Summerland Key, FL
Travel Guide
Visit Summerland Key
Where to stay in Summerland Key
Cutthroat Harbor Estates
While Cutthroat Harbor Estates isn't home to many top sights, Venture Out Keys and Upper Sugarloaf Key are some notable places to visit nearby.
Sugarloaf Shores
While Sugarloaf Shores isn't home to many top sights, Florida Keys Beaches and Sugarloaf Beach are some notable places to visit nearby.
Cudjoe Gardens
When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Venture Out Keys, some noteworthy sights in the nearby area.
Bay Point
Bay Point might not have many top sights, but Lower Sugarloaf Sound and Sugarloaf Beach are two attractions nearby that you can check out.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Newfound Harbor Keys and Cook Island are some notable places to visit nearby.
Parmer's Resort
Everything was excellent 5 stars we stayed at a lot of resorts this was best by far Sue was very helpful and even talked with cleaning staff was so friendly. They ALL go above and beyond. Will be back to our private little getaway.
Reviewed on 30 October 2025
Sugar Loaf Lodge
This was an excellent value for the price - the room was spacious and clean, the property was quiet. There was a beautiful view with a balcony. I could not have been happier with my experience!
Reviewed on 6 October 2025
Looe Key Reef Resort
We enjoyed our three night stay. We dived Looe Key reef every day through their dive shop. Safe shallow diving with excellent storage, easy access and excellent staff. Left the afternoon/evening open to relax or go into town. About 50 minutes from Key West. Recommend car rental for your stay
Reviewed on 17 October 2025
JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
Excellent stay Quiet clean and comfortable Thank you for making our vacation a fantastic experience
Reviewed on 8 September 2025
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
This home was a 10/10 experience. Everything was top notch from the cleanliness to the amenities available. It looks exactly like the pictures online but in person it was so much better. The view from the balcony was the best part about it as well as the boat access. We also spent lots of time at ...
Reviewed on 28 September 2025
Cudjoe Cottages, swimming pool, just 20 miles from Key West
was a great stay however i think the photos should be updated especially for the dock / boating areas, they are much more run down than the photos show. there were some ants but thats to be expected in an area like this. the tenants before us left dirty dishes in the dish washer. other than that ...
Reviewed on 7 July 2025
Popular places to visit
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key.
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Key
Commune with nature and explore the great outdoors at Upper Sugarloaf Key during your travels in Summerland Key.
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Squirrel Key
Commune with nature and explore the great outdoors at Squirrel Key during your travels in Summerland Key.
Pye Key
Commune with nature and explore the great outdoors at Pye Key during your travels in Summerland Key.
- Florida Keys Beaches
- Sugarloaf Beach
- Upper Sugarloaf Key
- Saddlebunch Keys
- Upper Sugarloaf Sound
- Lower Sugarloaf Sound
- Duval Street
- Southernmost Point
- Mallory Square
- Smathers Beach
- Sombrero Beach
- South Beach
- Ernest Hemingway Home and Museum
- Fort Zachary Taylor Historic State Park
- Stock Island Yacht Club & Marina
- Key West Golf Club
- Clarence S. Higgs Memorial Beach Park
- Seven Mile Bridge
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Key West Butterfly and Nature Conservatory
- Vaca Key
- Florida Keys National Marine Sanctuary
- Key West Lighthouse and Keeper's Quarters Museum
- Florida Keys Eco - Discovery Center
- Calusa Beach
