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Holiday Villas Florida Keys, FL

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From
$216
Per Night
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1 / 5
Long Key
1 Bedroom, 1 Bathroom, Sleeps 7
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$14,801
Per Month
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1 / 17
Islamorada
3 Bedrooms, 3 Bathrooms, Sleeps 8
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$1,159
Per Week
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1 / 20
Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 4
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From
$3,700
Per Month
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1 / 23
Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
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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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$185
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1 / 12
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Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
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 22 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 18 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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$137
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1 / 13
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Two bedroom home with ocean view from living room and deck. Living room has a queen size sleeper sofa, flat screen TV.Smart TV with Wifi for your devices. Kitchen is open and inviting with wood tone cabinets. Dining area located in a pleasant alcove near kitchen has a glass top table with seating... View all property information
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$3,700
Per Month
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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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$291
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1 / 23
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Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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 8 August 2014
This home is clean, very comfortable and well equipped. It has a charming island decor that really lends to the atmosphere and everything is well planned. You can enjoy a drink...
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$527
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1 / 6
Key Colony Beach
5 Bedrooms, 4 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Walk to Sunset Park - Located on Your Block! Tropical large five-bedroom, four bathroom home on a deep water canal with boat dockage in Key Colony Beach. Private upper level king master bedroom suite with bath, sitting room and balcony overlooks the water. On the main level there are three... View all property information
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$179
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1 / 14
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Tavernier
2 Bedrooms, 2 Bathrooms, Sleeps 4
Bookings
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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
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 22 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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$352
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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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$317
Per Night
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1 / 10
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Conch Key
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • 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
$950
Per Week
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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, sit and enjoy the sunsets at our rate payers park. Lots of parking in... View all property information
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From
$9,250
Per Month
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1 / 10
Islamorada
3 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
****This house cannot rent for less than 28 days, due to a County Ordinance**** You fall in love with The Cottage @ Schooner Bay Estate at first sight. Built in 1935, this once Red Cross building serves as a true historical reflection of the Florida Keys. Both bedrooms overlook the ocean, which is... View all property information
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5 of 5 stars Reviewed 3 December 2013
We were so lucky to have visited this home during November. We had the whole private gated compound to ourselves and even though we only leased the Cottage, the owners were so...
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From
$401
Per Night
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1 / 27
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Marathon
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • Internet Access
  • Private Fishing...
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
ATTENTION (Please Read): Due to the extreme popularity of this resort, most reservations must have a 4-6 month lead. On rare occasions, spontaneous bookings are available, but very unlikely. **** REMEMBER: IF YOU SEND AN INQUIRY ABOUT THIS LISTING, PLEASE CHECK YOUR JUNK OR SPAM MAIL FOR A... View all property information
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From
$327
Per Night
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1 / 32
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Sauna
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
About this property
Paradise found reservations must begin and end on a Saturday. You feel it the moment you arrive. It's a rhythm. A rhythm set into motion over a century ago by pirates, artists, writers and other champions of leisure. Today that same rhythm beckons you to discover the charm and grace of Old Key... View all property information
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5 of 5 stars Reviewed 31 May 2014
The vacation property is well worth the price. It's well maintain with beautiful views and perfect pool. Very spacious and quiet, perfect for a family. The condo is a 2 to 3...
3 of 5 stars Reviewed 2 February 2014
The unit waiting for us was not the unit promised in our reservation. The location was nice and very scenic. The center courtyard with large heated pool and large hot tub were...
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From
$5,550
Per Week
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1 / 24
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Marathon
4 Bedrooms, 5 Bathrooms, Sleeps 10
Booking
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Satellite TV
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
$308
Per Night
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1 / 41
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Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Beautiful 3 story 3 bedroom 2 baths home. Locate in key largo at MM 101 is on a canal which opens up to beautiful Tarpon Basin Bay with access to the Atlantic Ocean. Minutes from beautiful Penny Camp National Underwater Park. Close to local shopping, fine restaurants or just swimming with the... View all property information
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5 of 5 stars Reviewed 20 August 2014
We enjoy staying at this place. Very big place, very clean. I got my deposit back. I will visit again
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From
$86
Per Night
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1 / 13
Key Largo
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • Waterfront
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
SMUGGLER'S COVE is a wonderful Property you are literally on the Water. It joins our Fleet of Seven (7) other Properties in the same quiet Neighborhood, which we operate in. This a Kropft, 40Ft. late Model Park Trailer. Queen Size in the Master Bedroom, Queen Size Second Bed in the Loft, with... View all property information
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5 of 5 stars Reviewed 13 January 2013
This location was perfect. The trailer was clean and everything worked well. It was a great alternative to an expensive hotel and had more amenities than one. The bed was...
