Title: Book The Best Hotels in Windley Key, FL for 2025 from CA $144 - Fully Refundable Options - Expedia.ca [Windley Key Travel Guide](https://expedia.ca/Windley-Key.dx553248635976197663)[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) ![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find hotels in Windley Key, FL from CA $144 - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - 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Nov 21](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-20&endDate=2025-11-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 21 - Nov 22](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-21&endDate=2025-11-22&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-21&endDate=2025-11-23&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Compare 2,781 hotels, room rates, hotel reviews and availability. Most hotels are fully refundable. ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/b10fe59f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/be3c8b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/ca67d5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Cove Resort and Marina Islamorada 9.0/10 Wonderful (141) "Quiet and relaxing. Great place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Edward CA $214 CA $240 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/711bb33e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/7c261d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/449b99c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher Inn Resort & Marina Islamorada 8.2/10 Very good (1006) "Great experience, highly recommend staying at the Fisher Inn." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Eduardo CA $104 CA $163 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.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) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/c5948ba3.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) ![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 (111) "Beautiful place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $286 CA $416 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/42d378ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/29680b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Water view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/3997e962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drop Anchor Islamorada 8.8/10 Excellent (1001) "Beautiful property and the staff was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $145 CA $212 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Classic Room, Patio, Garden View | Terrace/patio](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/224c2448.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/01400ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, Patio, Garden View](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/5d3fac38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Classic Room, Patio, Garden View](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/5f27ae80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ocean View Inn & Pub Islamorada 9.6/10 Exceptional (7) "Awesome place to stay, restaurant and bar attached, outside bar and dining area overlooking the bay. Pool also very nice. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rick CA $222 CA $249 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Islamorada-Hotels-The-Ocean-View-Inn-Pub.h110683445.Hotel-Information) ![Private beach, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/fa9b6bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, hypo-allergenic bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/43f5c138.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort Matecumbe 9.2/10 Wonderful (1581) "Great breakfast very well kept grounds" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $179 CA $281 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/8e763282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/46aade65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier One Bedroom Waterfront Suite Bayview with Sofabed](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/dd3dbaaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Inn Key Largo Key Largo 8.6/10 Excellent (1607) "Great location and helpful staff !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nikki CA $165 CA $221 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.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) ![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) ![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) ### Lime Tree Bay Resort Long Key 9.2/10 Wonderful (1101) "Excellent stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joshua CA $159 CA $242 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45deddf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/45b47efd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront Pool View King Room | Terrace/patio](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/a348bb16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Pines & Palms Resort Matecumbe 9.2/10 Wonderful (1002) "Great staff and excellent customer service. Absolute beautiful place with great amenities." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jesse CA $196 CA $298 total includes taxes & fees Dec 8 - Dec 9 [](https://www.expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/9192d0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite | Beach/ocean view](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/ae06d5c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/b5cef261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pelican Key Largo Cottages Key Largo 8.8/10 Excellent (1006) "We were delighted with everything The Pelican said it was. The staff was friendly and courteous throughout the property. THE VIEWS were stunning! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ramiro CA $154 CA $173 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/9bcc8c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/w1485h1001x15y0-19c35a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/528adcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rock Reef Resort Rock Harbor 9.2/10 Wonderful (1062) "Everything was perfect. Very clean great staff beautiful place to relax ." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Miguel CA $129 CA $146 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.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) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/9b929f51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1272) "Everything about our stay was amazing and exceeded our expectations in every way!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary Frances CA $314 CA $449 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/af88a0b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/9a9545cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/bf4f58dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Marina Del Mar Resort and Marina Key Largo 8.4/10 Very good (1631) "Great location and laid back vibe!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $127 CA $183 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.