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Holiday Rentals in Florida Keys, FL

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    1 / 17
    5 of 5 stars (13) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 17
    5 of 5 stars (24) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 23
    4.5 of 5 stars (2) Very good
    Grassy Key
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 24
    5 of 5 stars (2) Excellent
    Grassy Key
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Air Conditioning
    • Patio
    • Parking
    • Internet Access
    • Satellite TV
    • Shared Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Our charming efficiencies are located 50 yards from the Atlantic Ocean. All units are fully furnished with well-equipped kitchens, linens, and baths. Each efficiency has a small outdoor space that share a tropical front yard with individual gas-BBQ grills, and picnic tables with umbrella's for... View all property information
    Location Information
    Grassy Key, Marathon 33050
    5 of 5 stars Reviewed 10 March 2015
    A very nice hideaway on Grassy Key - a cozy little studio for two- while it is located in a very quiet snowbird trailer park - it has a degree of privacy and all the amenities...
    5 of 5 stars Reviewed 12 June 2014
    We stayed for one week in January. We loved our one room efficiency with its beautiful art work and nice decor. The neighbors were great, the sunsets were awesome, the small...
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    1 / 17
    5 of 5 stars (9) Excellent
    Big Pine Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Waterfront
    • DVD Player
    • Satellite TV
    • Parking
    • Grill
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 stars Reviewed 5 August 2015
    This is a great place to enjoy the lower keys. Extremely clean and well appointed. We stay there as often as we can. I can't wait to go back.
    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...
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    1 / 22
    4.5 of 5 stars (13) Very good
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Grill
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Patio
    • Wi-Fi
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes <BR>Wifi, boat dock, trailer parking, and all amenities are included also, <BR><BR>Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee... View all property information
    Location Information
    Islamorada, Florida Keys 33037
    5 of 5 stars Reviewed 6 June 2016
    Wonderful vacation nice, relaxing. I would definitely return. Charlie was very informative on where to go to eat. Locals were very nice too.
    4 of 5 stars Reviewed 16 October 2015
    What a great little spot! Was quiet and very peaceful. Clean and cozy! Had everything we needed. Will be back to Stay again soon! :)
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    1 / 14
    5 of 5 stars (19) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 22 August 2015
    Traveled to Key West with my sister and my Mom to celebrate Moms 85th birthday. The house was so close to everything we wanted to do and see. The grocer nearby was great, the...
    4 of 5 stars Reviewed 2 May 2015
    We stayed for three nights in April. Checked in Saturday, and as we were unloading our car owner came by to say hi and ask if we had any questions. She answered the few...
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    1 / 13
    5 of 5 stars (4) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Balcony
    • Satellite TV
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 2 weeks ago
    Great Location, Great Space, Great amenities, Great balcony, and Great Owner...bed was comfy & bathroom had everything we needed...Thanks again!!
    5 of 5 stars Reviewed 11 July 2016
    Tom from Duval Balcony was wonderful. He communicated with me to confirm my visit and then to make arrangements to meet when it was time to check in. When we arrived he...
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    1 / 19
    Big Pine Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Wi-Fi
    • Hot Tub
    • Private Garden
    • Patio
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located in the heart of the national key deer preserve this bright chalet style home with many windows, with very comfortable memory foam mattresses in all the beds, master room has a queen size bed with a 40' flat screen TV, and the guest room is equipped with a very sturdy wood bunk bed with a... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 55
    5 of 5 stars (6) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Grill
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Its all about being newly renovated, on the top floor of the best building with the largest end unit with the most windows - twelve. You will have the most magnificent unobstructed ocean views from the living room, kitchen, master & guest bedrooms and balcony. This unit sleeps four adults, (the... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 stars Reviewed 4 days ago
    Beautiful property, very clean, and has a gorgeous view of the ocean.....from ALL ROOMS!!! Our stay was for a little over a week. The unit was ready to go with everything we...
    5 of 5 stars Reviewed 4 days ago
    Just returned from a week in Key Largo and this rental condo was a perfect home base. Clean, comfortable and well appointed, this 2 bedroom/2 bath unit gave us all the space we...
