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Holiday Villas Florida Keys, FL

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$754
Per Night
1 / 15
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Marathon
5 Bedrooms, 6 Bathrooms, Sleeps 10
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$176
Per Night
1 / 12
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Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 4
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$170
Per Night
1 / 14
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Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 4
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$205
Per Night
1 / 28
Key Largo
4 Bedrooms, 4 Bathrooms, Sleeps 10
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largo's newest oceanfront gated destination, with no other private... View all property information
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4 of 5 stars Reviewed 3 November 2014
This is a beautiful condo, in a beautiful resort, and I would love to spend another vacation here! We had four couples & never felt cramped. My only regret was not having more...
5 of 5 stars Reviewed 26 December 2013
We rented this unit for five nights in mid-December 2014. It had plenty of space for our party of seven and the price was a good value. We would have paid at least as much for...
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$3,517
Per Month
1 / 15
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Long Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • 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 5 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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$109
Per Night
1 / 16
Big Pine Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
980 Sf Moble home on Big Pine Key Fenced lot . 5mins from Baja Honda State park and 25 Mins from Key West. Baja Honda pass comes with rental for the week .Great fishing and snorking . Capt Ron next door for tripes. $650.00 a week for 2 people $ 25.00 for each person up to 6. Dopsit and 1/2 rent up... View all property information
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$205
Per Night
1 / 10
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Key West
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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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4 of 5 stars Reviewed 10 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.
4 of 5 stars Reviewed 24 May 2014
Condo was a great location. Near beaches and activities. Great place to relax. Owner was very courtious. Pool was a little small but the facilities were beautiful.
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$334
Per Night
1 / 5
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Marathon
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Situated on at natural Key's sandy sunning beach a scant few feet from the water's edge looking out to the Atlantic Ocean you'll find three of the most enchanting "honeymoon-type" Cottages in the Florida Keys. Made from Dade County Pine with vaulted beam ceilings these beach bungalows offer... View all property information
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5 of 5 stars Reviewed 18 April 2014
awesome place to stay for lots of relaxation!!! My kids loved it. The place was very clean, nice breakfast. The pool was very clean and warm. the water was perfect.
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$586
Per Night
1 / 24
Cudjoe Key
5 Bedrooms, 3 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This 5 bedroom 3 bath house with pool on ocean front property on Highway, located just 20 miles away from the famous Key west complete with WiFi. This lovely home has it's own huge pool area with full lounge chairs all the way around pool area, the pool is heated. Downstairs grill, upstairs grill,... View all property information
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$205
Per Night
1 / 22
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Housekeeping...
  • Internet Access
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
An island paradise situated in the heart of Key Largo, adjacent to John Pennekamp Coral Reef State Park and Molasses Reef. The property is located in Rock Harbor's most upscale neighborhood. The area has the distinction of being Key Largo's newest oceanfront gated destination, with no other private... View all property information
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5 of 5 stars Reviewed 19 March 2013
We were very pleased with our stay in this villa. Mariners Club is nicely landscaped, had wonderful pool, nice hot tub, and was a very safe area. It was a good location for Key...
5 of 5 stars Reviewed 29 July 2011
We stayed for two nights at Key Largo to Dive on our way to Key West.The townhouse vas very tastefully decorated, it had 2 bedrooms, 2 baths, giant flat TV, complete gourmet...
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From
$147
Per Night
1 / 20
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
If you want to experience the true meaning of a Key Largo Island Vacation, then look no further than our spacious villa on the ocean side of the world famous Key Largo, Florida... ..The Dive Capital of the World! This villa is located inside Kawama Yacht Club, a beautiful Hawaiian Island style... View all property information
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From
$232
Per Night
1 / 20
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Key West
1 Bedroom, 2 Bathrooms, Sleeps 4
Booking
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Located inside the Villas known as Old Town Garden Villas Enjoy a margarita while listening to songbirds in the courtyard, or work on your tan at the pool in the lushly landscaped courtyard right outside your door! The bedroom is decorated in rich tropical colors. A writing desk and chair completes... View all property information
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5 of 5 stars Reviewed 9 October 2014
Pictures are awesome and still don't do this unit justice. It is fabulous. Located midway between Southernmost point and Mallory Square, half block off Duval. You can get...
5 of 5 stars Reviewed 19 August 2014
