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
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Summerland Key cottages

Exterior

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.4 out of 10, Exceptional, (172 reviews)
"Great place "
United States
David
The price is SAR 845
SAR 1,549 total
includes taxes & fees
7 Jul - 8 Jul
Cottage with Pool and Dockage, just minutes to Key West
Outdoor dining

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (187 reviews)
"Clean and as described "
United States
Tim S.
The price is SAR 676
SAR 1,481 total
includes taxes & fees
5 Jul - 6 Jul
Waterfront Home
Outdoor dining

Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (101 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
The price is SAR 676
SAR 1,492 total
includes taxes & fees
6 Jul - 7 Jul
Canal front, dockage, 2 bedroom, 2 bath
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 760
SAR 1,506 total
includes taxes & fees
1 Aug - 2 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, (14 reviews)
"All was excellent "
United States
Bryan M.
The price is SAR 1,502
SAR 2,597 total
includes taxes & fees
24 Jul - 25 Jul
Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!
Property grounds

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, (31 reviews)
"Everything about this home is perfect!"
United States
Shari H.
The price is SAR 1,874
SAR 3,309 total
includes taxes & fees
4 Aug - 5 Aug
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
Exterior

OCEANIA... water front cottage retreat ~

OCEANIA... water front cottage retreat ~
Cudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Super beautiful place and the decor was just on point."
United States
Josefina S.
The price is SAR 3,000
SAR 4,591 total
includes taxes & fees
12 Jul - 13 Jul
OCEANIA... water front cottage retreat ~
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, (350 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is SAR 448
SAR 1,032 total
includes taxes & fees
6 Jul - 7 Jul
Old Wooden Bridge Resort and Marina
Exterior

Get your ISLAND STLYE on!

Get your ISLAND STLYE on!
Old Town Key West
9.6 out of 10, Exceptional, (84 reviews)
"Good location. Provided everything that was listed. The unit was very clean."
United States
Mary S.
The price is SAR 880
SAR 2,406 total
includes taxes & fees
23 Jul - 24 Jul
Get your ISLAND STLYE on!
Exterior

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, (30 reviews)
"Great location, freshly renovated "
United States
Jackie M.
The price is SAR 1,401
SAR 2,491 total
includes taxes & fees
12 Jul - 13 Jul
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
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, (148 reviews)
"Such a great stay. A nice walk to duval for nightlife!"
United States
Mercedes A.
The price is SAR 1,967
SAR 3,207 total
includes taxes & fees
9 Jul - 10 Jul
The Dancing Rooster: 2 Blocks from Duval in Old Town.
Outdoor dining

HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (101 reviews)
"All around amazing place! Location was perfect! "
United States
Daniel M.
The price is SAR 859
SAR 2,410 total
includes taxes & fees
12 Jul - 13 Jul
HIDDEN OASIS 3 blocks from Duval
Exterior

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (21 reviews)
"Location was great. "
United States
Karen B.
Find your zen at HIDDEN TREASURE
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

Springs Venture Out Dolphin House #386 with beautiful open water views

Springs Venture Out Dolphin House #386 with beautiful open water views

8/10 Good
"Beautiful location ! Everything was clean and lots of extras :) kayaks, and paddle boards were available. Really cool :) The community was very cozy.. would def recommend"
Allison F. 5-night trip
Posted 1 day ago
Springs Venture Out Dolphin House #386 with beautiful open water views

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between SAR 1,032 and SAR 4,591 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.