Title: The 10 Best 5 Star Hotels in Upper Matecumbe Key - 2025 Updated Prices | Expedia.co.uk [Upper Matecumbe Key Travel Guide](https://expedia.co.uk/Upper-Matecumbe-Key.dx553248635975749648)[Hotels in Upper Matecumbe Key](https://expedia.co.uk/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[Holiday Rentals in Upper Matecumbe Key](https://expedia.co.uk/Upper-Matecumbe-Key-Holiday-Rentals.d553248635975749648.Travel-Guide-HolidayRentals)[Flights to Upper Matecumbe Key](https://expedia.co.uk/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[Upper Matecumbe Key Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Upper-Matecumbe-Key.d553248635975749648.Car-Hire-Guide)[Upper Matecumbe Key Holidays](https://expedia.co.uk/Upper-Matecumbe-Key.d553248635975749648.Holidays-City-Breaks) ![Islamorada showing a beach bar](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191196-Islamorada.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Compare and book 5 Star hotels in Upper Matecumbe Key, Islamorada ![price find illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Upper Matecumbe Key 5 Star Hotels Tonight [9 Oct - 10 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2025-10-09&endDate=2025-10-10&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [10 Oct - 11 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2025-10-10&endDate=2025-10-11&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [10 Oct - 12 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [17 Oct - 19 Oct](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2025-10-17&endDate=2025-10-19&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Upper Matecumbe Key 5 Star Hotels ![Private beach, sun-loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/e32d7e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/9b929f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/79d31a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1220) "Beautiful and relaxing hotel!!" £167 includes taxes & fees 16 Oct - 17 Oct [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/9b3c41b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/0917a41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/2c922f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/5de75c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in the Keys Tavernier 8.4/10 Very good (10) "Thoroughly enjoyed our stay! The pool, beach area and pickleball courts were fantastic! Also enjoyed the premium cable. " [](https://www.expedia.co.uk/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/691ffb10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, memory-foam beds](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/478c87a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![75-inch Smart TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/e85faba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/4e0d8909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront House with Boat Dock Hammer Point 6.0/10 (1) "Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration." [](https://www.expedia.co.uk/Tavernier-Hotels-Waterfront-House-With-Boat-Dock.h109724487.Hotel-Information) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Upper-Matecumbe-Key-Hotels.s50-0-d553248635975749648.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Upper-Matecumbe-Key-Hotels.s50-0-d553248635975749648.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Upper Matecumbe Key. ![Hawks Cay Resort](https://images.trvl-media.com/lodging/1000000/10000/6100/6068/b1845555_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Hawks Cay Resort 61 Hawks Cay Blvd, Marathon, FL £299 23 Oct - 24 Oct includes taxes & fees 8/10 Very Good! (1,005 reviews) [](https://expedia.co.uk/Marathon-Hotels-Hawks-Cay-Resort.h6068.Hotel-Information) ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 97000 Overseas Hwy, Key Largo, FL £304 16 Oct - 17 Oct includes taxes & fees 8.6/10 Excellent! (1,006 reviews) [](https://expedia.co.uk/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Amara Cay Resort 80001 Overseas Hwy, Islamorada, FL £154 19 Oct - 20 Oct includes taxes & fees 8.8/10 Excellent! (1,253 reviews) [](https://expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Still don't see what you're looking for? [See all properties in Upper Matecumbe Key.](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635975749648&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635975749648&star=50&star=50&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635975749648&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635975749648&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635975749648&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=10%2F10%2F2025&endDate=11%2F10%2F2025®ionId=553248635975749648&star=50&star=50&amenities=WATER_PARK) 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. ## Learn more about Upper Matecumbe Key Venture to sights like Bud n' Mary's Dive Center and Florida Keys Brewing Co. as you discover Upper Matecumbe Key. [See all hotels in Upper Matecumbe Key](https://www.expedia.co.uk/Hotel-Search?startDate=2025-10-23&endDate=2025-10-24&adults=2®ionId=553248635975749648) ![Islamorada showing a beach bar](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191196-Islamorada.