Title: TOP Upper Matecumbe Key Beach Resorts for 2026 - Hotels on the Beach in Upper Matecumbe Key, FL | 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 Florida. Beautiful Beach and Amazing Fishing. What else can you ask for.](https://images.trvl-media.com/place/10768/414c55a9-82b2-4829-857c-fd7c26e0bd48.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Cameron Abbott # Find Beach Resorts in Upper Matecumbe Key, FL - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](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) - ![](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 Beach Resorts & Hotels Tonight [8 Dec - 9 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2025-12-08&endDate=2025-12-09&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Tomorrow [9 Dec - 10 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2025-12-09&endDate=2025-12-10&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) This weekend [12 Dec - 14 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2025-12-12&endDate=2025-12-14&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) Next weekend [19 Dec - 21 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635975749648&startDate=2025-12-19&endDate=2025-12-21&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true&travelerType=beach) ## Top Upper Matecumbe Key Beach Resorts & Hotels ![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/d330cb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/ac9bc991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 2 Queen Beds, Kitchenette, Bay View | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/c0d44f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Jolla Resort Matecumbe 9.0/10 Wonderful (1002) "Great stay. Friendly staff, great accommodations, very nice complex. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shela [](https://www.expedia.co.uk/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ![Private beach, white sand, sun-loungers, beach towels](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/fa9b6bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillow-top beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/43f5c138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor spa tub](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/12d77a84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort Matecumbe 9.2/10 Wonderful (1584) "Excellent hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ALEXANDER £174 includes taxes & fees 11 Dec - 12 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45b47efd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/a571015b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45deddf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pines & Palms Resort Matecumbe 9.2/10 Wonderful (1000) "Very nice place to stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan [](https://www.expedia.co.uk/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, in-room safe, desk, blackout curtains](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/6ec44483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Islander Suite Ocean View Two Bedroom | Private kitchen | Coffee/tea maker](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/3ea0faf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort Matecumbe 9.2/10 Wonderful (1004) "This resort is beautiful and the rooms are decorated so tastefully. I highly recommend The Islander Resort for family fun and couples get aways alike. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Suzanne £314 includes taxes & fees 18 Dec - 19 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cottage | 1 bedroom, free WiFi](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/b8fa0acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cottage | Living area | TV](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/7a0bffa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98496c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezy Palms Resort Matecumbe 8.8/10 Excellent (583) "we stayed in the beach front cottage kitchen was stocked room was clean and the views were great friendly staff " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Terry £120 includes taxes & fees 9 Dec - 10 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Alligator Reef Oceanfront Accessible Room King Bed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/1b5ced17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/28233e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite King | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/2f598fe7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1258) "Great location right on the ocean " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) GREG £208 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/7578de06.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, Multiple Beds (Casa de Coco) | Dining room](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/9c557f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a375b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas Matecumbe 8.8/10 Excellent (1001) "Great stay and beautiful space" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amir £177 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/70514579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, pool loungers](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/641fc549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/8ad54011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/29faa902.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Villas by Islander Resort Matecumbe 8.8/10 Excellent (400) "I loved the property, the staff and all the amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Janeth £248 includes taxes & fees 16 Dec - 17 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/9b929f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1270) "It was awesome, great service, staff members are helpful, clean and tidy room with excellent views!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sami £247 includes taxes & fees 16 Dec - 17 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Kitchenette, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/0cb6bab7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/2b7458ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, Refrigerator & Microwave | In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/d3f952a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, Refrigerator & Microwave | In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/b1df7837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sands of Islamorada Matecumbe 8.8/10 Excellent (391) "The rooms were recently remodeled and very nice. People are really nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Tammie £165 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information) 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. [View all properties](https://expedia.co.uk/Hotel-Search?startDate=2025-12-22&endDate=2025-12-23®ionId=553248635975749648&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Top Upper Matecumbe Key Hotel Reviews ![The Pelican Key Largo Cottages](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg) ### The Pelican Key Largo Cottages 10/10 Excellent "Magical spot. " [](https://expedia.co.uk/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Great location right on the ocean " [](https://expedia.co.uk/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "It was awesome, great service, staff members are helpful, clean and tidy room with excellent views!" [](https://expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "This resort is beautiful and the rooms are decorated so tastefully. I highly recommend The Islander Resort for family fun and couples get aways alike. " [](https://expedia.co.uk/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Waterside Suites & Marina](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Great property with boat slips " [](https://expedia.co.uk/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Casa Morada](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/46d4fa27_y.jpg) ### Casa Morada 10/10 Excellent "always a pleasant stay." [](https://expedia.co.uk/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) ![Sands of Islamorada](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/0cb6bab7_y.jpg) ### Sands of Islamorada 10/10 Excellent "The rooms were recently remodeled and very nice. People are really nice." [](https://expedia.co.uk/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information) ![Hadley Resort and Marina](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd_y.jpg) ### Hadley Resort and Marina 10/10 Excellent "Gisselle and her daughter who helped us were great. We enjoyed the property and thr room. Beautiful views, spacious and comfortable. Location was perfect. The front desk had just dealt with unkind clients but when it came to us they put aside whay they had just dealt with and greeted us with a smile. The ability to do thay was refreshing and they get A plus in customer serivce." [](https://expedia.co.uk/Islamorada-Hotels-Hadley-House-Islamorada.h12200.Hotel-Information) ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "Great stay and beautiful space" [](https://expedia.co.uk/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [5 Star Hotels in Islamorada ](https://www.expedia.co.uk/5Star-Islamorada-Hotels.s50-0-d10768.Travel-Guide-Filter-Hotels) - [Hotels Suites in Brickell ](https://www.expedia.co.uk/Brickell-Miami-Hotels-Hotel-Suites.0-n6240961-0-thotelsuites.Travel-Guide-Filter-Hotels) - [Hotels with a Bar in Brickell ](https://www.expedia.co.uk/Brickell-Miami-Hotels-Hotel-With-A-Bar.0-n6240961-0-thotelwithabar.Travel-Guide-Filter-Hotels) - [Hotels with Airport Transfers in Brickell ](https://www.expedia.co.uk/Brickell-Miami-Hotels-Hotel-With-Airport-Transfers.0-n6240961-0-thotelwithairporttransfers.Travel-Guide-Filter-Hotels) - 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