Search Summerland Key Cottage Rentals from CA $172

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Check prices for these dates

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Aug 15 - Aug 17
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Aug 22 - Aug 24
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Sep 5 - Sep 7
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Oct 3 - Oct 5

Browse Select Summerland Key Cottages

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Residential homes with diverse architectural styles and manicured lawns.

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

8.8 out of 10, Excellent, (161)
"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Canal front, dockage, 2 bedroom, 2 bath
Enjoy a waterfront retreat with a balcony overlooking the water, a covered outdoor area, and access to the dock.

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (85)
"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
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Enjoy scenic views of the ocean and surrounding landscape from this coastal property featuring a pool, residential buildings, and a lush garden with palm trees.

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
Cottage with Pool and Dockage, just minutes to Key West
Residential homes with unique architectural styles surround a large pool and well-manicured lawn.

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (151)
"Good Fishing, Good local eateries. "
Cottage with Pool and Dockage, just minutes to Key West
Quaint cottage, pool, dockage just minutes to Key West!
Residential homes with unique architectural styles and well-manicured lawns surround a serene body of water.

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
Relax on the beach with lounge chairs and a tranquil sea view.

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

8.8 out of 10, Excellent, (72)
"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
Charming cottages, dockage, pool, just minutes to Key West
Exterior

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. "
The price is CA $206
CA $437 total
includes taxes & fees
Aug 11 - Aug 12
Charming cottages, dockage, pool, just minutes to Key West
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Enjoy a romantic meal with a serene view of the marina and calm waters.

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

9.6 out of 10, Exceptional, (39)
"Property was very clean and well stocked. Perfect location on the water. Would definitely rent again "
**TURTLE COVE VIEWS @ VENTURE OUT** 2BR/2BA Cottage +35’ Private Slip | 80’ Pool
Direct Oceanfront Cottage-Sunrise View- #2,
Guests can relax on the lawn overlooking the serene body of water surrounded by lush greenery.

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (187)
"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!
Enjoy an outdoor space with a swimming pool and lush greenery surrounding this two-story house.

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

8.6 out of 10, Excellent, (144)
"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. "
The price is CA $172
CA $349 total
includes taxes & fees
Aug 27 - Aug 28
Cottage with Pool and Boat Dockage just minutes to Key West!
Cottage with swimming pool and dockage, just minutes to Key West!
Stylish single-story home with a covered entryway and lush garden surroundings.

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

9.0 out of 10, Wonderful, (153)
"Nice place and susan was an excellent hosts "
Cottage with swimming pool and dockage, just minutes to Key West!
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Stairs lead to a cozy seating area with a chair, surrounded by lush foliage.

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

10.0 out of 10, Exceptional, (29)
"We really enjoyed the mini vacation in the Florida Keys."
Wonderful Chalet, with Terrace & Private Patio – 20 miles from Key West.
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Enjoy breathtaking views of the marina from this balcony.

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!
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Enjoy a serene beachside picnic with a sailboat on the horizon.

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

9.6 out of 10, Exceptional, (27)
"It was an awesome time! Pool was nice and hot with an excellent location. Hope was a great hostess and look forward to coming back sooner than later "
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Waterfront Home
Enjoy a serene canal view from this balcony with seating for two.

Waterfront Home

8.8 out of 10, Excellent, (167)
"Great price great location "
Waterfront Home
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Detached houses with individual driveways and yards surround a swimming pool area adjacent to the beach.

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

9.0 out of 10, Wonderful, (49)
"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
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Overlooking a calm body of water, this serene property features a spacious two-story house with a balcony and lush greenery.

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

8.6 out of 10, Excellent, (49)
"Wonderful time "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Surrounded by palm trees and a body of water, this resort offers a tranquil atmosphere and a central swimming pool.

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
Relax by the pool or on the beach, surrounded by lush greenery and palm trees.

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

8.0 out of 10, Very good, (43)
"Was such a great stay clean and everything we needed "
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
**TIDEWATER VIEWS @ VENTURE OUT** 2BR/2BA Cottage + 35’ Private Slip | 80’ Pool
Relax in this beachside gazebo with ocean views, picnic tables, and a trash bin.

**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
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

Private Secluded Ocean View & Pool Near Key West

Private Secluded Ocean View & Pool Near Key West

10/10 Excellent
"Thank you so much for the great stay! The ocean view was beautiful! The landscaping with surrounding trees and flowers was lovely! The house was comfortable and had everything that we needed. It was perfect for our family!"
Deidra B. 4-night trip
Posted 1 day ago
Private Secluded Ocean View & Pool Near Key West