Search Cottages in Summerland Key

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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

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

8.6 out of 10, Excellent, (134)
"2nd time and it's a nice relaxing stay.Catch a few fish off the dock or to one of the bridges.And my dogs love it!!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Outdoor pool

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

8.8 out of 10, Excellent, (153)
"As always, we had a great time. Nothing fancy but just a quiet get-away. "
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cottage with Pool and Dockage, just minutes to Key West
Pool

Cottage with Pool and Dockage, just minutes to Key West

9.2 out of 10, Wonderful, (138)
"This was a good property was exactly what was advertised"
The price is HK$1,358
HK$2,703 total
includes taxes & fees
1 May - 2 May
Cottage with Pool and Dockage, just minutes to Key West
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Fridge, microwave, oven, stovetop

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

9.0 out of 10, Wonderful, (72)
"Scenic and convenient"
The price is HK$1,358
HK$2,795 total
includes taxes & fees
29 Apr - 30 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Beach

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

9.4 out of 10, Exceptional, (23)
"Really cool little "resort". Room was clean, nicely laid out, and it was nice to have a pool and laundry facilities. Location was great for me to dive in Key West or Middle Keys. Only complaint was TV not working correctly 2 out of 5 days and I have to watch morning news/weather and in the evening wind down. Could just be Direct TV issue? Regardless I would recommend the stay."
SEA SHELL COTTAGE, Sleeps 2 - Summer Vacation, Fishing & Lobster Season is Here!
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (173)
"My husband and I enjoyed the peacefulness of the area, the beautiful view, the prime location for great places to eat and things to do, the short drive to Key West and Bahia Honda. The cottage was clean, the bed comfy and all was as described. Susan was quick in responding to any questions we had. We will stay here again, I’m sure. "
Direct Oceanfront Cottage-Sunrise View- #2,
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Beach nearby

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

8.0 out of 10, Very good, (39)
"Was such a great stay clean and everything we needed "
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
Beach nearby

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

8.8 out of 10, Excellent, (68)
"This property could have been amazing but it needed a lot of TLC. The cottage was mostly clean but there were a few issues for me. Some crumbs still on kitchen counter top, dirty front porch and you could tell light switches we not wiped down - they were dirty. The property grounds were disappointing as well. the rusty grill, the torn up lawn chairs.thrown around. Definitely needed work around the property."
The price is HK$1,358
HK$2,795 total
includes taxes & fees
27 Apr - 28 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Charming cottages, dockage, pool, just minutes to Key West
Fridge, microwave, oven, stovetop

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

8.6 out of 10, Excellent, (112)
"We enjoyed are stay. The customer service was great. The area was quiet and had access to the water for a boat. "
The price is HK$1,280
HK$2,554 total
includes taxes & fees
26 Apr - 27 Apr
Charming cottages, dockage, pool, just minutes to Key West
Quaint cottage, pool, dockage just minutes to Key West!
Miscellaneous

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

9.0 out of 10, Wonderful, (135)
"Had issue with tv, but host resolved quickly. Close to many places to eat."
Quaint cottage, pool, dockage just minutes to Key West!
Canal front, dockage, 2 bedroom, 2 bath
Outdoor pool, a heated pool

Canal front, dockage, 2 bedroom, 2 bath

9.0 out of 10, Wonderful, (81)
"Property was adorable! Had all that we needed. Good use of space for a smaller home but decorated beautifully. The only issue was overflow parking as we had two cars and a boat trailer. We decided to put the trailer in overflow recommended but that was three miles away further than security said quarter mile. Where we stored though, Mitch and Rich, were great. We would come back again but with one less vehicle "
Canal front, dockage, 2 bedroom, 2 bath
Cottage with swimming pool and dockage, just minutes to Key West!
Miscellaneous

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

9.0 out of 10, Wonderful, (145)
"We have been staying at this property for over 20 years. It’s the perfect location for visiting all of the lower keys. "
Cottage with swimming pool and dockage, just minutes to Key West!
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!
Sun-loungers, beach towels

