Summerland Key, FL Cottages from SAR 908

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

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

Cudjoe Key

Carla R.

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

Cudjoe Key

BRIAN S.

SAR 1,967 total

includes taxes & fees

20 Aug - 21 Aug

3. Old Wooden Bridge Resort and Marina

Punta Brisa

Kathy

SAR 908 total

includes taxes & fees

1 Sep - 2 Sep

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

Old Town Key West

Bradley

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

Old Town Key West

Jessica C.

SAR 2,237 total

includes taxes & fees

5 Aug - 6 Aug

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

Old Town Key West

Mercedes A.

SAR 2,336 total

includes taxes & fees

23 Aug - 24 Aug

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Top Summerland Key Hotel Reviews

A Tropical Luxury Getaway, Your own private resort!!

10/10 Excellent

"This property is fantastic! It’s in perfect condition, both inside and out. The grounds were immaculate. They had everything you could need, from pool games and beach games to beach towels, life jackets, entertainment around the pool, large porches, a dock for a boat, a fish cleaning area at the dock’s end, paddle boards, kayaks, and more. The layout was ideal for a large group with multiple families. The host was super responsive and helpful with all our questions. We can tell they really care about the home and the property. Definitely recommend! We cannot wait to come back"

Sugarloaf Key Hotel at KOA Resort

8/10 Good

"Overall it was a great experience. All staff is really kind. Our room had dogs hair on the floor when I first swept and bed isn’t too comfortable but room overall looks beautiful and is well maintained. Bar and pool close a bit early but like everything else in the keys. Only annoying thing is marina rental closes super early and last call for rental is too early as well but the place is nice especially if you have children. It’s clean, easy to move around, close to Key West. Bartenders are all super nice and there are different activities like smores or live singers. It was a great experience. We will be back."

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

10/10 Excellent

"This property was perfect for our stay. My nine year old son caught and released over 50 fish right off the back. The water was beautiful and the things for families to do at Venture Out are great!"

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."

Frequently asked questions

How much do cottages in Summerland Key cost?

Cottages in Summerland Key range between SAR 908 and SAR 2,336 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.

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.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Summerland Key cottages

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

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

3. Old Wooden Bridge Resort and Marina

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

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

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

Find vacation rentals that suit your style

Top Summerland Key Hotel Reviews

A Tropical Luxury Getaway, Your own private resort!!

Sugarloaf Key Hotel at KOA Resort

Sugar Loaf Lodge

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

Cottage with Pool and Dockage, just minutes to Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West

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,

Frequently asked questions

Search Cottages in Summerland Key

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Summerland Key cottages

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

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

3. Old Wooden Bridge Resort and Marina

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

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

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

Find vacation rentals that suit your style

Top Summerland Key Hotel Reviews

A Tropical Luxury Getaway, Your own private resort!!

Frequently asked questions