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Upper Matecumbe Key Hotel Reviews ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Staff was extremely accommodating, Property is stunning with numerous activities. " [](https://expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ## Find out more about Upper Matecumbe Key ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [3 Star Hotels in Brickell](https://www.expedia.co.uk/3Star-Brickell-Miami-Hotels.s30-n6240961-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Coconut Grove](https://www.expedia.co.uk/3Star-Coconut-Grove-Miami-Hotels.s30-n11937-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Coral Gables](https://www.expedia.co.uk/3Star-Coral-Gables-Hotels.s30-0-d7654.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Duck Key](https://www.expedia.co.uk/3Star-Duck-Key-Hotels.s30-0-d184267.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Florida City](https://www.expedia.co.uk/3Star-Florida-City-Hotels.s30-0-d8101.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Homestead](https://www.expedia.co.uk/3Star-Homestead-Hotels.s30-0-d7744.Travel-Guide-Filter-Hotels) - 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[Visit Lignumvitae Key Botanical State Park](https://www.expedia.co.uk/Lignumvitae-Key-Botanical-State-Park.dx553248621532652349) - [Visit Plantation Key](https://www.expedia.co.uk/Plantation-Key.dx553248635083898347) - [All inclusive Holiday Packages Lignumvitae Key Botanical State Park](https://www.expedia.co.uk/lp/theme-holidays/all-inclusive-holidays/553248621532652349/Lignumvitae-Key-Botanical-State-Park) - [Ace Rental Cars in Windley Key](https://www.expedia.co.uk/Ace-Car-Rentals-In-Windley-Key.d553248635976197663-c2.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Plantation Key](https://www.expedia.co.uk/Avis-Car-Rentals-In-Plantation-Key.d553248635083898347-c41.Car-Rental-Guide-Suppliers) - [Car hire Islamorada](https://www.expedia.co.uk/Compare-Cheap-Car-Hire-In-Islamorada.d10768.Car-Hire-Guide) - [Discount Car Rentals Rental Cars in Lower Matecumbe Key](https://www.expedia.co.uk/Discount-Car-Rentals-Car-Rentals-In-Lower-Matecumbe-Key.d553248635975749077-c11.Car-Rental-Guide-Suppliers) - [Drive-A-Matic Rental Cars in Windley Key](https://www.expedia.co.uk/Drive-A-Matic-Car-Rentals-In-Windley-Key.d553248635976197663-c1082.Car-Rental-Guide-Suppliers) - [Goldcar Key’n Go Rental Cars in Windley Key](https://www.expedia.co.uk/Goldcar-Keyn-Go-Car-Rentals-In-Windley-Key.d553248635976197663-c1044.Car-Rental-Guide-Suppliers) - [Localiza Argentina Rental Cars in Windley Key](https://www.expedia.co.uk/Localiza-Argentina-Car-Rentals-In-Windley-Key.d553248635976197663-c1097.Car-Rental-Guide-Suppliers) - [Megadrive Rental Cars in Lower Matecumbe Key](https://www.expedia.co.uk/MegaDrive-Car-Rentals-In-Lower-Matecumbe-Key.d553248635975749077-c1074.Car-Rental-Guide-Suppliers) - [Record Rent A Car Rental Cars in Lower Matecumbe Key](https://www.expedia.co.uk/Record-Rent-A-Car-Car-Rentals-In-Lower-Matecumbe-Key.d553248635975749077-c30.Car-Rental-Guide-Suppliers) - [Sixt Rental Cars in Plantation Key](https://www.expedia.co.uk/Sixt-Car-Rentals-In-Plantation-Key.d553248635083898347-c35.Car-Rental-Guide-Suppliers) - [U-Save Rental Cars in Lower Matecumbe Key](https://www.expedia.co.uk/U-Save-Car-Rentals-In-Lower-Matecumbe-Key.d553248635975749077-c34.Car-Rental-Guide-Suppliers) - [Islamorada Holiday Rentals](https://www.expedia.co.uk/Islamorada-Holiday-Rentals.d10768.Travel-Guide-HolidayRentals) - [Things to do in Islamorada](https://www.expedia.co.uk/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities) - [Things to do in Plantation Key](https://www.expedia.co.uk/Things-To-Do-In-Plantation-Key.d553248635083898347.Travel-Guide-Activities) - [Things to do in Windley Key](https://www.expedia.co.uk/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities) - [Book 5 Star Hotels in Upper Matecumbe Key on Expedia.com](https://www.expedia.com/5Star-Upper-Matecumbe-Key-Hotels.s50-0-d553248635975749648.Travel-Guide-Filter-Hotels)