Summerland Key, FL
Travel Guide
Visit Summerland Key
Where to stay in Summerland Key
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.
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.
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, Newfound Harbor Keys and Cook Island are some notable places to visit nearby.
Looe Key Reef Resort
yes
Reviewed on Jan 14, 2026
Parmer's Resort
Excellent
Reviewed on Jan 5, 2026
Sugar Loaf Lodge
Great staff and great location!
Reviewed on Jan 7, 2026
Cottage with Pool and Boat Dockage just minutes to Key West!
This was exactly as advertised Small with everything you would need Not a luxurious 5 Star hotel but wasn’t advertised as one Cudjo key is perfect Several good restaurant (check out Morning Joint for breakfast) Will definitely come back
Reviewed on Dec 26, 2025
COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!
Great place!
Reviewed on Nov 29, 2025
Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
A/C cold. Room clean. Good service. Priced right. Super cute property on the water. Just what I was looking for.
Reviewed on Dec 14, 2025
Popular places to visit
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Upper Sugarloaf Sound
Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in 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.
Venture Key
Commune with nature and explore the great outdoors at Venture 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.
Things to do
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Key West Sunset Cruise & Glass Bottom Eco Tour
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Haunted Tour : Ghosts & Gravestones
- Duval Street
- Mallory Square
- Smathers Beach
- Southernmost Point
- Sombrero Beach
- Fort Zachary Taylor Historic State Park
- Ernest Hemingway Home and Museum
- South Beach
- Clarence S. Higgs Memorial Beach Park
- Key West Butterfly and Nature Conservatory
- Seven Mile Bridge
- Boca Chica Nude Beach
- Florida Keys National Marine Sanctuary
- Harry S. Truman Little White House
- Key West Lighthouse and Keeper's Quarters Museum
