Title: 4 Stars Hotels in Windley Key, Islamorada from CA $332 - Find Cheap Windley Key Hotels With 4 Stars | 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) ![Theater of the Sea](https://images.trvl-media.com/place/6069249/5a39f3a2-0de6-49e9-a8f9-b4e8e17b70ba.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Windley Key, Islamorada from CA $332 - ![](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 Windley Key 4 Star Hotels Tonight [Dec 12 - Dec 13](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-12&endDate=2025-12-13&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 13 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-13&endDate=2025-12-14&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-12&endDate=2025-12-14&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-19&endDate=2025-12-21&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Windley Key 4-star hotels ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/2728b985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Room King | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/43c465e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite Two Queens Lanai](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/a737b04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Matecumbe 8.8/10 Excellent (1262) "very nice staff, quiet and comfortable" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dana CA $248 CA $371 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/7c755dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/4de34d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch LCD TV with satellite channels, TV, iPod dock](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/3b0a2582.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) Key Largo 8.6/10 Excellent (1004) "Beautiful and relaxing stay " ![Sweden](https://a.travel-assets.com/egds/marks/flags/se.svg) Pauline CA $356 CA $476 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/8c74658c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/92d23e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/ba58782b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/d9cc2f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Largo Resort & Spa, Autograph Collection [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) Rock Harbor 8.8/10 Excellent (1000) "Beautiful location, great views, very clean property, room was great (great bed), friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Scott CA $453 CA $586 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/2bff44ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5d218fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/d49c45e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1002) "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 CA $379 CA $520 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Ocean View](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/c134a889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Ocean View | Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/b304e7ea.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/eed3d949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) Matecumbe 8.8/10 Excellent (1000) "Great stay and beautiful space" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amir CA $213 CA $332 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fcc01350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/55a08207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) Matecumbe 9.8/10 Exceptional (69) "Great for family vacation with kids. love it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dixania CA $825 CA $1,004 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/7d71db4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds, Private Pool, Garden View | Living room](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/b7e4c2f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Multiple Beds, Private Pool, Garden View | Living room](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/f68ce2f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/4c18eaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Caribbean Resort Coconut Palm North [](https://www.expedia.ca/Islamorada-Hotels-The-Caribbean-Resort-Hemingway-House-North.h60289884.Hotel-Information) Matecumbe [](https://www.expedia.ca/Islamorada-Hotels-The-Caribbean-Resort-Hemingway-House-North.h60289884.Hotel-Information) ![](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%2F4Star-Windley-Key-Hotels.s40-0-d553248635976197663.Travel-Guide-Filter-Hotels)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F4Star-Windley-Key-Hotels.s40-0-d553248635976197663.Travel-Guide-Filter-Hotels) ## Explore similar 5-star hotels Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Windley Key. ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Cheeca Lodge & Spa 81801 Overseas Highway, Mile Marker 82 Islamorada FL CA $271 CA $398 total Dec 16 - Dec 17 includes taxes & fees 9.2/10 Wonderful! (1,268 reviews) [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Condo in the Keys](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/9b3c41b7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Condo in the Keys 500 Burton Dr Tavernier FL [Get rates](https://expedia.ca/Hotel-Search?startDate=27%2F12%2F2025&endDate=28%2F12%2F2025&selected=93061348&PinnedHotelID=93061348&HadPinnedHotel=true®ionId=553248635976197663) 7.8/10 Good! (13 reviews) [](https://expedia.ca/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) ![Waterfront House with Boat Dock](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/5d9195bd_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Waterfront House with Boat Dock 213 Aberdeen Ct Tavernier FL [Get rates](https://expedia.ca/Hotel-Search?startDate=27%2F12%2F2025&endDate=28%2F12%2F2025&selected=109724487&PinnedHotelID=109724487&HadPinnedHotel=true®ionId=553248635976197663) 6/10 (1 review) [](https://expedia.ca/Tavernier-Hotels-Waterfront-House-With-Boat-Dock.h109724487.Hotel-Information) Still don't see what you're looking for? [See all properties in Windley Key.](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635976197663&star=40) You can also use these popular filters to refine your search. [Pool](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635976197663&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635976197663&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635976197663&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635976197663&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=14%2F12%2F2025&endDate=15%2F12%2F2025®ionId=553248635976197663&star=40&star=40&amenities=WATER_PARK) 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. ## Learn more about Windley Key Check out the local area in Windley Key as you venture to sights like Windley Key Fossil Reef Geological State Park. [See all hotels in Windley Key](https://www.expedia.ca/Hotel-Search?startDate=2025-12-27&endDate=2025-12-28&adults=2®ionId=553248635976197663) ![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Windley Key Hotel Reviews ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "very nice staff, quiet and comfortable" [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Baker's Cay Resort Key Largo, Curio Collection by Hilton](https://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 "Staff was amazing and process was fast and painless" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ## Find out more about Windley Key If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Windley Key are calling your name. Known for providing first-rate service in amazing locations, each of the Windley Key 4 Stars hotels lets discerning travelers bask in an unforgettable experience. Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day. It’s all waiting for you at the top four star hotels in Windley Key. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Windley Key, Islamorada, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Windley Key hotels with 4 Stars provide everything you need to unwind in style. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [1 Star Hotels in Eden Pines ](https://www.expedia.ca/1Star-Eden-Pines-Big-Pine-Key-Hotels.s10-n553248635976471710-0.Travel-Guide-Filter-Hotels) - [1 Star Hotels in Riviera Estates ](https://www.expedia.ca/1Star-Riviera-Estates-Miami-Hotels.s10-n553248635976469340-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Coconut Grove ](https://www.expedia.ca/2Star-Coconut-Grove-Miami-Hotels.s20-n11937-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Kendall ](https://www.expedia.ca/2Star-Kendall-Miami-Hotels.s20-n8226-0.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Key Largo ](https://www.expedia.ca/2Star-Key-Largo-Hotels.s20-0-d8369.Travel-Guide-Filter-Hotels) - [2 Star Hotels in Plantation Key ](https://www.expedia.ca/2Star-Plantation-Key-Hotels.s20-0-d553248635083898347.Travel-Guide-Filter-Hotels) - 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