4 of 5 stars Reviewed 18 September 2012
The accommodations were clean and comfortable. The place was very easy to find. The owners were super easy to deal with. Be aware though, this is not really oceanfront property...
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From
$463
Per Night
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1 / 9
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Key West
3 Bedrooms, 5 Bathrooms, Sleeps 10
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
1207 Heaven is Key West Casual at it's best! Decorated by a world travelling, gallery Curator/Artist/Entrepreneur- the place is a refreshing twist of elegant, sophisticated & funky with local & international art, contemporary & mid-century modern decor & comfort. The layout includes 2 bedrooms &... View all property information
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From
$617
Per Night
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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
  • Waterfront
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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From
$154
Per Night
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1 / 27
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Grassy Key
Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Two charming efficiencies located 50 yards from the Atlantic Ocean. Both are fully furnished with well-equipped kitchens and are decorated with a Caribbean flair. In the private front yard, each unit has a gas-BBQ grill, a picnic table with large umbrella's for shade. Unit 9 has two single beds... View all property information
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5 of 5 stars Reviewed 13 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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From
$382
Per Night
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1 / 30
Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
THE TRUMAN SUITES - Four Weekly Vacation Rentals - 3 to 5 Night Minimum Stay Requirement - Lavishly appointed 1 and 2 bedroom suites located ONE HALF BLOCK FROM DUVAL STREET - Each suite is furnished with kitchen, contemporary & comfortable living room furniture, new ultra comfortable mattresses... View all property information
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5 of 5 stars Reviewed 17 December 2014
My wife and I stayed at this location during Fantasy Fest. It was our first time at Fantasy Fest but we are Key West regulars. The rooms are newly remodeled, clean and well...
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$154
Per Night
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1 / 13
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Grassy Key
Studio, 1 Bathroom, Sleeps 2
Bookings
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Two charming efficiencies located 50 yards from the Atlantic Ocean. Both are fully furnished with well-equipped kitchens and are decorated with a Caribbean flair. In the private front yard, each unit has a gas-BBQ grill, a picnic table with large umbrella's for shade. View all property information
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4 of 5 stars Reviewed 1 May 2014
Our rental worked out great. We explored the Keys north and south from Marathon. Our "base" was attractive, clean, and thoughtfully equipped for our stay.
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From
$775
Per Night
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1 / 19
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Key Colony Beach
7 Bedrooms, 7 Bathrooms, Sleeps 16
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
his home offers 4,200 square feet of remodeled, re-decorated space under air with an amazing 7 bedrooms/7 baths! There are three lovely master suites upstairs, each with a king size bed, and an en-suite bath. Also upstairs is a fourth bedroom with a king size bed, and a fifth bedroom with twin bunk... View all property information
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From
$229
Per Night
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1 / 8
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Conch Key
Studio, 1 Bathroom, Sleeps 2
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • 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
$440
Per Night
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1 / 27
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Key West
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Reviews (11) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
SeaShadows is a townhouse located just 2 blocks from Duval Street and a few minutes walk from Mallory Square. Down the street is Ft. Zachary Taylor Park where you can spend the day fishing, swimming, barbecuing, walking, and anything else that you can think of doing in the sun. It sleeps 4... View all property information
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5 of 5 stars Reviewed 1 July 2013
The house was very nice and well kept and within walking distance to just about anything. We did a lot of walking and actually ate in most of our meals.
5 of 5 stars Reviewed 26 May 2013
An absolutely fantastic holiday home away from home. The cleanliness of the house is an absolute joy, and there is every household amenity to make your stay comfortable. It is...
