Title: Visit Upper Matecumbe Key: Best of Upper Matecumbe Key Tourism | Expedia Travel Guide - Expedia.ca [Hotels in Upper Matecumbe Key](https://expedia.ca/Upper-Matecumbe-Key-Hotels.d553248635975749648.Travel-Guide-Hotels)[Vacation Rentals in Upper Matecumbe Key](https://expedia.ca/Upper-Matecumbe-Key-Vacation-Rentals.d553248635975749648.Travel-Guide-VacationRentals)[Flights to Upper Matecumbe Key](https://expedia.ca/Cheap-Flights-To-Upper-Matecumbe-Key.d553248635975749648.Travel-Guide-Flights)[Upper Matecumbe Key Car Rentals](https://expedia.ca/Car-Rentals-In-Upper-Matecumbe-Key.d553248635975749648.Car-Rental-Guide)[Upper Matecumbe Key Vacation Packages](https://expedia.ca/Upper-Matecumbe-Key.d553248635975749648.Destination-Travel-Guides) # Upper Matecumbe Key ## Travel Guide ![Islamorada which includes a beach bar](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191196-Islamorada.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Islamorada which includes a beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191179-Islamorada.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Islamorada](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191198-Islamorada.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Islamorada featuring mangroves, a marina and general coastal views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63855-Islamorada.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ![Islamorada featuring a beach, tropical scenes and general coastal views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63859-Islamorada.jpg?impolicy=fcrop&w=1040&h=580&q=mediumHigh) ## Visit Upper Matecumbe Key Things to do - Upper Matecumbe Key Hotel Deals - Vacation Rentals in Upper Matecumbe Key ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Chesapeake Beach Resort 83409 Overseas Hwy Islamorada FL CA $183 CA $284 total Dec 16 - Dec 17 includes taxes & fees Book a stay at this beach hotel in Islamorada. Enjoy free breakfast, free WiFi, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. ... 9.2/10 Wonderful! (1,592 reviews) Excellent !!!!! Reviewed on Dec 14, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&selected=4170&PinnedHotelID=4170&HadPinnedHotel=true®ionId=553248635975749648) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Amara Cay Resort 80001 Overseas Hwy Islamorada FL CA $238 CA $360 total Dec 18 - Dec 19 includes taxes & fees Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in ... 8.8/10 Excellent! (1,261 reviews) very nice staff, quiet and comfortable Reviewed on Dec 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=18%2F12%2F2025&endDate=19%2F12%2F2025&selected=61976&PinnedHotelID=61976&HadPinnedHotel=true®ionId=553248635975749648) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cheeca Lodge & Spa 81801 Overseas Highway, Mile Marker 82 Islamorada FL CA $271 CA $398 total Dec 16 - Dec 17 includes taxes & fees Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff ... 9.2/10 Wonderful! (1,268 reviews) Everything was awsome Reviewed on Dec 7, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&selected=5780&PinnedHotelID=5780&HadPinnedHotel=true®ionId=553248635975749648) [See all 2,818 properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=16%2F12%2F2025&endDate=17%2F12%2F2025®ionId=553248635975749648) 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. ![Breezy Palms Resort](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Breezy Palms Resort 80015 Overseas Highway Islamorada FL Book a stay at this beach aparthotel in Islamorada. Enjoy free WiFi, a beach locale, and a marina. Our guests praise the helpful staff and the clean rooms in ... 8.8/10 Excellent! (584 reviews) Great place over all! The bathroom excellent and the bed very comfortable. Reviewed on Dec 9, 2025 [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![The Islands of Islamorada](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Islands of Islamorada 82779 Old Hwy Islamorada FL Book a stay at this beach villa in Islamorada. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions History of Diving Museum and Islamorada ... 