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Vacation rentals in Florida Keys, FL

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All 1,232 Rentals in Florida Keys
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From
$291
Per Night
1 / 41
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Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 8
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From
$332
Per Night
1 / 5
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Marathon
1 Bedroom, 1 Bathroom, Sleeps 4
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From
$406
Per Night
1 / 1
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Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$262
Per Night
1 / 12
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Matecumbe Key
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Grill
  • Patio
  • TV
  • Terrace
  • Refrigerator
  • Deck
  • Ceiling Fans
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Dive right into paradise while staying at Casa Rio. With a beautiful view from a raised master suite in the Florida Keys you can quickly relax and transform into 'island time.' This exclusive bayside home is situated in a secluded location on Islamorada with quick access to the Florida Bay and... View all property information
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$145
Per Night
1 / 27
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Grassy Key
Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Linens Provided
  • Parking
  • Dryer
  • TV
  • Internet Access
  • Ceiling Fans
  • Microwave
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Two charming efficiencies located 50 yards from the Atlantic Ocean. Both are fully furnished with well-equipped kitchens and are decorated with a Caribbean flair. In the private front yard, each unit has a gas-BBQ grill, a picnic table with large umbrella's for shade. Unit 9 has two single beds... View all property information
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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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$5,214
Per Week
1 / 16
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (38) Make Enquiry
Amenities & Details
  • Internet Access
  • Guest Count
  • # Of Bathrooms
  • Deck
  • Ceiling Fans
  • Air Conditioning
  • Number Of Bedrooms
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
An Old town Key West home, located in the Historic District and just one half a block off Duval Street. Guests are within walking distance of restaurants, the Atlantic Ocean, Southernmost Point of Key West and our sunset piers. All lovingly restored and cared for, this charming 1 & 1/2 story... View all property information
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5 of 5 stars Reviewed 17 October 2012
This amazing little house had everything you could need to make a Key West vacation even better. The whole house was clean, and with a tropical flair that told you the moment you...
5 of 5 stars Reviewed 1 September 2012
The house was spotless. Easy to live in. Close to everything. Comfortable. The small pool/grotto is where I hang out in my memories. Everyone was sweet, accommodating and...
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From
$145
Per Night
1 / 13
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Grassy Key
Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Two charming efficiencies located 50 yards from the Atlantic Ocean. Both are fully furnished with well-equipped kitchens and are decorated with a Caribbean flair. In the private front yard, each unit has a gas-BBQ grill, a picnic table with large umbrella's for shade. View all property information
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4 of 5 stars Reviewed 30 April 2014
Our rental worked out great. We explored the Keys north and south from Marathon. Our "base" was attractive, clean, and thoughtfully equipped for our stay.
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From
$149
Per Night
1 / 17
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Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Ceiling Fans
  • DVD Player
  • Dishwasher
  • Microwave
  • Safe
  • Garage
  • Patio
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The condo is located in a complex called Moon Bay More like a resort than a condominium. Free tennis courts, saunas, a private boat slip, and a dock for fishing and saltwater swimming, to mention just a few of the amenities. The unit is on the fourth floor of an elevator building, making for... View all property information
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4 of 5 stars Reviewed 8 October 2013
We stayed in condo B-106, owned by Gloria, who prepared everything for our arrival. Erin, her housekeeper met us on arrival and showed us round. Everything was as promised. The...
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From
$581
Per Night
1 / 39
Marathon
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • DVD Player
  • Safe
  • Washer
  • Refrigerator
  • Patio
  • Dishwasher
  • Parking
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Create a memory that will last a Lifetime! Never on the Rental Market before, this newly renovated Million Dollar House will become your vacation destination year after year. 4 bedrooms, 3 bathrooms, 28 foot Pool, 44 foot patio, 40 foot concrete pier, endless views, and privacy. You can bring your... View all property information
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From
$128
Per Night
1 / 12
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Key Largo
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
This newly finished studio with queen bed, reclining sofa,40 inch tv w/comcast cable, wifi, large screened in porch with outdoor kitchen with toaster oven, coffee maker, 2 burner stovetop, barbecue, microwave. view over gardens, sit and enjoy the sunsets at our rate payers park. Lots of parking in... View all property information
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From
$215
Per Night
1 / 5
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Key West
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Historic 'conch' house has been completely redesigned and custom crafted by 2 architects as our home away from home. Featured on HGTV in 2007 (!), this intimate house boasts many fun and thoughtful features which will help make your stay in Key West special. It is located in a wonderfully private... View all property information
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5 of 5 stars Reviewed 8 December 2014
This is a wonderful conch house in Old Town, Key West. The house is just around the middle of Old Town, so you can walk or bike to the harbor, the ocean, and the great music at...
