Upper Sugarloaf Key Tours and Activities
Visit Upper Sugarloaf Key
Plan a trip to see Upper Sugarloaf Key
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Miami Beach
Mid Beach
Price was CA $1,815, price is now CA $991 per person
CA $991
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
8/10 Very Good! (1,097 reviews)
Bad condition of the rooms. The glass door doesn’t close properly, leaving gaps. There weren’t enough loungers for the number of people on the beach; many had to lie directly on towels.
Reviewed on Aug. 27, 2025
Bentley Hotel South Beach
South Beach
Price was CA $2,128, price is now CA $1,120 per person
CA $1,120
per person
Oct 27 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Miami (MIA)
9.2/10 Wonderful! (294 reviews)
We loved our stay at the Bentley Hotel! The staff was so friendly and always took the initiative to help us out. It was my girlfriend's birthday and when they learned aboit it they brought champagne, snacks to the room and left us a heartfelt card.
Thank you again for your hospitality. We cannot wait to be back again!
Reviewed on Aug. 24, 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.
Florida Keys Beaches
Why not spend a lazy afternoon at Florida Keys Beaches during your trip to Long Beach Estates?
Shark Key
Commune with nature and explore the great outdoors at Shark Key during your travels in Key West. In the area, take in the great live music and beautiful sunsets.
Venture Key
Commune with nature and explore the great outdoors at Venture Key during your travels in Summerland Key.
Sugarloaf Beach
Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key?
Crab Key
Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key.
Best Lodging Options Near Upper Sugarloaf Key
Check availability on hotels close to Upper Sugarloaf Key
Sugarloaf Key Hotel at KOA Resort
251 Co Rd 939, Summerland Key, FL
Escape to the Keys! Pet-Friendly Sugarloaf Key Bungalow - Great Amenities (84)
Summerland Key
Pet-Friendly Bungalow in Sugarloaf Key, FL - Fantastic Amenities (83)
Summerland Key
Pet-Friendly Lakefront Bunglaow - Sugarloaf Key - Great Amenities (21)
Summerland Key
Lakefront Bungalow - Pet-Friendly - Sugarloaf Key - Great Amenities (22)
Summerland Key
Pelico Palms Estate.
Monroe County
The Villa of Pelico Palms
Monroe County
The Sunset Suites of Pelico Palms
Monroe County
Sublimely private luxury home with enveloping oceanfront views near Key West
Near Key West
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Vacations and getaways similar to Upper Sugarloaf Key
- Other Hotels near Upper Sugarloaf Key, Summerland Key
- Hotels near popular Summerland Key Attractions
- Duval Street
- Southernmost Point
- Mallory Square
- Smathers Beach
- Sombrero Beach
- South Beach
- Fort Zachary Taylor Historic State Park
- Clarence S. Higgs Memorial Beach Park
- Seven Mile Bridge
- Boca Chica Nude Beach
- Harry S. Truman Little White House
- Florida Keys National Marine Sanctuary
- Key West Lighthouse and Keeper's Quarters Museum
- Florida Keys Eco - Discovery Center
- Sugar Loaf Lodge
- Pet friendly amazing location in paradise
- Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot
- Cudjoe Cabana, Escape to Cudjoe Cabana
- Gorgeous New 4/3 With Heated Pool/Spa And Large Deep Water Boat Dock
- Getaway to the Quiet Florida Keys
- Magnificent Ocean views, privacy abounds on this well appointed mini estate.
- Private Secluded Ocean View & Pool Near Key West
- Ocean View 4/2 Estate with Private Pool 15 minutes from Key West
- Atlantic View Luxury Villa with Pool
- Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West
- Cottage with Pool and Boat Dockage just minutes to Key West!
- Hotels near Florida Keys Beaches
- Hotels near Boca Chica Nude Beach
- Hotels near Key West Naval Station
- Hotels near Boca Chica Beach
- Hotels near Sugarloaf Beach
- Hotels near Key West Visitors Center
- Hotels near National Key Deer Refuge Visitor Center
- Hotels near Saddlebunch Keys
- Hotels near Looe Key National Marine Sanctuary
- Hotels near Shark Key
- Hotels near Big Pine Key Flea Market
- Hotels near Upper Sugarloaf Sound
- Hotels near Cook Island
- Hotels near Coupon Bight Aquatic Preserve
- Hotels near Lower Sugarloaf Sound
- Hotels near Blue Hole
- Hotels near Florida Keys Wilderness