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Vacation Rentals in Sugarloaf Key, FL and nearby

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All 64 Rentals in the Sugarloaf Key Area
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From
$300
Per Night
1 / 20
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Sugarloaf Key
3 Bedrooms, 4 Bathrooms, Sleeps 6
Bookings
Details Reviews (1) Make Inquiry
From
$130
Per Night
1 / 25
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Sugarloaf Key
3 Bedrooms, 4 Bathrooms, Sleeps 6
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From
$333
Per Night
1 / 31
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Sugarloaf Key
4 Bedrooms, 4 Bathrooms, Sleeps 8
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The following rentals are within 10 miles of Sugarloaf Key, Florida Keys, Florida.

From
$115
Per Night
1 / 17
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Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • 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
Tropical, Affordable Rental in Gated Community, Wi-Fi & Gas Grill Colorful tropical vacation home. The living room nicely decorated with tropical flare, has a flat screen TV with DVD, Directv W/DVR,two sofas, one is a queen size sleeper and comfortable bamboo chair. Dining area conveniently... View all property information
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From
$500
Per Week
1 / 12
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Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Gym
  • Hot Tub
  • 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
Cute and Cozy Mobile Home located in gated community of Venture Out MM 23 in the Florida Keys. Fully equipped kitchen, new refrigerator, self cleaning oven, free internet, Cable, 50 inch flat screen TV in living room 2 queen size beds 1 queen size sofa bed 1 bathroom gas grill washer &... View all property information
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4 of 5 stars Reviewed September 3, 2014
Overall was a great week, had a small issue but the owner quickly resolved it and the stay was awesome. Would recommend venture out to anyone
3 of 5 stars Reviewed August 21, 2014
This is an older trailer that could use some updating. It is not perfect by far but it is definitely doable for the price. The doors do not lock at all and I was not really...
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From
$250
Per Night
1 / 22
Summerland Key, FL
4 Bedrooms, 3 Bathrooms, Sleeps 8
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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
Welcome Tropical Villa which is a large home on a clear, flow through swimming canal. With 65 feet of seawall, and 4.5 feet of control depth, even large sailboats can be accommodated here! We only three minutes to the ocean, only fifteen minutes to Looe Key reef (one of the Key's premier dive... View all property information
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From
$250
Per Night
1 / 19
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Cudjoe Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Relax in our traditional keys style stilt home. The home is located on a channel with immediate access to the Atlantic Ocean. The concrete dock allows for easy access and quick drive to the open water. With the ocean at your whim, finding your favorite spots for fishing, lobstering, diving, and... View all property information
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From
$107
Per Night
1 / 11
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Ramrod Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
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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
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
10 minutes to the OCEAN - DEEP WATER CANAL READY FOR LOBSTER SEASON!!!!! 3 bedroom 2 bath Stilt house on a canal. Nice screened in porch (mosquito proofed) to relax in the evening. 10 minutes to the Ocean!! Just 25 minutes to Key West. Walking distance to Looe Key Reef Resort and Tikki Bar... View all property information
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From
$1,300
Per Week
1 / 36
Ramrod Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Make Inquiry
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
$130
Per Night
1 / 54
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Cudjoe Key
3 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Fishing...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Waterfront 120' Dock - Extensive Tropical Gardens Abound - Privacy - New Stainless Steel Appliances - 3 Bedrooms - Home Newly Remodeled and Redecorated - 300 sq' Elevated Deck - Pets Welcome w/ Fenced Backyard - New Bathroom Featuring Large 3 Head Shower - New King Size Sleep Number Bed - Fully... View all property information
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From
$200
Per Night
1 / 15
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Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (2) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Beach
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 January 10, 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 April 7, 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
$136
Per Night
1 / 8
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
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From
$225
Per Night
1 / 24
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Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
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 October 25, 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
$236
Per Night
1 / 23
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Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
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 August 7, 2014
This home is clean, very comfortable and well equipped. It has a charming island decor that really lends to the atmosphere and everything is well planned. You can enjoy a drink...