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    1 / 10
    5 of 5 stars (8) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Washer
    • Air Conditioning
    • Waterfront
    • Internet Access
    • Grill
    • Satellite TV
    • DVD Player
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    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
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 stars Reviewed 11 July 2016
    We rented this house from Captain Ron and had a great time. We brought a boat and were able to dock it in the canal with no problems. The house was outfitted with everything we...
    5 of 5 stars Reviewed 31 May 2015
    My husband and I came to Big Pine Key for a second honeymoon. We immediately fell in love with the house and the atmosphere. Very clean and cozy! We had a fantastic time and...
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    1 / 13
    5 of 5 stars (9) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    • Waterfront
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 stars Reviewed 20 December 2015
    My wife and I were looking for a place on the water that was quiet, comfortable and inexpensive. Captain Ron provided all of that and more. The house is the perfect getaway and...
    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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    1 / 21
    5 of 5 stars (1) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Ocean Views
    • Air Conditioning
    • Waterfront
    • Sauna
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. For a couple with 2 kids or two couples. The two new extra long twin beds in 2nd bedroom convert to a comfy King Bed! This direct oceanfront, well-cared for 5th floor corner unit is right on the ocean in Islamorada at... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 10 July 2016
    Beautiful ocean views! Nicely decorated and well-cared for condo. We hope to return next year. We had everything we needed and felt like we were at home, a lovely relaxing home.
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    1 / 19
    5 of 5 stars (3) Excellent
    Islamorada
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Patio
    • DVD Player
    • Wi-Fi
    • Ocean Views
    • Children's Pool
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful / tropical decorated one bedroom, one bath water front condo in Summer Sea Condominiums located at Mile Marker 88.5 Bayside Islamorada, FL. Bayside means amazing open water views & world famous Florida Keys sunsets from your own private balcony overlooking the Florida Bay. You can also... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 5 May 2016
    This condo was to die for. The decor was fabulous and the location was perfect and close to many restaurants. The sunset from the balcony was breathtaking. The owner was a...
    5 of 5 stars Reviewed 6 April 2016
    Very nice, quiet, low key place to stay. Great location, in walking distance of many restaurants. Would love to stay again in the near future!
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    1 / 17
    4 of 5 stars (7) Very good
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Washer
    • Balcony
    • Shared Outdoor Pool...
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area.... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 26 October 2014
    Lovely, clean and well furnished condo with great view onto the Gulf. Condo was large with ample room for all six of us with screened verandah ideal for relaxing and watching...
    5 of 5 stars Reviewed 18 July 2014
    Really enjoyed our stay. Two adults and four teenagers. We had more than enough space. Also grocery stores close by and only an hour drive from the keys. Also a great snorkel...
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    1 / 20
    5 of 5 stars (15) Excellent
    Key Largo
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Air Conditioning
    • Patio
    • Ocean Views
    • Wi-Fi
    • Washer
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Charming and secluded CBS construction seaside cottage with all of the comforts. Two bedrooms each with queen size bed and private bath. Also a third bathroom in the main area for your convenience. Fully equipped kitchen/dining room with a bar cabinet and a washer/dryer closet. For your outdoor... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 stars Reviewed 1 week ago
    Casa Cay is a stunning bungalow 50 yards from Florida Bay directly next to a small channel leading to the Bay. We had a splendidly lazy week of relaxation following a very busy...
    5 of 5 stars Reviewed 4 weeks ago
    My wife and I stayed at this house during the mini season week. The house is very clean and has everything we needed to live in as a home away from home. We brought our jet skis...
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    1 / 9
    5 of 5 stars (1) Excellent
    Marathon
    Studio, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
    • Grill
    • Patio
    • Waterfront
    • Parking
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Comfortable studio condo with full kitchen and a full size pull-out couch for extra guests. This condo has full resort amenities from a marina with boat dockage, heated pool, tennis & basketball courts, bicycles, canoes, kayaks, paddle boats, tiki huts with picnic tables and charcoal grill, along... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 4 weeks ago
    We loved it here. Perfect accommodations for three and in the heart of Marathon. Has everything u need to enjoy a wonderful vacation.
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    1 / 24
    Cudjoe Key
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Shared Outdoor Pool...