My husband and I had an awesome time in this villa. It's the perfect location, so close to all the hot spots. The Caribbean Suite was very cute and clean. The decor was fun and...
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$938
Per Night
1 / 34
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Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Welcome to "SANDY BEACH" in Key Largo, Fl. Enjoy amazing sunsets from your own private white sandy beach and swaying palm trees that leads you into the warm ocean blue waters of the Florida Bay. This gated 1 acre 3/3 pool home has been updated and beautifully decorated. It can sleep 8 to 10... View all property information
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5 of 5 stars Reviewed 10 June 2014
This place is truly amazing! The beach is clean and the good sand extends out into the water. The amenities are endless in the house. Kids loved the pool as it gave them a...
5 of 5 stars Reviewed 16 March 2014
My family of 7 including 2 babies just had a wonderful week at Sandy Beach. The house is perfect for a group with large quiet bedrooms. The outdoor kitchen and beautiful private...
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$1,084
Per Week
1 / 15
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 5
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Amenities & Details
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Minimum Rental: 7 Nights Calling all fishermen and divers... Whether you plan to fish or dive on your next visit to the Keys, you will find these exceptional accommodations first class and affordable. World famous dive sites are minutes away and phenomenal fishing is at your door step. Bring... View all property information
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5 of 5 stars Reviewed 1 May 2014
The place was clean and felt like home. A little noisy from a running pump and the exit gate got stuck closed, no outside deck or water view. But all in all it was great, I would...
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From
$322
Per Night
1 / 5
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Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Penthouse unit has designer furniture in this two bedroom (master has king size bed and guest bedroom has a queen) with a comfortable queen sleeper sofa in the living room. Two full bathrooms, full kitchen, dishwasher, microwave, cook top and electric oven, and outside balcony overlooking the... View all property information
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3 of 5 stars Reviewed 4 September 2013
Our first night I was kept up until 4 AM by noisy you people and I love to hang and have fun but come on they were really poorly behaved. The following night Saturday of Labor Day...
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$674
Per Night
1 / 24
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Marathon
4 Bedrooms, 5 Bathrooms, Sleeps 10
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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
$199
Per Night
1 / 15
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Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Key Largo Home with 2 bedrooms large kitchen great for entertaining, access to ratepayers park with boat launch where you can dock your boat for 72hrs at a time. Great sunsets. Home features screened in porch with seating area, barbecue, internet, tv, 2 reclining sofa's, comfy pillowtop mattress's,... 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
$264
Per Night
1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Private Fishing...
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • 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. Three free ocean kayaks(one 2-person kayak, and two single-person kayaks), one paddleboard, two bicycles, free... View all property information
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5 of 5 stars Reviewed 26 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
$301
Per Night
1 / 10
Conch Key
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Garden
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Our Florida Keys tradional island home is a fully furnished 2 bedroom, 1 bath plus Florida room with a deck overlooking the bay. It is surrounded by lush vegetation and large towering coconut palm trees. The house has been decorated in a nautical flavor with many fine antiques collected from around... View all property information
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4 of 5 stars Reviewed 29 April 2014
Comfortable, homey/cozy feeling cottage with the bonus of the daily use of a compact sailboat! A/C, ceiling fans, full kitchen, comfortable queen sized beds, BBQ, porch with fans...
5 of 5 stars Reviewed 10 February 2014
Captain Tom and Peggy's hospitality is second to none! The current managers, Danny and Michele go out of their way to ensure you're comfortable and have everything you need...
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From
$410
Per Night
1 / 18
Key Largo
4 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Two stories with guest quarters in main level! Strategically located in a deep water canal next to the Atlantic Ocean. A 75 ft of private dock with davits. Four comfortable bedrooms with 2 and 1/2 baths, private heated pool. Great room with large fully equipped , open kitchen with island and dining... View all property information
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From
$586
Per Night
1 / 8
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Islamorada
4 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
About this property
This large 4 bedroom house sits jst 10 feet from a 116 foot dock. You are right around the corner from 4 bridges in a row where yo can get to the Ocean or Bay within a few minutes. View all property information
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5 of 5 stars Reviewed 27 August 2014
We had a great stay! Ended up renting both houses for a weekend stay. Had 15 people and 4 boats. We had a great weekend, Helen and her son Rob were very accommodating and quickly...
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$264
Per Night
1 / 21
Marathon
