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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 Jan

Our top choices for Summerland Key cottages

A covered outdoor deck with a sofa and table, overlooking a marina with boats and palm trees.

1. Canal front, dockage, 2 bedroom, 2 bath

Canal front, dockage, 2 bedroom, 2 bath
Cudjoe Key
8.8 out of 10, Excellent, (110 reviews)
"The place was better than listed. Extremely well taken care. Highly recommend"
United States
Joseph L.
The price is £397
includes taxes & fees
14 Nov - 15 Nov
Canal front, dockage, 2 bedroom, 2 bath
A floating houseboat with a covered deck and seating area, docked at a marina.

2. Old Wooden Bridge Resort and Marina

Old Wooden Bridge Resort and Marina
2.5 star property
Punta Brisa
8.6 out of 10, Excellent, (382 reviews)
"Very clean for Florida keys room - no complaints easy check in and out"
United States
Anthony
The price is £164
includes taxes & fees
4 Dec - 5 Dec
Old Wooden Bridge Resort and Marina
A cozy outdoor patio area with a wooden deck, a white table, and a cushioned seating area.

3. 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, (63 reviews)
"The place is very clean and AC works great. Access to pool was super convenient. Pool is very nice. Landscaping is tropical and tidy."
United States
Juan B.
The price is £420
includes taxes & fees
12 Nov - 13 Nov
OSPREY STUDIO @ The Colony-Sleeps up to 4
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, (37 reviews)
"Wonderful property! We enjoyed our stay! Property hosts were very attentive to every question we had. Highly recommend!"
United States
Sheri J.
The price is £400
includes taxes & fees
29 Nov - 30 Nov
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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Learn more about Summerland Key

Snorkel the vibrant coral reefs at Looe Key, where rangers can direct you to spots with fewer boats. Rent kayaks to explore the mangrove trails, then ask locals about their favourite seafood shacks serving fresh-caught Keys lobster.

See all hotels in Summerland Key
A coastal pier extending into the sea, surrounded by rocky shores and greenery.

Frequently Asked Questions

How much do cottages in Summerland Key cost?

Cottages in Summerland Key range between £164 and £420 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 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?

Settle in at Old Wooden Bridge Resort And Marina and make your family visit to Summerland Key an easy one. This family-friendly cottage has a 2.5-star rating and conveniences like a picnic area and a firepit. After checking in and kicking back together in your home away from home, it's time to head out and visit some of the local sights. No Name Key and Florida Keys Beaches are popular family-friendly attractions in Summerland Key.

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 favourite 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.