Title: Windley Key Guest Houses from CA $132 | 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 Guest Houses in Windley Key from CA $132 ![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 3 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-03&endDate=2025-10-05&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-10&endDate=2025-10-12&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windley Key Guest Houses ## Our top choices for Windley Key guest houses ![Exterior](https://images.trvl-media.com/lodging/57000000/56960000/56952700/56952622/b0a43673.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/57000000/56960000/56952700/56952622/b1bfc483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/57000000/56960000/56952700/56952622/b442c959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/57000000/56960000/56952700/56952622/b27f4d1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ragged Edge Resort & Marina Islamorada 9.4/10 Exceptional (192) "We enjoyed our stay very much and have already recommended this hotel to friends. Thanks for accommodating our check in and check out. " CA $118 CA $132 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Islamorada-Hotels-Ragged-Edge-Resort-Marina.h56952622.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/ac0b6e27.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 1 Bedroom, Kitchen (25) | Terrace/patio](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/0c8ddcdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterview King (26)](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/fd4b899f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/724424f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Bay Resort Key Largo Key Largo 9.6/10 Exceptional (187) "beautiful place." CA $228 CA $257 total includes taxes & fees Sep 24 - Sep 25 [](https://www.expedia.ca/Key-Largo-Hotels-Coconut-Bay-Resort-Key-Largo.h10531753.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=2025-10-07&endDate=2025-10-08®ionId=553248635976197663&adults=2&lodging=GUEST_HOUSE&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-Guest-Houses.d553248635976197663-aaGuestHouses.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Guest-Houses.d553248635976197663-aaGuestHouses.Travel-Guide-Accommodation) ## Top Windley Key Hotel Reviews ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](//images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 10/10 Excellent "Great experience- plenty to do or you can do nothing- very clean property- food was great- drinks were cold- Plenty of boats going by- Staff was friendly always asking if they could help with anything- highly recommended. " [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Waterside Suites & Marina](//images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Love the location and the room. Made for a great fishing trip with my son & grand daughter. Well be return in the near future." [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Staff has been so accommodating, the pool and the grounds are beautiful, rooms are very comfortable. Great place!" [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.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 "Bakers Cay was a wonderful place to stay and unwind. The service was outstanding and location perfect. Thank you" [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Beautiful and relaxing hotel!!" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Alot of fun things to do including kayaking, paddle board, vollyball,ping pong and bikes." [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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 "Loved " [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Rock Reef Resort](//images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "Room was like an efficiency apartment, even had a full kitchen. " [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![The Pelican Key Largo Cottages](//images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg) ### The Pelican Key Largo Cottages 10/10 Excellent "Very friendly staff and cool property. Also the beach area and snorkeling!" [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ## Find out more about Windley Key ## Windley Key Guest Houses information | Number of reviews | 379 | | --- | --- | | Accommodation | 2 Guest Houses | | Lowest Price | CA $132 | | Highest Price | CA $257 | ## 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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