    • Wi-Fi
    • Ocean Views
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This luxurious home overlooking the Atlantic Ocean is part of Sunrise Beach Resort, an exclusive gated community built in 2007 with only 10 other homes. Our home is third from the waters edge facing Southwest. Lounge in your private hammock or enjoy the gorgeous tropical landscaping and cool... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 21
    Grassy Key
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Private Garden
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Our efficiencies/Studio apartments are located 50 yards from the Ocean. All units are fully furnished with equipped Kitchens,lines, and baths. Each efficiency has a small outdoor space sharing a common front yard with tropical foliage, individual gas-BBQ grills, picnic tables and umbrella's for... View all property information
    Location Information
    Grassy Key, Marathon 33050
    1 / 22
    4.5 of 5 stars (2) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    Recently renovated, two bedroom, one bathroom, high end kitchen, luxurious living room, and balcony over looking garden restaurant. Tile throughout, modern kitchen, top-of-the-line appliances, are just a few nice features of this perfect vacation rental. Just moments from some of the best dinning... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 5 July 2015
    My Husband, I and my sister spent 6 days in Key West. This was a home like condo to stay in. It had a kitchen,dining room and living room on the main level with a bathroom(all one...
    4 of 5 stars Reviewed 8 April 2014
    Just got back from Key West and this condo is in a prime location on Duval St. It is towards the back so noise is not a problem-other than roosters crowing (they are all over the...
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    1 / 14
    4.5 of 5 stars (26) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Outdoor Dining Area
    • Air Conditioning
    • Balcony
    • Parking
    • Washer
    • Grill
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Just steps away from shops, restaurants, and the excitement of Duval Street, yet set on a quiet side street in a world of its own. With 3 bedrooms and 2 Baths, The Grand Bahama Suite has plenty of room for a large gathering or group of friends. Experience endless sunshine and the incomparable... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 weeks ago
    Loved the Bahama House Close to Duval Street Clean and beautiful Pool was great Had problem with smoke detector beeping because battery was low Called and it was fixed...
    5 of 5 stars Reviewed 11 July 2016
    This is actually the second time we have stayed at the Bahama house. We stayed in different suites each time but both were clean and well stocked for us. We really enjoyed having...
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    1 / 15
    5 of 5 stars (4) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Porch
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 9 March 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another couple...
    5 of 5 stars Reviewed 18 March 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
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    1 / 20
    5 of 5 stars (1) Excellent
    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Satellite TV
    • Patio
    • Washer
    • DVD Player
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Amazing canal front 3 bed 2 bath open concept house located in prestigious community of Summerland Key Cove. It is the first canal from open water and one of just a few flow-through canals providing excellent water quality. The canal is deep and wide. Expect to see lobsters, crabs and other sea... View all property information
    Location Information
    Summerland Key, Lower Keys 33042
    5 of 5 stars Reviewed 26 March 2016
    Whatever I'd hoped for, this vacation home has without question, surpassed any and all expectations! Excellent location; in a quiet and beautiful strip. Loved relaxing on the...
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    1 / 41
    5 of 5 stars (2) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Wi-Fi
    • Ocean Views
    • Sauna
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Located in Islamorada, Florida Keys, Ocean Harbour is our beautiful and luxurious home away from home surrounded by the tropical beauty of the Florida Keys. The location is in the perfect proximity for visiting Key West & Miami. With its exceptional location and gated security, this premium... View all property information
    Location Information
    Islamorada, Florida Keys FL 33036
    5 of 5 stars Reviewed 2 February 2016
    We loved our stay at Ocean Harbour Apartments. After viewing photos on your website, we chose this based on the beautiful grounds and lovely accomodations. We could not have...
    5 of 5 stars Reviewed 5 January 2015
    This spacious condo is beautifully furnished and equipped. The gated community is very quiet and has a heated salt water pool. There is a nice spot to see the moon and sunrise...
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    1 / 19
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    2 bedroom 2 bath 1700 square foot of total luxury. Master bath offers jacuzzi for two. Living room offers 82 inch TV with Wi-Fi and cable. Outside grill for a great cooking experience. Sleeps up to eight with great views of swimming canal. No boat access at property. Closest marina within one mile... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 6
    Tavernier
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
    • Housekeeping...
