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

Search Summerland Key Cottage Rentals from CA $341

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 CA $125
CA $341 total
includes taxes & fees
Oct 12 - Oct 13
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.
The price is CA $237
CA $831 total
includes taxes & fees
Oct 13 - Oct 14
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 CA $711
CA $1,172 total
includes taxes & fees
Oct 20 - Oct 21
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, (36 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 CA $711
CA $1,155 total
includes taxes & fees
Oct 25 - Oct 26
NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location
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

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

10/10 Excellent
"We had a great stay! Everything was clean, comfortable, and worked out perfectly for our trip. Having access to the boat ramp and convenient parking for both our boat and trailer was extremely helpful. The marina store was a nice added convenience, and having a pressure washer available made cleaning up after a day on the water much easier. Overall, we really enjoyed our stay and would definitely stay here again."
Sterling D. 2-night trip
Posted 2 hours ago
Oceanside Paradise Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews
644
Accommodation
49 Cottages
Lowest Price
CA $341
Highest Price
CA $1,172

Frequently asked questions

How much do cottages in Summerland Key cost?
Cottages in Summerland Key range between CA $341 and CA $1,172 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 49 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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