Summerland Key Cottages

Aerial view of road to Key West with turquoise water and small island, Summerland Key, Florida, United States.

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In two weeks

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Our top choices for Summerland Key cottages

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key

David

includes taxes & fees

3 Jun - 4 Jun

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cudjoe Key

Bryan M.

includes taxes & fees

14 Jun - 15 Jun

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key

Anonymous traveller

includes taxes & fees

4 Jun - 5 Jun

Waterfront Home

Cudjoe Key

Karen H.

includes taxes & fees

23 Jun - 24 Jun

2BR,2BA w KING Master,35' SeaWall-SS and Quartz Kitchen,Bikes, Kayaks and VIEWS

Cudjoe Key

Shari H.

includes taxes & fees

7 Jun - 8 Jun

Old Wooden Bridge Resort and Marina

Punta Brisa

Sofia

includes taxes & fees

28 Jun - 29 Jun

HIDDEN OASIS 3 blocks from Duval

Old Town Key West

Daniel M.

includes taxes & fees

3 Jun - 4 Jun

NEW! - The Jolly Rooster Cottage Steps to Duval - Prime and Quiet Location

Old Town Key West

Jackie M.

includes taxes & fees

14 Jun - 15 Jun

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Top Summerland Key Hotel Reviews

Looe Key Reef Resort

10/10 Excellent

"Great place to stay!"

SEA SHELL COTTAGE, Sleeps 2 - ESCAPE THE COLD; OUR POOL IS HEATED!

8/10 Good

"The bed was overly soft. Making sleeping a challenge. The area and the pool were great. I never did find the beach with in a 6 minute walk. Room was clean could use a comfortable chair to sit in. All in all it was a great place to stay."

Cottage with swimming pool and dockage, just minutes to Key West!

8/10 Good

"We had a nice stay at this property, which was clean and nicely presented. It is in a calm area by the water and has some good food options close by as well. We did use the pool on 2 days and it felt like a private pool just when we used it."

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews	342
Accommodation	55 Cottages
Lowest Price	€236
Highest Price	€236

Frequently asked questions

How much do cottages in Summerland Key cost?

Cottages in Summerland Key range between €236 and €236 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.

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 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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Summerland Key cottages

Cottage with Pool and Dockage, just minutes to Key West