Title: Upper Sugarloaf Key Tours - Book Now | Expedia.com [Upper Sugarloaf Key Hotels](https://expedia.com/Upper-Sugarloaf-Key-Hotels.0-l553248635975865768-0.Travel-Guide-Filter-Hotels)[Flights to Summerland Key](https://expedia.com/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.com/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Car Rentals in Upper Sugarloaf Key](https://expedia.com/Car-Rentals-In-Upper-Sugarloaf-Key.d553248635975865768.Car-Rental-Guide)[Summerland Key Vacation Packages](https://expedia.com/Summerland-Key.d6177802.Destination-Travel-Guides) # Upper Sugarloaf Key Tours ## Visit Upper Sugarloaf Key Activities --- --- When you've finished up at this urban area in [Sugarloaf Key](https://www.expedia.com/Sugarloaf-Key.dx183126), why not make your way to Florida Keys Beaches, Sugarloaf Beach, and Upper Sugarloaf Sound? They're not too far from Upper Sugarloaf Key and also a favorite with many travelers. ## Plan a trip to see Upper Sugarloaf Key Price found within the past 48 hours. Click for updated prices. ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Creekside Inn Save 100% on your flight $1,201 per person Jun 14 - Jun 21 found 22 hours ago Roundtrip flight included Boston (BOS) to Miami (MIA) 7.8/10 Good! (1,027 reviews) The staff, place, everything was great. Just some irrationals guest let children play and screening around …3 am.. believe me 3:00 am.. l couldn’t believe. Children under 11-10 years old play and yelling around 3:00 am.. ridiculous !! Reviewed on Mar 29, 2026 ![The Penguin Hotel](https://images.trvl-media.com/lodging/1000000/70000/62900/62824/d4ab7ebb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Penguin Hotel South Beach $1,440 per person Jun 21 - Jun 28 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8.2/10 Very Good! (1,725 reviews) Everything was wonderful. Reviewed on Mar 29, 2026 ### Popular places to visit ![Aerial view from Venture Out on Cudjoe Key Florida., Shutterstock ID 757510879, Purchase Order: Wave 0 First Batch, Order Number: , Client/Licensee: Hotels.com / BEX, Other: Mixed Budget](https://images.trvl-media.com/place/553248635976496782/a20a9413-7e85-4fd2-95ee-846207681027.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Florida Keys Beaches 4/5(525 reviews) Nothing says vacation like spending a carefree day at Florida Keys Beaches, a popular beach in Long Beach Estates. [](https://expedia.com/Florida-Keys-Beaches-Florida.d553248635976496782.Vacation-Attraction) ![Sugarloaf Beach](https://images.trvl-media.com/place/553248635983994028/1d746f78-98d9-4591-8682-e70514df330b.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Sugarloaf Beach Why not spend a lazy afternoon at Sugarloaf Beach during your trip to Summerland Key? [](https://expedia.com/Sugarloaf-Beach-Summerland-Key.d553248635983994028.Vacation-Attraction) ![Shark Key vegetation and water, Keys Islands, FL - USA](https://images.trvl-media.com/place/553248635976194849/ad7d3af1-00b1-4385-a55a-a8c6038c75da.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### 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. [](https://expedia.com/Shark-Key-Key-West.d553248635976194849.Vacation-Attraction) #### Upper Sugarloaf Sound Commune with nature and explore the great outdoors at Upper Sugarloaf Sound during your travels in Summerland Key. [](https://expedia.com/Upper-Sugarloaf-Sound-Summerland-Key.d553248635976195391.Vacation-Attraction) #### Venture Key Commune with nature and explore the great outdoors at Venture Key during your travels in Summerland Key. [](https://expedia.com/Venture-Key-Summerland-Key.d874556559894753280.Vacation-Attraction) #### Crab Key Commune with nature and explore the great outdoors at Crab Key during your travels in Summerland Key. [](https://expedia.com/Crab-Key-Summerland-Key.d874555154127626240.Vacation-Attraction) --- ## Best Lodging Options Near Upper Sugarloaf Key ## Check availability on hotels close to Upper Sugarloaf Key [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=2026-03-30&endDate=2026-03-31)[Mar 30 - Mar 31](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=2026-03-30&endDate=2026-03-31) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=2026-03-31&endDate=2026-04-01)[Mar 31 - Apr 1](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=2026-03-31&endDate=2026-04-01) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026)[Apr 3 - Apr 