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From
$285
Per Night
1 / 30
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Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 9
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Ceiling Fans
  • Garage
  • Microwave
  • Dryer
  • Refrigerator
  • Washer
  • Grill
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful 2 story 3 bedroom 2 baths home. Located in Key Largo at MM 103 on the bayside and close to John Pennekamp Park, local shopping, fine restaurants, diving, charter fishing or just swimming with the dolphins! This home has an open water view overlooking the beautiful Florida Keys bay, Relax... View all property information
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5 of 5 stars Reviewed 22 July 2014
Gorgeous views, easy boat and water access, clean house with fun beach decor, all for a great price. Thank you, we will be coming back!
5 of 5 stars Reviewed 20 June 2014
This rental was as nice as pictured. Everything is new and very tastefully decorated. Beds were comfortable with fresh and clean smelling sheets. House is in a very quiet area...
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From
$242
Per Night
1 / 26
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Key West
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Linens Provided
  • Internet Access
  • Parking
  • Patio
  • Satellite TV
  • Grill
  • Balcony
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • ?
  • ?
About this property
Brand New to the Rental Market! Part of Banana's Foster Guest House This cozy 2nd floor studio is perfect for a couple looking to be in the middle of the Duval action! After entering the compound from the shared off street parking into the courtyard with shared plunge pool and BBQ grill, go... View all property information
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5 of 5 stars Reviewed 11 November 2014
This place was perfect for what we were looking for: Close to Duval, Close to Front Street, Pet Friendly, Shared Space but still alot of privacy. It is a small one bedroom, one...
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From
$220
Per Night
1 / 6
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Key Largo
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Microwave
  • DVD Player
  • Pool
  • Ceiling Fans
  • Refrigerator
  • Canoe
  • Air Conditioning
  • Patio
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving.... View all property information
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5 of 5 stars Reviewed 23 July 2014
Our unit was just big enough for the two of us having one bedroom, one bath. Walk out about 15 ft. to the pool and another 20 ft to the water. Beautiful sunsets! Diving nearby...
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1 / 8
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 4
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From
$1,047
Per Night
1 / 47
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Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (6) Make Enquiry
Amenities & Details
  • Deck
  • TV
  • Microwave
  • Refrigerator
  • Dryer
  • Ceiling Fans
  • Safe
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Only 5 minutes offshore by boat, Seabird Key is a ten acre private island available for rental by the week featuring an architecturally stunning home with gracious porches and multi level decks; a private, sandy beach and beautiful, tropical gardens throughout. This is the Island that has it... View all property information
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5 of 5 stars Reviewed 23 September 2014
From the moment you step foot on this beautiful island paradise, you'll feel like you've been transported to your own little private world! Every amenity has been thought of from...
5 of 5 stars Reviewed 25 June 2014
This paradise has to be experienced to believe. We have stayed at Seabird Key every year for the last 15 years. Our sons now grown with families of their own, look forward to our...
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From
$58
Per Night
1 / 27
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Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Washer
  • Microwave
  • Ceiling Fans
  • Central Heating
  • Internet Access
  • DVD Player
  • Satellite TV
  • Air Conditioning
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Look No Further As This Is An Excellent Deal!!!! Best Value For Your Money!!!! You will truly enjoy this key Largo vacation home!! It is conveniently located at a mile marker 103.5, Adjacent to world famous John Pennekamp Coral Reef State Park, where you can experience... View all property information
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4 of 5 stars Reviewed 27 March 2014
Unit was very comfortable & clean! If you are traveling on a tight Vacation Budget this is the spot! Close to many FINE Restaurants The Fish House/Encore for Dinner, Evelyn's is...