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This beautiful, newly decorated, three bedroom unit, plus convertible bed, is perfect for the larger family. Sleeps up to eight (8) people. Large master bedroom has King-size bed,TV, private bath, and walk-in closet. The condo also has a completely equipped kitchen with all new appliances and... View all property information
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5 of 5 stars Reviewed 7 May 2014
The townhome was everything we hoped. Great location with many activities on site. Condo was spacious and accommodated our large family. Great pool. Only negative pool water was...
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From
$1,084
Per Week
1 / 20
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Grill
  • Internet Access
  • Pool
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
MINIMUM STAY: 7 NIGHTS. This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens and fresh paint add... View all property information
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From
$129
Per Night
1 / 12
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Key Largo
Studio, 1 Bathroom, Sleeps 2
Bookings
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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, access to ratepayers park with boat launch where you can leave your... View all property information
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From
$1,005
Per Night
1 / 9
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Grassy Key
5 Bedrooms, 4 Bathrooms, Sleeps 12
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Imagine gazing across a large, sparkling swimming pool to see a natural in-ground aquarium..... Big enough to swim in and filled with tropical fish. The dock accommodates large boats drawing 5' + The home sits on almost 3 acres of landscaped property The house is large and can handle big groups... View all property information
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From
$186
Per Night
1 / 15
Tavernier
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Mile Marker 92.5.....Ocean Pointe Suites at Key Largo is an all-suite resort located directly on the Atlantic Ocean. Just two(2) hours to Key West(90 miles) and 71 miles from Miami, our 60 acres are part of a protected mangrove forest entered through a private gatehouse and road. Ocean Pointe... View all property information
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3 of 5 stars Reviewed 25 July 2014
This property is ffalsely advertised as a hotel resort with suites. It is an apart rental complex. So if you would like to spend your vacation staying in someone else's apartment...
4 of 5 stars Reviewed 27 February 2014
Just back to cold and snowy Ottawa Canada, after some fine days of sun at Ocean Pointe Suites. We really enjoyed our short stay there. Location was an easy drive from Miami and...
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From
$176
Per Night
1 / 12
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Matecumbe Key
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Garden
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • 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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From
$218
Per Night
1 / 8
Conch Key
Studio, 1 Bathroom, Sleeps 2
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Garden
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Nested in the coconut palms on the quaint little fishing village of Conch Key.This stand alone Tropical Studio Cottage is perfect for a couples getaway! It has a private yard and is located across the street from our bayside docks.The unit has a full kitchen,bath,and full size bed.There is an... View all property information
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5 of 5 stars Reviewed 11 May 2014
The studio cottage was very clean and quaint (nautical theme) it was a lot newer than we expected it to be, very comfortable and completely equipped we didn’t have to bring...
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From
$205
Per Night
1 / 9
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Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
Details Reviews (2) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Lovely beachfront 2 bedroom, 2 bath condo. Incredible bay views and sunsets from your huge, screen enclosed porch. Walk directly onto a sandy beach from from your porch. This ground floor unit has been newly furnished and decorated in a tropical motif. Comfy, queen sized pillow top bed in master... View all property information
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5 of 5 stars Reviewed 28 July 2014
I was looking to rent a house again to enjoy the keys with the family but at the last minute ended up renting this quite and convenient ground level condo that was more than i...
5 of 5 stars Reviewed 2 June 2014
A beautiful location which is on the ground floor, giving you access straight onto the beach. Plenty of furniture to sit and enjoy the wonderful view and very private. The...
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From
$179
Per Night
1 / 2
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Marathon
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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
$264
Per Night
1 / 15
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Long Key
4 Bedrooms, 3 Bathrooms, Sleeps 9
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautiful canal front, clean, home located on ocean side in Long Key. MM 68. 4 bedrooms 3 baths total: 3 bedroom, 2 bath upstairs, 1 bedroom/bath (studio) downstairs. Great fishing and diving moments away. This is our family's vacation hideaway. Never rented prior to December 2012. Direct TV w HBO,... View all property information
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5 of 5 stars Reviewed 15 June 2014
Currently staying here and couldn't be happier. Comfortably sleeping 9 people in our party (4 adults, 4 kids/teens and a baby). The kitchen is stocked very well. Gorgeous view of...
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From
$1,055
Per Night
1 / 25
Key Largo
5 Bedrooms, 4 Bathrooms, Sleeps 12