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From
$170
Per Night
1 / 12
Summerland Key, FL
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Inquiry
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
Seasonal Rates Start at 1190.00 per week based on 7 night miniimum stay. Extremely private two bedroom two full bathrooms on beautiful Little Torch Key , Oceanside . Deep Water swimming canal . Plenty of room for docking and parking of trailers etc... house was completely renovated less than... View all property information
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From
$230
Per Night
1 / 15
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Summerland Key, FL
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
Details Make Inquiry
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
Waterfront 2 bedroom home with 2 full baths with tubs, large great room, fully stocked kitchen, cable, wifi, interenet, washer/ dryer, central a/c. `house is located on a clean, swimmable deepwater flow through canal with a 60 ft cement dock. Ladder for easy exit. Property large enough to handle... View all property information
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From
$285
Per Night
1 / 30
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Summerland Key, FL
2 Bedrooms, 3 Bathrooms, Sleeps 10
Details Make Inquiry
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
Change Your Whole Latitude. Parrot Heads Welcome! 24 miles from Margaritaville. Not far to interactive Dolphin Research Center. Fish off the dock or bring your boat and ocean fish in the Atlantic or Gulf. Inviting crystal clear water for swimming and snorkeling in your yard!! Snorkel and/or dive... View all property information
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From
$329
Per Night
1 / 22
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (4) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
2 Bedroom+/2 Bath+ Tropical Paradise Home with floating dock, small beach, heated dipping pool and hot tub. This has been a popular honeymoon and anniversary celebration home for over 10 years. Very romantic. You wake up to the sunrise reflecting on the water and don't even have to get out of... View all property information
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5 of 5 stars Reviewed January 26, 2013
All we can say is WOW! We stayed here two weeks. Beautiful sunrises, ocean view, birds to watch and Iggy the resident Iguana. Perfect property for two couples or a small...
4 of 5 stars Reviewed February 2, 2012
Our extended family including grandparents, teenagers and a dog stayed at this house for one week in early January. Although we had some unseasonably cool weather at first, we had...
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From
$1,290
Per Week
1 / 24
Ramrod Key
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
Details Reviews (24) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dryer
  • Grill
  • Internet Access
  • Washer
  • Waterfront
  • Water Views
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Only Sleeps 2 People (Child or Infant count as a Person) Only 5 Steps to Climb. Most Houses in the Keys are Built on Stilts and have lots of Steps to Climb. Tiki Hut is Only 4 inches from the Water There is a Gas Grill located 3 feet from the Seawall ( Enjoy the View while cooking your Dinner)... View all property information
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5 of 5 stars Reviewed August 12, 2014
Most perfect place to stay in the keys. Judy and Tom are the best at providing anything you need and know everything you need to know about the area
5 of 5 stars Reviewed July 7, 2014
The stay, in short, was a dream come true. For a honeymoon--or any holiday, for that matter--the spot was romantic, charming, impeccably clean, cozy, and incredibly comfortable...
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From
$111
Per Night
1 / 13
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Inquiry
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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From
$136
Per Night
1 / 9
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Relax enjoying water views from both front and back decks. This home was recently redecorated with comfy upscale furniture and art. Large open living room has flat screen TV with DVD. Furniture is microfabric sleeper sofa, love seat and an armchair with hassock. Kitchen is conveniently laid... View all property information
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5 of 5 stars Reviewed November 10, 2014
We had a wonderful stay at Venture Out. It was very peaceful and enjoyable. The internet was fast and the cable TV had plenty of channels. The appliances and furniture are modern...
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From
$107
Per Night
1 / 10
Cudjoe Key
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (2) Make Inquiry
Amenities & Details
  • Grill
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Enjoy fabulous canal and open water views from the dining room, living room, and covered deck. 35‘ dock with cleats, dock posts, swim ladder and picnic table. Florida living room has TV with DVD & VCR, two queen sleeper sofas, two wicker chairs and love seat. Dining area with wood dining table... View all property information
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4 of 5 stars Reviewed May 27, 2014
My family and I loved it. We had a great time. We don't have a boat or anything so we just fished off the back area. The kids fished while my wife and I had drinks in the sun...
4 of 5 stars Reviewed November 15, 2013
I really liked the Ventue Out Experience, Nice clean, quaint, charming, Island Condo Style unit…Located in an VERY upscale RV park, on the water… 30 mins to Key West.. …ONE BAD...
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From
$100
Per Night
1 / 11
Cudjoe Key
1 Bedroom, 1 Bathroom, Sleeps 4
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
38' seawall with dock posts, cleats, fish cleaning table and swim ladder. This home has a large covered, screened porch with upscale patio furniture including a large table with four comfortable chairs, a swinging love seat and several swivel chairs. The master bedroom has a queen size bed with... View all property information
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4 of 5 stars Reviewed April 23, 2014
The unit was nice and clean. Everything worked good. The screen porch was very popular.. I did not have a chance to have my boat there but the dock area was in good shape. The...
