Title: Hotels by Hersha Hospitality in Upper Matecumbe Key from CA $383 | 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 Hotels by Hersha Hospitality in Upper Matecumbe Key from CA $383 - ![](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 prices for these dates Tonight [Nov 2 - Nov 3](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-02&endDate=2025-11-03&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 3 - Nov 4](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-03&endDate=2025-11-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975749648&startDate=2025-11-14&endDate=2025-11-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Upper Matecumbe Key Hersha Hospitality Hotels ![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) ![1 bedroom, premium bedding, in-room safe, desk](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](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort Matecumbe 9.2/10 Wonderful (1014) "Staff at resort were extremely friendly and helpful. Highly recommend if visiting Islamorada" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thalia CA $265 CA $393 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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) ![Restaurant](https://images.trvl-media.com/lodging/4000000/3870000/3861400/3861342/29faa902.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) ![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 (392) "The property was quiet and clean" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leah CA $256 CA $383 total includes taxes & fees Nov 20 - Nov 21 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.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=2025-11-16&endDate=2025-11-17®ionId=553248635975749648&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FUpper-Matecumbe-Key-Hotels-Hersha-Hospitality.0-0-d553248635975749648--bHershaHospitality.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FUpper-Matecumbe-Key-Hotels-Hersha-Hospitality.0-0-d553248635975749648--bHershaHospitality.Travel-Guide-Filter-Hotels) ## Top Upper Matecumbe Key Hotel Reviews ![Breezy Palms Resort](//images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg) ### Breezy Palms Resort 10/10 Excellent "Room was wonderful " [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Staff were fantastic, the property was very clean, room was good." [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "I was very pleased with the resort. It’s a quiet hidden gem with a friendly and helpful staff. I would love to stay here again." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.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 "peaceful" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Rock Reef Resort](//images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "Clean, lovely grounds, park right at room" [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "A few problems with the room, ex. Coffee maker, sink in bathroom, shower, but over all excelent " [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Pines & Palms Resort](//images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "Wonderful place! Love all the new upgrades and remodeling since our last stay years ago. Our little bungalow was so cozy and private. Look forward to coming back in the future. " [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.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 "Everything was cleaning and good working order staff was wonderful." [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.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 "Buen servicio " [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [5 Star Hotels in Islamorada](https://www.expedia.ca/5Star-Islamorada-Hotels.s50-0-d10768.Travel-Guide-Filter-Hotels) - [Hilton Hotels in Big Pine Key](https://www.expedia.ca/Big-Pine-Key-Hotels-Hilton-Hotels.0-0-d7195--bHiltonHotels.Travel-Guide-Filter-Hotels) - [Aimbridge Hospitality Hotels in Blue Waters](https://www.expedia.ca/Blue-Waters-Tavernier-Hotels-Aimbridge-Hospitality.0-n553248635976472188-0--bAimbridgeHospitality.Travel-Guide-Filter-Hotels) - [Marriott Hotels & Resorts in Country Walk](https://www.expedia.ca/Country-Walk-Miami-Hotels-Marriott-Hotels-Resorts.0-n553248635975848802-0--bMarriottHotelsResorts.Travel-Guide-Filter-Hotels) - 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