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Holiday Villas Florida Keys, FL

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$171
Per Night
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1 / 28
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Key West
Studio, 1 Bathroom, Sleeps 4
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$331
Per Night
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1 / 26
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Key West
2 Bedrooms, 1 Bathroom, Sleeps 6
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$9,272
Per Month
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1 / 10
Islamorada
3 Bedrooms, 1 Bathroom, Sleeps 6
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$2,473
Per Week
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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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$3,091
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1 / 37
Key West
1 Bedroom, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
This vacation home is only licensed for stays of 28 nights or more. Southard Square Hideaway is a newly renovated first floor corner condo perfect for 2 plus space for visiting friends and family! Monthly Rental A surprise awaits you inside the gates of the Southard Square village. Nestled in the... View all property information
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$103
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1 / 34
Key West
Studio, 1 Bathroom, Sleeps 2
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Amenities & Details
  • Air Conditioning
  • Dryer
  • Internet Access
  • Ocean Views
  • Satellite TV
  • Washer
  • Waterfront
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautifully Renovated First Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the first floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located only 1.5 blocks from the Historic Seaport and 4.5 blocks from Duval Street.... View all property information
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$309
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1 / 26
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Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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5 of 5 stars Reviewed 17 November 2014
my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located. they would definitely stay...
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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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$136
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1 / 17
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Matecumbe Key
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
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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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$2,102
Per Week
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1 / 11
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Conch Key
1 Bedroom, 1 Bathroom, Sleeps 2
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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
$495
Per Night
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1 / 25
Key West
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This home has a unique pricing structure. While it can rent for less than 30 days, the owner prefers Monthly rentals. Because of this, this home offers substantial (25% off) Monthly Rental discounts. Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full... View all property information
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5 of 5 stars Reviewed 8 June 2011
This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is first...
5 of 5 stars Reviewed 6 March 2010
The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A...
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$2,847
Per Week
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1 / 19
Islamorada
3 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious... View all property information
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5 of 5 stars Reviewed 20 January 2015
This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
5 of 5 stars Reviewed 23 December 2014
We have stayed at Bay Harbor several times in this condo and love it. The condo feels like home and has everything you would ever need during your stay The complex is very well...
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From
$292
Per Night
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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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$177
Per Night
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1 / 8
Key Colony Beach
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Hot Tub
  • Satellite TV
  • Shared Outdoor Pool...
  • Waterfront
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Maria's Place is a two-bedroom, two-bath duplex Marathon Vacation Rental located right on the water in the city of Key Colony Beach in Marathon Key, Florida. This resort location is great for the family or fishing party and we strive to make sure this rental home is cleaner than any other in the... View all property information
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$1,236
Per Week
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1 / 16
Key Colony Beach
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
14 NIGHT MINIMUM STAY Each unit is fully furnished and has two bedrooms, two bathrooms, dining area, full kitchen, washer/dryer, central heat/airconditioning and a private patio or balcony. This unit has a great corner view of the ocean! The kitchen is equipped with stove, refrigerator, dishwasher,... View all property information
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$371
Per Night
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1 / 35
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Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Gym
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This remodeled 2 bedroom 2 bath condo is directly on the Atlantic Ocean with ground access via a spiral staircase. Stunning views from the Master bedroom and balcony. Wake up to the sunrise and enjoy your leisurely day on the boat, at the nearby sand bar, or lounge in the zero entry pool. There... View all property information
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5 of 5 stars Reviewed 7 January 2012
My husband and I stayed here for almost 2 weeks for our honeymoon/vacation over the Christmas holiday. We were nervous about renting something over the internet that we had never...
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From
$278
Per Night
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1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
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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
$247
Per Night
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1 / 15
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Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Florida Keys Charm meets Genuine Island Style describes our Ocean Front, 3 bedroom, 2 bath Oasis in the Lower Keys. Take advantage of our upper and lower decks offering Ocean Views with glorous sunrises and star filled night skies. Boaters will appreciate the easy deep water ocean access with no... View all property information
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5 of 5 stars Reviewed 11 January 2013
Stayed at Little Sleeves End and loved it. Went with friends and have to say the location and views were incredible. The house was very nice and well equiped. Bring your boat and...
5 of 5 stars Reviewed 8 April 2012
This is a wonderfully cute waterfront house in a great neighborhood. The house sits high so the views are just beautiful. There is an outdoor shower which is a little slice of...
