Title: Windley Key Guest Houses | 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 ![](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 [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-31&endDate=2025-11-02&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [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) In two months [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=GUEST_HOUSE&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select 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/b442c959.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) ![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 (196) "The location was quiet and relaxing. We never heard a peep out of any of the other guests and it seemed that they were up early and in bed early which left us to enjoy the hotel grounds later in the evening... We had the pool to ourselves the entire week. Pretty view of the ocean. Close to everything you'll need or want including great restaurants and convenience stores. The staff was helpful and kind and we would def go back for a restful vacation. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cassidy CA $130 CA $147 total includes taxes & fees Oct 29 - Oct 30 [](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) ![Exterior](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/724424f3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 2 Queen Beds (Room 24) | Private kitchen](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/56547671.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) ### Coconut Bay Resort Key Largo Key Largo 9.6/10 Exceptional (190) "beautiful place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karl CA $259 CA $291 total includes taxes & fees Oct 26 - Oct 27 [](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=2025-11-08&endDate=2025-11-09®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 ![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 "Cottages are clean and comfortable. Just be sure to get one of the larger units. I had cottage with 2 Queens and a full kitchen. Staff is friendly and very helpful. Within walking distance of 3 decent restaurants and a Walgreens." [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Fisher Inn Resort & Marina](//images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg) ### Fisher Inn Resort & Marina 10/10 Excellent "Beautiful place, nice room" [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Beautiful resort, pools and property. Glad we found this place. Great for families, young kids and adults! Zero entry pool was a hit with our daughter. Excellent service and friendly staff. " [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "The front desk lady was very pleasant upon my check-in. She answered all my questions and made me feel comfortable driving to my room where I was staying. I slept late the next day with the do not disturb sign and I received a personal text from the front desk in the early afternoon asking me to respond when I was ready for them to make up my room. I did eat breakfast at the resort each morning. The chefs were extremely friendly and I enjoyed a sunrise breakfast overlooking the water. The breakfast is complimentary as well! Other than that, I wasn’t T the resort to stay the entire time. The rest of the time I was out and about, but I looked forward to jumping in the super comfy bed each evening when I would get back. I’ll be back the next time I’m in Islamorada!!" [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.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 and property. We would stay here again. " [](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 "Our room was clean and updated. The woman at the front desk was very nice during the check in process. The view was beautiful and the grounds had a nice layout. We would definitely stay here again! " [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![Drop Anchor](//images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "Great" [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.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 "We only spent one night but we loved it! There's a little beach and a great tiki bar where we met some very nice people. Our room was fine; clean & convenient to everything. Plenty of parking. We'll stop again next time we are in the area!" [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.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 "Super friendly staff. Very well maintained property. Music and areas of entertainment were fantastic. Sunsets on beach priceless. Walk-in pool. Walk-in beach with aquabanas. " [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ## Find out more about Windley Key ## Windley Key Guest Houses information | Number of reviews | | | --- | --- | | Accommodation | Guest Houses | | 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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