5 stars Reviewed 2 June 2014
    Our Trip was amazing!! During the crazy christmas season it was so nice to get away and enjoy a relaxing vacation with friends. The condo we stayed at was very well kept and...
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    4 of 5 stars (1) Very good
    Grassy Key
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Two charming efficiencies located 50 yards from the Atlantic Ocean. Both are fully furnished with well-equipped kitchens and are decorated with a Caribbean flair. In the private front yard, each unit has a gas-BBQ grill, a picnic table with large umbrella's for shade. View all property information
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    4 of 5 stars Reviewed 1 May 2014
    Our rental worked out great. We explored the Keys north and south from Marathon. Our "base" was attractive, clean, and thoughtfully equipped for our stay.
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    5 of 5 stars (3) Excellent
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Ocean Views
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Upscale 'Yacht and Breakfast'! 3 bedroom, (4th convertible bed), 2bath luxury yacht. Please search for or see Key West Yacht and Breakfast for more information. Otherwise, the system only allows you and us to converse via the online system and will block any attempts to send phone numbers, etc.... View all property information
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    5 of 5 stars Reviewed 10 March 2015
    We enjoyed our visit and stay. The Marina and boating way of life is slow and relaxing which is exactly what we were looking for. The boat was as advertised and we found it clean...
    5 of 5 stars Reviewed 5 March 2015
    The owners of this property were helpful in so many ways. I feel they went above and beyond to help us out with a lot of questions about Key West and activities that we were...
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    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Overview
    Amenities & Details
    • Balcony
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    LONG TERM RENTAL Available 4-15-2015 - Completely Furnished. 12 months preferred will consider 6+ months. Luxurious 2 bedroom, 2 bath townhome in gated bayfront complex with pool, hot tub, and tennis courts. This wonderful townhome is nestled in a tropical hardwood hammock. Enjoy... View all property information
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    5 of 5 stars (6) Excellent
    Matecumbe Key
    3 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    Overview Reviews (6)
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    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Fishing...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    3 bedroom, 2.5 bath home at the end of a quiet private road in Islamorada. Queen bed in the master with a fantastic view of the ocean from your pillow. Two queen beds in the second bedroom with en suite bath The third bedroom is used as an office. From the moment you open the front door you have... View all property information
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    5 of 5 stars Reviewed 18 January 2015
    Stayed at this fabulous home again, and once again the title is absolutely correct... I did not want to leave. This time, we bought groceries on our way down, and with that...
    5 of 5 stars Reviewed 9 July 2014
    This was our first trip to the Keys and not knowing the area, we splurged on this house. We were not disappointed! It was very peaceful, roomy, clean, nicely decorated, and the...
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    5 of 5 stars (3) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a... View all property information
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    5 of 5 stars Reviewed 12 April 2015
    The owners were amazing to work with and very quick to answer any questions. The condo was beautiful and very well stocked with anything you would need for a vacation in the Keys...
    5 of 5 stars Reviewed 7 March 2015
    The Daniels unit in Executive Bay Club is great. Very clean and modern up to date. People were very friendly and helpful nice events in clubhouse. Large rooms upstairs and...
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    4.5 of 5 stars (2) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Private Fishing...
    • Safe
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    The condo is located in a complex called Moon Bay More like a resort than a condominium. Free tennis courts, saunas, a private boat slip, and a dock for fishing and saltwater swimming, to mention just a few of the amenities. The unit is on the fourth floor of an elevator building, making for... View all property information
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    5 of 5 stars Reviewed 9 January 2015
    We stayed in A407. This condo unit is nicely set up with everything you could need. The beds are very comfortable with the master bedroom having a view of the bay, so nice to...
    4 of 5 stars Reviewed 8 October 2013
    We stayed in condo B-106, owned by Gloria, who prepared everything for our arrival. Erin, her housekeeper met us on arrival and showed us round. Everything was as promised. The...
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    4.5 of 5 stars (2) Very good
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Condo, 2 Bedrooms + 2 Baths (Sleeps 4-7) in Port Largo Villas Perfectly located condo across the street from Ocean Divers and Sharkey’s Pub and Galley in the heart of Key Largo. Quiet, serene and relaxed, yet still close to all ithe main fishing, diving and boating amenities. Recently updated,... View all property information
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    4 of 5 stars Reviewed 25 March 2014
    Walking distance to snorkel, dive and evening cruises. Nice pool, good views from our balcony over the canal. Ate at many nice restaurants, liked the Fish House and Lazy Days...
    5 of 5 stars Reviewed 8 January 2014
    Clean, well maintained and stocked. Nicely decorated. You can tell the owners use the condo. We walked to the Scuba charters and training pools. Several locations within...
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Coral Hammock is one of the newest gated communities with 55 luxury... View all property information
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    3 of 5 stars Reviewed 8 April 2014
    The house is as described. Clean and comfortable. The condo is very pleasant and safe. Pool was very much appreciated by our children. The main inconvenient is the noise. The...
    4 of 5 stars Reviewed 20 April 2013
    We enjoyed our stay and will plan to come again. The only complaints we had was that the lower bedroom dresser had the bottoms missing out of two drawers so unpacking the suitcase...
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    4 of 5 stars (1) Very good
    Key Largo
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Paradise point! This is a newly renovated (Spring 2014) home in a private gated community. Located at mile marker 106 on the bayside in Key Largo, this home is an ideal location for those looking to enjoy life on the water in the Florida keys. The home is situated for convenient access to... View all property information
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    4 of 5 stars Reviewed 8 January 2015
    I stayed at the Bayside home from 12/31/14-1/6/15 and it was wonderful. Joy and Doug were very accommodating and available for any and all questions. The place was perfect to sit...
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    5 of 5 stars (2) Excellent
    Key Largo
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Dishwasher
    • Dryer
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    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
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    • Elder access
    • ?
    About this property
    Beautiful 2 bedroom, 2 bathroom Conch House located minutes from Pennekamp State Park. Fully equiped modern kitchen, spacious living area. Two comfortable decks for leisure and entertainment. Hot and cold outdoor shower. Steps away from home owner's park complete with covered picnic area, sandy... View all property information
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    5 of 5 stars Reviewed 10 January 2015
    We thoroughly enjoyed our holiday stay in the Keys So Happy house. It’s a wonderfully restored and appointed mid-century cottage with private access to Largo Sound and proximity...
    5 of 5 stars Reviewed 23 March 2014
    Charming bungalow...great outdoor deck and patio... Fully equipped...easy access to shopping restaurants and nightlife...highly recommend
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    5 of 5 stars (1) Excellent
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Enjoy your getaway in Casa Solis, on the docks awaiting a gorgeous sunrise or a cool breeze at sunset on the deck. This brand new home provides the views and relaxing setting you are looking for! The two bedrooms and en-suite bathrooms are designed to perfection. Each room comes with its own LED... View all property information
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    5 of 5 stars Reviewed 6 April 2015
    Just stay there. It's one of the nicest condos available to rent! The place looks like it is brand new. It has a large double car carport under the raised condo to keep cars...
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    5 of 5 stars (11) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Ocean Pointe Suites is located directly on the Atlantic Ocean. This unit is completely renovated and is located in building 4 which is the most desirable building. Featuring magnificent ocean views from the living room, master bedroom and porch. This unit offers 1 King bed in master bedroom, 1... View all property information
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    5 of 5 stars Reviewed 12 April 2015
    The accomodation is first class and really well maintained and so comfortable for a weeks relaxing break. The wifi worked well , the TV channels had everything imaginable and even...
    5 of 5 stars Reviewed 30 November 2014
    My wife, daughter and I stayed at Kim's condo while we visiting family for Thanksgiving and we were very pleased. The location of the unit was conveniently close to...
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    From
    €2,597
    / Month
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    Overview
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    28 NIGHT MINIMUM STAY REQUIREMENT - THE TREETOP APT AT THE SAILMAKER'S HOUSE Beautifully Renovated Second Floor Apartment for Two - Incredible Location in Historic Old Town Gorgeous one bedroom apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental... View all property information
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    Florida Keys Vacation Rentals