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From
$179
Per Night
1 / 8
Summerland Key, FL
3 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Private Outdoor...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Lovely three Bedroom/2 Bath home with pool and hot tub located on Summerland Key. Mile marker 25. Deep water swimming canal with boat ramp and dockage. Large screened in porch for outdoor dining and BBQ grill. Tropical landscape and extra sleeping. Sleeps up to 8. 28 day rental. Please... View all property information
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4 of 5 stars Reviewed April 2, 2012
The home and pool were clean, comfortable and nicely furnished. Kitchen is simply furnished and could use a variety of serving dishes and sharp knives. You will need to purchase...
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From
$329
Per Night
1 / 8
Summerland Key, FL
4 Bedrooms, 2 Bathrooms, Sleeps 8
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
4 Bedrooms, 2 Bathrooms, Sleeps 8 Come enjoy the cool clear blue waters of the Florida Keys. The weather is great, lobster season is open.. This is a spacious oceanfront 4/2 home with a heated pool/spa and breathtaking open water views! It is located on beautiful Ramrod Key 110 ft concrete... View all property information
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5 of 5 stars Reviewed November 10, 2014
This oceanfront home in Ramrod Key is beautiful! It is clean and well kept. The owner ensures that you are comfortable in your home away from home. The view is gorgeous. The...
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From
$3,450
Per Week
1 / 18
Cudjoe Key
6 Bedrooms, 4 Bathrooms, Sleeps 12
Details Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Oceanfront 6 bed/4 bath home with panoramic ocean view on Cudjoe Key. Sleeps 12+. Beach, Hot Tub, Floating Dock, Heated Pool, Kayaks and 540 square foot screened in porch overlooking the Atlantic ocean. This house has been very popular with large groups. Floating dock is great to fish and swim... View all property information
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5 of 5 stars Reviewed July 11, 2014
The house was clean and in good shape. The kitchen was well stocked with cooking and eating utensils. The beach was gravel, and it was clean with no grass or sand. There were...
5 of 5 stars Reviewed May 27, 2014
This property was very clean, spacious and perfect for our large party. Every morning you would find me on the lanai, enjoying the Cudjoe Bay view, with my computer on my lap...
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From
$3,400
Per Week
1 / 20
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (6) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Designed as the ultimate vacation rental. Five Bedroom/Three Bath Oceanview Home with Heated Pool and Hot Tub. Panoramic Ocean Views. Sleeps 10+. Located on Cudjoe Key. Includes private boat dock, private beach, kayaks, and bikes. Weber BBQ grill, Lot's of lounge chairs and two hammocks.... View all property information
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5 of 5 stars Reviewed July 28, 2014
We rented this home for a week in July for a quiet family getaway. This was my first time renting a home in the keys, I have done so many times in the Smokey Mountains but never...
5 of 5 stars Reviewed March 3, 2014
We had a great experience at Fandango! The house looks exactly like online photos. The kitchen is well equipped, house is very clean, lots of bath and beach towels and a good...
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From
$3,800
Per Week
1 / 22
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 12
Details Reviews (1) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Hot Tub
  • Internet Access
  • Ocean Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Beautiful four thousand plus square foot home located on Cudjoe Key. Private beach and 30 foot swimming pool with 10 foot waterfall hot tub. Huge master suite overlooking the ocean. The house comes with BBQ grill and single and double kayaks. Spectacular views can be enjoyed from the screened... View all property information
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5 of 5 stars Reviewed January 5, 2014
We are 3 families, 5 adults and 3 teenagers. The 4 bedrooms are each very private and quiet. There are 2 master bedrooms each with ensuite bathrooms; 1 upstairs and 1 downstairs...
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From
$118
Per Night
1 / 12
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Freshly redecorated canal front home. Living room has a 32' flat screen TV with DVD, two sleeper sofas . Master bedroom has full size bed, mirror closet and a vanity with drawers. Guest bedroom has twin trundel bed with mirror closet and slider doors to patio and canal. Spacious open kitchen... View all property information
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4 of 5 stars Reviewed November 23, 2013
Two bedrooms, living room, full kitchen and bathroom was enough to accommodate five people. Place is quiet, but not very close to public beaches. For the end of October there are...
