Title: Book the Best Upper Matecumbe Key LUXURY Hotels - Upscale Hotels in Upper Matecumbe Key, FL | Expedia.ca [Upper Matecumbe Key Travel Guide](https://expedia.ca/Upper-Matecumbe-Key.dx553248635975749648)[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) ![Islamorada which includes 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) # Find luxury hotels in Upper Matecumbe Key, FL ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](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 Luxury Hotels Tonight [Oct 20 - Oct 21](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-20&endDate=2025-10-21&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Tomorrow [Oct 21 - Oct 22](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-21&endDate=2025-10-22&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-24&endDate=2025-10-26&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-31&endDate=2025-11-02&adults=2&propertyStyle=LUXURY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=luxury_property) ## Top Upper Matecumbe Key Luxury Hotels ## 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 "Nice room with everything you need." [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](//images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544_y.jpg) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 10/10 Excellent "We had the absolute best fall break vacation here and will most definitely be back" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Resort offered alot considering it was somewhat smaller. Excellent staff and rooms/amenities..will definitely go back. " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Beautiful place. Would go back again." [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Playa Largo Resort & Spa, Autograph Collection](//images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg) ### Playa Largo Resort & Spa, Autograph Collection 10/10 Excellent "In the beginning the reception counter didn’t give me good service, she assigned a bad room when I complained she assigned another bad room, until the manager came and find an appropriate one for me" [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Pines & Palms Resort](//images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "This place is a gem. Rented the 3 bedroom with ocean view. Very clean and everyone was great Highly recommd" [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "This was our second stay there and will definitely go back. The location is great and there is plenty of well-maintained beach area to enjoy. The room was large, clean and updated. However, the view from the room left a lot to be desired. We booked a standard room so we didn't have expectations one way or the other, but the window was located chest-up (bottom half was wall) and overlooked the roof of the restaurant. We did have a partial view of the ocean, but only if you looked out the corner. The Rum Runner (water taxi) and free shuttle were great amenities to have!" [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![La Siesta Resort & Villas](//images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "Excellent stay with great amenities." [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Holiday Inn Key Largo by IHG](//images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg) ### Holiday Inn Key Largo by IHG 10/10 Excellent "Awesome trip stayed there for seven days had a blast down by the pool and the tiki hut and the iguanas are fun to watch as are the curly tail lizards no problem we had in the room was the toilet didn’t flush very well. It did flush but it was slow. The restaurant next-door within walking distance is nice pool tables and some other games and all we had a great time if you do go here make sure you go to Rob’s Marina feed the tarpon and go along the snorkeling trip to the lighthouse. You will be amazed. Happy travels." 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[Ski Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Ski-Hotel.0-0-d178286-tSkiHotel.Travel-Guide-Filter-Hotels) - [Waterpark Hotels in Miami](https://www.expedia.ca/Miami-Hotels-Waterpark-Hotels.0-0-d178286-tWaterparkHotels.Travel-Guide-Filter-Hotels) - [Cheap Hotels in North Key Largo](https://www.expedia.ca/North-Key-Largo-Hotels-Cheap-Hotels.0-0-d553248635976475358-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in North Key Largo](https://www.expedia.ca/North-Key-Largo-Hotels-Luxury-Hotel.0-0-d553248635976475358-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Book Luxury Hotels in Upper Matecumbe Key on Expedia.com](https://www.expedia.com/Upper-Matecumbe-Key-Hotels-Luxury-Hotel.0-0-d553248635975749648-tLuxuryHotel.Travel-Guide-Filter-Hotels)