Title: Book the Best BEACH RESORTS in Upper Matecumbe Key, FL from CA $165 - Upper Matecumbe Key Hotels on the Beach| 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 beach hotels in Upper Matecumbe Key, FL from CA $165 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.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 Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![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 Beach Hotel Tonight [Sep 27 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-09-27&endDate=2025-09-28&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 28 - Sep 29](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-09-28&endDate=2025-09-29&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-03&endDate=2025-10-05&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-10-10&endDate=2025-10-12&adults=2&amenities=BEACH&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Upper Matecumbe Key Beach Hotel ![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) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/ac9bc991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/31d6a642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 2 Queen Beds, Kitchenette, Bay View](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 (1007) "The location is great..nice beach and dock area..room was very nice.. will definitely plan to return for a longer stay" CA $112 CA $165 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/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) ![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) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop 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) ### Chesapeake Beach Resort Matecumbe 9.2/10 Wonderful (1540) "Great location, clean rooms, great amenities and the staff is very friendly. " CA $171 CA $270 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/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, sun 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 (1004) "Very nice place to stay " CA $149 CA $245 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/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) ![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 Suite Ocean View Two Bedroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/b513b652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort Matecumbe 9.2/10 Wonderful (1020) "Absolutely wonderful place, great view and staff was outstanding " CA $261 CA $387 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/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) ![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/5e728c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cottage](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/b8fa0acc.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 (541) "Spacious rooms and location was great for what we needed. " CA $102 CA $187 total includes taxes & fees Oct 2 - Oct 3 [](https://www.expedia.ca/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/1000000/70000/62000/61976/60b7c04d.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) ![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) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1259) "Great hotel with a perfect location and friendly staff." CA $220 CA $341 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Outdoor pool, sun 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) ![Beach/ocean view](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a11bb47b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun 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 8.6/10 Excellent (1006) "Great rooms" CA $179 CA $294 total includes taxes & fees Sep 29 - Sep 30 [](https://www.expedia.ca/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) ![Brand New Two King Bay Front | Private kitchen](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/4b05ab7b.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) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/641fc549.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Villas by Islander Resort Matecumbe 8.8/10 Excellent (390) "Great place to stay" CA $333 CA $468 total includes taxes & fees Oct 23 - Oct 24 [](https://www.expedia.ca/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) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/e32d7e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1214) "Beautiful and relaxing hotel!!" CA $115 CA $224 total includes taxes & fees Oct 1 - Oct 2 [](https://www.expedia.ca/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) ![Beach umbrellas, beach towels](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/658c83a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Family Suite, 2 Queen Beds, Refrigerator & Microwave](https://images.trvl-media.com/lodging/13000000/12660000/12653500/12653483/d3f952a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sands of Islamorada Matecumbe 8.8/10 Excellent (389) "The hotel was reasonably priced and while a little dated, the rooms were large and clean. The staff was SUPER nice. All in all, a great place to stay a couple nights in the keys at a reasonable price. Would definitely recommend!" CA $224 CA $271 total includes taxes & fees Sep 28 - Sep 29 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2025-10-11&endDate=2025-10-12®ionId=553248635975749648&adults=2&travelerType=beach&sort=RECOMMENDED&openPlayBack=true) ## Top Upper Matecumbe Key Hotel Reviews ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Clean room, ocean view, friendly staff. Highly recommended!" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Hampton Inn Key Largo Manatee Bay](//images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233_y.jpg) ### Hampton Inn Key Largo Manatee Bay 10/10 Excellent "The location is very nice, with a small private beach and beautiful views. The rooms were clean and spacious. The hot/cold breakfast was delicious. The pool and gym were good. Nicole the bartender at the tiki bar was friendly and great." [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Everything was perfect and beautiful " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "The resort had free kayaking and paddle boarding which was a great addition. " [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.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 "By far one of the best hotels in the keys. " [](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 "Very nice place to stay " [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "I love it" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Breezy Palms Resort](//images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg) ### Breezy Palms Resort 10/10 Excellent "Quaint" [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.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 "Great rooms" [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ## Explore a world of travel with Expedia - 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[Adults Only Resorts & in Islamorada](https://www.expedia.ca/Islamorada-Hotels-Adults-Only-Resorts.0-0-d10768-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Islamorada](https://www.expedia.ca/Islamorada-Hotels-All-Inclusive-Hotel.0-0-d10768-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Islamorada](https://www.expedia.ca/Islamorada-Hotels-Beach-Hotel.0-0-d10768-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Islamorada](https://www.expedia.ca/Islamorada-Hotels-Boutique-Hotel.0-0-d10768-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Cheap Hotels in Islamorada](https://www.expedia.ca/Islamorada-Hotels-Cheap-Hotels.0-0-d10768-tCheapHotels.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Islamorada](https://www.expedia.ca/Islamorada-Hotels-Couples-Resorts-Hotels.0-0-d10768-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Family Hotels in Islamorada](https://www.expedia.ca/Islamorada-Hotels-Family-Hotel.0-0-d10768-tFamilyHotel.Travel-Guide-Filter-Hotels) - 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