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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Summerland Key cottages

A floating houseboat with a covered deck and seating area, docked at a marina.

1. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (373 reviews)
"Best stop over before going to Key west. We enjoyed here a lot, parking our trailer was never a problem."
United States
Daisybel
The price is SAR 727
SAR 1,345 total
includes taxes & fees
2 Oct - 3 Oct
Old Wooden Bridge Resort and Marina
A building with a white exterior, a brick pathway, and lush greenery including palm trees and flowering plants.

2. Get your ISLAND STLYE on!

Get your ISLAND STLYE on!
Old Town Key West
9.6 out of 10, Exceptional, (84 reviews)
"Good location. Provided everything that was listed. The unit was very clean."
United States
Mary S.
Get your ISLAND STLYE on!
A two-story building with balconies, surrounded by lush greenery and palm trees.

3. 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, (151 reviews)
"Perfect for what we needed. Close to Duval and all the action."
United States
Jonnye W.
The price is SAR 1,878
SAR 3,058 total
includes taxes & fees
20 Oct - 21 Oct
The Dancing Rooster: 2 Blocks from Duval in Old Town.
A two-story building with balconies, surrounded by lush greenery and palm trees.

4. 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, (35 reviews)
"The location of jolly rooster was great, and we managed to get parking right outside. Very clean property. Host was very responsive to emails while we were there. Would definitely book again"
United States
Pauline B.
The price is SAR 1,690
SAR 2,805 total
includes taxes & fees
3 Oct - 4 Oct
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
A small, single-story building with a white exterior and a metal roof, surrounded by lush greenery and a paved patio area.

5. Find your zen at HIDDEN TREASURE

Find your zen at HIDDEN TREASURE
Old Town Key West
9.2 out of 10, Wonderful, (22 reviews)
"Great location, clean and well equipped."
United States
Richard M.
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

Sugarloaf Key Hotel at KOA Resort

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent
"Very clean, great drinks. Friendly staff, Tammy was very helpful in sending us some recommendations for snorkeling in the area!"
Nikolas 4-night trip
Posted 2 days ago
Sugarloaf Key Hotel at KOA Resort

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between SAR 1,345 and SAR 3,058 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 51 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.