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Check prices for these dates

Next weekend
11 Apr - 13 Apr
In two weeks
18 Apr - 20 Apr
In one month
2 May - 4 May
In two months
30 May - 1 Jun

Compare 55 Cottages in Summerland Key with updated reviews, rates, and availability.

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, (133)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
The price is AED 551
AED 1,025 total
includes taxes & fees
8 Apr - 9 Apr
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, (152)
"Cottage 1 was right by the water. A walk down a long path to a dock was a nightly trip to watch the sunset. Located between Marathon Key and Key West was perfect for restaurants and stores without the crowding from tourists. About 20-30 minutes to Key West"
The price is AED 606
AED 1,095 total
includes taxes & fees
7 Apr - 8 Apr
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, (136)
"Very nice"
The price is AED 643
AED 1,283 total
includes taxes & fees
17 Apr - 18 Apr
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

9.2 out of 10, Wonderful, (68)
"Beach towels!! The cottage is very cute. Very basic kitchen supplies and bathroom supplies. No extra comfort amenities...travel mugs, beach chairs, hot pads for kitchen, toilet paper, beach towels. And if you plan to wash anything bring coins. 1.50 per wash "
The price is AED 643
AED 1,345 total
includes taxes & fees
6 Apr - 7 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
SEA SHELL COTTAGE UNIT #2 Sleeps 2
Beach

SEA SHELL COTTAGE UNIT #2 Sleeps 2

9.4 out of 10, Exceptional, (20)
"We stayed in the sea shell cottage, perfect for two. The unit was clean and the grounds were beautiful. There is a grill and a flattop griddle you can use. We went out for most meals so we didn’t use them. Close to a ton a restaurants, good recommendations in the book Had a great time! Will be back"
SEA SHELL COTTAGE UNIT #2 Sleeps 2
Direct Oceanfront Cottage-Sunrise View- #2,
On the beach

Direct Oceanfront Cottage-Sunrise View- #2,

8.6 out of 10, Excellent, (173)
"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."
The price is AED 551
AED 1,165 total
includes taxes & fees
16 Apr - 17 Apr
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, (38)
"This rental is in a perfect, peaceful location! We brought our paddleboards and fishing poles and enjoyed the Florida sun. Great getaway - we will definitely be back!"
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, (65)
"These are great older cottages. Not luxurious, great for fishing, relaxing away from the bustle of Key West but a short drive to all the fun. Local restaurants are great Tonio's was definitely our favorite. Lobster and local fish. Skewered shimp with rice and great sauce. We had a relaxing time "
The price is AED 643
AED 1,323 total
includes taxes & fees
7 Apr - 8 Apr
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from 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, (132)
"It is what it is, only wish the furniture was not worn out. "
The price is AED 863
AED 1,561 total
includes taxes & fees
19 Apr - 20 Apr
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, (79)
"We really liked the location of this rental. It is situated in a quiet community, on the beautiful canal, and close to other things in the area. We did not spend a ton of time at the house due to family events but the property had everything we needed for our short weekend trip. The only reason I gave it a 4 star is because of the air conditioning rule. The house rules state you cannot turn the AC down lower than 75 degrees, which is not a comfortable setting. "
The price is AED 826
AED 1,657 total
includes taxes & fees
5 Apr - 6 Apr
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, (141)
"This little cottage was perfect for our stay. Clean and comfortable. No frills but all essentials. Property manager gave very helpful clear directions to find the cottage. Would stay again. "
The price is AED 551
AED 1,047 total
includes taxes & fees
16 Apr - 17 Apr
Cottage with swimming pool and dockage, just minutes to Key West!
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit # 3 Sleeps 4
Sun loungers, beach towels

THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit # 3 Sleeps 4

9.6 out of 10, Exceptional, (47)
"We would highly recommend this rental. The host,Hope was so nice and recommended many highlights of the area to visit and restaurants.The owners, Glenn and Trina were also so friendly and accommodating to us. Very clean unit. Equipped with everything we needed. Heated pool was a nice added bonus."
THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit # 3 Sleeps 4
ISLE BE BACK To The Sunny Keys
Fridge, microwave, oven, stovetop

ISLE BE BACK To The Sunny Keys

9.6 out of 10, Exceptional, (26)
"This property has all the items that you would expect in the kitchen and more. It was a wonderful time, sitting in the back, relaxing with coffee in the morning . Supper time around the outdoor table. Grilled fish on the barbecue. I would definitely go back."
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, (126)
"Everything great ,"
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 UNIT #1 Sleeps 4
Beach

FLAMINGO COTTAGE UNIT #1 Sleeps 4

9.8 out of 10, Exceptional, (38)
"We managed to check in a little early, which was great. Flamingo cottage #1 is cute. Some technical difficulties with the TV were had, but between Glenn and his brother in law, it was easily resolved. Tonios is easy walking distance but you need to be mindful of crossing the highway. The Pool was lovely and relaxing after spending the day exploring. Key West was an easy 40 minute drive. The muffins and cookies left by Hope were yummy and much appreciated. Having use of a washing machine was a...
FLAMINGO COTTAGE UNIT #1 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 Sleeps 4
Sun loungers, beach towels

PALM COTTAGE Sleeps 4

9.8 out of 10, Exceptional, (40)
"Our family enjoyed our stay at the Palm Cottage. The owners went the extra mile in every way. They made us feel welcome, the pool was perfect and clean, the owner cut fresh coconuts for our girls to try, we had donuts and muffins dropped to our door lastly their recommendations were spot on and made our whole Florida Keys vacation. We highly recommend this place and would return.lastly "
PALM COTTAGE 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 ~
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Exterior

Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)

9.8 out of 10, Exceptional, (12)
"Great spot. Very quiet and clean. "
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
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)
"The location and views are great. It was a comfortable stay. There were some deferred maintenance items which were shared with the property manager. Completion of these items will greatly enhance the experience at the property and make it a '10' rating."
The price is AED 551
AED 1,165 total
includes taxes & fees
16 Apr - 17 Apr
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, (133)
"Perfect location for us 23 miles to key west. Restaurants near by, pool, fishing pier. Can't wait to come back and do it all over again!"
The price is AED 551
AED 1,025 total
includes taxes & fees
8 Apr - 9 Apr
Cottage with Pool and Boat Dockage just minutes to Key West!
Old Florida Style, wrap around porch, boat basin for dockage, open water
Property grounds

Old Florida Style, wrap around porch, boat basin for dockage, open water

9.6 out of 10, Exceptional, (71)
"We really enjoyed our short stay in your cute cottage style home. Great views of the water and comfortable, pretty decor. What a nice surprise Kiki Sand Bar restaurant was! Overall very nice, relaxing couple of days. "
Old Florida Style, wrap around porch, boat basin for dockage, open water
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.

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between AED 551 and AED 863 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 55 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.
How can I find cheap cottages in Summerland Key?
Expedia is here to help you track down cheap cottages in Summerland Key. To book your perfect stay in a few quick keystrokes, try out our handy filter tool to refine your search results by star rating, budget and amenities.