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Holiday Rentals in Florida Keys, FL

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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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    Big Pine Key
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 14
    4.5 of 5 stars (25) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Big Pine Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Private Garden
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    About this property
    Beautiful home very centrally located in the heart of Big Pine key this 3 bedroom 2 bathroom home is close to everything that lower keys has to offer, Bahia Honda State Park which has one of the most beautiful beaches in the country is only 3.5 miles away as well as 29 miles away from Key West and... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    1 / 17
    5 of 5 stars (12) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The Nassau Suite is one of the largest suites in The Bahama House. Featuring 2 King Bedrooms, 2 Bath and 2 Day-rooms with Futons. Quietly Tucked away in a world of it's own, yet literally only steps away from all that Key West has to offer. Whether your looking for a place to meditate or find an... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 8 February 2016
    This is a roomy two bedroom apartment, very clean and nicely decorated. You couldn't ask for a better location to all things around downtown Key West - one block off of Duval...
    5 of 5 stars Reviewed 4 February 2016
    This is a beautiful unit in a perfect location. There are 2 bedrooms with very comfortable beds, and two bathrooms. One bathroom is full size and the other is rather small, but...
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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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    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 23 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 3 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 / 18
    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
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    A Vacation Rental for View Lovers! FREE WIFI Best location in the complex. Fantastic Autumn Rates! Welcome to this direct oceanfront, well-cared for 5th floor corner unit right on the ocean in Islamorada. Enjoy your stay with spectacular panoramic ocean views in this private, serene... View all property information
    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 1 week ago
    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 / 17
    5 of 5 stars (22) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Located in the heart of Old Town, this split 2 Bedroom plan is just blocks from everything Key West has to offer. The famous Southernmost Point, Hemingway House, Lighthouse, Beaches and more. Just 1/2 block from Duval Street. Completely updated for your comfort and convience with new furnitire,... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 1 week ago
    We just stayed in the Bimini Suite at the Bahama House! The pictures on here don't do it justice! We all loved it which made me feel good since I picked it out. Everything was...
    5 of 5 stars Reviewed 5 June 2016
    Enjoyed our stay. The 2 bedroom suite was clean, comfortable, and convenient to Duval Street. The kitchen allowed us to have breakfast as we awoke and the pool was relaxing. The...
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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
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    • Waterfront
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    • Pet-friendly
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    • ?
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    • 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 1 week ago
    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 / 20
    5 of 5 stars (12) Excellent
    Key Largo
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
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    • Ocean Views
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    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 2 weeks ago
    My husband and I enjoyed Casa Cayo for a week in June. From the minute we arrived, until the minute we left - we enjoyed this convenient canal-front property! The inside of the...
    5 of 5 stars Reviewed 3 weeks ago
    We loved this cottage and the fact that it was on the channel with a family of manatees and various other sea life made it that much more amazing. The outside kitchen became our...
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    1 / 12
    5 of 5 stars (2) Excellent
    Duck Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Hot Tub
    • DVD Player
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    • Pet-friendly
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    • x
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    • x
    About this property
    SPA VILLA ON BLUE WATER CANAL AVAILABLE JULY 5-12TH, JULY 17 TO 23 Nestled within the charming island resort of Hawk's Cay Escape to your very own Tropical Paradise in the heart of the Florida Keys. Although we are not affiliated with Hawks Cay Resort the Marina, Spa, Dolphin Facility,... View all property information
    Location Information
    Duck Key, Florida Keys 33050
    5 of 5 stars Reviewed 24 May 2016
    This is a great place to spend a week. The unit is clean with a beach decor, accommodating four adults with no problem. The location is half way down the Keys so it was not too...
    5 of 5 stars Reviewed 17 November 2015
    Beautiful condo with high end furnishings, pictures on here not do justice to how nice this condo is. I could not be happier that we rented this condo unit instead of the resort...
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    1 / 11
    4.5 of 5 stars (3) Very good
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 2 days ago
    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 1 January 2016
    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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    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
    Location Information
    Big Pine Key, Florida Keys 33043
    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
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
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    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 21 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 11 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 / 46
    4.5 of 5 stars (10) Very good
    Matecumbe Key
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Private Outdoor...
