Title: Browse the Best Windley Key Resorts | 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) # Search Resort Hotels in Windley Key - ![](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 prices for these dates Next weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-12&endDate=2025-12-14&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-09&endDate=2026-01-11&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windley Key Resorts ![Private beach, sun loungers, beach towels, scuba diving](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/c5948ba3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/cb9f9f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4dfe75fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Islamorada 9.0/10 Wonderful (109) "Our view of the beach was beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $309 CA $440 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/393ff3a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/4b49fc53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Standard King Bed](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/e7a0378c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lime Tree Bay Resort Long Key 9.2/10 Wonderful (1091) "Excellent stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua CA $158 CA $241 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.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) ![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) ![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) ![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) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1252) "The rooms were clean, staff was friendly and helpful, food was delicious, the property was beautiful and loved how there was connections to the other resorts through van transportation or the Rum runner boat! Would definitely stay again! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lucia CA $197 CA $315 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.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) ![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) ![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) ### Playa Largo Resort & Spa, Autograph Collection Rock Harbor 9.0/10 Wonderful (1003) "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 $335 CA $454 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.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) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1267) "It was absolutely beautiful and the staff was always super nice!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary CA $269 CA $398 total includes taxes & fees Dec 17 - Dec 18 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/3b0a2582.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 (1010) "Beautiful and relaxing stay " ![Sweden](https://a.travel-assets.com/egds/marks/flags/se.svg) Pauline CA $378 CA $503 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.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) ![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) ![Beach/ocean view](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a11bb47b.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 8.8/10 Excellent (1001) "Clean rooms, great ambiance and service. Would definitely go again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gary CA $176 CA $292 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Private beach, white sand](https://images.trvl-media.com/lodging/113000000/112180000/112177000/112176968/e786ed3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment, 2 Bedrooms, Patio, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/113000000/112180000/112177000/112176968/7a0dd395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/113000000/112180000/112177000/112176968/3678f39a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, Ocean View | Living area](https://images.trvl-media.com/lodging/113000000/112180000/112177000/112176968/a6fc4b95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Matecumbe Resort Matecumbe 8.8/10 Excellent (83) "Safe covered parking and stocked kitchen" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Bonnie CA $170 CA $191 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Islamorada-Hotels-Matecumbe-Resort.h112176968.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=2025-11-30&endDate=2025-12-01®ionId=553248635976197663&adults=2&lodging=HOTEL_RESORT&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-Resort-Hotels.d553248635976197663-aaResortHotels.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Resort-Hotels.d553248635976197663-aaResortHotels.Travel-Guide-Accommodation) ## Top Windley Key Hotel Reviews ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Rooms were clean big and had a great view. The staff was amazing. " [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ### Cheeca Lodge & Spa 10/10 Excellent "Amazing!" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ### Chesapeake Beach Resort 10/10 Excellent "Room was clean, breakfast and staff were good " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Rock Reef Resort](//images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "This place was awesome. Friendly staff. Would definitely stay again if in the area." [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.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 "Clean room , coconut beach was wonderful, the other beach too. Nice rooms with nice views " [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ### Coconut Cove Resort and Marina 10/10 Excellent "Really really enjoyed the laid back style at this resort and what a beautiful property. Will be back soon!" [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Waterside Suites & Marina](//images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Nice room. Great staff" [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ### Amara Cay Resort 10/10 Excellent "Very nice resort! Nice pool and the tiki bar was amazing. Great service and so close to Bud and Mary’s since we were fishing a few days. Definitely will return." [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ### Lime Tree Bay Resort 10/10 Excellent "Room was spotless the view was to die for and the staff absolutely amazing " [](https://expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ## Find out more about Windley Key ## Windley Key Resorts information | Number of reviews | | | --- | --- | | Accommodation | Resorts | | Lowest Price | | | Highest Price | | ## Explore a world of travel with Expedia - Lodging - Packages - Cars - More ways to book - [2 Star Hotels in Plantation Key](https://www.expedia.ca/2Star-Plantation-Key-Hotels.s20-0-d553248635083898347.Travel-Guide-Filter-Hotels) - [B&B in Coopertown](https://www.expedia.ca/Coopertown-Bed-And-Breakfast.d6177715-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Coopertown](https://www.expedia.ca/Coopertown-Guest-Houses.d6177715-aaGuestHouses.Travel-Guide-Accommodation) - [B&B in Elliott Key](https://www.expedia.ca/Elliott-Key-Bed-And-Breakfast.d553248621532652848-aaBedAndBreakfast.Travel-Guide-Accommodation) - 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