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    • Washer
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Our 'House Boats' are a boat lovers dream with all the comforts of home, including full bathroom (head) with stand up full size shower, full kitchen (galley) with all amenities, living area with sofa, dining table and TV. It has a generous outdoor patio with seating for two along with a complete... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 15
    5 of 5 stars (8) Excellent
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • DVD Player
    • Parking
    • Shared Garden
    • Air Conditioning
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    When you arrive, you know you've come somewhere very special. This condo has the most spectacular views of the the Atlantic Ocean and a pristine heated pool. Located on Coco Plum Beach in Marathon, Florida Keys, you're in a secluded yet central base for all Keys sightseeing and activities, if you... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 24 April 2016
    We traveled with our adult children and 2 grandchildren. Condo #33 has everything you need, and is roomy. Screened in balcony keeps and bugs that may be around outside. View is...
    5 of 5 stars Reviewed 18 August 2015
    We had a great time on our first family vacation to the Keys. Marathon is perfectly situated right in the middle. Lots to do right in Marathon. A visit to the Sea Turtle...
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    Marathon Shores
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Child-friendly
    • x
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    • x
    About this property
    The vacation villas at this bayside resort are perfectly situated to give you views of nature and wildlife you might never have seen before. Survey the lagoon to find parrotfish, tarpon and lobster. Admire the beauty of egrets, herons and pelicans among the mangroves. You might even see an... View all property information
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    Marathon Shores, Marathon 33050
    1 / 36
    5 of 5 stars (7) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Ocean Views
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 4 weeks ago
    I stayed in this condo for a week with my 3 children (ages 12, 19, and 20) and a friend and her child (age 20). The condo was located near all that we wanted to explore in...
    5 of 5 stars Reviewed 23 November 2014
    Really enjoyed this home, clean,secure, owner answered all questions in a timely fashion. Highly recommended!
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    1 / 20
    5 of 5 stars (2) Excellent
    Conch Key
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Patio
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    • Pet-friendly
    • Child-friendly
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    About this property
    If Comfort, Fun, Fishing and Views Are on Your List, Stay Here! We have ground level or second floor units. We provide outside table and chairs, and just around the corner the barbecue grill is located to grill up those freshly caught Florida Keys' lobster or our wonderful assortment of Keys'... View all property information
    Location Information
    Conch Key, Florida Keys 33050
    5 of 5 stars Reviewed 1 week ago
    My wife and I stayed with Stewart and Katie this past May. They were very helpful and our efficiency apartment was great. We were on the second floor and the views were awesome...
    5 of 5 stars Reviewed 8 December 2015
    We just returned from staying at the Conch Key Villas and couldn't have been happier with our stay. The unit was clean, comfortable and quiet. We were the only guests while we...
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    1 / 96
    5 of 5 stars (9) Excellent
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Key Colony Beach house (duplex) description SPECIAL rate of $999.00 for 4 guests (may have 6 (Spring break 04/02-04/09 is $1300.00), $10 per extra person per day, 6 max total) Valid for Spring and Fall (except Thanksgiving), Summer is $1200 per week, excluding lobster weeks which are $1850. Please... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    5 of 5 stars Reviewed 2 weeks ago
    This was a wonderful vacation rental and a great base for touring the keys. Booking with Dee was easy and the cold beverages on our arrival were a welcome surprise! Our family...
    4 of 5 stars Reviewed 3 weeks ago
    This property had many amenities and was satisfactory with six people. Did have a little problem with the AC unit in dining room. Owner was as courteous and helpful as possible...