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From
$3,709
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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From
$282
Per Night
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1 / 10
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Key Colony Beach
3 Bedrooms, 3 Bathrooms, Sleeps 7
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
An updated 3 bedroom, 3 bath ground level half duplex. Large bedroom with 1 king, 1 queen, and 2 full size beds. Three full bathrooms. Four TV's - 3 flat screens and 2 DVD players, high speed wireless internet. You can watch the kids from living room, dining room, kitchen as they play in 8x14... View all property information
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From
$5,563
Per Month
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1 / 43
Key West
4 Bedrooms, 3 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
28 NIGHT MINIMUM STAY REQUIREMENT - SEABREEZE 4 Bedroom 3 Bath with Off Street Parking, Private Heated Pool, Fitness Center, Gorgeous!! A warm color scheme and meticulous design details lend an elegant tropical ambience to this spacious four bedroom, 3 bath home located in the 'Sanctuary' on the... View all property information
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4 of 5 stars Reviewed 2 May 2014
We rented Seabreeze for a month! It was in the Golf Course a gated community. It was a great home away from home. Very comfortable, stocked well. Had a few glitches with the...
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From
$173
Per Night
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1 / 24
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Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 7
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Plan your next Shore Leave at this gorgeous waterfront Key Largo home on Largo Sound, Oceanside near Mile Marker 103! Beautifully furnished and updated, with living room, kitchen and half-bath at ground level & 3 bedrooms & 2 bathrooms upstairs. Master bedroom has a Queen bed. Guest bedroom #1 has... View all property information
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5 of 5 stars Reviewed 5 March 2014
My husband and I greatly enjoyed our Valentines weekend at this house. It was very clean and comfortable. The backyard was awesome to fish from and the kayaks were so much fun...
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$3,956
Per Week
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1 / 7
Duck Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
All the comforts of home! Each beautiful unit features a full kitchen, comfortable living space, multiple bedrooms, private porches or lanais, tropical island décor and much more! With access to all the features of Hawk's Cay Resort. Be sure to visit Calm Waters Spa, voted in the top 25 hotel... View all property information
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4 of 5 stars Reviewed 10 January 2015
Happy New Year!! We just returned from Hawk's Cay in Duck Key, FL. I traveled with 2 adults and 2 kids. My son is severely autistic. We found the resort welcoming and...
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From
$104
Per Night
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1 / 36
Key West
Studio, 1 Bathroom, Sleeps 2
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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
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
28 NIGHT MINIMUM STAY REQUIREMENT - THE STUDIO AT THE SAILMAKER'S HOUSE Beautifully Renovated Second Floor Studio for Two - Incredible Location in Historic Old Town Gorgeous studio apartment on the second floor of the historic Sailmaker's House. This 28 night minimum vacation rental is located... View all property information
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5 of 5 stars Reviewed 3 September 2014
I really enjoyed my stay at the sailmaker's studio. The staff as well as the owner were very easy to work with and very helpful. My small dog was with me and he enjoyed it too. It...
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From
$319
Per Night
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1 / 20
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Key West
1 Bedroom, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Duval Delight is a breathtaking, newly-renovated 2-story condo located at the historic 'Cuban Club' on the 'quieter' side of world famous Duval St. This high end vacation rental features a huge 55-inch flatscreen TV in the living room and all brand new furniture including a comfy, pull-out queen... View all property information
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From
$12,363
Per Month
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1 / 19
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Duck Key
3 Bedrooms, 3 Bathrooms, Sleeps 6
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Private residence on Duck Key. 2 bedrooms and 2 baths upstairs with a seperate one bedroom one bath apartment downstairs. Apartment has own kitchen and family room. Private dock with heated pool. Ocean kayak and fishing rods included. Catch tarpon right off the dock. House extensively... View all property information
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5 of 5 stars Reviewed 10 October 2014
Stayed at Key Breeze with some old friends for a week of fishing. As the one that booked it, I came away a hero. The house was just perfect for our needs. Clean and up to date...
3 of 5 stars Reviewed 5 February 2014
We didn't realize the strength of the current behind this house when we booked it. Swimming is next to impossible and the fishing wasn't that great. We ended up renting boats for...
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From
$4,945
Per Month
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1 / 1
Islamorada
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Amenities & Details
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This home, located in the Plantation Key Colony neighborhood, is a fantastic home for a family or just a couple who wants to enjoy an escape to the Florida Keys. Home is located on a canal with 50ft of concrete dockage, along with a fish cleaning station. The yard is completely fenced in, has a... View all property information
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From
$319
Per Night
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1 / 21
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Islamorada
2 Bedrooms, 3 Bathrooms, Sleeps 6
Bookings
Details Reviews (2) Make Enquiry
Amenities & Details
  • Balcony
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • Internet Access
  • Safe
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
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5 of 5 stars Reviewed 3 September 2014
Looked far and wide for a place in the keys that was on one level for my mom that uses a walker. Finally found the one! The owner is very helpful and communicative and worked...