9.6/10 Exceptional! (69 reviews) Beautiful accommodations and location, very clean, many activities available at resort Reviewed on Nov 25, 2025 [](https://expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Treasure Harbor](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Treasure Harbor 200 Treasure Harbor Dr Islamorada FL Stay at this hotel in Islamorada. Enjoy free WiFi, free parking, and premium bedding. Our guests praise the helpful staff in our reviews. Popular attractions ... 8.8/10 Excellent! (117 reviews) I am obsessed with tiny houses and this one floats! It was so relaxing to sit on the deck and enjoy the view. The bed was very comfy and the gentle motion of the water put me right to sleep. The staff are friendly and helpful. Islamorada is beautiful and fun to explore. Reviewed on Nov 25, 2025 [](https://expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) [See all properties in Upper Matecumbe Key](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=553248635975749648&sort=VACATION_RENTAL) 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. ## Check Upper Matecumbe Key hotel availability [Tonight ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975749648&startDate=2025-12-15&endDate=2025-12-16)[Dec 15 - Dec 16](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975749648&startDate=2025-12-15&endDate=2025-12-16) [Tomorrow night ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975749648&startDate=2025-12-16&endDate=2025-12-17)[Dec 16 - Dec 17](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975749648&startDate=2025-12-16&endDate=2025-12-17) [This weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975749648&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025)[Dec 19 - Dec 21](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975749648&startDate=19%2F12%2F2025&endDate=21%2F12%2F2025) [Next weekend ](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975749648&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025)[Dec 26 - Dec 28](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=553248635975749648&startDate=26%2F12%2F2025&endDate=28%2F12%2F2025) ### Popular places to visit ![Florida Keys Brewing Co.](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497961-florida-keys-brewing-co.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Florida Keys Brewing Co. You can take time to visit Florida Keys Brewing Co. during your travels to Islamorada. [](https://expedia.ca/Florida-Keys-Brewing-Co-Islamorada.d553248635997958830.Vacation-Attraction) ![History of Diving Museum](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/497000/497744-history-of-diving-museum.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### History of Diving Museum 4/5(1 review) Trace one of the world’s most astonishing watersports back through the centuries to see some of the first diving suits as you explore this interactive museum, featuring the world's largest international collection of diving artifacts. [](https://expedia.ca/History-Of-Diving-Museum-Matecumbe.d6069257.Vacation-Attraction) ![Hurricane Monument showing outdoor art and a monument](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63861-Islamorada.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Hurricane Monument 4/5(1 review) The memories of those lost to the 1935 Labor Day Hurricane live on at this moving tribute and burial site along the Overseas Highway. [](https://expedia.ca/Hurricane-Monument-Matecumbe.d6063543.Vacation-Attraction) #### Bud n' Mary's Dive Center 1/5(1 review) Explore the waterfront of Bud n' Mary's Dive Center and enjoy other activities such as fishing in Islamorada. Discover the beautiful sunsets and seafood restaurants in this family-friendly area. [](https://expedia.ca/Bud-N-Marys-Dive-Center-Islamorada.d6069243.Vacation-Attraction) #### Islamorada Brewery & Distillery You can take time to visit Islamorada Brewery & Distillery during your travels to Islamorada. [](https://expedia.ca/Islamorada-Brewery-Distillery-Matecumbe.d885113391451107328.Vacation-Attraction) #### Keys History & Discovery Center You can spend time exploring the galleries in Keys History & Discovery Center during your trip to Islamorada. [](https://expedia.ca/Keys-History-Discovery-Center-Matecumbe.d885113749766311936.Vacation-Attraction) ## Cities near Upper Matecumbe Key ![Islamorada which includes tropical scenes and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63860-Islamorada.