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    1 / 22
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    PEAK A BOO BAY VIEWS & QUICK ACCESS TO THE OPEN WATERS; GULF & OCEAN. Very Clean 2 bedrooms, 2 bath home with over sized master bdrm & bath. Cathedral ceiling in spacious living room that includes a queen size sleep sofa. Home is bright & airy. Wide, open covered deck with wrap around walkway.... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 6
    3 of 5 stars (1) Average
    Big Pine Key
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Cabana in beautiful Sunshine Key Resort, Golf Cart,great fishing, breezes, and relaxation. 1 bedrooms, 1 bath, kitchen and living room. Outdoor tiki. enjoy the island living of the Florida Keys. Great resort amenities.Marina available in resort, park your boat, jet sky, and enjoy your vacation... View all property information
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    Big Pine Key, Florida Keys 33043
    3 of 5 stars Reviewed 1 week ago
    Good RV park with marina. No live bait @ bait shop in marina but had ice, chum and gas. Cabana was clean with fresh sheets and towels. Shower faucet very difficult to work...
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    1 / 9
    5 of 5 stars (3) Excellent
    Islamorada
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • ?
    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 26 May 2016
    I recommend this B&B to anyone who just wants a beautiful property to relax and enjoy the company of your significant other. The staff is very attentive and accommodating and the...
    5 of 5 stars Reviewed 9 September 2015
    Enjoyed my 2 night stay. Bombay room was quiet, uniquely furnished, clean, and well-air conditioned. Refreshing pool and nice seating areas with plantings, water features, and...
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    1 / 6
    Marathon Shores
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
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    • Central Heating
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Perfect resort to decompress. Keys feeling with class. Friendly and accommodating staff. You can’t beat this location, in the middle of everything! Hammocks of Marathon is an affordable paradise. Immediately adjacent to property Jerry's Water Sports offers very reasonable boat and other watercraft... View all property information
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    Marathon Shores, Marathon 33050
    1 / 16
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • ?
    About this property
    This house is in a very quiet section of a quiet island . It is surrounded by palm trees. There is a large screened deck which catches the breeze. At the end of the canal (approximately a block ) you will be in a large open area between Big Pine and Little Torch ; from there you can easily travel... View all property information
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    Big Pine Key, Florida Keys 33043
    1 / 26
    5 of 5 stars (38) Excellent
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    BRAND NEW WHISPER QUIET $5300/42,000 BTU'S TRI-ZONE AIR CONDITIONING/HEATING SYSTEM PROFESSIONALLY INSTALLED AND COMPLETED IN MAY 2014. Simple and unpretentious, the Oceanfront Bungalow Hideaway is a mobile home located right on the water at Boot Key Harbor. Only 45 miles south to Key West. One... View all property information
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    Marathon, Florida Keys 33050
    4 of 5 stars Reviewed 19 June 2016
    Bill the owner of the Property was excellent to deal with and answered all questions promptly regarding the property and surrounding areas . The Property was exactly as as...
    5 of 5 stars Reviewed 22 October 2015
    Ok this is a small trailer, in a trailer park but don't let that put you off. The trailer is remodeled and is just like the pictures. It's very clean and cozy. The neighborhood is...
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    1 / 11
    5 of 5 stars (4) Excellent
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • ?
    • ?
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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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    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 21 July 2016
    The Florida Keys is a big place, with literally thousands of places to stay between Key Largo and Key West. Nestled almost exactly in the middle, on a quaint little key called...
    5 of 5 stars Reviewed 31 December 2015
    A somewhat eclectic cottage flair with a nice solid sandy beach right outside the door. This place is a lovely place to lay out on the beach or find solace on the cottage front...
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    1 / 27
    Key Largo
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    5BR ONLY IN 2017 - $699/night w/ 4 night min - $4,250/week (2017 Non-Holiday Prices) - Request Holiday Pricing for 2017 ** Please note that the advertised nightly rate is for the 3BR upper unit of the home that can accommodate 7 guests at maximum. Guests have the exclusive option to add the 2BR... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    1 / 15
    4 of 5 stars (5) Very good
    Tavernier
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Sauna
    • Satellite TV
    • Waterfront
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
    • x
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    • x
    About this property
    Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on sea. Once this salt air gets in you you will never want... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 stars Reviewed 8 February 2016
    Very relaxing, friendly environment, with an excellent view of the ocean, we had a great time during our stay. The owner "Tad" was very helpful, whenever we had questions about...
    4 of 5 stars Reviewed 1 February 2016
    The location is in a very good position and permit to visit all the most important site of Keys, Everglades and Miami in a daily tour. The set up of the apartment is complete and...