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From
$2,500
Per Night
1 / 40
Little Torch Key
10 Bedrooms, 11 Bathrooms, Sleeps 24
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Hot Tub
  • Internet Access
  • Satellite TV
  • Water Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
The Lost Pelican Fish Camp is the perfect Florida Keys destination for family reunions, corporate events, and just the perfect place for a family vacation where there is room for the entire family. Located close to mile marker 28.5 and close to just about anything you will want to do or can do... View all property information
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From
$213
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
180 degree wrap around porch with patio furniture. 42' seawall with dock posts, cleats, fish cleaning table, swim ladder and outdoor shower. Panoramic view from front room with three sets of glass sliders. TV, DVD player, queen sleeper sofa. Kitchen island, side by side refrigerator with water... View all property information
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From
$186
Per Night
1 / 10
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Panoramic open water view! Enjoy this hypnotic view from living room, dining area and kitchen. Unusually large 50' seawall with cleats, swim ladder and fish cleaning table. Flat screen TV with DVD conveniently placed for viewing from living room, dining area and kitchen. Living area has... View all property information
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4 of 5 stars Reviewed October 27, 2014
Enjoyed our stay. Lots to see and do! The view was breathtaking and the resort was in a great location. The pools and hot tub were very convenient. We would definitely visit again!
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From
$171
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Amenities & Details
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Just three lots in from the open water!! Newly renovated and sophisticatedly decorated vacation home has an ocean view from 35’ concrete seawall. Dock has posts and cleats for mooring your boat also lounge furniture and mosaic picnic table for relaxing and dining al fresco. Living room with canal... View all property information
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1 of 5 stars Reviewed July 9, 2014
we are a working family and so when we take a vacation we want to really relax. we spent 1500 dollars plus a 450 dollar deposit for this small double wide trailer it was nicely...
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From
$121
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Reviews (1) Make Inquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Canal front home with spacious ambiance. 35’ seawall with dock posts, cleats, fish cleaning table with hose and outdoor shower. Covered back deck with ceiling fan, drop shades and patio furniture. Living room has large Flat Screen TV with DVD, sleeper sofa, two rockers, recliner and door to... View all property information
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1 of 5 stars Reviewed September 18, 2014
Upon entering the house, floors were dirty. Cabinets had roach feces all through out and live roaches in the oven drawer and in cabinets. Did not cook food in the home the last...
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From
$200
Per Night
1 / 12
Little Torch Key
3 Bedrooms, 2 Bathrooms, Sleeps 8
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Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Hot Tub
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Monthly, 28 day minimum inquiries please! Luxury waterfront monthly vacations Villa Torchwood Cay on Little Torch Key. Spectacular Key West Style - spectacular boating/pool home Direct ocean access from 100 ft private deep water Dock, Hideaway heated In- Ground Pool, Hot Tub Spa, Lush... View all property information
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From
$86
Per Night
1 / 7
Cudjoe Key
Studio, 1 Bathroom, Sleeps 6
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  • Grill
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Private backyard with dining/lounging furniture. Bright open Florida room with TV and two sleeper sofas. Attractive dining area with glass and white wood table. Kitchen conveniently arranged with appliances. Bedroom with full size bed. With this rental enjoy all the Venture Out amenities - pool,... View all property information
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From
$100
Per Night
1 / 3
Cudjoe Key
Studio, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
35' concrete dock/seawall with dock posts, cleats and swim ladder. Additional amenities include: pet friendly 150.00 nr pet fee. View all property information
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From
$136
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Dishwasher
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Canal front home with 35’ dock and covered screened porch. Dock has cleats, posts, swim ladder, fish cleaning table, hose and patio furniture with sun umbrella. Large covered and screened porch that overlooks the canal and has table with chairs for outside dining or lounging . Glass sliders into... View all property information
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From
$114
Per Night
1 / 7
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Internet Access
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Newly renovated canal front home. 35’ seawall with dock posts and swim ladder. Glass sliders to Florida room with view of canal, flat screen TV, sofa and beautiful dark wood furniture. Living room also with glass sliders to off street parking has a flat screen TV in decorator wood armoire,... View all property information
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1 / 21
Ramrod Key
2 Bedrooms, Sleeps 6
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  • Dishwasher
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Brand new home with high end features just two canals from open water. Large seawall with dock posts, fish cleaning table and swim ladder. Upstairs relax or dine on huge screened deck overlooking canal with dining furniture and two lounge chairs. Two sets of double glass sliders lead into main... View all property information
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From
$129
Per Night
1 / 8