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From
$262
Per Night
1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dryer
  • Dishwasher
  • Hot Tub
  • DVD Player
  • Washer
  • Safe
  • Microwave
  • TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Dock you boat or jet skis behind this nicely decorated 2 bedroom 2 bathroom(sleeps up to six people) on a deep water canal just a stone's throw from the open water of the Atlantic Ocean. On-site amenities include an 80 foot heated swimming pool, seperate pool for the kiddies, jacuzzi, marina, boat... View all property information
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5 of 5 stars Reviewed 25 October 2014
Awesome Cudjoe Key get a way. Good sized personal dock behind the house for my boat and great Atlantic Ocean access, was in deep water in about 10-15 minutes. Good fishing off the...
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From
$5,237
Per Week
1 / 24
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Marathon
4 Bedrooms, 5 Bathrooms, Sleeps 10
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Ceiling Fans
  • Microwave
  • Parking
  • Refrigerator
  • Dryer
  • Patio
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Gorgeous, 4 bedroom, 4 full bath home, plus 1/2 bath, located on exclusive Tingler Island and near Sombrero Beach! This 3297 square feet tri- level floor plan provides space and privacy for visitors, while the softly lit pool area create a wonderful atmosphere for entertaining and relaxation. With... View all property information
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From
$178
Per Night
1 / 2
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Marathon
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Amenities & Details
  • Microwave
  • Satellite TV
  • DVD Player
  • Refrigerator
  • Parking
  • Fax
  • Highchair
  • Grill
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The Cats Eye has a queen bed in the bedroom and a sleeper sofa in the living/dining room. Cable color TV, A/C, paddle fans and full kitchen. BBQ grill. Light and bright. Recommended for 2 but will accommodate 4 people including children. View all property information
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From
$275
Per Night
1 / 23
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Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
3 bedroom, 2 full bathroom, 1 outdoor shower, Sleeps 8 This three bedroom home boasts of many special features and offers a perfect location. The unit can sleep 6-8 . Laying at the corner of Dolphin Marina and Little Palm Island you'll vacation in one of Key's finest neighborhoods. A 60 second... View all property information
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5 of 5 stars Reviewed 7 August 2014
This home is clean, very comfortable and well equipped. It has a charming island decor that really lends to the atmosphere and everything is well planned. You can enjoy a drink...
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From
$204
Per Night
1 / 10
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Key West
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (6) Make Enquiry
Amenities & Details
  • Hot Tub
  • Microwave
  • Fitness Room
  • Refrigerator
  • Soap/Shampoo...
  • Balcony
  • Air Conditioning
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
About this property
Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
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5 of 5 stars Reviewed 11 December 2014
This condo at Sunrise at Seaside is perfect for a family vacation. We stayed there last Thanksgiving weekend and had a wonderful time. The condo is very well maintained and...
4 of 5 stars Reviewed 9 June 2014
Very good price for a 2 bed 2 bath in Key West! It Was clean and just what we needed! It was also not right in downtown close to everything so we could get away hen we wanted.
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From
$524
Per Night
1 / 15
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Key West
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (4) Make Enquiry
Amenities & Details
  • Grill
  • Stereo System
  • Dryer
  • Washer
  • VCR
  • Microwave
  • Refrigerator
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • 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
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5 of 5 stars Reviewed 16 August 2014
I came down with my family and we loved this place. We had a direct view of the water and it was amazing waking up every morning to see that. Very relaxing. Friendly people...
5 of 5 stars Reviewed 29 May 2014
This was our first trip to Key West and everything was great including the condo. Very nice view, great pool, short walk to very nice beach. What more would you want.