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Imagine a Perfect Sunset with Porpoises Swimming on the Horizon - This is Key Largo at its Very Best. Enjoy our newly remodeled and gated – 5 bedroom, 4 bath house directly on the bay. We call our house CASA de IVY. The house features an infinity pool, large sandy beach, and a newly... View all property information
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5 of 5 stars Reviewed 4 September 2014
Our extended family (children, spouses, grandparents) stayed for a week at this beautiful home. We brought our boat (32') and docked it right behind the house. The dock was new...
5 of 5 stars Reviewed 19 July 2014
Beautiful updated house with private beach, kayak, stand up paddleboard, dock for a boat, and perfect sunsets. What could be better
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From
$1,172
Per Night
1 / 71
Key Largo
6 Bedrooms, 4 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Housekeeping...
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
About this property
Why would anyone want to rent a house on a canal right next to other houses and no real place to swim when you could rent this private stunning place surrounded on 3 sides by water. We have the most charming and spectacular and intimate property in Key Largo for your vacation rental. With our own... View all property information
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5 of 5 stars Reviewed 9 October 2014
I've been spending the majority of my birthdays at Shadow Point over the last decade with my favorite people in the world, and my 60th this year was the best so far! Marlee is a...
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From
$501
Per Night
1 / 14
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Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Garden
  • Grill
  • Internet Access
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
WHAT IS UNIQUE ABOUT THIS VACATION RENTAL? This vacation rental puts you on your own tropical island in a quiet cove of protected mangroves in the Gulf of Mexico. You stay on a 2 bedroom houseboat that is docked on the island. You have your own 17 foot boat for the entire week! HOW MANY PEOPLE CAN... View all property information
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4 of 5 stars Reviewed 3 January 2012
Renting the houseboat was a unique experience. I was concerned about the logistics of our stay, but we were well instructed on the workings of the houseboat and island, and felt...
4 of 5 stars Reviewed 22 February 2011
If you like semi rustic conditions and loads of privacy, this is the spot! We booked this rental for a week in February for our first "getaway from it all" vacation. Though Key...
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From
$1,339
Per Night
1 / 28
Key West
6 Bedrooms, 7 Bathrooms, Sleeps 16
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Private Home, DownTown, Villa description Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theatres and shops, this sprawling six bedroom, seven bath compound has two private heated swimming pools, endless porches, terraces and a... View all property information
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From
$184
Per Night
1 / 25
Islamorada
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (9) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Internet Access
  • Private Beach
  • Satellite TV
  • Shared Outdoor Pool...
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, basketball and... View all property information
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3 of 5 stars Reviewed 5 March 2014
This was a nice rental. There seems to have been a nice soft update done not to long ago, and it appeared that some features were still being upgraded. The building is clean...
5 of 5 stars Reviewed 14 January 2012
The condo was great! It was clean and located in a great place in the Keys. There were many excellent restaurants in the area when you wanted to go out, and a full kitchen when...
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From
$251
Per Night
1 / 11
Conch Key
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (11) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This one bedroom, one bath cottage is located high in the swaying coconut trees overlooking the water. The living room area has sliding glass doors that open onto a small deck area with a water view. The bedroom is tastefully furnished with an antique double bedroom set and the entire cottage is... View all property information
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5 of 5 stars Reviewed 16 June 2014
Stayed here for a week in May with a good friend......really cute, clean, apartment looking out over the cove and the boats, palm tree foliage right off the balcony. Easy to get...
5 of 5 stars Reviewed 15 June 2014
This was our best vacation ever with a beautiful, well equipped apartment room and so many interesting things to do. The sailing was perfect for us (with light winds and a very...
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From
$410
Per Night
1 / 59
Payment Protection
Key Largo
3 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Villa Los-Montes Beautiful Summer Gate away, Paradise in the Keys. Rates quoted are all inclusive, taxes and other fees are calculated and added including Reservation/Security Deposit. We have NO hidden fees. Rates quoted are also reflect standard Cleaning Fee and PDP Fee. There being no... View all property information
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From
$205
Per Night
1 / 23
Payment Protection
Tavernier
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Garden
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Find a “Peace of mind” in this beautiful Tropical Paradise. This two bedroom home is conveniently located at Mile Marker 92 in Historical Tavernier, Florida. It is only 69 miles from Miami International Airport, and the residence will truly captivate your mind and help you relax! Want to... View all property information
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5 of 5 stars Reviewed 21 August 2014
10 dagen met veel plezier doorgebracht in de woning Peace in the Keys. Een woning in een grote tuin met mooie palmbomen waar je al snel een "thuisgevoel" krijgt. De woning is...
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From