5 of 5 stars Reviewed 25 January 2014
This condo exceeded our expectations. It was truly a home away from home. It has all the amenities you will need to have a great vacation. The kitchen is fully furnished, the...
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From
$340
Per Night
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1 / 27
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Islamorada
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (3) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Internet Access
  • Private Fishing...
  • Satellite TV
  • Shared Outdoor Pool...
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
$1,607
Per Week
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1 / 36
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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From
$431
Per Night
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1 / 1
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Marathon
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
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About this property
Ocean View Cottage Periwinkle 2 bedroom - 2 bath This is an ocean view cottage perched in the air 12 feet on pilings open to fabulous views. With a full gourmet kitchen and great attention to detail, this cottage has a warm feel at home ambiance. Kick back and enjoy the beautiful water vistas... View all property information
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$1,669
Per Week
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Key Largo
3 Bedrooms, 2 Bathrooms, Sleeps 10
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Ocean Views
  • Private Fishing...
  • Safe
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • 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
$3,427
Per Month
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Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 8
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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
  • ?
  • ?
About this property
Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing... View all property information
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5 of 5 stars Reviewed 3 January 2015
I have two small children and the condo was perfect and comfortable for the entire family. It was nicely remodeled. The pool and dock area were very nice. Security was visible and...
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From
$601
Per Night
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1 / 19
Key West
3 Bedrooms, 3 Bathrooms, Sleeps 5
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Grill
  • Internet Access
  • Safe
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Private home of three bedrooms and 2 1/2 Baths within a gated community. High definition plasma TV found in every bedroom in addition to the living room and high speed internet available throughout. There is access to a large private association pool. This beautiful home is close to ocean and the... View all property information
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5 of 5 stars Reviewed 1 March 2014
This three bedroom condo (two upstairs bedrooms with king and twin beds and ensuite baths and a downstairs bedroom with full-sized bed and right-next-door half-bath) exceeded all...
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From
$158
Per Night
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1 / 29
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Key West
Studio, 1 Bathroom, Sleeps 2
Bookings
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Amenities & Details
  • Air Conditioning
  • Grill
  • Gym
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This wonderful unit is set apart from the others with cathedral ceilings and a skylight in each room; light and airy and yet very cozy and comfortable. This efficiency condo is perfect for 2 and can even accommodate the occasional guest with the living room sleeper sofa. The bedroom has a... View all property information
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3 of 5 stars Reviewed 8 October 2014
The place was pretty decent overall however it is not in the safest feeling part of town. We learned that it is right next to public housing and there are some loud neighbors at...
2 of 5 stars Reviewed 21 August 2014
The property was cute, but the surrounding areas are quite scary. The pool is a few blocks away... No Wi-Fi. The location is quite convenient and the suite was rather clean...
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From
$319
Per Night
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Key West
2 Bedrooms, 3 Bathrooms, Sleeps 7
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Gym
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Short walk to Fort Zachary State Park and South Beach! This spacious unit is only steps from a large pool and covered gazebo. On the ground floor is a secured garage for parking your vehicle. Lush and tropical gardens surround this beautiful development in the heart of historic Old Town.... View all property information
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5 of 5 stars Reviewed 28 September 2014
Very, very nice! Comfortable and clean too. Only complaint is the roosters next door crowing early in the morning. Very audible on the master bedroom side of the unit.
5 of 5 stars Reviewed 20 August 2014
Traveling with a group of six people, we found Casa Bonita to be the perfect location for our stay in Key West. The property is gorgeous and incredibly well taken care of; and...
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From
$495
Per Night
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1 / 17
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Matecumbe Key
3 Bedrooms, 3 Bathrooms, Sleeps 5
Bookings
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Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Fishing...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
3 bedroom, 2.5 bath home at the end of a quiet private road in Islamorada. Queen bed in the master with a fantastic view of the ocean from your pillow. Two queen beds in the second bedroom with en suite bath The third bedroom is used as an office. From the moment you open the front door you have... View all property information
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5 of 5 stars Reviewed 18 January 2015
Stayed at this fabulous home again, and once again the title is absolutely correct... I did not want to leave. This time, we bought groceries on our way down, and with that...
5 of 5 stars Reviewed 10 July 2014
This was our first trip to the Keys and not knowing the area, we splurged on this house. We were not disappointed! It was very peaceful, roomy, clean, nicely decorated, and the...
