Title: 4 Stars Hotels in Windley Key, Islamorada from CA $256 - 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) ![](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) # 4 Stars Hotels in Windley Key, Islamorada from CA $256 ![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 Windley Key 4 Star Hotels Tonight [Oct 2 - Oct 3](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-02&endDate=2025-10-03&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 3 - Oct 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-03&endDate=2025-10-04&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-03&endDate=2025-10-05&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-10&endDate=2025-10-12&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windley Key 4 Star Hotels ![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) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/1f0afa1e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/6e0cfc6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/7c755dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton Key Largo 8.6/10 Excellent (1001) "The food at Dry Rocks was great" CA $365 CA $488 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![One Bedroom Oceanfront Suite King](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 (1263) "Great hotel with a perfect location and friendly staff." CA $168 CA $282 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.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) ![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 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 (1001) "Stunning resort with great amenities and excellent service! " CA $268 CA $395 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58.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) ![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) ![House, 3 Bedrooms, Pool Access, Bay View (Balcony/Patio, Private Pool) | Beach](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/10dd6c61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Largo Resort & Spa, Autograph Collection Key Largo 9.0/10 Wonderful (1000) "By far one of the best hotels in the keys. " CA $333 CA $452 total includes taxes & fees Oct 8 - Oct 9 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![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) ![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, 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) ### La Siesta Resort & Villas Matecumbe 8.6/10 Excellent (1001) "Great rooms" CA $145 CA $256 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/531fe0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fa0090c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/5be55ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada Matecumbe 9.8/10 Exceptional (66) "Absolutely outstanding resort. Legitimate 5 star property. " CA $602 CA $754 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/4c18eaad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/d2d6a27b.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) ![Room, Multiple Beds, Private Pool, Garden View | Living room](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/5f28c00b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Caribbean Resort Coconut Palm North 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, Marker 82, Islamorada, FL CA $144 CA $257 total Oct 5 - Oct 6 includes taxes & fees 9/10 Wonderful! (1,221 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, 1313, Tavernier, FL [Get rates](https://expedia.ca/Hotel-Search?startDate=16%2F10%2F2025&endDate=17%2F10%2F2025&selected=93061348&PinnedHotelID=93061348&HadPinnedHotel=true®ionId=553248635976197663) 8.6/10 Excellent! (8 reviews) [](https://expedia.ca/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) ![Waterfront House with Boat Dock](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/691ffb10_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=16%2F10%2F2025&endDate=17%2F10%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=03%2F10%2F2025&endDate=04%2F10%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=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=553248635976197663&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=553248635976197663&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=553248635976197663&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%2F2025®ionId=553248635976197663&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=03%2F10%2F2025&endDate=04%2F10%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=2025-10-16&endDate=2025-10-17&adults=2®ionId=553248635976197663) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340299-Windley-Key-Fossil-Reef-Geological-State-Park.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ## Top Windley Key Hotel Reviews ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Loved the stay at Amara Cay! Will be back. Staff was amazing." [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Stunning resort with great amenities and excellent service! " [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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 "Beautiful place awesome staff very helpful ❤️❤️❤️❤️" [](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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[Book 4 Star Hotels in Windley Key on Expedia.com](https://www.expedia.com/4Star-Windley-Key-Hotels.s40-0-d553248635976197663.Travel-Guide-Filter-Hotels)