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

9.6 out of 10, Exceptional, (51)
"Thank you for a wonderful stay Glen and Hope! We loved the location it was convenient to travel to the Key West, yet far enough from the noise and party. Summerland Key itself is gorgeous! Few great spots for breakfast and lunch/dinner. Also every place around had fresh seafood and live music in the evening. Pool on the property was very clean and heated, which I loved since we got a few cooler days.Overall wonderful atmosphere. If we will be back to Key West next year, we will be back to stay...
STAR FISH COTTAGE, Sleeps 4 - Summer Vacation, Lobster & Fishing Season is Here!
ISLE BE BACK To The Sunny Keys
Fridge, microwave, oven, stovetop

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (28)
"Very nice, location and property. The people at the park were wonderful. We joined the pancake breakfast at the shelter house and had a great time and wonderful pancakes and sausage for 6. Great deal. "
ISLE BE BACK To The Sunny Keys
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Outdoor dining

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

9.8 out of 10, Exceptional, (128)
"Had a wonderful stay. The cottage is well maintained. The deck outback was the perfect place for evening cocktails. The owner was very responsive to any questions. One thing worth mentioning is you can’t take showers back to back, the hot water will run out. The hot water struggled through one shower.. my husband and I don’t mind tepid water so it wasn't a big deal to us. Other than that everything was fabulous. "
35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
Waterfront Home
Terrace/patio

Waterfront Home

8.8 out of 10, Excellent, (161)
"Venture out is more of a retirement community than a family resort. The location is ideal and the house was well appointed "
Waterfront Home
FLAMINGO COTTAGE - Summer vacation Lobster and Fishing season- sleeps 4
Beach

FLAMINGO COTTAGE - Summer vacation Lobster and Fishing season- sleeps 4

9.8 out of 10, Exceptional, (39)
"Our hosts were very kind and accommodating. Whenever we had a question or request, Hope would respond right away, and she always seemed to have some sweets for us, which were a hit with the kids. We enjoyed our stay immensely."
FLAMINGO COTTAGE - Summer vacation Lobster and Fishing season- sleeps 4
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Exterior

Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)

9.8 out of 10, Exceptional, (9)
"We arrived to a spotless cabana! The bed was perfect! Just awesome accommodations that I would definitely book again!!! Highly recommend- it was close to Key West but quiet and relaxing. And our pet stayed with us."
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4
Sun-loungers, beach towels

PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4

10.0 out of 10, Exceptional, (43)
"This is the place. The place to listen to birds and rustling palms. Our Nineteen fifties chic bungalow was perfect, clean, and quiet. We enjoyed our mornings poolside with Five Brothers Cuban coffee and pastelitos. The location is amazing for a short drive to Key West or Marathon.The Hosts are amazing, delivering pastries and information regularly.We're very much looking forward to our next stay."
PALM COTTAGE Summer vacation Lobster and Fishing season! sleeps 4
NAUTILUS...ocean front cottage retreat ~
Beach nearby, sun-loungers, beach towels

NAUTILUS...ocean front cottage retreat ~

8.4 out of 10, Very good, (5)
"Great property and location. Very clean. Had everything we needed- kitchen, bath , towels, kayaks and bikes. Venture Out is the resort property- nice pool, hot tub, community store. Everyone was very friendly and helpful. I almost forgot about Pickleball, Tennis and basketball court. Equipment available on loan to use- so convenient!!"
NAUTILUS...ocean front cottage retreat ~
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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Other property types in Summerland Key

Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (173)
"My husband and I enjoyed the peacefulness of the area, the beautiful view, the prime location for great places to eat and things to do, the short drive to Key West and Bahia Honda. The cottage was clean, the bed comfy and all was as described. Susan was quick in responding to any questions we had. We will stay here again, I’m sure. "
Direct Oceanfront Cottage-Sunrise View- #2,
Cottage with Pool and Boat Dockage just minutes to Key West!
Exterior

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

8.6 out of 10, Excellent, (134)
"2nd time and it's a nice relaxing stay.Catch a few fish off the dock or to one of the bridges.And my dogs love it!!"
Cottage with Pool and Boat Dockage just minutes to Key West!
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Fridge, microwave, oven, stovetop

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

8.8 out of 10, Excellent, (145)
"We have stayed in the Keys often. This place has it all…great water views, kitchen of glass with more great views and an open floor plan full of light. The house is clean and nicely decorated. Dock was perfect for the boat we rented…caught lots of lobster the last several days of the season!"
Direct Oceanfront-Atlantic Side-Dockage-Pool and 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.