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    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
    Location Information
    Matecumbe Key, Florida Keys 33036
    5 of 5 stars Reviewed 10 November 2015
    Having this much private sandy beach front was a rare treat. We have stayed in some beautiful homes in the past 14 years in the Keys, but this was the first with so much sandy...
    5 of 5 stars Reviewed 18 December 2014
    My Dad's 70th birthday celebration was a wonderful time with family. We enjoyed the pool, hot tub, and view every day; and the kitchen and grills served us well for making a feast...
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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
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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 6 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 7 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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    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    No. 1 rated resort in Marathon Completely renovated w/ dock. We will be ready to take reservations for Thanksgiving. 3 bedrooms 1 King, 2 queens and a queen size sleeper. 2.5 bathrooms. Walking distance to Marathon and Key Colony activities. Representing a new concept that offers... View all property information
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    Marathon, Florida Keys 33050
    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    1 / 36
    5 of 5 stars (6) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Ocean Views
    • DVD Player
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    • Waterfront
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    • Pet-friendly
    • Child-friendly
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    • 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 23 November 2014
    Really enjoyed this home, clean,secure, owner answered all questions in a timely fashion. Highly recommended!
    5 of 5 stars Reviewed 30 May 2014
    We spent seven wonderful days at Blue Heaven . When we arrived we were astonished by the clean, modern,well equipped home . Located centrally in Marathon, it was a great central...
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    1 / 19
    5 of 5 stars (2) Excellent
    Islamorada
    3 Bedrooms, 6 Bathrooms, Sleeps 8 | Quick View
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    • Hot Tub
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    • Ocean Views
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    • Pet-friendly
    • Child-friendly
    • x
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    About this property
    Luxurious end unit in Bay Harbour with a boat slip. Upon entering the unit you are greeted with the tranquil views of the harbor and ocean. Enjoy the ocean breeze from the large screen porch. Beautiful Bay Harbour gated condo community on lower Matecumbe, mm 74 1/2. Enjoy the sunrise or sunset... View all property information
    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 12 February 2016
    Great place. The condo was exactly as described in Tripadvisor. Located halfway between Miami and Keywest it is the perfect place to sight see the keys from.
    5 of 5 stars Reviewed 19 September 2015
    We spent Labor Day weekend at this condo (Friday through Tuesday) and had one of our most memorable vacations with our adult kids! The condo is beautiful and large, with excellent...
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    1 / 55
    5 of 5 stars (4) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
    • x
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    • 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 3 weeks ago
    This condo was exactly as described only better! Everything you could think of was there, from the fully equipped kitchen to great beds, vacuum, washer and dryer, hair dryers in...
    5 of 5 stars Reviewed 3 June 2016
    We stayed in this beautiful condo over the Memorial Day weekend, and at peak occupancy for Ocean Point it was still quiet and felt secure. The unit is tastefully furnished and the...
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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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    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
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    • 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 30 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 / 14
    5 of 5 stars (8) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    • Terrace
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    • Pet-friendly
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    • x
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    • x
    About this property
    Tropical 2 bedroom, 2 bath condo 1/2 mile from Smather's Beach in Key West. Fully appointed kitchen and living room. Balcony overlooking Salt Ponds and distant ocean view. Large heated pool on property, perfect for sunbathing. Jacuzzi and gym. Tennis court. Small boats on trailer allowed.... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 stars Reviewed 16 April 2016
    The condo was clean and equipped with the necessities and a washer/dryer. Location is away from downtown but we knew that when we booked it. Would definitely rent again and price...
    5 of 5 stars Reviewed 5 March 2016
    Condo is a $25 cab ride including tip (2016 prices) from Duval Street area where most bars/restaurants/shopping/tourist sites are located. However all cab companies were familiar...
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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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    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
    Location Information
    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 / 17
    4 of 5 stars (7) Very good
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Top floor suite! Beautifully furnished condo overlooking the aqua-blue waters of the Gulf of Mexico! This 1,700 sq. ft. , custom decorated condominium offers a unique water vista from the living areas. The split floor plan provides privacy as the bedrooms are on each side of the living/dining area.... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 27 October 2014
    Lovely, clean and well furnished condo with great view onto the Gulf. Condo was large with ample room for all six of us with screened verandah ideal for relaxing and watching...
