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 Key and Venture Out Keys 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 Newfound Harbor Keys are some notable places to visit nearby.
Looe Key Reef Resort
Clean, very hospitable, will return.
Reviewed on Feb 27, 2026
Parmer's Resort
Clean, quiet. Waterfront. Minimal “breakfast”. Plenty parking. Pricey. Standard room very small but functional. Showing some wear but freshly painted, well landscaped. Free bikes.
Reviewed on Feb 28, 2026
Sugarloaf Key Hotel at KOA Resort
The property is immaculate. The room is more like an apartment and it feels brand new. So spacious and just perfect for a family. The staff could not have been nicer!
Reviewed on Feb 28, 2026
Private Oceanfront Cottage with dockage, pool just minutes to Key West!
Did not use tge pool, it looked nice. The place is a little worn and dated. It was clean, everything worked as it should. Tough thing to find in the keys, it was very private. 4 places spred out over a long property. I could only see 2 houses, about the same when you went on the dock. Dock was nice, ...
Reviewed on Dec 30, 2025
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
This is a large, comfortable house close to Key West, but far enough away from the hustle and bustle
Reviewed on Jan 26, 2026
Private Secluded Ocean View & Pool Near Key West
Terrible experience! Booked house for group for wife's birthday - months in advance, only to have canceled at 2am the night before check-in! Would not return emails, phone calls or any other communication! Very sketchy! ALSO there are 2 identical bookings on VRBO for this house so be very careful ...
Reviewed on Feb 2, 2026
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.
Venture Key
Commune with nature and explore the great outdoors at Venture 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.
Things to do
Key West Sunset Cruise & Glass Bottom Eco Tour
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Haunted Tour : Ghosts & Gravestones
Key West Dolphin & Snorkeling Tour - Small Group
- Duval Street
- Southernmost Point
- Mallory Square
- Smathers Beach
- Ernest Hemingway Home and Museum
- Sombrero Beach
- Fort Zachary Taylor Historic State Park
- South Beach
- Key West Butterfly and Nature Conservatory
- Seven Mile Bridge
- Clarence S. Higgs Memorial Beach Park
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Florida Keys National Marine Sanctuary
