A coastal road with a beach on one side and a marina with boats on the other.

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sep - 27 Sep
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Summerland Key cottages

Outdoor dining

1. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (102 reviews)
"The bedrooms and bathrooms were a little small but everything else was fantastic. We loved the outdoor spaces."
United States
Carla R.
The price is SAR 845
SAR 1,693 total
includes taxes & fees
2 Aug - 3 Aug
Canal front, dockage, 2 bedroom, 2 bath
Property grounds

2. 2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Cudjoe Key
9.8 out of 10, Exceptional, (32 reviews)
"This place was great! As advertised. It is located within a resort community, so it is safe with lots of amenities. "
United States
BRIAN S.
The price is SAR 813
SAR 1,871 total
includes taxes & fees
11 Aug - 12 Aug
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Exterior

3. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (360 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
United States
Kathy
The price is SAR 365
SAR 939 total
includes taxes & fees
11 Aug - 12 Aug
Old Wooden Bridge Resort and Marina
Interior

4. Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
3.0 star property
Old Town Key West
9.8 out of 10, Exceptional, (7 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is SAR 1,186
SAR 2,426 total
includes taxes & fees
12 Aug - 13 Aug
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Exterior

5. The Dancing Rooster: 2 Blocks from Duval in Old Town.

The Dancing Rooster: 2 Blocks from Duval in Old Town.
Old Town Key West
9.8 out of 10, Exceptional, (150 reviews)
"Such a great stay. A nice walk to duval for nightlife!"
United States
Mercedes A.
The price is SAR 1,299
SAR 2,189 total
includes taxes & fees
23 Aug - 24 Aug
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Exterior

6. NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Old Town Key West
10.0 out of 10, Exceptional, (33 reviews)
"Great stay in Key West! Clean, well-located, and exactly as advertised. Easy check-in and responsive host. Would definitely book again."
United States
Jessica C.
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
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

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

8/10 Good
"Overall it was a great experience. All staff is really kind. Our room had dogs hair on the floor when I first swept and bed isn’t too comfortable but room overall looks beautiful and is well maintained. Bar and pool close a bit early but like everything else in the keys. Only annoying thing is marina rental closes super early and last call for rental is too early as well but the place is nice especially if you have children. It’s clean, easy to move around, close to Key West. Bartenders are all super nice and there are different activities like smores or live singers. It was a great experience. We will be back."
Loik 4-night trip
Posted 2 days ago
Sugarloaf Key Hotel at KOA Resort

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between SAR 939 and SAR 2,426 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 54 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.