    5 of 5 stars Reviewed 19 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 / 23
    5 of 5 stars (1) Excellent
    Little Torch Key
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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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    Little Torch Key, Florida Keys 33043
    1 / 15
    5 of 5 stars (8) Excellent
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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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    1 / 10
    5 of 5 stars (4) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    <BR><BR>Luxurious direct bayfront townhome with dock, upgraded unit.<BR><BR> best location in the 50's overlooking large green yard and open bay with slip in front.<BR><BR>3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat, beautiful pool, mins to ocean through vaca... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 13 August 2015
    it was just a great place , we just loved it there , the location to all , the pool and marina was just great , and the sunsets with a drink were just wonderful.
    5 of 5 stars Reviewed 4 July 2014
    This was my second rental through Keys Caribbean . Excellent Price, excellent service, excellent location . A hidden jewel in Marathon.
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    1 / 22
    5 of 5 stars (1) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    This house has everything! You can rent 1/2 or the whole house. The top unit has 2bd/ 2bths. Lower spacious unit has 1bd/1bth. Enjoy dinner on breezy upper or lower outdoor patios. This house is more convenient and offers much more than your ordinary 3/3. Each unit is very spacious, sleeps up to... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 stars Reviewed 29 January 2016
    We had a great time at Paradise In Marathon. First, the place was extremely easy to book compared to every other property we checked in the area (and we checked a lot), and the...
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    1 / 26
    5 of 5 stars (37) Excellent
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 4 weeks ago
    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 23 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 / 96
    5 of 5 stars (7) Excellent
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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 3 weeks ago
    We truly enjoyed our stay. Dee, the owner, could not have been nicer and went way beyond expectations of being able available with helpful information and resources. She was a...
    4 of 5 stars Reviewed 22 September 2015
    We stayed at this wonderful home for a week , but wished it was longer ,the home provided us with a perfect taste of life in the keys , The home was clean comfortable and very...
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    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    About this property
    Rental amount includes all fees boat dock fee.. This newly renovated modern 4th floor condo in a private gated community has a spectacular Florida Bay sunset view. Futura Yacht Club is just 68 miles south of Miami. Amenities include heated pool, screened in Lanai, 2 lighted tennis courts, and... View all property information
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    Islamorada, Florida Keys 33036
    1 / 10
    4.5 of 5 stars (2) Very good
    Key Largo
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    This fully furnished 4 Bedroom, 3 1/2 Bath Canal Front Home is the ideal Escape to Paradise. One thing that cannot be seen through photos is the amount of privacy this location has, at the end of the Cul-de-sac with the canal and mangroves surrounding the home. Double Boat Dockage, Large Tiki Hut... View all property information
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    Key Largo, Florida Keys 330037
    4 of 5 stars Reviewed 9 April 2016
    The house was just as seen on Trip Advisor post. We stayed for a week with our 2 boys (25 & 28) and our daughter 22 . We used the canoes every morning to fish and paddle the area...
    5 of 5 stars Reviewed 30 March 2016
    This was our families first trip to the Keys. We were absolutely impressed with this property. The game room was a big hit with kids and adults alike. The house was up to...
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    Islamorada
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Children's Pool
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    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on... View all property information
    Location Information
    Islamorada, Florida Keys 33023
    Marathon Shores
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    About this property
    This private vacation home is situated at a great location close to the middle of Marathon with just a lovely short walk or bike ride to the famous Sombrero Beach. 6 bedroom/ 3 bathroom with comfortable and inviting coastal designed decor. Attention to detail with fine linens and beach towels. 2... View all property information
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    Marathon Shores, Marathon 33050
    1 / 41
    5 of 5 stars (2) Excellent
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Sauna
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    • Pet-friendly
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    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 6 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 / 22
    4.5 of 5 stars (2) Very good
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    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
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    Key West, Florida Keys 33040
    5 of 5 stars Reviewed 6 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 9 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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    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    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 (1) Excellent
    Summerland Key
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    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 / 17
    5 of 5 stars (14) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    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
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 stars Reviewed 17 August 2015
    The apt. Was beautiful in an awesome location. Close to shopping areas. Marina was great. Fishing was awesome. There were lots of people diving. Lots to do too little time...