$234
Per Night
1 / 23
Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Fireplace
  • Grill
  • Satellite TV
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
The Owner's Unit is also right in front of the bay with 2 bedrooms; it can sleep 2 adults and 1 to 3 kids plus plus. The main bedroom has a queen size bed, the second bedroom has a queen size loft bed and a twin bed on the ground floor. Theres also a queen size pullout sofa bed in the living... View all property information
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From
$3,517
Per Month
1 / 23
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Balcony
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
MINIMUM STAY: 28 DAYS Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to... View all property information
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5 of 5 stars Reviewed 14 August 2014
Was a very clean house with all the amenities. I would stay again. Easy access to the Ocean for fishing and plenty of dock for your boat.
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From
$205
Per Night
1 / 21
Payment Protection
Key West
1 Bedroom, 4 Bathrooms, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Housekeeping...
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • 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 16 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 3 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
$1,223
Per Night
1 / 14
Islamorada
5 Bedrooms, 4 Bathrooms, Sleeps 16
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Beach
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new kitchen... View all property information
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4 of 5 stars Reviewed 7 November 2014
We had a wonderful time, wedding on the beach, beautiful view, snorkeling of the beach, lots of birds visiting. But when it rains you need your wellingtons, the drive way up to...
5 of 5 stars Reviewed 12 May 2013
We booked this fabulous ocean front home for our 20th Anniversary as we decided to bring our four teenagers with us. This was the first time we had ever rented a vacation...
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From
$244
Per Night
1 / 26
Payment Protection
Key West
Studio, 1 Bathroom, Sleeps 2
Booking
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Brand New to the Rental Market! 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 upstairs to a large shared deck, perfect... View all property information
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5 of 5 stars Reviewed 12 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
$352
Per Night
1 / 11
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Duck Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Rest and Relax as you sip your favorite beverage on one of the 3 decks at our Hawks Cay Villa. Kitchen is stocked with all necessities. Cable and internet provided. We do not participate in the Hawks Cay amenities. you can also check out a video and more pics at (website: hidden) The 3rd... View all property information
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From
$410
Per Night
1 / 24
Key Largo
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (12) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Garden
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This is a designer built home on a full acre estate with 300' on the water and 80' dock. Drive to dock to load and unload boat. Covered parking. Lush tropical landscaping throughout estate. Roof is a beautiful Bermuda stepped design. Cathedral cypress wood ceiling that gives the home an... View all property information
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From
$5,745
Per Week
1 / 29
Islamorada
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Grill
  • Internet Access
  • Private Pool
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Alligator Reef is a truly special slice of Paradise with 4 individual homes nestled on a privately gated oceanfront estate. This home, the Conch House (pronounced konk), is a 3 bedroom, 2 bathroom ocean front home featuring beautiful views, ocean breezes, and your own private pool (heated in the... View all property information
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5 of 5 stars Reviewed 23 August 2011
This property is a collection of 4 houses, 2 closer to the ocean, each with their own pool and three bedrooms (Conch and Pelican Houses), the other two behind, with no pool and...
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From
$336
Per Night
1 / 10
Payment Protection
Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Housekeeping...
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • 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 4 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 21 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
$21,103
Per Month
1 / 11
Islamorada
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Housekeeping...
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and... View all property information
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5 of 5 stars Reviewed 17 June 2013
Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching...
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From
$1,524
Per Week
1 / 36
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Ramrod Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
A paradise is immersed when entering Ramrod Key. It offers you a close relationship with the nature displaying an exuberant vegetation bordering the sea water canals. Ramrod Key is known as Breezeswept because of the breezes that sweep it through. This is a well located house, walking distance to... View all property information
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Florida Keys Vacation Rentals

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

Florida Keys attractions and activities

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

Live like a local in a Florida Keys rental

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

Florida Keys vacation rentals for families

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

Saving money on Florida Keys vacation rentals

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