Title: Browse the Best Windley Key Resorts from CA $239 | 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 from CA $239 ![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 prices for these dates Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=HOTEL_RESORT&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [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) ## Browse Select Windley Key Resorts ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/9b929f51.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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1223) "Beautiful and relaxing hotel!!" CA $144 CA $257 total includes taxes & fees Oct 2 - Oct 3 [](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) ![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) ### 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 $487 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![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) ![3 outdoor pools, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/8de2bfdc.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) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Islamorada 9.0/10 Wonderful (89) "Beautiful place to stay" CA $259 CA $384 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.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/1000000/70000/62000/61976/28233e0b.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 (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) ![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) ![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) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/8f8fe319.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 $451 total includes taxes & fees Oct 7 - Oct 8 [](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) ![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) ![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 8.6/10 Excellent (1001) "Great rooms" CA $146 CA $257 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.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) ![Room | Private kitchen](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/4077334d.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 (1094) "So close to the ocean was amazing. " CA $157 CA $239 total includes taxes & fees Oct 22 - Oct 23 [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.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) ![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) ![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, Sea View | Private kitchen](https://images.trvl-media.com/lodging/113000000/112180000/112177000/112176968/372df6b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Matecumbe Resort Matecumbe 8.8/10 Excellent (78) "Great place to stay if you like fishing and even if you don't. " [](https://www.expedia.ca/Islamorada-Hotels-Matecumbe-Resort.h112176968.Hotel-Information) ![Beach](https://images.trvl-media.com/lodging/110000000/109910000/109905800/109905778/c291b1d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/110000000/109910000/109905800/109905778/09dad71d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/110000000/109910000/109905800/109905778/0955307f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/110000000/109910000/109905800/109905778/35a4d45d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL Matecumbe 9.0/10 Wonderful (2) "We enjoyed our stay here, although units are older and do need some sprucing up.It was nice to have a beach onsite, as well as a heated pool, the use of (older) bikes and kayaks. We were only a few miles from the action of Islamorada, including restaurants, tourist attractions, shopping, breweries" [](https://www.expedia.ca/Islamorada-Hotels-2-BD2BA-VILLA-WITH-BOAT-SLIP-IN-ISLAMORADA.h109905778.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74230000/74229000/74228939/30bff6fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/75000000/74230000/74229000/74228939/8ff22b2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74230000/74229000/74228939/7e98bc23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74230000/74229000/74228939/8335aab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Keys Villa Matecumbe 10/10 Exceptional (7) "Wonderful place to stay. It was quiet with a private beach. Just what we were looking for. " [](https://www.expedia.ca/Islamorada-Hotels-Keys-Villa.h74228939.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/106000000/105230000/105220500/105220440/w1290h963x0y5-e98b98f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105230000/105220500/105220440/w1290h2119x0y1-d73d9fd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105230000/105220500/105220440/w1290h954x0y0-93deecf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/106000000/105230000/105220500/105220440/w1290h890x0y0-5adb22a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 2 Bedrm / 2 Bath Private Beach Boat Dock Fishing Pier Pool Hot Tub Dream Vacay Matecumbe [](https://www.expedia.ca/Islamorada-Hotels-2-Bedrm-2-Bath-Private-Beach-Boat-Dock-Fishing-Pier-Pool-Hot-Tub-Dream-Vacay.h105220440.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/79000000/78080000/78072500/78072441/e0ad2c05.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/79000000/78080000/78072500/78072441/74274b77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/79000000/78080000/78072500/78072441/80b1d3b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, offices](https://images.trvl-media.com/lodging/79000000/78080000/78072500/78072441/w1024h673x0y4-b2d09f3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beautiful oceanfront resort located at mile marker 73.8 Matecumbe [](https://www.expedia.ca/Islamorada-Hotels-Beautiful-Oceanfront-Resort-Located-At-Mile-Marker-738.h78072441.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147207/w973h1235x0y0-221a49ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147207/ff71f914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147207/0853f7a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147207/b85c9c6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub Matecumbe [](https://www.expedia.ca/Islamorada-Hotels-Sleeps-6-WATER-BEACH-2-Bedrooms-2-Bath-Boat-Slip.h39147207.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/88000000/87380000/87370400/87370340/w1280h718x0y0-7bf5f357.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, WiFi](https://images.trvl-media.com/lodging/88000000/87380000/87370400/87370340/edc12668.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/88000000/87380000/87370400/87370340/88be4c95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/88000000/87380000/87370400/87370340/b10f5d15.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### On the water in Islamorada elevated detached unit!!! Matecumbe [](https://www.expedia.ca/Islamorada-Hotels-On-The-Water-In-Islamorada-Elevated-Detached-Unit.h87370340.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=2025-10-15&endDate=2025-10-16®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 ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Yes" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Holiday Inn Key Largo by IHG](//images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg) ### Holiday Inn Key Largo by IHG 10/10 Excellent "September is the quietest month and this has been exceptionally quiet apparently, still staff were very attentive, no reason to think it unusual ," [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ![Rock Reef Resort](//images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "The staff were friendly and funny. The room was comfortable. I had fun. " [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Excellent recommendation for a small budget." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Playa Largo Resort & Spa, Autograph Collection](//images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg) ### Playa Largo Resort & Spa, Autograph Collection 10/10 Excellent "The entire environment " [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![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) ![Hampton Inn Key Largo Manatee Bay](//images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233_y.jpg) ### Hampton Inn Key Largo Manatee Bay 10/10 Excellent "There’s a small but cozy beach area with the best view for sunset during happy hour at the tiki bar. We saw other guests have easy access to kayaks and paddle boarding and pets were welcomed!" [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.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) ![Bayside Inn Key Largo](//images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg) ### Bayside Inn Key Largo 10/10 Excellent "Yes everything was just amazing i felt so safe It was just me and my sister and we would definitely come back " [](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ## Find out more about Windley Key ## Windley Key Resorts information | Number of reviews | 6,791 | | --- | --- | | Accommodation | 14 Resorts | | Lowest Price | CA $239 | | Highest Price | CA $487 | ## 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) - 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