    5 of 5 stars Reviewed 24 July 2015
    Super clean and lovely,everything in order and everything needed to enjoy our stay, Super comfortable beds,boards games and spectacular view from the apartment. The awesome time...
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    Big Pine Key
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    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
    Location Information
    Big Pine Key, Florida Keys 33043
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Our Private Bay Front Key Largo Cottage is our home away from home. Located in Kings Kamp RV park, we have Spectacular Views of Florida Bay as we are 25′ from the waters edge. Our Large Kitchen and Living area are all one with central air conditioning. The 12’x15′ Screened porch with Hammock is... View all property information
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    Key Largo, Florida Keys 33037
    1 / 13
    5 of 5 stars (3) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    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 1 week ago
    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...
    5 of 5 stars Reviewed 22 October 2015
    Being a Florida local, I travel to Key West quite often for the past 13 years and have never had a better and more pleasant stay than at the Duval Balcony. The owner was waiting...
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    Key Colony Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    Key Colony Beach Canal Front Property. Nnew deep water boat dock (37.5 ft) directly at your back door with a fish cleaning table, water and power on dock. bait freezer 5 min. boat ride through the 100' wide canal leads toVaca Cut and the Atlantic Ocean and quick access to the Gulf of Mexico... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    1 / 29
    4.5 of 5 stars (3) Very good
    Marathon
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Ask About our Specials! Seaside Escape! Boater's Paradise! In the heart of the Florida Keys, "La Casita Sol" is on MM 52. "La Casita Sol" is a quaint 1/2 duplex canal home with 2 bedrooms and 1 bathroom that can comfortably accommodate 4-6 guests. 'La Casita Mar', it's sister vacation rental, is... View all property information
    Location Information
    Marathon, Florida Keys 33050
    4 of 5 stars Reviewed 29 March 2016
    An extremely clean and comfortable venue to vacation. Spacious deck for outdoor dining, sunning and fishing. Beautiful view of the Atlantic. There were 4 of us in our family and...
    5 of 5 stars Reviewed 8 July 2015
    My husband and 3 girls aged 16, 14, and 10 stayed from June 13-28th. The house was immaculate, quiet, clean, and had all the necessities. The house is on a canal on the Atlantic...
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    1 / 19
    4 of 5 stars (10) Very good
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Located in the centre of Marathon. This destination is perfect for discovering the beautiful Florida Keys. One hour's drive from Key West or Key Largo. Marathon is famous for the sportfishing including but not limited to Marlin, Sailfish, Mahi-Mahi and there are numerous places to rent a boat,... View all property information
    Location Information
    Marathon, Florida Keys 33050
    4 of 5 stars Reviewed 8 October 2015
    My husband and I rented the condo for one week and enjoyed our stay. We'll rent again when in the Keys. PROS: Owner is friendly, responsive, and the rental process was simple...
    3 of 5 stars Reviewed 30 July 2015
    I've been going to Sombrero Resort for many years now and am sad to see what has been happening to it. While at one time it was a resort, it has now become resort/condo. Many...
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    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    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
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This beautifully furnished and newly renovated condo is airy and offers all the comforts of your own home. Walk in to a spacious living room with an adjacent dining area and then onto a full kitchen with everything necessary to prepare and serve your meals. The kitchen has granite counter tops, a... View all property information
    Location Information
    Marathon, Florida Keys 33050
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    About this property
    WIFI -3 LED 42' TV -DOC SPACE ROOM FOR TRALER PARKING All New Fans & new Lighting New Appliancess, Pets Allowed Enjoy Ocean Views and Tranquil Breezes from this fully equipped tropical 2/2 Vacation Home with Private Deep Water Dock Direct To The Ocean. This 1200 Sf Private Two Story Home Comes... View all property information
    Location Information
    Marathon, Florida Keys 33050
    Key Colony Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Welcome to our Key Colony Beach vacation home. We are located at the end of the canal between 8th and 9th streets and enjoy an unobstructed views from the kitchen, sitting area, dining room, and living room directly down our beautiful canal. Our home is bright, much wider than most with twice the... View all property information
    Location Information
    Key Colony Beach, Florida Keys 33051
    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.