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, Upper Sugarloaf Sound and Florida Keys Beaches are some notable places to visit nearby.
Cudjoe Gardens
When in Cudjoe Gardens, you can plan a visit to Upper Sugarloaf Key and Upper Sugarloaf Sound, some noteworthy sights in the nearby area.
Breezeswept Beach Estates
While Breezeswept Beach Estates isn't home to many top sights, Cook Island and Crab Key are some notable places to visit nearby.
Looe Key Reef Resort
Staff very polite and accommodating.
Reviewed on 21 December 2025
Parmer's Resort
Room was clean and comfortable.
Reviewed on 10 December 2025
Sugar Loaf Lodge
Exceeded expectations. Nothing to complain about. Nice water scenery back of rooms. Spacious parking. Quiet, off road.
Reviewed on 16 December 2025
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
It was a nice location. 30” from Key West.
Reviewed on 21 November 2025
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Great place!
Reviewed on 29 November 2025
Private Secluded Ocean View & Pool Near Key West
A wonderful time was had by all. Host was very responsive and we had no issues. Beautiful home and views!
Reviewed on 18 November 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 Sound
- Upper Sugarloaf Key
- Saddlebunch Keys
- Lower Sugarloaf Sound
- Duval Street
- Mallory Square
- Smathers Beach
- Southernmost Point
- Sombrero Beach
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home and Museum
- South Beach
- Seven Mile Bridge
- Stock Island Yacht Club & Marina
- Key West Butterfly and Nature Conservatory
- Clarence S. Higgs Memorial Beach Park
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Key West Golf Club
- Vaca Key
- Florida Keys National Marine Sanctuary
- Key West Tropical Forest and Botanical Garden
- Key West Lighthouse and Keeper's Quarters Museum
- Calusa Beach
