Summerland Key Cottage: Find The Top Holiday Cottages in Summerland Key

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

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

Cudjoe Key

Anthony

includes taxes & fees

2 Aug - 3 Aug

Island Oasis ~ YOUR Paradise awaits in Venture Out Resort!

Cudjoe Key

Bryan M.

includes taxes & fees

24 July - 25 July

Canal front, dockage, 2 bedroom, 2 bath

Cudjoe Key

Anonymous traveller

includes taxes & fees

3 Aug - 4 Aug

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

Cudjoe Key

BRIAN S.

includes taxes & fees

4 Aug - 5 Aug

Old Wooden Bridge Resort and Marina

Punta Brisa

Maya

includes taxes & fees

7 Aug - 8 Aug

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

Old Town Key West

Juleigh N.

includes taxes & fees

5 Aug - 6 Aug

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

Old Town Key West

Mercedes A.

includes taxes & fees

1 Aug - 2 Aug

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Top Summerland Key Hotel Reviews

Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"We luved everything about it !!! The staff in the cabana (Marlo) were super !!! The hotel was spotless and well appointed. The pool area and marina were fun and well maintained! From kayak rentals to bike rentals and even inflatable play area in the water- it really offers a great Key experience!"

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."

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Summerland Key Cottages information

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Frequently asked questions

How much do cottages in Summerland Key cost?

You can expect to pay between and per night for cottages in Summerland Key. Whatever your budget, an awesome stay is just clicks away on Expedia. This price was 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?

Surround yourself with nature in one of the cottages available in Summerland Key. To help you reserve a place that's right for you, take advantage of our filters to search for amenities or perks you need.

What is there to do in Summerland Key near my cottage?

You'll find plenty of superb things to do in Summerland Key. Discover well-known attractions like Florida Keys Beaches, Sugarloaf Beach and Big Pine Key Flea Market. Blue Hole, Cook Island and Upper Sugarloaf Sound are other must-see's.

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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