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From
$258
Per Night
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1 / 21
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Key Largo
1 Bedroom, 1 Bathroom, Sleeps 5
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Safe
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Ever wondered what it was like to live on a boat? Here is your chance. Take a dip in the swimming pool. Build a sand castle on the beach. Enjoy a romantic evening. Venture out on an invigorating kayak trip. Photograph an incredible Keys sunset. Lounge at the tiki bar. Watch Manatees while... View all property information
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5 of 5 stars Reviewed 9 September 2014
My husband and I had the pleasure of staying here twice! It was perfect for us, we were able to do what we love with ease (i.e. fish and jet ski). The owners were more than...
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From
$278
Per Night
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1 / 12
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Matecumbe Key
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Waterfront
  • 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
$136
Per Night
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1 / 17
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Matecumbe Key
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Directly on your private beach. Ocean views from every room of your two bedroom one bath Keys style duplex villa. You will experience the true 'old Keys' charm of bird watching on the wraparound deck to fishing on the beach...or perhaps just relaxing on the sand. With over a half acre of tropical... View all property information
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From
$264
Per Night
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1 / 11
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Conch Key
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (12) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
  • Waterfront
  • 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 12 December 2014
My wife and I stayed in the treetop cottage during the first week of December. We had so much fun!!! Capt Tom, Peggy, Danny and Michelle are great hosts. The treetop cottage...
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...
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From
$339
Per Night
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1 / 27
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Islamorada
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling,... View all property information
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From
$216
Per Night
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1 / 10
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Key West
2 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • 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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5 of 5 stars Reviewed 12 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 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.
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From
$233
Per Night
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Key Largo
1 Bedroom, 1 Bathroom, Sleeps 4
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • 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 24 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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From
$210
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1 / 4
Key West
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This cozy upper level unit is perfect for a quiet relaxing week in Key West. Explore the island's history all while being just one block away from Duval Street. This unit is only minutes from attractions like the Southernmost Point, Hemingway House, Mallory Square, and the Historic Seaport. This... View all property information
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From
$216
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1 / 21
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Key West
1 Bedroom, 4 Bathrooms, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
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
$257
Per Night
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Key West
Studio, 1 Bathroom, Sleeps 2
Bookings
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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! 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 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
$216
Per Night
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1 / 23
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Tavernier
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • 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
$3,700
Per Week
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1 / 16
Grassy Key
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (7) 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
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
3 bedroom 'suites' villa on the Gulf of Mexico on exclusive and private Morton Street on beautiful Grassy Key, next to Marathon, the 'heart of the Keys'. Each private suite has its own bathroom-completely renovated in the fall of 2010, its own seating area and flatscreen TV. Beautifully landscaped... View all property information
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5 of 5 stars Reviewed 22 June 2014
We stayed here with another family. From the 6 yr old to the 58 yr old, this was a place for all. Kayaks with life vests, bikes, dock with lots of fish, momma manatee with calf...
4 of 5 stars Reviewed 14 March 2014
This house was great but beware of outside wildlife. Iguanas, lizards, raccoons and spiders just to name a few.Be aware that there are steps going into the house and down to the...
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From
$189
Per Night
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Marathon
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
  • Internet Access
  • 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
$1,110
Per Night
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Marathon
3 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (6) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
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 24 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 26 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
$278
Per Night
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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
$302
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1 / 22
Key Largo
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Gym
  • Hot Tub
  • 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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$278
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1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Shared Outdoor Pool...
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. 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 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
$6,475
Per Month
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1 / 16
Key West
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Strikingly set in the oft-missed Key West Beachside neighborhood, we find Island Elegance ~ Near the Beach, making a seriously smart curbside statement showing a tall white privacy wall topped with shimmering green louvers. Completely renovated in summer 2012, to modern luxury standards, this... View all property information
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From
$1,166
Per Week
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1 / 10
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Key Largo
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (2) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
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 6 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
$793
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Marathon
5 Bedrooms, 5 Bathrooms, Sleeps 10
Bookings
Details Reviews (1) 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
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Great Heron House Ocean Front - Estate Luxury in ever detail and design with spectacular ocean views throughout. Private pool and spa. Spacious 5 bedroom 5.5 bath sleeps up to 10 guests. Sister property to the Grand Mangrove. Both accommodations reflect a meticulous attention to detail. Granite... View all property information
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From
$370
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1 / 28
Key Largo
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
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
Make Enquiry
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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From
$185
Per Night
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1 / 20
Key Largo
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
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
$247
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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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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.