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Cottages in Summerland Key

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, (141)
"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, (86)
"Quiet and off the beaten path, old school, old style Key’s homes,would stay again."
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Waterfront Home

8.6 out of 10, Excellent, (171)
"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, (152)
"Good Fishing, Good local eateries. "
The price is SAR 563
SAR 1,190 total
includes taxes & fees
22 Sep - 23 Sep
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!

8.8 out of 10, Excellent, (162)
"We have been coming here for the past few years, usually during Memorial Day. We are always so relaxed and pleased with all aspects of our stay. Already working on booking again for next year! "
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)
"House was well equipped and everything we needed was there and clean. I'm not great at writing reviews, but we really couldn't been happier with our stay there. Location on the canal was perfect, we snorkeled and dove between Looe Key and American shoals every day. Even when the weather isn't great, the boat ride is really short. I'll definitely be looking to book again next year."
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, (191)
"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, (147)
"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 time, great place!"
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

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between SAR 1,190 and SAR 1,190 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.
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.