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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Summerland Key cottages

Exterior

Cottage with Pool and Boat Dockage just minutes to Key West!

Cottage with Pool and Boat Dockage just minutes to Key West!
Cudjoe Key
8.6 out of 10, Excellent, (162 reviews)
"Stayed one night, conveniently located. "
United States
Wendy H.
Cottage with Pool and Boat Dockage 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, (167 reviews)
"Great place "
United States
David
The price is AED 744
AED 1,408 total
includes taxes & fees
22 Apr - 23 Apr
Cottage with Pool and Dockage, just minutes to Key West
Property grounds

Direct Oceanfront Cottage-Sunrise View- #2,

Direct Oceanfront Cottage-Sunrise View- #2,
Little Torch Key
8.6 out of 10, Excellent, (199 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.
The price is AED 826
AED 1,516 total
includes taxes & fees
18 Apr - 19 Apr
Direct Oceanfront Cottage-Sunrise View- #2,
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, (29 reviews)
"Very nicely remodeled Vrbo, excellent location for a quick drive down to Key West or exploring the other Keys!"
United States
Patrick M.
The price is AED 1,154
AED 2,363 total
includes taxes & fees
19 Apr - 20 Apr
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, (321 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
The price is AED 426
AED 996 total
includes taxes & fees
26 Apr - 27 Apr
Old Wooden Bridge Resort and Marina
House (1 Bedroom) | 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
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, (141 reviews)
"Great place to stay"
United States
JEFFREY Z.
The price is AED 1,638
AED 2,775 total
includes taxes & fees
3 May - 4 May
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, (100 reviews)
"Parking was easy. This was we a great place for me and my pup!"
United States
Tiffany H.
The price is AED 1,069
AED 2,629 total
includes taxes & fees
19 Apr - 20 Apr
HIDDEN OASIS 3 blocks from Duval
Exterior

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.
The price is AED 2,146
AED 4,012 total
includes taxes & fees
15 May - 16 May
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

Parmer's Resort

Parmer's Resort

8/10 Good
"Cool place, nice staff, very nice location"
jamie 4-night trip
Posted 5 hours ago
Parmer's Resort

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between AED 996 and AED 4,012 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.