Title: 4 Stars Hotels in Windley Key, Islamorada from CA $312 - 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) ![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # 4 Stars Hotels in Windley Key, Islamorada from CA $312 - ![](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 [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-23&endDate=2025-11-24&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 24 - Nov 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-24&endDate=2025-11-25&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-28&endDate=2025-11-30&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-05&endDate=2025-12-07&adults=2&star=40&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windley Key 4 Star Hotels ![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 (1266) "Great place and great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $214 CA $335 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/7c755dc1.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) ![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) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton Key Largo 8.6/10 Excellent (1001) "Beautiful and relaxing stay " ![Sweden](https://a.travel-assets.com/egds/marks/flags/se.svg) Pauline CA $357 CA $480 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.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) ![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) ![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 Rock Harbor 9.0/10 Wonderful (1002) "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 $337 CA $457 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.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) ![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) ![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 (1011) "The room and amenities were great and it was quiet.. just what we needed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $339 CA $477 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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) ![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) ![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) ### La Siesta Resort & Villas Matecumbe 8.8/10 Excellent (1001) "Excellent stay with great amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $194 CA $312 total includes taxes & fees Nov 30 - Dec 1 [](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) ![Poolside bar](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/5be55ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a93dc7d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada Matecumbe 9.8/10 Exceptional (68) "Great for family vacation with kids. love it" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dixania CA $987 CA $1,188 total includes taxes & fees Nov 30 - Dec 1 [](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) ![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) ![Lake](https://images.trvl-media.com/lodging/61000000/60290000/60289900/60289884/1d5cc14d.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 Islamorada FL CA $358 CA $498 total Dec 1 - Dec 2 includes taxes & fees 9/10 Wonderful! (1,270 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=07%2F12%2F2025&endDate=08%2F12%2F2025&selected=93061348&PinnedHotelID=93061348&HadPinnedHotel=true®ionId=553248635976197663) 7.8/10 Good! (11 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=07%2F12%2F2025&endDate=08%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=24%2F11%2F2025&endDate=25%2F11%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=24%2F11%2F2025&endDate=25%2F11%2F2025®ionId=553248635976197663&star=40&star=40&amenities=POOL)[Spa](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F11%2F2025&endDate=25%2F11%2F2025®ionId=553248635976197663&star=40&star=40&amenities=SPA_ON_SITE)[Hot tub](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F11%2F2025&endDate=25%2F11%2F2025®ionId=553248635976197663&star=40&star=40&amenities=HOT_TUB)[Breakfast included](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F11%2F2025&endDate=25%2F11%2F2025®ionId=553248635976197663&star=40&star=40&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=24%2F11%2F2025&endDate=25%2F11%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=2025-12-07&endDate=2025-12-08&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 ![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 "As always great staff and amenities. I go there as often as I can , always love it. This time it was off season and they upgraded me to an ocean view for my birthday! 😊" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Rooms were clean, landscape was beautiful, staff was friendly. Access to the (2) other resorts were a plus. Would stay again." [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.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)