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This charming two bedroom, two bath home has been totally renovated and updated for your comfort and enjoyment! Spacious, open floor plan in the living room/dining room/kitchen area is excellent for entertaining!! Nice covered patio area - perfect for relaxing or reading your favorite book. 35'... View all property information
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From
$93
Per Night
1 / 9
Cudjoe Key
1 Bedroom, 1 Bathroom, Sleeps 4
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Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This clean and very well maintained canal front vaction home features 1Bd/1Ba with master bedroom king size bed with access to the full size bathroom. Living room features a futon sleeper with 32' flat screen television with DVD player. 35'concrete seawall features dock posts, cleats, swim... View all property information
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From
$121
Per Night
1 / 9
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Check-out this vacation home! It is situated on the widest canal in Venture Out!! Located on a 35' concrete dock with cleats and dock posts. Beautiful views of the open water from the living room, dining area and kitchen. Recently remodeled, clean fresh decor. Living room has a 26' flat screen TV... View all property information
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From
$171
Per Night
1 / 11
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 4
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Amenities & Details
  • Grill
  • Internet Access
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Wrap around open water view with a huge 61' concrete dock/seawall, complete with cleats, padded aluminum dock posts,mooring whip holders,and hose. Covered deck with lounge furniture to dine out or enjoy an evening drink. Or eat inside on upscale dining set and still enjoy the million dollar... View all property information
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From
$393
Per Night
1 / 3
Summerland Key, FL
2 Bedrooms, 2 Bathrooms, Sleeps 4
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  • Air Conditioning
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Beachfront home located on privately owned Sugarloaf Beach. This gated estate offers 350 feet of private beach and 4 acres of tropical gardens. The gardens have tropical plants and bananas that have been collected from all around the world. This 2 bedroom home is beautifully and fully furnished... View all property information
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From
$100
Per Night
1 / 10
Cudjoe Key
2 Bedrooms, 1 Bathroom, Sleeps 6
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Amenities & Details
  • Grill
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Affordable vacation home beautifully decorated in peaceful pastel colors. This home has many nice features including being bright, spacious and tropically decorated. The living room area has a Flat screenTV with DVD & VCR, queen size sleeper sofa, glass top table and comfy chairs. Master bedroom... View all property information
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From
$157
Per Night
1 / 10
Cudjoe Key
2 Bedrooms, 2 Bathrooms, Sleeps 6
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Amenities & Details
  • Grill
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
You will fall in love with the happy colorful tropical decorations in this canal front home. 35' seawall with whips, high end dock posts, cleats, swim ladder. Large table, comfortable patio chairs and lounging furniture to enjoy the seawall view and shade under the home. Upper deck has a view of... View all property information
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From
$500
Per Night
1 / 21
Payment Protection
Summerland Key, FL
4 Bedrooms, 3 Bathrooms, Sleeps 10
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Details Reviews (4) Make Inquiry
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
  • ?
About this property
Windswept, is a 4 bedroom 3 bath, two story home for rent located on Summerland Key (Mile Marker 25). This breezy island get-a-way fashioned in the casual style of Key West & The Bahama Islands offers you the perfect vacation spot. Peaceful, charming and quaint. Right on the ocean with its own... View all property information
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5 of 5 stars Reviewed January 6, 2013
We were at Windswept for Christmas week 2012. Relaxing and exciting at the same time. Beautiful home right on the water. Location is perfect. Morning sunrises, gentle ocean...
5 of 5 stars Reviewed January 3, 2013
Perfect house for extended family group including a toddler. The house had everything you could ask for, lots of places to sit and relax, plastic kayaks, fishing poles, bicycles...
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From
$500
Per Night
1 / 34
Cudjoe Key
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Reviews (5) Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Unwind and take a deep breath, you have finally found your tropical paradise vacation home. This 4 vacation home is the perfect getaway from the hustle and bustle of everyday life. Only 20 minutes from Key West! If you are ready to kick off your shoes and sit by the pool or grab that fishing pole... View all property information
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5 of 5 stars Reviewed March 16, 2014
This home is just as described--bright, sunny, clean, and has fabulous ocean views. Close to anything you could possibly want to do in Key West or Marathon. There was lots to do...
3 of 5 stars Reviewed February 17, 2014
The location at the water front is fantastic with a marvelous sunrise and shallow water in the bay. That is hardly found any better anywhere at the Keys. The kayaks were very...
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From
$100
Per Night
1 / 11
Summerland Key, FL
1 Bedroom, 2 Bathrooms, Sleeps 4
Details Make Inquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Satellite TV
  • Washer
  • Waterfront
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
'The Pisces House' is a cozy cottage perfectly located on a deep water canal with open water views. This adorable 'keys style' cottage has everything you need for a relaxing getaway. This 1 bedroom/2bath cottage features a FULL kitchen, quaint living quarters with a sofa bed, and a peaceful patio... View all property information
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