Title: Hotels by Hersha Hospitality in Windley Key from CA $350 | Expedia.ca [Windley Key Travel Guide](https://expedia.ca/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Vacation Rentals in Windley Key](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Flights to Windley Key](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Windley Key Car Rentals](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[Windley Key Vacation Packages](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340299-Windley-Key-Fossil-Reef-Geological-State-Park.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels by Hersha Hospitality in Windley Key from CA $350 ![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 prices for these dates Tonight [Sep 22 - Sep 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-09-22&endDate=2025-09-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Sep 23 - Sep 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-09-23&endDate=2025-09-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Sep 26 - Sep 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-09-26&endDate=2025-09-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-03&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windley Key Hersha Hospitality Hotels ## Our top choices for Windley Key Hersha Hospitality ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.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) ![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 Resort Matecumbe 9.2/10 Wonderful (1012) "Absolutely wonderful place, great view and staff was outstanding " CA $228 CA $350 total includes taxes & fees Sep 28 - Sep 29 [](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) ![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 (388) "Great place to stay" CA $272 CA $399 total includes taxes & fees Sep 28 - Sep 29 [](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=2025-10-06&endDate=2025-10-07®ionId=553248635976197663&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%2FWindley-Key-Hotels-Hersha-Hospitality.0-0-d553248635976197663--bHershaHospitality.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Hotels-Hersha-Hospitality.0-0-d553248635976197663--bHershaHospitality.Travel-Guide-Filter-Hotels) ## Top Windley Key Hotel Reviews ![Waterside Suites & Marina](//images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Love the location and the room. Made for a great fishing trip with my son & grand daughter. Well be return in the near future." [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Staff has been so accommodating, the pool and the grounds are beautiful, rooms are very comfortable. Great place!" [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.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 "Bakers Cay was a wonderful place to stay and unwind. The service was outstanding and location perfect. Thank you" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Beautiful and relaxing hotel!!" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Alot of fun things to do including kayaking, paddle board, vollyball,ping pong and bikes." [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Marina Del Mar Resort and Marina](//images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg) ### Marina Del Mar Resort and Marina 10/10 Excellent "Loved " [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Rock Reef Resort](//images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "Room was like an efficiency apartment, even had a full kitchen. " [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![The Pelican Key Largo Cottages](//images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg) ### The Pelican Key Largo Cottages 10/10 Excellent "Very friendly staff and cool property. Also the beach area and snorkeling!" [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Very clean property, good breakfast included and the views are spectacular!! Beautiful beach location!! Would go back anytime!! 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[Pickup Car Rentals in Islamorada](https://www.expedia.ca/Pickup-Car-Rentals-In-Islamorada.d10768-tPickup.Car-Rental-Guide-Class) - [Pickup Car Rentals in Plantation Key](https://www.expedia.ca/Pickup-Car-Rentals-In-Plantation-Key.d553248635083898347-tPickup.Car-Rental-Guide-Class) - [Sixt Rental Cars in Islamorada](https://www.expedia.ca/Sixt-Car-Rentals-In-Islamorada.d10768-c35.Car-Rental-Guide-Suppliers) - [Thrifty Car Rental Rental Cars in Islamorada](https://www.expedia.ca/Thrifty-Car-Rental-Car-Rentals-In-Islamorada.d10768-c45.Car-Rental-Guide-Suppliers) - [Islamorada Vacation Rentals](https://www.expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals) - [Things to do in Islamorada](https://www.expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities) - [Book Hersha Hospitality in Windley Key on Expedia.com](https://www.expedia.com/Windley-Key-Hotels-Hersha-Hospitality.0-0-d553248635976197663--bHershaHospitality.Travel-Guide-Filter-Hotels)