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From
$233
Per Night
1 / 15
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Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Ceiling Fans
  • Dryer
  • Washer
  • Refrigerator
  • Parking
  • Safe
  • Patio
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Beautiful 2 bedroom, 2 bathroom Conch House located minutes from Pennekamp State Park. Fully equiped modern kitchen, spacious living area. Two comfortable decks for leisure and entertainment. Hot and cold outdoor shower. Steps away from home owner's park complete with covered picnic area, sandy... View all property information
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5 of 5 stars Reviewed 23 March 2014
Charming bungalow...great outdoor deck and patio... Fully equipped...easy access to shopping restaurants and nightlife...highly recommend
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From
$291
Per Night
1 / 27
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Indigo Reef #3 ~ Seaside Escape by Coco Plum Vacation Rentals INDIGO REEF FLORIDA KEYS VACATION RENTAL HOME #3 Spacious and like new 3 BR 2.5 BA at one of Marathon, Florida Keys most prestigious resorts, "INDIGO REEF Marina Resort Florida Keys" ~ Magnificent views from this home and 30 feet of... View all property information
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From
$64
Per Night
1 / 10
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Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (7) Make Enquiry
Amenities & Details
  • Satellite TV
  • Microwave
  • VCR
  • Grill
  • Deck
  • Refrigerator
  • Ceiling Fans
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Look No Further As This Is An Excellent Deal!!!! Best Value For Your Money!!!! You will truly enjoy this key Largo vacation home!! It is conveniently located at a mile marker 103.5, Adjacent to world famous John Pennekamp Coral Reef State Park, where you can experience... View all property information
Make Enquiry
5 of 5 stars Reviewed 16 October 2014
This rental home really fulfilled our vacation needs. We had access to a private boat ramp (we brought our boat) and it had plenty of space to the park the boat on the side of the...
5 of 5 stars Reviewed 18 August 2014
We had the best vacation at this home. It was perfect for two couples. It was close to everything. The community was quiet. The private beach was great. Hope to go back again!
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From
$204
Per Night
1 / 24
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Key West
1 Bedroom, 4 Bathrooms, Sleeps 2
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Microwave
  • DVD Player
  • Garden
  • Dishwasher
  • Dryer
  • Parking
  • Washer
  • Hot Tub
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Beautiful New large modern Home on very quiet street . Location , Location Location ! Share .5 Star $2.4m Home in Old Town Key West.. Own fully furnished bedroom with Queen size bed for 1 - 2 max ( see photos ) with flat screen t.v. and dvr and 2 french doors leading onto private balcony... View all property information
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5 of 5 stars Reviewed 15 November 2014
This house was great!!! Don was not only a gracious host but absolutely funny. House is EXACTLY as pictures online show, but better. The location for us was perfect as it was...
5 of 5 stars Reviewed 2 September 2014
This was such a rare find. We will be back and refer our friends. Loved that we had access to the pool. Absolutely the perfect spot!
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From
$157
Per Night
1 / 10
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Key Largo
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (2) Make Enquiry
Amenities & Details
  • Washer
  • Internet Access
  • Linens Provided
  • Microwave
  • Air Conditioning
  • Ceiling Fans
  • Parking
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
1 Bedroom in Key Largo steps to homeowners park with great sunsets. Kingsized bed and day bed, wifi, cable and air con. screened front porch. Canoe for use. We are located close to grocery store and restaurants on the bayside. There is also a 2br upper and studio available for rent in this triplex. View all property information
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4 of 5 stars Reviewed 8 July 2014
We stayed here 4th of July weekend. The unit itself was nice and clean, pots and dishes were there to prepare breakfast etc. Good size bathroom and living/ dining room area...
4 of 5 stars Reviewed 5 March 2014
Nice older rental in quiet neighborhood. Part of a home that was divided into several units. The unit will sleep up to four since it has a day bed. However, you'll notice in...
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From
$3,491
Per Month
1 / 15
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Long Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Guest Count
  • # Of Bathrooms
  • Number Of Bedrooms
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
I’ve owned this house for over 25 years. It’s available for rental throughout the calendar year. I rent the house monthly, as per the rules by the city of Layton in Long Key, Florida. The house is on a dead end street just off mile marker 69. It’s a very tranquil and peaceful neighborhood; everyone... View all property information
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5 of 5 stars Reviewed 4 December 2013
Loved this place, I will not stay in a hotel again when visiting the keys! Great Price! Excellent Location near to stores, bars, and fun. Just an hour drive to key west and...
