Title: Windley Key Villas | 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 Windley Key Villa Rentals - ![](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 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windley Key Villas ![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 (68) "Beautiful property!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Betty CA $981 CA $1,181 total includes taxes & fees Nov 4 - Nov 5 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.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=2025-11-17&endDate=2025-11-18®ionId=553248635976197663&adults=2&lodging=VILLA&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-Villas.d553248635976197663-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Villas.d553248635976197663-aaVillas.Travel-Guide-Accommodation) ## Top Windley Key Hotel Reviews ![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 "Clean room, great pool and tiki bar and skippers was a great short walk for happy hour " [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.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 "Staff was outstanding from the front desk, cleaning staff, tiki bar (Nicole made excellent cocktails!). Breakfast was amazing as well. You have a good group of people there in key largo working for you!!" [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.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, great staff " [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Friendly staff clean room!!!" [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Very comfortable and professional " [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Marina Del Mar Resort and Marina](//images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg) ### Marina Del Mar Resort and Marina 10/10 Excellent "The staff was friendly and helpful throughout my stay, always greeting guests with a smile and offering great local recommendations. My room was clean, comfortable, and had everything I needed for a relaxing trip. I especially loved waking up to the peaceful marina view every morning! The pool area and hot tub were beautiful, and the atmosphere was calm and inviting. Having restaurants and water activities just steps away made everything super convenient — we even took a sunset cruise right from the marina!" [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Treasure Harbor](//images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3_y.jpg) ### Treasure Harbor 10/10 Excellent "The houseboat was so cute! The staff was very friendly and helpful. We really enjoyed out stay. The pool was new and clean. We would definitely come back." [](https://expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![Drop Anchor](//images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "Quiet peaceful nice beds view kitchen 😍" [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.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 "It's a beautiful resort and the staff was friendly and helpful. We only encountered 2 disappointments: The first day the music at the pool was so loud we couldn't converse among ourselves, but after requesting the volume was reduced. The second was the temperature of the pool was HOT, I mean easily in the 90s or higher! We felt it coming out of the input valves and it felt like hot tub temps! We asked the staff and we saw people checking the water, but it was still uncomfortably hot when we checked out. " [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ## Find out more about Windley Key ## Windley Key Villas information | Number of reviews | | | --- | --- | | Accommodation | Villas | | 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) - [Condo Rentals in Elliott Key](https://www.expedia.ca/Elliott-Key-Condos.d553248621532652848-aaCondos.Travel-Guide-Accommodation) - 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