Summerland Key Cottages ￥41,968

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

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In two weeks

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In four months

Our top choices for Summerland Key cottages

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key

Carla R.

￥74,824 total

includes taxes & fees

Aug 3 - Aug 4

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

Cudjoe Key

BRIAN S.

￥81,611 total

includes taxes & fees

Aug 11 - Aug 12

Old Wooden Bridge Resort and Marina

Punta Brisa

Kathy

￥41,968 total

includes taxes & fees

Aug 3 - Aug 4

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

Old Town Key West

Bradley

￥105,841 total

includes taxes & fees

Aug 12 - Aug 13

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

Old Town Key West

Mercedes A.

￥101,840 total

includes taxes & fees

Aug 23 - Aug 24

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

Old Town Key West

Jessica C.

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Top Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

10/10 Excellent

"Bring extra coffee pods sugar and creamer."

Sugarloaf Key Hotel at KOA Resort

8/10 Good

"Enjoyed our stay here with a lovely pool area with bar and small private beach area. Also the hot tub is wonderful. Rooms are really nice and staff are very friendly and helpful. Our bedroom door was broken and the maintenance team fixed it efficiently. The mattress in the bedroom and the sofa bed wasn’t great but everything else was very good!"

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!!"

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."

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Summerland Key Cottages information

Number of reviews	529
Accommodation	54 Cottages
Lowest Price	￥41,968
Highest Price	￥105,841

Frequently asked questions

How much do cottages in Summerland Key cost?

Cottages in Summerland Key range between ￥41,968 and ￥105,841 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 54 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

Canal front, dockage, 2 bedroom, 2 bath

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

Old Wooden Bridge Resort and Marina

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

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

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

Find vacation rentals that suit your style

Top Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Sugarloaf Key Hotel at KOA Resort

Parmer's Resort

A Tropical Luxury Getaway, Your own private resort!!

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

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

Private Oceanfront Cottage with dockage, pool just minutes to Key West!

Direct Oceanfront Cottage-Sunrise View- #2,

Springs Venture Out Dolphin House #386 with beautiful open water views

Find out more about Summerland Key

Summerland Key Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Summerland Key Cottage Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Summerland Key cottages

Canal front, dockage, 2 bedroom, 2 bath

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

Old Wooden Bridge Resort and Marina

Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!

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

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

Find vacation rentals that suit your style

Top Summerland Key Hotel Reviews

Sugarloaf Key RV Resort & Cottages

Find out more about Summerland Key

Summerland Key Cottages information

Frequently asked questions

Explore a world of travel with Expedia