    Relaxing in a hammock under a swaying palm tree. Sipping a margarita. Enjoying a cheeseburger in paradise. Life in the Florida Keys is unique, laid-back and fun. Spending your stay in a cramped, sterile hotel room just doesn’t seem to fit the lifestyle. You should consider a vacation rental. We’ll help you find special deals on beach houses, condos, townhouses, cottages and cabins in a variety of settings in Key Largo, Marathon, Islamorada, Big Pine Key and the Lower Keys, Key West and other locales. Better still, you’ll have lots of space to spread out and relax as well as a fully-equipped kitchen where you can fix the perfect margarita.

    Florida Keys attractions and activities

    From phenomenal scuba diving and snorkeling to world-class ocean sportfishing and flats fishing to eco-tours and sunset watch parties, the Florida Keys has something for everyone. Each section of the Keys has its own unique attractions. In Key Largo, visit John Pennekamp Coral Reef State Park, a spectacular undersea park. In Islamorada, the Theater of the Sea Marine Mammal Park, offers opportunities to swim with dolphins and other creatures. At Marathon’s Crane Point, you can hike through a preserved tropical hardwood grove. In the Lower Keys, beach enthusiasts love the Bahia Honda State Park with its white sandy beaches. Key West is home to the Ernest Hemingway Home and Museum, the Key West Butterfly & Nature Conservatory and Mel Fisher’s Maritime Heritage Museum.

    Live like a local in a Florida Keys rental

    A vacation rental allows you the freedom to pursue the Florida Keys getaway perfect for you and your family. You’ll have ample space to store your fishing equipment, scuba and snorkeling gear, beach toys and other necessities for a great beach vacation. When it’s time to dine, a fully equipped kitchen allows you to save money and prepare a delicious meal that might even include the big fish you caught earlier in the day. With a vacation rental in the Florida Keys, you can stop imagining what it’s like to live there and actually do it for a short time.

    Florida Keys vacation rentals for families

    From Key Largo to Key West, we have an inventory of vacation rentals ideal for family getaways. We’ve got plenty of low-cost, budget-helping rentals that will allow you to spend money on things like swimming with dolphins or scuba diving instead of on a pricey hotel room.

    Saving money on Florida Keys vacation rentals

    Obviously, you want the best deal available to stay within your budget. Whether you want an amenity-rich beachfront estate home, a condo affording stunning sunset views or a cozy cottage or cabin, we have special deals and discounts in every price range.