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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

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
9.2 out of 10, Wonderful, (170 reviews)
"Great place "
United States
David
The price is SAR 676
SAR 1,332 total
includes taxes & fees
9 Jun - 10 Jun
Cottage with Pool and Dockage, just minutes to 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.
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, (100 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
The price is SAR 676
SAR 1,491 total
includes taxes & fees
5 Jun - 6 Jun
Canal front, dockage, 2 bedroom, 2 bath
Outdoor dining

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (187 reviews)
"Clean, great view, wonderful porch, comfortable bed"
United States
Karen H.
The price is SAR 751
SAR 1,595 total
includes taxes & fees
23 Jun - 24 Jun
Waterfront Home
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, (30 reviews)
"Everything about this home is perfect!"
United States
Shari H.
The price is SAR 1,179
SAR 2,426 total
includes taxes & fees
7 Jun - 8 Jun
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS
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, (343 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is SAR 447
SAR 1,031 total
includes taxes & fees
17 Jun - 18 Jun
Old Wooden Bridge Resort and Marina
Outdoor dining

HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (100 reviews)
"All around amazing place! Location was perfect! "
United States
Daniel M.
HIDDEN OASIS 3 blocks from Duval
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, (26 reviews)
"Great location, freshly renovated "
United States
Jackie M.
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
Terrace/patio

OSPREY STUDIO @ The Colony-Sleeps up to 4

OSPREY STUDIO @ The Colony-Sleeps up to 4
Old Town Key West
9.4 out of 10, Exceptional, (61 reviews)
"As ex Key west’s, we were very specific in the location that we wanted to bi in. This property was perfect for us. The compound was calm and quiet as well as extremely well kept. The communication with the management company was seamless."
United States
Donald
The price is SAR 929
SAR 2,484 total
includes taxes & fees
19 Jun - 20 Jun
OSPREY STUDIO @ The Colony-Sleeps up to 4
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.
The price is SAR 1,657
SAR 3,441 total
includes taxes & fees
16 Jun - 17 Jun
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

Tranquility Bayview House-Ocean Front with pool, boat basin and boat ramp

Tranquility Bayview House-Ocean Front with pool, boat basin and boat ramp

10/10 Excellent
"Amazing property and well stocked with amenities. Check in was smooth and great communication with owner and local property manager. Book your trip to the keys! The middle keys is where it’s at!"
Kelley K. 6-night trip
Posted 1 day ago
Tranquility Bayview House-Ocean Front with pool, boat basin and boat ramp

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between SAR 1,031 and SAR 3,441 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.