Title: The 10 Best 5 Star Hotels in Windley Key - 2025 Updated Prices | Expedia.co.uk [Windley Key Travel Guide](https://expedia.co.uk/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.co.uk/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Holiday Rentals in Windley Key](https://expedia.co.uk/Windley-Key-Holiday-Rentals.d553248635976197663.Travel-Guide-HolidayRentals)[Flights to Windley Key](https://expedia.co.uk/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.co.uk/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Windley Key Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Windley-Key.d553248635976197663.Car-Hire-Guide)[Windley Key Holidays](https://expedia.co.uk/Windley-Key.d553248635976197663.Holidays-City-Breaks) ![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) # Compare and book 5 Star hotels in Windley Key, Islamorada - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 5 Star Hotels Tonight [27 Nov - 28 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976197663&startDate=2025-11-27&endDate=2025-11-28&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [28 Nov - 29 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976197663&startDate=2025-11-28&endDate=2025-11-29&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976197663&startDate=2025-11-28&endDate=2025-11-30&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=553248635976197663&startDate=2025-12-05&endDate=2025-12-07&adults=2&star=50&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Windley Key 5 Star Hotels ![Private beach, sun-loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/e32d7e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/79d31a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/9b929f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1278) "Everything about our stay was amazing and exceeded our expectations in every way!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Frances £214 includes taxes & fees 15 Dec - 16 Dec [](https://www.expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/9b3c41b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/0917a41a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/ab76abc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/94000000/93070000/93061400/93061348/5de75c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Condo in the Keys Tavernier 8.0/10 Very good (12) "This is going to be my go to whenever I go to the Key Largo area. Very comfortable accommodations. What amazed me is that the full kitchen not only jad appliances but dishes, silverware, pots and pans. Great pool area and on site cafe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sheila [](https://www.expedia.co.uk/Tavernier-Hotels-Condo-In-The-Keys.h93061348.Hotel-Information) ![Design Villa, Canal View | Balcony](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/5d9195bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, memory-foam beds](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/478c87a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/cc96c50e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/4e0d8909.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront House with Boat Dock Hammer Point 6.0/10 (1) "Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew [](https://www.expedia.co.uk/Tavernier-Hotels-Waterfront-House-With-Boat-Dock.h109724487.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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Windley-Key-Hotels.s50-0-d553248635976197663.Travel-Guide-Filter-Hotels)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2F5Star-Windley-Key-Hotels.s50-0-d553248635976197663.Travel-Guide-Filter-Hotels) ## Explore similar 4-star hotels Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Windley Key. ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Amara Cay Resort 80001 Overseas Hwy Islamorada FL £170 4 Dec - 5 Dec includes taxes & fees 8.8/10 Excellent! (1,268 reviews) [](https://expedia.co.uk/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?impolicy=resizecrop&rw=402&ra=fit) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton 97000 Overseas Hwy Key Largo FL £253 30 Nov - 1 Dec includes taxes & fees 8.6/10 Excellent! (1,003 reviews) [](https://expedia.co.uk/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Playa Largo Resort & Spa, Autograph Collection](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Playa Largo Resort & Spa, Autograph Collection 97450 Overseas Highway Key Largo FL £258 2 Dec - 3 Dec includes taxes & fees 8.8/10 Excellent! (1,002 reviews) [](https://expedia.co.uk/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) Still don't see what you're looking for? [See all properties in Windley Key.](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F11%2F2025&endDate=29%2F11%2F2025®ionId=553248635976197663&star=50) You can also use these popular filters to refine your search. [Pool](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F11%2F2025&endDate=29%2F11%2F2025®ionId=553248635976197663&star=50&star=50&amenities=POOL)[Spa](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F11%2F2025&endDate=29%2F11%2F2025®ionId=553248635976197663&star=50&star=50&amenities=SPA_ON_SITE)[Hot tub](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F11%2F2025&endDate=29%2F11%2F2025®ionId=553248635976197663&star=50&star=50&amenities=HOT_TUB)[Breakfast included](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F11%2F2025&endDate=29%2F11%2F2025®ionId=553248635976197663&star=50&star=50&amenities=FREE_BREAKFAST)[Waterpark](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Hotel&startDate=28%2F11%2F2025&endDate=29%2F11%2F2025®ionId=553248635976197663&star=50&star=50&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 Venture to sights like Windley Key Fossil Reef Geological State Park as you discover the local area in Windley Key. [See all hotels in Windley Key](https://www.expedia.co.uk/Hotel-Search?startDate=2025-12-11&endDate=2025-12-12&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 ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Nice place " [](https://expedia.co.uk/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ## Find out more about Windley Key ## Explore a world of travel with Expedia - Accommodation - Flights - Packages - Cars - Holiday Homes - Other - More ways to book - [3 Star Hotels in Brickell](https://www.expedia.co.uk/3Star-Brickell-Miami-Hotels.s30-n6240961-0.Travel-Guide-Filter-Hotels) - [3 Star Hotels in Coconut Grove](https://www.expedia.co.uk/3Star-Coconut-Grove-Miami-Hotels.s30-n11937-0.Travel-Guide-Filter-Hotels) - 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