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Our top choices for Summerland Key cottages

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (179 reviews)
"Place was as advertised! We LOVE Venture out! There are park rules but if you follow them, you become family! Home was stocked and clean. Screened in back patio was a nice touch! Would stay in this unit again!"
United States
Thomas B.
$406 nightly
The price is $451
Apr 10 - Apr 11
Total with taxes and fees
Waterfront Home

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, (167 reviews)
"Great place "
United States
David
$346 nightly
The price is $383
Apr 22 - Apr 23
Total with taxes and fees
Cottage with Pool and Dockage, just minutes to Key West

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
8.6 out of 10, Excellent, (197 reviews)
"Excellent location for staying in the Lower Keys. Sunrise view. Nice neighborhood setting. Close to real good places to eat, listen to music and chill. Would come back. "
United States
Ihor C.
$372 nightly
The price is $413
Apr 11 - Apr 12
Total with taxes and fees
Direct Oceanfront Cottage-Sunrise View- #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, (28 reviews)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
$586 nightly
The price is $650
Apr 19 - Apr 20
Total with taxes and fees
2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

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.
$704 nightly
The price is $782
Apr 24 - Apr 25
Total with taxes and fees
Beautiful Cottage & Amenities in Gated Community

Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (317 reviews)
"Staff was great. Walking distance to No Name Pub. Water view was terrific. The bridge to nowhere was a good walk."
United States
Amado
$267 nightly
The price is $300
Apr 22 - Apr 23
Total with taxes and fees
Old Wooden Bridge Resort and Marina

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, (57 reviews)
"We loved our stay here. It was calm and quiet--such a nice place to lounge and enjoy a morning coffee when you're not hanging out on Duval or exploring the island! We loved it!"
United States
Dean H.
$624 nightly
The price is $683
Apr 14 - Apr 15
Total with taxes and fees
OSPREY STUDIO @ The Colony-Sleeps up to 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
10.0 out of 10, Exceptional, (6 reviews)
"Property was clean and quiet nice amenities "
United States
Bradley
$877 nightly
The price is $986
Apr 15 - Apr 16
Total with taxes and fees
Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

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, (141 reviews)
"Great place to stay"
United States
JEFFREY Z.
$646 nightly
The price is $717
Apr 22 - Apr 23
Total with taxes and fees
The Dancing Rooster: 2 Blocks from Duval in Old Town.

HIDDEN OASIS 3 blocks from Duval

HIDDEN OASIS 3 blocks from Duval
Old Town Key West
9.6 out of 10, Exceptional, (100 reviews)
"Parking was easy. This was we a great place for me and my pup!"
United States
Tiffany H.
$709 nightly
The price is $777
Apr 19 - Apr 20
Total with taxes and fees
HIDDEN OASIS 3 blocks from Duval

Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
9.0 out of 10, Wonderful, (16 reviews)
"Great place to stay! "
United States
sarah R.
$1,147 nightly
The price is $1,263
May 3 - May 4
Total with taxes and fees
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

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
1,013
Accommodation
59 Cottages
Lowest Price
$300
Highest Price
$1,263

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between $300 and $1,263 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 59 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.
Are there any family-friendly cottages in Summerland Key?
You bet there are! Reserve a room at Old Wooden Bridge Resort And Marina, a top base for enjoying the great outdoors in Summerland Key. This family-friendly cottage has a 2.5-star rating and comes with handy amenities such as a firepit and a picnic area. Once you've checked in and unpacked your suitcase, there are lots of family-friendly attractions to see around Summerland Key. Florida Keys Beaches and Sugarloaf Beach promise fun for all ages.
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.
What is there to do in Summerland Key near my cottage?
The ideal travel accessory is a well-planned itinerary. Florida Keys Beaches is a wonderful place to begin your exploration of Summerland Key.

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