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From
$122
Per Night
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Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
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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
  • x
About this property
87200 Overseas Hwy Islamorada, Florida An ample 1,400 sq ft. town home in the heart of Islamorada. Two bedrooms and one bathroom upstairs. One bedroom has two queen beds and cable television. Second bedroom is set up with one queen bed and cable television. Sofabed and bathroom downstairs.... View all property information
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From
$335
Per Night
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1 / 17
Key Colony Beach
3 Bedrooms, 2 Bathrooms, Sleeps 6
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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
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
KEY COLONY BEACH IS in the heart of the Florida Keys The city, called the 'Gem of the Florida Keys,' is a on an island just south of the Overseas Highway connected via a causeway with a very small bridge. Par 3 golf course, restaurants, boating, biking, fishing, etc. This beautiful 3... View all property information
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5 of 5 stars Reviewed 6 January 2015
Kathi was super helpful and the house was wonderful. Great location, central to lots of fun activities. Cabana club was a fun bonus. Fished right off the dock and caught nice...
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From
$25,962
Per Month
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1 / 15
Islamorada
5 Bedrooms, 5 Bathrooms, Sleeps 10
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
****This house cannot rent for less than 28 days, per County Ordinance**** Breathtaking Sunset's, Breathtaking Home. Pineapple Plantation is an unbelievable gated, New Bay Front home. It is perfectly located a Mile Marker 89, Islamorada. Boasting 5 Bedroom Suite's, Gourmet kitchen with an ocean... View all property information
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From
$216
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1 / 5
Long Key
1 Bedroom, 1 Bathroom, Sleeps 7
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
About this property
Enjoy staying in the heart of the Florida Keys at Fiesta Key RV Resort! Discover the lush greenery and tropical feel of our spacious 28 acre resort located on an island all our own. We are surrounded by incredible Gulf of Mexico ocean views, have an onsite marina, and plenty of areas where you can... View all property information
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5 of 5 stars Reviewed 21 November 2014
Rented the water front cottage. It was clean and pretty. We got there after the office closed but Raul in security took care of us. Fishing, swimming, and boating. Near Dolphin...
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From
$1,854
Per Week
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1 / 22
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Islamorada
3 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beautiful bayside condo, 3bedrooms 2baths, sleeps 6 comfortably, new sealy beds in all rooms with cable and wifi. Newly furnished and clean. Comes with 36 foot boat slip in the marina. There is a boat ramp on the property along with a brand new pool. Deep water dockage and deep channel to... View all property information
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4 of 5 stars Reviewed 16 June 2014
We spent a full week at this Futura Yacht Club rental, which we enjoyed very much. Here are the pro's and con's: Pro: Boat slip accommodated our 29 foot boat well Fresh water...
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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
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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
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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$1,168
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1 / 10
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Key Largo
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
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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
$340
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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
  • Satellite TV
  • Shared Outdoor Pool...
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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From
$234
Per Night
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Key Largo
1 Bedroom, 1 Bathroom, Sleeps 2
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
$1,484
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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
  • 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. Great sunsets. Home features screened in porch with seating area, barbecue, internet, tv, 2 reclining sofa's, comfy pillowtop mattress's, large high top dining table seating for 8ppl. Steps to park. Lots... View all property information
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4 of 5 stars Reviewed 25 August 2014
This was our first time staying outside of the known major hotel chains or resorts for vacation thoroughly enjoyed this location. The home is adequately furnished and clean. Also...
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From
$371
Per Night
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1 / 15
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Islamorada
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
We also have monthly and 3 day weekend rates! Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2... View all property information
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5 of 5 stars Reviewed 16 January 2015
The Daniels' property was an outstanding vacation rental. It is centrally located in the middle of Islamorada. This is a two story end unit condo that is in perfect, (yes...
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From
$1,236
Per Night
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1 / 42
Key Largo
6 Bedrooms, 7 Bathrooms, Sleeps 14
Details Reviews (4) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Grill
  • Hot Tub
  • Internet Access
  • Private Fishing...
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
About this property
This is a monthly rental, please contact for rates, as they vary depending on how many people and how many days are occupied during the month.... Minutes from the mainland and an hour from Miami Airport...This giant estate with 2 separate residences come with contemporary mediterrean style... View all property information
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5 of 5 stars Reviewed 4 August 2014
What can I say that would do this place justice? Privacy with a gated entrance on famed Millionaire's Row in Key Largo. Or Maybe the spectacular views from all over the...
5 of 5 stars Reviewed 31 December 2013
This luxurious double house is ideal for a large family group. The location is convenient, the houses are spacious and well equipped, the pool and spa are very comfortable, and...
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From
$989
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1 / 17
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Key Largo
1 Bedroom, 1 Bathroom, Sleeps 4
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
1 / 1 Apartment Key Largo in Pennekamp Recently remodeled one bedroom apartment centrally located in the Heart of Key Largo. Private, Safe and Quiet residential neighborhood within walking distance to John Pennekamp National Park. Kayak right into the parks beautiful mangrove canals and beaches... 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.