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1 / 12
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Grill
  • Microwave
  • Satellite TV
  • TV
  • Refrigerator
  • Ceiling Fans
  • Deck
  • Washer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Look no further you have found a beautiful 2 bedroom 2 bath "Shot-Gun" house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size... View all property information
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From
$334
Per Night
1 / 10
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Marathon
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Patio
  • Dishwasher
  • DVD Player
  • Safe
  • Microwave
  • TV
  • Gym
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
Luxurious direct bayfront townhome with dock, upgraded unit. Jan, March and April 2015 are now available. $6,500/month. best location in the 50's overlooking large green yard and open bay with slip in front. 3 bedroom, 2.5 bath. Built in 2006. gated waterfront community. Dock for 32 ft boat,... View all property information
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5 of 5 stars Reviewed 3 July 2014
This was my second rental through Keys Caribbean . Excellent Price, excellent service, excellent location . A hidden jewel in Marathon.
5 of 5 stars Reviewed 20 June 2014
Best condo we have ever rented Very spacious, well maintained, nicely decorated. Beautiful view, excellent boat dockage. Only complaint: no HD cable for World Cup
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From
$349
Per Night
1 / 35
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Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Washer
  • Dishwasher
  • Refrigerator
  • Microwave
  • Hot Tub
  • Gym
  • Ceiling Fans
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
This remodeled 2 bedroom 2 bath condo is directly on the Atlantic Ocean with ground access via a spiral staircase. Stunning views from the Master bedroom and balcony. Wake up to the sunrise and enjoy your leisurely day on the boat, at the nearby sand bar, or lounge in the zero entry pool. There... View all property information
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5 of 5 stars Reviewed 6 January 2012
My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never...
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From
$145
Per Night
1 / 19
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Marathon
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Internet Access
  • Ceiling Fans
  • Satellite TV
  • Refrigerator
  • VCR
  • Patio
  • Balcony
  • Microwave
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
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
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4 of 5 stars Reviewed 9 November 2014
Really liked the location and balcony on the front & back. The TV's were nice. The bed was very comfortable. The kitchen was suitable. It may need new carpeting soon. Over all...
5 of 5 stars Reviewed 28 October 2014
We stayed in this one bedroom unit, in a complex of about 6 buildings, overlooking a canal off the ocean side of marathon key, fl. We used the key west transit bus to travel to...
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$303
Per Night
1 / 28
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Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
Details Reviews (6) Make Enquiry
Amenities & Details
  • Washer
  • Dishwasher
  • Parking
  • TV
  • Microwave
  • Patio
  • Refrigerator
  • Garage
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • 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
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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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From
$141
Per Night
1 / 14
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Sauna
  • Microwave
  • Dryer
  • Parking
  • Ceiling Fans
  • Refrigerator
  • DVD Player
  • Satellite TV
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
We want your business...Popular vacation spot for this 2 bedroom condo Master Queen bed , 2nd bedrm : 2 twin beds and living area has sleeper sofa. Completely and tastefully furnished with most everything you will need. Has Wi-Fi and cable TV Complex: Pool, wading pool for kiddies , tennis ct,... View all property information
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From
$663
Per Night
1 / 27
Payment Protection
Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Reviews (10) Make Enquiry
Amenities & Details
  • Grill
  • Deck
  • Refrigerator
  • Waterfront
  • Dryer
  • Dishwasher
  • Washer
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own private tropical island in the Gulf of Mexico named Pretty Joe Rock. You have your own 17 foot boat for the entire week! ARE WE THE ONLY PEOPLE ON THE ISLAND? Your family or group will be the only people on Pretty... View all property information
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5 of 5 stars Reviewed 16 February 2014
For my son's 26th birthday, I wanted to find something special and unusual. This place is amazing! It is very popular, stays booked for most of the year, so you should plan...
