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Compare 57 Cottages in Summerland Key with updated reviews, rates, and availability.

Cottage with Pool and Boat Dockage just minutes to Key West!

8.6 out of 10, Excellent, (139)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
The price is AED 496
AED 978 total
includes taxes & fees
10 Jun - 11 Jun
Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (143)
"Clean cottage, very helpful host, comfortable beds, great location --enjoyable stay."
Cottage with Pool and Dockage, just minutes to Key West

Quaint cottage, pool, dockage just minutes to Key West!

9.0 out of 10, Wonderful, (137)
"It is what it is, only wish the furniture was not worn out. "
The price is AED 643
AED 1,280 total
includes taxes & fees
31 May - 1 Jun
Quaint cottage, pool, dockage just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

8.8 out of 10, Excellent, (157)
"This is a great place to stay if you’re looking for a quiet home base for your vacation. Key West is a quick drive away and we found lots of fun activities and great food locally. "
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (57)
"Great time, great place!"
Waterfront Cozy Cottage with Boat Ramp & Dock!

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (79)
"My family and I enjoyed our stay. It was very convenient to everything we wanted to do. Would definitely stay again."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Waterfront Home

8.8 out of 10, Excellent, (163)
"Loved this property and the community. Great property, near some great restaurants. Would definitely stay again."
Waterfront Home

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.8 out of 10, Excellent, (71)
"Place was everything we needed, would definitely stay again "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

9.0 out of 10, Wonderful, (48)
"We enjoyed our stay. Place is exactly as described. We really enjoyed the lanai. Wanted somewhere close to Key West and this turned out perfect. Would definitely stay here again. Thanks!"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Charming cottages, dockage, pool, just minutes to Key West

8.6 out of 10, Excellent, (115)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
The price is AED 606
AED 1,235 total
includes taxes & fees
17 Jun - 18 Jun
Charming cottages, dockage, pool, just minutes to Key West

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (82)
"Excellent appearance, location, amenities and comfort. Bedrooms are a little tight but manageable. Host was very responsive and easy to work with. "
Canal front, dockage, 2 bedroom, 2 bath

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.0 out of 10, Very Good, (41)
"It's a good quiet place about 20 miles from Key West. The property itself has seen its best years-- it has aged now but functional. The entrance is a bit tricky to find, right off of the highway. Overall a good place if you don't mind driving back and forth between Key West attractions. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

9.6 out of 10, Exceptional, (51)
"Clean, convenient, great host. Would definitely stay again! Especially enjoyed the daily pastries!!"
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!

SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

9.6 out of 10, Exceptional, (25)
"Lovely, quiet property. I really enjoyed my stay. Pool was heated. Wonderful place to relax under the stars."
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season

9.4 out of 10, Exceptional, (26)
"Perfect, spacious, cozy and cleanWe had a great timeWonderful hosts and a great property, location, amenities, all around just right"
OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

8.6 out of 10, Excellent, (47)
"A great value"
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

9.8 out of 10, Exceptional, (129)
"We had a great time, there for lobstering. Very clean place, great location!"
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool

Cozy, Perfect Conch Cottage! - VO315

9.2 out of 10, Wonderful, (30)
"Stay was good"
Cozy, Perfect Conch Cottage! - VO315

Beautiful Cottage & Amenities in Gated Community

10.0 out of 10, Exceptional, (2)
"Beautiful home, perfect for our needs"
Beautiful Cottage & Amenities in Gated Community

Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!

9.8 out of 10, Exceptional, (24)
"Thank you so much for such a wonderful stay at a great location. Really enjoyed riding the bikes down to the seawall at night and seeing the sea life. Perfect location to Key West. Wonderful screened in porch to watch the sunrise! "
The price is AED 1,098
AED 2,297 total
includes taxes & fees
9 Jun - 10 Jun
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks, SUPs, Washer,Dryer!
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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Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between AED 496 and AED 1,098 per night. These stays offer a chance to reconnect with nature — at a price you can afford. 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?
Reconnect with nature in one of the 57 cottages waiting for you in Summerland Key. To help you select a stay that’s right for you, use our filter tool to search for must-have amenities.
Why book your cottage in Summerland Key with Expedia?
We think that vacays should be stress-free, so if you’re after cottages in Summerland Key at a competitive rate, Expedia has your back. Keep the budget in check and select a thrifty option far from the rush of the city, or splurge on an upscale cottage to spoil your favorite people.