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Featured Cottages in Summerland Key and around

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (86)
"The facility is very nice with lots of amenities. It was clean and located close to everything we wanted to do."
Canal front, dockage, 2 bedroom, 2 bath

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

8.6 out of 10, Excellent, (119)
"Amazing place for a getaway. Very calm quiet area and close to 2 nice beaches. "
Charming cottages, dockage, pool, just minutes to Key West

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

9.0 out of 10, Wonderful, (142)
"We had an excellent time , property was an excellent place for our vacation.We hope to come back next year"
Quaint cottage, pool, dockage just minutes to Key West!

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

9.0 out of 10, Wonderful, (88)
"Quiet and off the beaten path, old school, old style Key’s homes,would stay again."
The price is €306
includes taxes & fees
7 Oct - 8 Oct
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Waterfront Home

8.6 out of 10, Excellent, (172)
"Venture out resort is a great vaca spot"
Waterfront Home

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (154)
"Good Fishing, Good local eateries. "
The price is €277
includes taxes & fees
15 Oct - 16 Oct
Cottage with Pool and Dockage, just minutes to Key West

Cottage with swimming pool and dockage, just minutes to Key West!

9.0 out of 10, Wonderful, (155)
"Clean and comfortable."
Cottage with swimming pool and dockage, just minutes to Key West!

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

9.6 out of 10, Exceptional, (29)
"Perfect little place. "
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!

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

8.6 out of 10, Excellent, (163)
"The property is ideally situated, providing convenient access to key destinations within the Florida Keys. While the residence may benefit from some modernization, its value proposition remains highly competitive."
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

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

8.8 out of 10, Excellent, (73)
"Very nice quiet place for your lower key vacation. Nice accommodations and easy drive to Key West and Islamorada and several state parks. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cozy, Perfect Conch Cottage! - VO315

9.2 out of 10, Wonderful, (30)
"We had an amazing trip staying at cudjoe key. It’s a cute little trailer, very clean. The property was great. The renters are very attentive to questions. Highly recommend! "
Cozy, Perfect Conch Cottage! - VO315

Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

10.0 out of 10, Exceptional, (29)
"Clean bungalo perfect for a fishing vacation. I look forward to staying here again!"
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

9.6 out of 10, Exceptional, (12)
"Even if it was a short stay, we enjoyed it and will be staying here again in the future."
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

10.0 out of 10, Exceptional, (7)
"Property was clean, and staff were nice and helpful. Good location too"
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)

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, Extra Frig/Bait Frz

9.8 out of 10, Exceptional, (26)
"This was the perfect place to rent for a boat It was clean and had everything we needed"
Updated 2BR,2BA w KING Master,35' SeaWall-Bikes,Kayaks,SUPs, Extra Frig/Bait Frz

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (192)
"Quiet area, ocean view, roomy place for family of 3. Will stay again, thank you! "
Direct Oceanfront Cottage-Sunrise View- #2,

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

8.6 out of 10, Excellent, (148)
"We had a nice stay at the cottages. Location worked well for our fishing excursions and access across the street to old RT 1 to walk the dogs. "
Cottage with Pool and Boat Dockage just minutes to Key West!

Waterfront Cozy Cottage with Boat Ramp & Dock!

10.0 out of 10, Exceptional, (60)
"Great place to stay everything is close by"
Waterfront Cozy Cottage with Boat Ramp & Dock!

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

9.6 out of 10, Exceptional, (53)
"Wonderful and finally an affordable vacation spot!"
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!
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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Top Summerland Key Hotel Reviews

Find out more about Summerland Key

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
1,722
Accommodation
59 Cottages
Lowest Price
€277
Highest Price
€306

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between €277 and €306 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 59 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.
Are there any family-friendly cottages in Summerland Key?
You bet there are! Reserve a room at Old Wooden Bridge Resort And Marina, a top base for enjoying the great outdoors in Summerland Key. This family-friendly cottage has a 2.5-star rating and comes with handy amenities such as a firepit and a picnic area. Once you've checked in and unpacked your suitcase, there are lots of family-friendly attractions to see around Summerland Key. Florida Keys Beaches and Sugarloaf Beach promise fun for all ages.