4 of 5 stars Reviewed 17 September 2013
Island is about 5 acres located 500 yards from Marathon Florida. The house comes with a boat, kayaks, and fishing equipment. Not to be scared but there are Iguanas on the...
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From
$315
Per Night
1 / 11
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Marathon
4 Bedrooms, 4 Bathrooms, Sleeps 12
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Parking
  • Microwave
  • Dishwasher
  • Terrace
  • Washer
  • Ceiling Fans
  • Refrigerator
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Fisherman's Dream!! Clean comfortable duplex with huge yard on the water and close to everything. Plenty of parking and deepwater access/ dockage for up to 2 boats. Waterfront 4BR/4BA Duplex with ample dockage and parking for groups from 1 to 12 people. Can be split into 2- 2BR/2BA units that will... View all property information
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5 of 5 stars Reviewed 6 July 2014
Perfect all the way. This is perfectly located to easily access all of the surrounding attractions. I would highly recommend this rental to anyone that wants a great home on the...
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From
$175
Per Night
1 / 12
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Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (13) Make Enquiry
Amenities & Details
  • Dishwasher
  • TV
  • Ceiling Fans
  • Parking
  • Washer
  • Dryer
  • Microwave
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
2 bedroom 2 bath ocean view condo in Islamorada Florida Keys has 2 sets of sliding glass doors both leading to balconies with ocean view property has everything you need on site or close for the vacation of your dreams pool, jacuzzi, tennis courts, volleyball courts, basketball net, playground,... View all property information
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4 of 5 stars Reviewed 21 August 2014
Last week we stayed in a 2/2 condo (3207) with our daughter and son-in-law. The condo was very clean and conveniently located in Key Largo. I think they are individually owned...
3 of 5 stars Reviewed 17 August 2014
We stayed at Ocean Point Suites in 2013 unit 3409 and it was fabulous. What a great unit, everything worked, bedroom at the rear facing the Ocean what an experience. In April we...
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From
$1,397
Per Week
1 / 15
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Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • DVD Player
  • Dryer
  • Internet Access
  • Grill
  • Dishwasher
  • Microwave
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Key Largo Home with 2 bedrooms large kitchen great for entertaining, access to ratepayers park. Great sunsets. Home features screened in porch with seating area, barbecue, internet, tv, 2 reclining sofa's, comfy pillowtop mattress's, large high top dining table seating for 8ppl. Steps to park. Lots... View all property information
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4 of 5 stars Reviewed 25 August 2014
This was our first time staying outside of the known major hotel chains or resorts for vacation thoroughly enjoyed this location. The home is adequately furnished and clean. Also...
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From
$291
Per Night
1 / 5
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Tavernier
3 Bedrooms, 2 Bathrooms, Sleeps 10
Details Make Enquiry
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
This keys getaway is nestled perfectly between Islamorada and Key Largo on the ocean side.Cable and wifi Internet is available also. Really laid back atmosphere super comfortable and meant for enjoying yourself with love ones..Swimming and boating friendly 3.5 miles away from John Pennenkamp Coral... View all property information
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From
$233
Per Night
1 / 17
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Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (10) Make Enquiry
Amenities & Details
  • Refrigerator
  • TV
  • Terrace
  • Dryer
  • DVD Player
  • Hot Tub
  • Ceiling Fans
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Ocean Pointe Suites is located directly on the Atlantic Ocean. This unit is completely renovated and is located in building 4 which is the most desirable building. Featuring magnificent ocean views from the living room, master bedroom and porch. This unit offers 1 King bed in master bedroom, 1... View all property information
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5 of 5 stars Reviewed 30 November 2014
My wife, daughter and I stayed at Kim's condo while we visiting family for Thanksgiving and we were very pleased. The location of the unit was conveniently close to...
5 of 5 stars Reviewed 5 June 2014
We had a wonderful time at this Ocean Pointe condo. The facilities are fantastic. The pool is very clean. The condo was like new. The complex is staffed 24/7. We felt very safe...
