Find 5 Star Hotels in Summerland Key, FL
- Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Check availability on Summerland Key 5 Star Hotels
Compare Summerland Key 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.
Learn more about Summerland Key
Check out the local area in Summerland Key—home to attractions like Florida Keys Beaches and Sugarloaf Beach.

Explore a world of travel with Expedia
Explore a world of travel with Expedia
Summerland Key Hotels by Star Rating
Hotels in Summerland Key Neighborhoods
Stay near popular Summerland Key attractions
- Hotels near Duval Street
- Hotels near Smathers Beach
- Hotels near Mallory Square
- Hotels near Southernmost Point
- Hotels near Sombrero Beach
- Hotels near Ernest Hemingway Home and Museum
- Hotels near South Beach
- Hotels near Fort Zachary Taylor Historic State Park
- Hotels near Key West Golf Club
- Hotels near Clarence S. Higgs Memorial Beach Park
- Hotels near Seven Mile Bridge
- Hotels near Stock Island Yacht Club & Marina
Explore more hotels
- THE NEW HIDDEN HAMMOCK RESORT - Pink Cottage Unit # 3 Sleeps 4
- Little Torch Cottages
- Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Just 20 miles from Key West! Oceanfront, dockage, swimming pool
- Gated Community on Open Water with Dock, Heated Pool, Kayaks, Bikes
- Cudjoe Cottages, swimming pool, just 20 miles from Key West
- Private Secluded Ocean View & Pool Near Key West
- SEA SHELL COTTAGE UNIT #2 Sleeps 2
- Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
- JUDY'S PLACE ~ 2 Bedroom, 1 Bathroom Home in Venture Out Community!
- One of the very few beach houses with a daily, rental license in the Keys.
- Oceanside Paradise in the FL Keys Free Kayaks Bikes Wifi Outdoor BBQ Grill
- ISLE BE BACK To The Sunny Keys
- Canal front, dockage, 2 bedroom, 2 bath
- Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Charming cottages, dockage, pool, just minutes to Key West
- OCEAN FRONT PARADISE/290 ft PRIVATE DOCK/AWESOME VIEWS
- Waterfront Home
- 35' Seawall Sparkling , 30min from Keywest, WIFI, BBQ Grill, Pool
- Oceanside Paradise: Kayaks, Free WiFi, A/C, Grill, Elevated Deck, 24hr Security