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Featured Cottages in Summerland Key

Our top choices for Summerland Key cottages

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

9.0 out of 10, Wonderful, (85)
"My husband and I stayed with our son in the cottage and it was everything we needed. Great location, beautiful pool on the water, and just enough space. "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (86)
"I will sum it up by saying it was ok. It was a place to stay, would I book it again? No"
Canal front, dockage, 2 bedroom, 2 bath

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (152)
"Good Fishing, Good local eateries. "
Cottage with Pool and Dockage, just minutes to Key West

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

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! "
The price is AU$412
includes taxes & fees
1 Sept - 2 Sept
Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (190)
"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, (145)
"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 Home

8.8 out of 10, Excellent, (169)
"Great price great location "
Waterfront Home

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!

**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

9.6 out of 10, Exceptional, (39)
"My family had a great time. Enjoyed the sunrises and sunsets from the back porch overlooking the bay. Very peaceful and quiet. Everyone was very friendly and helpful. Wish we could have stayed longer. Would definitely stay at the trailer again. Loved the turtle decor."
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool

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

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

9.0 out of 10, Wonderful, (154)
"The cottage was comfortable, and the bed was just right. We were in the Keys for a funeral, so not much running around."
Cottage with swimming pool and dockage, just minutes to Key West!

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

10.0 out of 10, Exceptional, (29)
"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

9.0 out of 10, Wonderful, (50)
"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

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

9.4 out of 10, Exceptional, (28)
"Great private location"
OCEAN BREEZE HOUSE Summer Vacation bring the family. Fishing and Lobster season

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!

**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

9.8 out of 10, Exceptional, (211)
"We had a great time staying here. House was perfect for us and the location was perfect to explore many of the keys! The bikes and kayaks that were provided were a great treat for the kids. We had fun biking around the village and swimming in the pool during down time. Would definitely stay here again! "
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool

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

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)

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

8.2 out of 10, Very good, (45)
"Was such a great stay clean and everything we needed "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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.
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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
404
Accommodation
51 Cottages
Lowest Price
AU$412
Highest Price
AU$412

Frequently asked questions

How much do cottages in Summerland Key cost?
You can expect to pay between AU$412 and AU$412 per night for cottages in Summerland Key. Whatever your budget, an awesome stay is just clicks away on Expedia. This price was 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?
Surround yourself with nature in one of the 51 cottages available in Summerland Key. To help you reserve a place that's right for you, take advantage of our filters to search for amenities or perks you need.
What is there to do in Summerland Key near my cottage?
You'll find plenty of superb things to do in Summerland Key. Discover well-known attractions like Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market. Blue Hole, Cook Island and Upper Sugarloaf Sound are other must-see's.