A coastal road with a beach on one side and a marina with boats on the other.

Book a Summerland Key Cottage

  • 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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Summerland Key cottages

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)
The price is NZ$620
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, (15 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, (102 reviews)
"The bedrooms and bathrooms were a little small but everything else was fantastic. We loved the outdoor spaces."
United States
Carla R.
Canal front, dockage, 2 bedroom, 2 bath
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, (356 reviews)
"We stayed in the 2 bedroom condo. It was spacious and clean. We enjoyed our time there."
United States
Kathy
The price is NZ$444
includes taxes & fees
9 Aug - 10 Aug
Old Wooden Bridge Resort and Marina
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
The price is NZ$1,112
includes taxes & fees
12 Aug - 13 Aug
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, (149 reviews)
"Such a great stay. A nice walk to duval for nightlife!"
United States
Mercedes A.
The price is NZ$1,069
includes taxes & fees
1 Aug - 2 Aug
The Dancing Rooster: 2 Blocks from Duval in Old Town.
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

Parmer's Resort

Parmer's Resort

10/10 Excellent
"A very nice property, friendly and helpful staff. Very relaxing stay by the water."
John 1-night trip
Posted 16 hours ago
Parmer's Resort

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
726
Accommodation
54 Cottages
Lowest Price
NZ$444
Highest Price
NZ$1,112

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between NZ$444 and NZ$1,112 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.
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.