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 $679 per person May 21 - May 25 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 7.8/10 Good! (1,013 reviews) It’s totally sufficient for the type of hotel. Older but clean. Great location Reviewed on Mar 9, 2026 ![Casablanca Miami Beach](https://images.trvl-media.com/lodging/32000000/31660000/31652200/31652150/f54c02bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Casablanca Miami Beach North Beach $2,703 per person May 23 - May 28 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 5.8/10 (320 reviews) Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great. It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it. Reviewed on Feb 22, 2026 ![The Retreat Collection at 1 Hotel & Homes South Beach](https://images.trvl-media.com/lodging/13000000/12320000/12316600/12316590/e518a34f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Retreat Collection at 1 Hotel & Homes South Beach South Beach $7,428 per person May 20 - May 24 found 1 day ago Roundtrip flight included Boston (BOS) to Miami (MIA) 8/10 Very Good! (1 review) ### 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 Why not spend a lazy afternoon at Florida Keys Beaches during your trip to Long Beach Estates? [](https://expedia.com/Florida-Keys-Beaches-Florida.d553248635976496782.Vacation-Attraction) ![Stopped by the sea on a ride down the Overseas Highway from Miami to Key West. The bike is a KZ750 lent to me by the guy living in the condo next door. #TheKeys #florida #beach #kawasaki ](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=2026-03-11&endDate=2026-03-12)[Mar 11 - Mar 12](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=2026-03-11&endDate=2026-03-12) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=2026-03-12&endDate=2026-03-13)[Mar 12 - Mar 13](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=2026-03-12&endDate=2026-03-13) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026)[Mar 13 - Mar 15](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=3%2F13%2F2026&endDate=3%2F15%2F2026) [Next weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=3%2F20%2F2026&endDate=3%2F22%2F2026)[Mar 20 - Mar 22](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.Package&adults=2&openPlayBack=true®ionId=553248635975865768&startDate=3%2F20%2F2026&endDate=3%2F22%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/a76c0bc7_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 with Stunning Views](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/27d3efc7_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Starlight Serenity - Hideaway with Stunning Views Summerland Key FL [](https://expedia.com/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-With-Stunning-Views.h111873736.Hotel-Information) ![Sublimely private luxury home with enveloping oceanfront views near Key West](https://images.trvl-media.com/lodging/67000000/66820000/66812200/66812190/cc839a3f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sublimely private luxury home with enveloping oceanfront views near Key West Near Key West FL [](https://expedia.com/Sugarloaf-Key-Hotels-Luxurious-Oceanfront-Home-W-A-Private-Pool.h66812190.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) ![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) ![15% OFF PROMO: 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool](https://images.trvl-media.com/lodging/110000000/109870000/109860900/109860814/15f749fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 15% OFF PROMO: 3BR Lower Keys Remodel, Waterfront with 90-fT dock & private pool Cudjoe Key FL [](https://expedia.com/Summerland-Key-Hotels-July-25-Deal-Cudjoe-Cabana-New-CanalFront-With-Pool.h109860814.Hotel-Information) [See all 813 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. 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