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Islamorada ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - [5 Star Hotels in Islamorada ](https://www.expedia.ca/5Star-Islamorada-Hotels.s50-0-d10768.Travel-Guide-Filter-Hotels) - [Hotels near Florida Keys Brewing Co. ](https://www.expedia.ca/Florida-Keys-Brewing-Co-Hotels.0-l553248635997958830-0.Travel-Guide-Filter-Hotels) - [Aparthotels in Islamorada ](https://www.expedia.ca/Islamorada-Apart-Hotels.d10768-aaApartHotels.Travel-Guide-Accommodation) - [Apartments in Islamorada ](https://www.expedia.ca/Islamorada-Apartments.d10768-aaApartments.Travel-Guide-Accommodation) - [B&B in Islamorada ](https://www.expedia.ca/Islamorada-Bed-And-Breakfast.d10768-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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[Flights from Toronto to Islamorada ](https://www.expedia.ca/lp/flights/178314/10768/toronto-to-islamorada) - [Flights from Tampa to Islamorada ](https://www.expedia.ca/lp/flights/602996/10768/tampa-to-islamorada) - [Visit Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key.dx553248635083902001) - [Visit Doctor's Arm ](https://www.expedia.ca/Big-Pine-Key-Doctors-Arm.dx553248635976472396) - [Visit Big Pine Key ](https://www.expedia.ca/Big-Pine-Key.dx7195) - [Visit Duck Key ](https://www.expedia.ca/Duck-Key.dx184267) - [Visit Florida City ](https://www.expedia.ca/Florida-City.dx8101) - [Visit Grassy Key ](https://www.expedia.ca/Grassy-Key.dx3000451823) - [Visit Homestead ](https://www.expedia.ca/Homestead.dx7744) - [Hurricane Monument ](https://www.expedia.ca/Hurricane-Monument-Matecumbe.d6063543.Vacation-Attraction) - [Visit Lower Matecumbe Beach ](https://www.expedia.ca/Islamorada-Lower-Matecumbe-Beach.dx553248635976195207) - [Visit Matecumbe ](https://www.expedia.ca/Islamorada-Matecumbe.dx855587555438403584) - [Visit Seabreeze Trailer Park ](https://www.expedia.ca/Islamorada-Seabreeze-Trailer-Park.dx553248635976480972) - [Visit Venetian Shores ](https://www.expedia.ca/Islamorada-Venetian-Shores.dx553248635976470270) - [Islamorada Vacations ](https://www.expedia.ca/Islamorada.d10768.Destination-Travel-Guides) - [Visit Islamorada ](https://www.expedia.ca/Islamorada.dx10768) - [Visit Anglers Park ](https://www.expedia.ca/Key-Largo-Anglers-Park.dx553248635976468912) - [Visit Buccaneer Point ](https://www.expedia.ca/Key-Largo-Buccaneer-Point.dx553248635976481137) - [Visit Largo Sound Village ](https://www.expedia.ca/Key-Largo-Largo-Sound-Village.dx553248635976481003) - [Visit Wynken Blynken and Nod ](https://www.expedia.ca/Key-Largo-Wynken-Blynken-And-Nod.dx553248635976473708) - [Visit Key Largo ](https://www.expedia.ca/Key-Largo.dx8369) - [Visit Layton ](https://www.expedia.ca/Layton.dx6177793) - [Visit Leisure City ](https://www.expedia.ca/Leisure-City.dx553248635975873036) - [Visit Little Torch Key ](https://www.expedia.ca/Little-Torch-Key.dx177498) - [Visit Long Key ](https://www.expedia.ca/Long-Key.dx177527) - [Visit Lower Matecumbe Key ](https://www.expedia.ca/Lower-Matecumbe-Key.dx553248635975749077) - [Visit Marathon ](https://www.expedia.ca/Marathon.dx2437) - [Visit No Name Key ](https://www.expedia.ca/No-Name-Key.dx553248635976193734) - [Visit No Name Key ](https://www.expedia.ca/No-Name-Key.dx862057009059553280) - [Visit Plantation Key ](https://www.expedia.ca/Plantation-Key.dx553248635083898347) - [Visit Ramrod Key ](https://www.expedia.ca/Ramrod-Key.dx6156102) - [Visit Rock Harbor ](https://www.expedia.ca/Rock-Harbor.dx553248635975874039) - [Visit Hammer Point ](https://www.expedia.ca/Tavernier-Hammer-Point.dx553248635976468900) - [Visit Plantation Key Colony ](https://www.expedia.ca/Tavernier-Plantation-Key-Colony.dx855588080238100480) - [Alamo Rent A Car Rental Cars in Islamorada ](https://www.expedia.ca/Alamo-Rent-A-Car-Car-Rentals-In-Islamorada.d10768-c6.Car-Rental-Guide-Suppliers) - [Car rental Islamorada ](https://www.expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide) - 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