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
7 Aug - 9 Aug
In two months
18 Sep - 20 Sep
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Summerland Key cottages

Exterior

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
Cudjoe Key
8.6 out of 10, Excellent, (98 reviews)
"Perfect location. Privacy and comfort."
United States
Anthony
The price is SAR 657
SAR 1,375 total
includes taxes & fees
2 Aug - 3 Aug
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
Property grounds

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Cudjoe Key
9.6 out of 10, Exceptional, (15 reviews)
"All was excellent "
United States
Bryan M.
The price is SAR 1,201
SAR 2,210 total
includes taxes & fees
24 Jul - 25 Jul
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Outdoor dining

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (102 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
The price is SAR 1,183
SAR 2,129 total
includes taxes & fees
2 Aug - 3 Aug
Canal front, dockage, 2 bedroom, 2 bath
Exterior

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (355 reviews)
"We had a great time! It was family, friendly, and we saw a ton of key deer. Pool was perfect as well!"
United States
Maya
The price is SAR 386
SAR 962 total
includes taxes & fees
3 Aug - 4 Aug
Old Wooden Bridge Resort and Marina
Interior

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
10.0 out of 10, Exceptional, (6 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
The price is SAR 1,186
SAR 2,425 total
includes taxes & fees
12 Aug - 13 Aug
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Exterior

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, (149 reviews)
"Such a great stay. A nice walk to duval for nightlife!"
United States
Mercedes A.
The price is SAR 1,400
SAR 2,460 total
includes taxes & fees
27 Jul - 28 Jul
The Dancing Rooster: 2 Blocks from Duval in Old Town.
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

A Tropical Luxury Getaway, Your own private resort!!

A Tropical Luxury Getaway, Your own private resort!!

10/10 Excellent
"You will not find a better property, managed and thought out to every detail. If you don’t book this place now, you will regret it immensely!!!"
Todd A. 7-night trip
Posted 2 days ago
A Tropical Luxury Getaway, Your own private resort!!

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between SAR 962 and SAR 2,460 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.