Summerland Key Cottages from CA $381

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

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Our top choices for Summerland Key cottages

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Key

David

CA $538 total

includes taxes & fees

Jul 16 - Jul 17

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

Cudjoe Key

Anthony

CA $561 total

includes taxes & fees

Aug 1 - Aug 2

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cudjoe Key

Bryan M.

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key

Anonymous traveller

CA $864 total

includes taxes & fees

Aug 2 - Aug 3

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

Cudjoe Key

BRIAN S.

CA $1,156 total

includes taxes & fees

Aug 4 - Aug 5

Old Wooden Bridge Resort and Marina

Punta Brisa

Sofia

CA $381 total

includes taxes & fees

Aug 7 - Aug 8

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

Old Town Key West

Juleigh N.

CA $831 total

includes taxes & fees

Aug 5 - Aug 6

The Dancing Rooster: 2 Blocks from Duval in Old Town.

Old Town Key West

Mercedes A.

CA $890 total

includes taxes & fees

Aug 1 - Aug 2

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Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"Room was very clean. Staff was very nice. Unfortunately when I was there, the pool was under Construction, but everything else was great."

Parmer's Resort

10/10 Excellent

"We happened upon this quaint resort on a weekend to the Keys. What a great spot! It is not on one of the main keys but is close to Key West and other fun locations. The resort had hammocks to relax in, a pool, docks, outdoor activities and a small breakfast (don't plan on filling up on it if you are hungry though). Room was quiet even though it was right next to the pool and there are so many different options there! We would definitely stay there again! Beds were comfortable and the bathroom was spacious."

Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball

10/10 Excellent

"Everything was fantastic! The house was wonderfully furnished, from the kitchen, linens, towels, coolers, bikes, fishing poles, ice machine! The location for us was perfect since my Dad lives right down the road from Venture Out. He picked us up at the store with the boat! The Key Lime pie was a delicious surprise! We will be back!"

Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security

10/10 Excellent

"This house was great for our whole family! Easy to get to. Quick and easy check in process. Tons to do and the host provided a lot to use if wanted (bikes for kids/adults, kayaks..). Our kids loved the pool more than anything, which was great!! Our host had all the amenities. Full kitchen with all we needed. Sheets/blankets pillows provided; washer/dryer worked well. We loved sitting out on the balcony while there. Overall, great experience!!"

A Tropical Luxury Getaway, Your own private resort!!

10/10 Excellent

"The owners take great pride in their property. The house was immaculate and they have honestly thought of everything! Great location right between Key West and Marathon. The house, pool, dock, everything was top notch. The kayaks and paddle boards were definitely a bonus! The house looks just like the pictures. We will definitely be back!"

Direct Oceanfront Cottage-Sunrise View- #2,

8/10 Good

"The property is listed accurately. It is a very basic fishing cottage, but clean. It could be a better experience if they would fix a couple things: > Most Importantly for safety, repair the back stairs. The 2x4 holding up the left side is ready to fall off. I was tempted to fix it. > Clean the kitchen cupboard with the pot & pans more often. > Replace the Microwave, the inside bottom is rusting. > Connect the very nice refrigerator's ice maker to a water line. > As it is Mid Summer in the Florida Keys, the little window AC units were struggling to keep up. The kitchen could use it's own window AC unit. > The driveway could use a load of gravel, since it is muddy. My recommendation is for the owner to put a little more TLC into the property, and we may stay there again."

Find out more about Summerland Key

Summerland Key Cottages information

Number of reviews	1,033
Accommodation	55 Cottages
Lowest Price	CA $381
Highest Price	CA $1,156

Frequently asked questions

How much do cottages in Summerland Key cost?

Cottages in Summerland Key range between CA $381 and CA $1,156 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 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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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

Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West