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From
$169
Per Night
1 / 14
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Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Grill
  • Microwave
  • Refrigerator
  • Washer
  • TV
  • DVD Player
  • Ceiling Fans
  • Dryer
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Come enjoy all that the Florida Keys has to offer in this 'home away from home'. Great for a quick get-away or Mini-vacation! Located in the prestigious Hammer Point community, this water front home is a treasure! With its crystal clear waters and abundant sea life, your backyard... View all property information
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5 of 5 stars Reviewed 21 November 2014
Appreciated that the owner was prompt and timely with follow up, and gracious in every communication. The property was very comfortable and well met our needs. My adult daughter...
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From
$4,073
Per Week
1 / 6
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Key Largo
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (3) Make Enquiry
Amenities & Details
  • Satellite TV
  • DVD Player
  • Dishwasher
  • Refrigerator
  • Washer
  • Grill
  • Ceiling Fans
  • Waterfront
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Island style, waterfront home with exclusive private white sand beach, A pool and protected dockage. 5 bedrooms, 4 bathrooms should be enough room for any size group. Living Room, Dining Room, Kitchen all have unsurpassed views of the open water and Sunset. On the first level is the pool. This home... View all property information
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5 of 5 stars Reviewed 21 January 2014
We needed space for 10 adults who were willing to share beds. This place was perfect. The stacking condos was a good idea and there was enough space in the top condo for everyone...
2 of 5 stars Reviewed 3 March 2012
This property is two condos stacked - each unit has a kitchen and small living area. One is a two bedroom/two bath the top floor is a three bedroom/two bath. The top condo is...
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From
$291
Per Night
1 / 6
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Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Waterfront
  • Dishwasher
  • Washer
  • Satellite TV
  • Microwave
  • Grill
  • Ceiling Fans
  • Refrigerator
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
  • x
About this property
2 bedroom, 1 bath waterfront condo with a Center console boat at your front door. The unit is located in a small complex within walking distance to restaurants, bars and Park. Comes with Flat screen tv's, wifi, dvd player, washer and dryer. Barbecue on patio. Boat is equipped with VHF, GPS and... View all property information
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5 of 5 stars Reviewed 22 July 2013
The owner lives here is always gone tending to business so you have the place all to yourself. The pool is wonderful and you can swim in the canal. The boat was great to have...
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From
$320
Per Night
1 / 29
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Hot Tub
  • Dryer
  • Parking
  • Ceiling Fans
  • Dishwasher
  • Microwave
  • Refrigerator
  • DVD Player
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • x
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Instantly feel the warmth of the island spirit as you enter this inviting 3-bedroom, 3-bath, tri-level townhouse at Mariners Club Resort. Enjoy the relaxing atmosphere the Florida Keys are known for...a perfect setting for family fun or a private romantic get-a-way. Experience the joyful... View all property information
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From
$173
Per Night
1 / 25
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Key West
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
Details Reviews (10) Make Enquiry
Amenities & Details
  • Refrigerator
  • Satellite TV
  • Hot Tub
  • Safe
  • Ceiling Fans
  • Microwave
  • Grill
  • Dishwasher
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
The Jungle Breeze condo at LaBrisa Condominiums is a 1 bedroom, 1 bath apartment with a king size bed in the bedroom and a queen size sleeper sofa in the living area. It accommodates 2-4 people. This property is rented by the week from Saturday to Saturday, it is not a hotel; it is a privately... View all property information
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5 of 5 stars Reviewed 14 October 2014
My wife and I stayed here from Oct 4th thru the 11th. The Condo is situated minutes away from the airport so it was a quick taxi ride. The grounds of the complex are well taken...
5 of 5 stars Reviewed 11 August 2014
My wife, 2 adult daughters, and I, stayed at Pam's La Brisa "Jungle Breeze" condo from August 2 - 9, 2014. The condo is located in a very safe and friendly gated community. Pam...