5](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=4%2F3%2F2026&endDate=4%2F5%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026)[Apr 10 - Apr 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=4%2F10%2F2026&endDate=4%2F12%2F2026) ![Sugarloaf Key Hotel at KOA Resort](https://images.trvl-media.com/lodging/102000000/101140000/101135800/101135765/afeef809_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sugarloaf Key Hotel at KOA Resort 251 Co Rd 939 Summerland Key FL [](https://expedia.com/Sugarloaf-Key-Hotels-Sugarloaf-Key-Hotel.h101135765.Hotel-Information) ![Pelico Palms Estate.](https://images.trvl-media.com/lodging/90000000/89470000/89464500/89464403/cc4665fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Pelico Palms Estate. Monroe County FL [](https://expedia.com/Summerland-Key-Hotels-Pelico-Palms-Estate.h89464403.Hotel-Information) ![The Sunset Suites of Pelico Palms](https://images.trvl-media.com/lodging/90000000/89470000/89464500/89464402/c1a611df_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Sunset Suites of Pelico Palms Monroe County FL [](https://expedia.com/Summerland-Key-Hotels-The-Sunset-Suites-Of-Pelico-Palms.h89464402.Hotel-Information) ![Starlight Serenity - Hideaway w Stunning Views](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/3d9bbd48_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Starlight Serenity - Hideaway w Stunning Views Summerland Key FL [](https://expedia.com/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111872953.Hotel-Information) ![Waterfront, Pet Friendly - Loggerhead Lagoon](https://images.trvl-media.com/lodging/104000000/103050000/103048900/103048811/be66eeff_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront, Pet Friendly - Loggerhead Lagoon Sugarloaf Key FL [](https://expedia.com/Summerland-Key-Hotels-Loggerhead-Lagoon-Canalfront.h103048811.Hotel-Information) ![Waterfront home with a large dock, pool, and deck area. Can accommodate pets.](https://images.trvl-media.com/lodging/37000000/36720000/36716900/36716823/b7c7e563_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Waterfront home with a large dock, pool, and deck area. Can accommodate pets. Summerland FL [](https://expedia.com/Summerland-Key-Hotels-Pet-Friendly-Amazing-Location-In-Paradise.h36716823.Hotel-Information) ![Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot](https://images.trvl-media.com/lodging/72000000/71740000/71734600/71734548/ab2742cd_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Castaway To Sugarloaf Key Waterfront—Bring Your Boat—Corner Lot Upper Sugarloaf Key FL [](https://expedia.com/Summerland-Key-Hotels-Castaway-To-Sugarloaf-Key-WaterfrontBring-Your-BoatCorner-Lot.h71734548.Hotel-Information) ![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/8ae32688_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sugar Loaf Lodge 17001 Overseas Hwy Summerland Key FL [](https://expedia.com/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information) ![Oceanside, pet friendly, smart home with plenty of paddle equipment](https://images.trvl-media.com/lodging/28000000/27140000/27130500/27130490/5d1dacb4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Oceanside, pet friendly, smart home with plenty of paddle equipment Cudjoe Key FL [](https://expedia.com/Cudjoe-Key-Hotels-Oceanside.h27130490.Hotel-Information) [See all 787 properties in Upper Sugarloaf Key](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package®ionId=553248635975865768) 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 - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Key West Hotels ](https://www.expedia.com/Key-West-Hotels.d1187.Travel-Guide-Hotels) - [Cudjoe Key Hotels ](https://www.expedia.com/Cudjoe-Key-Hotels.d3000430966.Travel-Guide-Hotels) - [Rv Parks in Cudjoe Key ](https://www.expedia.com/Cudjoe-Key-RV-Parks.d3000430966-aaRVParks.Travel-Guide-Accommodation) - [Cottages in Cudjoe Key ](https://www.expedia.com/Cudjoe-Key-Cottages.d3000430966-aaCottages.Travel-Guide-Accommodation) - [Resorts in Cudjoe Key ](https://www.expedia.com/Cudjoe-Key-Resorts.d3000430966-aaResorts.Travel-Guide-Accommodation) - [Beach Hotels in Cudjoe Key ](https://www.expedia.com/Cudjoe-Key-Hotels-Beach-Hotel.0-0-d3000430966-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels with Restaurants in Cudjoe Key ](https://www.expedia.com/Cudjoe-Key-Hotels-Hotels-With-Restaurants.0-0-d3000430966-tHotelswithRestaurants.Travel-Guide-Filter-Hotels) - 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