Search Cottages in Summerland Key

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
12 Jun - 14 Jun
In two months
24 Jul - 26 Jul
In three months
21 Aug - 23 Aug
In four months
18 Sep - 20 Sep

Our top choices for Summerland Key cottages

Exterior

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (172 reviews)
"Everything was nice and clean. Loved the location . Would definitely stay at the property again. "
United States
Shawn M.
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
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 675
SAR 1,328 total
includes taxes & fees
31 May - 1 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)
"Host was great!!! Unit very clean well stocked with beautiful view."
United States
Lisa F.
The price is SAR 675
SAR 1,562 total
includes taxes & fees
2 Jun - 3 Jun
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, (99 reviews)
"We stayed one night, everything was as described"
United States
Anonymous traveler
The price is SAR 760
SAR 1,601 total
includes taxes & fees
4 Jun - 5 Jun
Canal front, dockage, 2 bedroom, 2 bath
Exterior

Beautiful Cottage & Amenities in Gated Community

Beautiful Cottage & Amenities in Gated Community
Cudjoe Key
10.0 out of 10, Exceptional, (2 reviews)
"Beautiful home, perfect for our needs"
United States
Lindsay S.
The price is SAR 784
SAR 2,268 total
includes taxes & fees
31 May - 1 Jun
Beautiful Cottage & Amenities in Gated Community
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)
"The view to watch the sunrise was amazing for our stay. House was clean and easy instructions to get inside. "
United States
Megan M.
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, (342 reviews)
"Very nice, clean and cozy, with the deers walking around."
United States
Sofia
The price is SAR 436
SAR 1,018 total
includes taxes & fees
31 May - 1 Jun
Old Wooden Bridge Resort and Marina
Outdoor dining

Living Life Dockside

Living Life Dockside
Stock Island
10.0 out of 10, Exceptional, (3 reviews)
"This place was welcoming to pets & humans alike, what a place."
United States
Stephen R.
Living Life Dockside
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 920
SAR 2,470 total
includes taxes & fees
19 Jun - 20 Jun
OSPREY STUDIO @ The Colony-Sleeps up to 4
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, (25 reviews)
"Great location, freshly renovated "
United States
Jackie M.
The price is SAR 1,400
SAR 2,474 total
includes taxes & fees
14 Jun - 15 Jun
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key RV Resort & Cottages

10/10 Excellent
"I prefer Communication via email or text. This was the plus for me with the resort. It was very easy to check in after hours and the reach the resort. Welcome package with all you need to get to the cottage. Beautiful, clean and just ready to start your vacation. This place is 25 min from Key West! Love it and will definitely coming back."
Yesenia 3-night trip
Posted 2 days ago
Sugarloaf Key RV Resort & Cottages

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between SAR 1,018 and SAR 2,474 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.