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From
$418
Per Night
1 / 22
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Key West
2 Bedrooms, 2 Bathrooms, Sleeps 5
Details Reviews (22) Make Enquiry
Amenities & Details
  • Gym
  • Microwave
  • Refrigerator
  • Parking
  • TV
  • Dishwasher
  • Sauna
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • Smoking allowed
  • Elder access
  • x
About this property
Location: Stock Island, Key West Area, Florida Keys, Florida, USA (160 Miles from Miami ) Accommodations: Condo, 2 Bedrooms, 2.5 Baths (Sleeps 4-5) Our beautifully landscaped property and contemporary housing will provide you with a serene tropical setting ideal for a relaxing vacation getaway.... View all property information
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4 of 5 stars Reviewed 30 November 2014
Room is very nice and clean. Facility is gated, very quite and clean. There is a excelent restaurant next to room.
5 of 5 stars Reviewed 19 November 2014
This facility was tucked away from the hustle & bustle of downtown Key West. Close enough, but yet offered solitude. Extremely clean and well kept. The restaurant was GREAT!! II...
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From
$413
Per Night
1 / 28
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Key Colony Beach
5 Bedrooms, 5 Bathrooms, Sleeps 10
Booking
Details Reviews (3) Make Enquiry
Amenities & Details
  • Ceiling Fans
  • Parking
  • DVD Player
  • Fireplace
  • Patio
  • Microwave
  • Washer
  • Safe
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • Smoking allowed
  • Elder access
  • x
About this property
Enjoy a resort experience with multiple family generations or friends along with the comfort of a real home. Five bedrooms (two master bedrooms with attached baths, two first floor guest rooms with a shared bath, and a second floor guest room with half bath) provide ample private space; fully... View all property information
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5 of 5 stars Reviewed 7 August 2014
The home was in a beautiful location with all the amenities we could have dream off. Clean, very comfortable, spacefull and quite. We had a wonderful familly time (5 adults, 2...
5 of 5 stars Reviewed 23 June 2014
The home was in a beautiful location with all the amenities. Clean, comfortable, and priced affordable. We had a wonderful time from the moment we got there, to the moment we...
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From
$128
Per Night
1 / 7
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Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Refrigerator
  • DVD Player
  • Patio
  • Washer
  • Parking
  • Microwave
  • Playground
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • x
  • ?
  • Smoking allowed
  • Elder access
  • ?
About this property
Minimum rental is 30 days. Our 2/2 modern comfortable house has plenty of dock space (over 100 ft.) and is very close to our community boat ramp. Do you like back-country (shallow water and remote) or deep sea fishing, scuba diving or snorkeling, sailing, nature-watching, canoeing or just... View all property information
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5 of 5 stars Reviewed 9 April 2014
I rent a house in Key Largo every year, and this canal side paradise is the best I've ever had. The house is spacious, comfortable and clean. The location is convenient to the...
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From
$14,664
Per Week
1 / 24
Key West
5 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (18) Make Enquiry
Amenities & Details
  • # Of Bathrooms
  • Hot Tub
  • Deck
  • Air Conditioning
  • Guest Count
  • Parking
  • Internet Access
  • Ceiling Fans
Suitability
  • Pet-friendly
  • Wheelchair access
  • Child-friendly
  • ?
  • ?
  • ?
  • Smoking allowed
  • Elder access
  • x
  • ?
About this property
Luxury on Duval Street in historic Key West? Luxury is not what most people visiting Key West associate with Duval Street until you look at Dreaming On Duval! There are very few private homes on Duval, let alone a single family vacation rental that is steps away from everything Key West has to... View all property information
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5 of 5 stars Reviewed 19 August 2014
This is a beautiful 5 bedroom house in a great location right on Duval Street which makes it very convenient . The layout of the house though keeps you in the back of the house...
5 of 5 stars Reviewed 26 March 2014
Absolutely loved this house. I came with my wife, 4yo and 1 yo along with my cousin and his wife and two 4yos. There is tons of space and the pictures really don't do the...
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Florida Keys Vacation Rentals

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

Florida Keys attractions and activities

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

Live like a local in a Florida Keys rental

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

Florida Keys vacation rentals for families

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

Saving money on Florida Keys vacation rentals

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