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Compare 40 Cottages in Summerland Key with updated reviews, rates, and availability.

Waterfront Home
Terrace/patio
Waterfront Home
8.8 out of 10, Excellent, (149)
"Has a nice seawall that can accomodate about a 30 foot boat. Cleaning station for fish was nice also. Actual house unit was older, but nice. We really just used it for cooking our fish and sleeping. The main perks of this place is that it has a seawall on a protected canal to keep a boat, has good channel access to both the oceanside and gulf, and is clean. Marina with boat fuel and boat ramp is in Venture Out neighborhood just a few hundred feet away from this actual unit. Overall a good...
Waterfront Home
SEA SHELL COTTAGE UNIT #2
Beach
SEA SHELL COTTAGE UNIT #2
9.2 out of 10, Wonderful, (11)
"We thoroughly enjoyed our stay here, the room we rented was perfect for us it definitely has an old school vibe. The pool was nice on the hot summer days but they were going through a bit of a crab invasion while we were there. But that was no big deal for us. Hope was super nice and have a bunch of suggestions for things to do and places to eat while down there. Ask in all we had a great time and will try to return in the future."
SEA SHELL COTTAGE UNIT #2
Waterfront Cozy Cottage with Boat Ramp & Dock!
Property grounds
Waterfront Cozy Cottage with Boat Ramp & Dock!
10.0 out of 10, Exceptional, (51)
"I really enjoyed it there we / my 12 year old and I . Took out charters everyday that we were there . They will pick you up from your dock ! We will be back .. Great experience!"
Waterfront Cozy Cottage with Boat Ramp & Dock!
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.8 out of 10, Excellent, (53)
"The grounds are good. The pools were clean and plenty of deck and dock space. The cottage itself needs help. It needed general maintenance on it. It needs caulking in the bathroom. It needs weather strips around door as it is not tight. There was not enough hand towels and there are no oven mitts in the kitchen. The exhaust fan has been taken out. The ceiling fan in one room only works on high. The ac vents and exhaust fan in the bathroom needs cleaning. We were happy about the porch except the...
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS
Beach
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS
9.4 out of 10, Exceptional, (14)
"The property was clean and nicely decorated. It was centrally located to all of the lower keys. We enjoyed our stay and all of the suggestions and ideas that Hope, the property manager, offered. Definitely family friendly!"
OCEAN BREEZE COTTAGE AT HIDDEN HAMMOCKS
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.0 out of 10, Very Good, (29)
"Just as advertised. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Blue Mind - Venture Out Unit 225
Property grounds
Blue Mind - Venture Out Unit 225
9.4 out of 10, Exceptional, (65)
"nice place 3rd time there"
Blue Mind - Venture Out Unit 225
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Property grounds
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
9.6 out of 10, Exceptional, (29)
"Great location, close to family that lives there. The place was nice and had a Awesome view "
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool
Canal front, dockage, 2 bedroom, 2 bath
9.0 out of 10, Wonderful, (72)
"OUR TRIP WAS AMAZING.THE HOUSE AND LOCATION WAS GREAT.EASY PEOPLE TO DEAL WITH AND RESPONSE VERY FAST.WOULD STAY AGAIN."
Canal front, dockage, 2 bedroom, 2 bath
HIDDEN HAMMOCK RESORT Palm cottage
Sun loungers, beach towels
HIDDEN HAMMOCK RESORT Palm cottage
10.0 out of 10, Exceptional, (27)
"Great place and pool! Great communication with the manager. Convenient to everything. I loved the cottage, a few other rentals on this property to choose from for bigger groups if needed."
HIDDEN HAMMOCK RESORT Palm cottage
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
A heated pool
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
10.0 out of 10, Exceptional, (15)
"awesome place"
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
9.2 out of 10, Wonderful, (61)
"The house was nice. It does have a few flaws but the price reflects that. Could use a few more dishes. Kitchen amenities are minimal but the basics are there. We used the large pool by the coin laundry and it was evrything we needed. We would stay again."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
Sun loungers, beach towels
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
9.6 out of 10, Exceptional, (40)
"The property was just as it was listed as, very clean and very inviting. We loved that it was so quiet! We will definitely go back again!"
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit #3 Sleeps 4
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Fridge, microwave, oven, stovetop
FL Keys Cottage with Ocean Views - Venture Out Unit 395
8.0 out of 10, Very Good, (2)
"Great location and nice park amenities. Kids really liked the Venture Out pool."
FL Keys Cottage with Ocean Views - Venture Out Unit 395
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Property grounds
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
9.8 out of 10, Exceptional, (8)
"Our stay was amazing. The property was immaculate. The amenities were great. We will be back next year. The location was perfect. Close to Key West and alot to do in the area. Thank you for making our stay wonderful. See you next year!"
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Property grounds
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
9.6 out of 10, Exceptional, (10)
"Our stay was wonderful! The room was perfect for our stay. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Property grounds
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
10.0 out of 10, Exceptional, (10)
"It was great. Very unique place. I will def be back with the pet’s next time. 5 stars"
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Property grounds
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
10.0 out of 10, Exceptional, (5)
"Took my grandmother on her bucket list trip. Great location and set up for myself, my mom and grandmother!"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
8.6 out of 10, Excellent, (37)
"Well located to visit Key West as well as other Keys both East and West. House needs some attention. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
waterfront cottage near key west, sleeps 6
Property grounds
waterfront cottage near key west, sleeps 6
9.4 out of 10, Exceptional, (16)
"We had a great stay! Other than the weather, everything was perfect! We had plans to dock our boat up at the house but it was too windy to take the boat out. We still enjoyed the patio and grilled out one night! We took showers across the street at the camp restrooms bc there were four of us and we would’ve ran out of hot water but that was no problem. We enjoyed our stay!"
waterfront cottage near key west, sleeps 6
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Summerland Key

Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Outdoor dining
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
9.0 out of 10, Wonderful, (179)
"The view was wonderful. Great place to see sunrise every morning. This was a girls trip. If you are just there for fishing, this place is perfect. The refrigerator and freezer smelled of fish. Even after 3 nights, the smell was strong. I recommend bringing some arm and hammer baking soda for both fridge and freezer. The place is pretty close to Key West, so location is great. The neighbors were cleaning their fish right off the dock, so there were many seagulls. With seagulls, comes poop. They...
Ocean Perch, Dock, Open Water Views, 80' Heated Pool, Tennis, 20 Min to Key West
Waterfront Home
Terrace/patio
Waterfront Home
8.8 out of 10, Excellent, (149)
"Has a nice seawall that can accomodate about a 30 foot boat. Cleaning station for fish was nice also. Actual house unit was older, but nice. We really just used it for cooking our fish and sleeping. The main perks of this place is that it has a seawall on a protected canal to keep a boat, has good channel access to both the oceanside and gulf, and is clean. Marina with boat fuel and boat ramp is in Venture Out neighborhood just a few hundred feet away from this actual unit. Overall a good...
Waterfront Home
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
A heated pool
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
9.6 out of 10, Exceptional, (173)
"The house had everything to stay comfortably. We stayed a week there. Enjoyed watching sunrise every morning and fished right there from the dock."
Dock, Htd 80' Pool, Deep Channel, 15 Min To Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

How much do cottages in Summerland Key cost?
You’ll pay between and per night for cottages in Summerland Key. Whatever your budget, a wonderful stay is only a click away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Summerland Key?
Lock in your vacation dates and then choose from 40 cottages in Summerland Key. Yearning for a place where you can surround yourself with nature? Expedia will help you find the ideal escape in a few simple clicks.
Why book your cottage in Summerland Key with Expedia?
Reserving a cottage in Summerland Key is as easy as working out your travel dates and picking an ideal place for a vacation in nature. From high-end retreats to affordable properties and cottages that have amenities like a kitchenette, Expedia has something for all styles and tastes. As for irresistible deals? We’ve got them too!
How can I find cheap cottages in Summerland Key?
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What is there to do in Summerland Key near my cottage?
If you want to fill up your itinerary in Summerland Key, make tracks to Florida Keys Beaches. It’s a winner among locals and visitors alike.