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    1 / 14
    4.5 of 5 stars (8) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 9 February 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 stars Reviewed 29 December 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    1 / 25
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
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    Cudjoe Key, Florida Keys 33042
    1 / 20
    5 of 5 stars (2) Excellent
    Marathon
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Spacious 2 bedroom, 2 1/2 bath, 1400 square foot condo located on the Vaca Cut Beautiful open quiet waterfront location directly on the Gulf of Mexico at MM 53. This spacious 1400 sq. ft. unit includes 2 Bedrooms, 2 Full Baths, 1 Half Bath. New 42" flat screen T.V. in living room. King size bed in... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 6 days ago
    Best the Florida Keys has to offer. Wonderful and spacious 2 bedroom condo with plenty of room for 6. TV each bedroom and WIFI. 2 1/2 Bath made easier for everyone to get ready...
    5 of 5 stars Reviewed 3 weeks ago
    The condo was fantastic, very clean and with all the amenities you needed, it felt really spacious and had a good layout. The wifi worked perfectly, which was important for our...
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    1 / 30
    5 of 5 stars (2) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 5 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    You are downtown with a pool at Flip Flop Retreat- just 2 blocks from Duval Street in a quiet poolside condo in Truman Annex. We have 33 all 5 Star Reviews on a competing website- our guests are very pleased with their vacations. You are in Old Town for convenient entertainment, shopping,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 4 January 2016
    My wife and I along with our son and daughter have been travelling to Key West for several years now and the past few we have stayed at the Flip Flop. As of now I can not think...
    5 of 5 stars Reviewed 15 December 2015
    My husband and I stayed here from 12/5-12/2015. Flip Flop was immaculate, perfectly located in Old Town Key West and well furnished. The owner took all of the steps to make...
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    1 / 21
    5 of 5 stars (3) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We are offering for rent our beautiful, 2/2 condominium located directly on the ocean in Key Largo (Tavernier), Florida. As this is an 'END' unit there are many windows that provide an open, bright feel and offer views of the ocean throughout. The elevator carries you quickly to our unit located... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 stars Reviewed 1 May 2016
    We really enjoyed this condo and the owners are fantastic to work with. The condo complex is really well maintained and is located right where you want to be to enjoy the Florida...
    5 of 5 stars Reviewed 1 April 2016
    We come here every year for the month of January because we absolutely love this condo, the amenities in the gated community and the location which is perfect to enjoy all that...
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    1 / 99
    4.5 of 5 stars (2) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Patio
    • Grill
    • Porch
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 9 November 2015
    Enjoyed our stay here. Fairly sparse furnishings, but clean and functional. Location and price were the best points for this cottage. Short walk to everything, location is just...
    5 of 5 stars Reviewed 20 July 2015
    Great place to sleep-we spent most of the time touring-courtyard was great for meeting new friends-place was very clean and plenty of space for 3 couples-location was very...
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    1 / 23
    Marathon Shores
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    4/3 villa in Marathon, FL that has what you are looking for. It's a Brand New unit that has was professionally decorated.The spacious layout is more than 1,700 square feet and can house a large family. It has a fully equipped luxury kitchen with stainless steel appliances, granite in the kitchen... View all property information
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    Marathon Shores, Marathon 33050
    1 / 7
    Islamorada
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
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    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • ?
    About this property
    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast.LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,... View all property information
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    Islamorada, Florida Keys 33036
    1 / 18
    Big Pine Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Enjoy this tranquil waterfront house located on a canal in Big Pine Key with easy access to the Flats, Gulf side, Ocean side or an easy boat ride to popular Picnic Island for Sunday Fundays. Launch the Kayaks from the easy step down dock and explore the many canals while fishing or taking in the... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 24
    Cudjoe Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Private Outdoor...
    • Internet Access
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    WATERFRONT POOL HOME, MINUTES TO KEY WEST, CONVIENT TO RESTATURANTS AND LOCAL ATTRACTIONS. A perfect vacation get away. But please note we only rent weeks from Saturday to Saturday. Three separate living/sleeping areas. 1)Main house is fully appointed with flat screen TV, DVD, DVR, Comcast cable,... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    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.