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) ![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) ![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) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1265) "Great place and great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Christian CA $198 CA $317 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Outdoor pool, free cabanas](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/25606792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/711b38d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 2 Double Beds, Kitchenette](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/4c5cb130.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/31000000/30570000/30568100/30568049/92298919.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Inn Matecumbe 9.4/10 Exceptional (1003) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Heather CA $158 CA $193 total includes taxes & fees Nov 25 - Nov 26 [](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.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) ![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) ![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) ![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) ### Playa Largo Resort & Spa, Autograph Collection Rock Harbor 9.0/10 Wonderful (1002) "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 $336 CA $455 total includes taxes & fees Dec 2 - Dec 3 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/9d3b800e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio Suite | Private kitchen](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/0f203959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/9c95fe9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterside Suites & Marina Key Largo 9.0/10 Wonderful (1122) "Great place to stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chad CA $153 CA $212 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/a375b426.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas Matecumbe 8.8/10 Excellent (1000) "Excellent stay with great amenities." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $179 CA $295 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/2a78a3da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/cb9ea3a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/e8b845d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/3dad51c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seafarer Key Largo Rock Harbor 9.4/10 Exceptional (124) "Everything was especially clean and the breakfast was incredible " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) FATIMA CA $146 CA $185 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Key-Largo-Hotels-Seafarer-Key-Largo.h111555855.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, in-room safe, desk](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/6ec44483.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Islander Suite Ocean View Two Bedroom | Private kitchen](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/20ed25e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/b513b652.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort Matecumbe 9.2/10 Wonderful (1009) "The room and amenities were great and it was quiet.. just what we needed" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sandra CA $327 CA $464 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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=2025-12-05&endDate=2025-12-06®ionId=553248635976197663&adults=2&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-Hotels.d553248635976197663.Travel-Guide-Hotels)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=HTG_BF_PROMO_553248635976197663) ## Learn more about Windley Key Check out the local area in Windley Key as you venture to sights like Windley Key Fossil Reef Geological State Park. [See all hotels in Windley Key](https://www.expedia.ca/Hotel-Search?startDate=2025-12-05&endDate=2025-12-06&adults=2®ionId=553248635976197663) ![Windley Key Fossil Reef Geological State Park](https://images.trvl-media.com/place/6282211/331e71ab-ee65-4e64-bb08-32876871cf53.jpg?impolicy=fcrop&w=900&h=506&p=1&q=high) ### Stay near popular Windley Key attractions [](https://expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Hotels.0-l6282211-0.Travel-Guide-Filter-Hotels) ![Windley Key Fossil Reef Geological State Park](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340296-Windley-Key-Fossil-Reef-Geological-State-Park.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Windley Key Fossil Reef Geological State Park Explore the fossilized reef of a former quarry in this island park, as you learn about the history and ecology from the interpretive trails. [See properties](https://expedia.ca/Hotel-Search?rfrrid=TG.LP..PointOfInterests®ionId=6282211) ## More cheap stays in Windley Key ![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Marina Del Mar Resort and Marina 527 Caribbean Drive Key Largo FL CA $127 CA $183 total Dec 1 - Dec 2 includes taxes & fees 8.4/10 Very Good! (1,630 reviews) [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Creekside Inn](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/5e43c05b_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Creekside Inn 90611 Old Highway Tavernier FL CA $176 CA $198 total Dec 2 - Dec 3 includes taxes & fees 7.8/10 Good! (1,005 reviews) [](https://expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) ![Rock Reef Resort](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Rock Reef Resort 97850 Overseas Hwy Key Largo FL CA $129 CA $146 total Dec 21 - Dec 22 includes taxes & fees 9.2/10 Wonderful! (1,057 reviews) [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Drift Hotel](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/f3e504e7_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### Drift Hotel 95320 Overseas Hwy Key Largo FL CA $114 CA $144 total Nov 30 - Dec 1 includes taxes & fees 8.8/10 Excellent! (1,003 reviews) [](https://expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.Hotel-Information) ![The Pelican Key Largo Cottages](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/f35b06df_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### The Pelican Key Largo Cottages 99340 Overseas Highway Key Largo FL CA $154 CA $173 total Dec 7 - Dec 8 includes taxes & fees 8.8/10 Excellent! (1,002 reviews) [](https://expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![La Jolla Resort](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92_y.jpg?impolicy=resizecrop&rw=402&ra=fit) ### La Jolla Resort 82216 Overseas Highway Islamorada FL CA $107 CA $160 total Dec 18 - Dec 19 includes taxes & fees 9/10 Wonderful! (1,003 reviews) [](https://expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ## Hotels in Windley Key with star-rating ![5 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/25600/25559/c6e0103a_z.jpg) 5 Star Hotels 3 properties [](https://expedia.ca/5Star-Windley-Key-Hotels.s50-0-d553248635976197663.Travel-Guide-Filter-Hotels) ![4 Star Hotels](https://images.trvl-media.com/lodging/1000000/30000/23700/23677/6ae928dd_z.jpg) 4 Star Hotels 7 properties [](https://expedia.ca/4Star-Windley-Key-Hotels.s40-0-d553248635976197663.Travel-Guide-Filter-Hotels) ![3 Star Hotels](https://images.trvl-media.com/lodging/20000000/19690000/19681400/19681371/84fffc75_z.jpg) 3 Star Hotels 79 properties [](https://expedia.ca/3Star-Windley-Key-Hotels.s30-0-d553248635976197663.Travel-Guide-Filter-Hotels) ![2 Star Hotels](https://images.trvl-media.com/lodging/92000000/91830000/91828000/91827910/6717a2ac_z.jpg) 2 Star Hotels 128 properties [](https://expedia.ca/2Star-Windley-Key-Hotels.s20-0-d553248635976197663.Travel-Guide-Filter-Hotels) ## Find out more about Windley Key ### Top reasons to visit Windley Key - **Outdoor Adventures:** Windley Key is a paradise for outdoor enthusiasts, featuring scenic hiking trails and engaging virtual tours. - **Windley Key State Park:** A highlight for nature lovers, offering stunning landscapes and opportunities for exploration. - **Fossil Reef Discovery:** Experience the unique Windley Key Fossil Reef, a fascinating glimpse into the area's geological history. - **Nearby Beaches:** Relax on beautiful beaches in Islamorada, just a short distance away, enhancing your coastal experience. - **Diverse Accommodations:** Choose from a range of lodging options, from budget-friendly to luxurious, accommodating every traveler's needs. ### Find great hotels near Windley Key Discover the charm of Windley Key, Florida, where a variety of hotel accommodations cater to every traveler's preference. From budget-friendly options to luxurious resorts, you can find the perfect stay, whether you're seeking adventure, a beach getaway, or pet-friendly lodgings. Explore Windley Key vacation rentals and experience the beauty of Florida’s Keys while enjoying comfortable amenities tailored to make your holiday unforgettable. - **[Amara Cay Resort:](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information)** Nestled 8.0km away from Windley Key, Amara Cay Resort is a family-friendly, 3.5-star beachside haven ideal for adventure seekers and families alike. With direct beach access, guests can immerse themselves in a variety of outdoor activities, from onsite kayaking and snorkelling to nearby hiking and biking trails. The resort ensures a worry-free stay for families with amenities like cribs and a first aid kit. Amara Cay provides a perfect blend of relaxation and adventure, making it an excellent choice for those looking to create lasting memories. - **[Cheeca Lodge & Spa:](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information)** Located just 6.4km from Windley Key, Cheeca Lodge & Spa is a luxurious 4-star resort that caters to beach lovers and golf enthusiasts. This stunning property offers direct access to the beach and features a scenic golf course for guests to enjoy. Adventure awaits with onsite windsurfing and fishing, while nearby hiking opportunities abound. The resort combines elegance with a laid-back atmosphere, providing a variety of dining options and a full-service spa for a truly indulgent experience. It’s the perfect retreat for those seeking both relaxation and excitement. - **[Islander Resort:](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information)** Just 4.8km from Windley Key, Islander Resort is a charming 3-star hotel that caters to families and adventure seekers. With direct beach access, guests can partake in an array of watersports, including kayaking and parasailing. The resort also features family-friendly amenities such as onsite mini-golf and ping pong, ensuring entertainment for all ages. Whether you’re looking to relax on the beach or explore the local waters, Islander Resort provides a fun-filled atmosphere perfect for creating unforgettable holiday experiences. ### Where to stay near Windley Key Windley Key, nestled in the stunning Florida Keys, offers an idyllic getaway for those seeking outdoor adventures and relaxation. With its family-friendly atmosphere and romantic settings, visitors can explore the enchanting landscapes of the Upper Florida Keys. Nearby, the charming village of Islamorada beckons with its beautiful beaches and vibrant local culture. Whether you're diving into the crystal-clear waters or lounging on the shore, Windley Key promises an unforgettable vacation experience. - **[Islamorada:](https://www.expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)** Known as the "Village of Islands," Islamorada is a picturesque destination that offers stunning coastal views and a laid-back atmosphere. Located directly on Windley Key, this city is a haven for outdoor enthusiasts and families looking to escape the hustle and bustle. Visitors can enjoy a variety of activities, from relaxing on beautiful beaches to exploring shopping areas and local resorts. The peak travel seasons, from March to April and July, see a vibrant influx of tourists, creating a lively ambiance perfect for family fun and adventure. Key landmarks include pristine beaches and a lively tourist precinct that add to its charm. - **[Tavernier:](https://www.expedia.ca/Tavernier-Hotels.d10047.Travel-Guide-Hotels)** Just 9.7km from Windley Key, Tavernier is a quaint city that captures the heart of the Florida Keys. With a focus on outdoor activities and family adventures, Tavernier is an ideal spot for those looking to immerse themselves in nature. The peak tourist seasons are similar to its neighbour, with March to April and July drawing the most visitors. Guests can explore local shopping areas and enjoy the beautiful beaches nearby. The town is surrounded by lush landscapes and offers easy access to various recreational activities, making it a perfect addition to your itinerary. - **[Venetian Shores:](https://www.expedia.ca/Venetian-Shores-Islamorada-Hotels.0-n553248635976470270-0.Travel-Guide-Filter-Hotels)** Nestled only 805m from Windley Key, Venetian Shores is a charming neighbourhood that boasts a relaxed vibe and a strong sense of community. This area is less seasonal, attracting visitors year-round, with peak times in February to March and July. Families and outdoor lovers will find plenty to enjoy, from recreational areas to beautiful beaches. The local shopping options and nearby islands provide a delightful experience for all. Venetian Shores is perfect for those seeking a tranquil getaway without straying too far from the attractions of the Florida Keys. ### Things to do near Windley Key Windley Key offers a fantastic outdoor getaway, perfect for adventure seekers. Explore scenic hiking trails, enjoy a leisurely walk through beautiful landscapes, or take part in engaging virtual tours. With its stunning natural beauty, Windley Key invites you to immerse yourself in various outdoor activities, making it an ideal destination for your vacation. **Shopping** For shopping in Windley Key, visit Rain Barrel Village, a charming spot just 1.6km away, offering a family-friendly atmosphere. If you're up for a drive, check out Kiffney's Firearms and Indoor Range, located 32.2km away, where you can find unique gifts and souvenirs. **Recreation** [Jacob's Aquatic Center](https://www.expedia.ca/Jacobs-Aquatic-Center-Hotels.0-l553248621532652370-0.Travel-Guide-Filter-Hotels) offers a family-friendly atmosphere with refreshing pools, perfect for unwinding. For a touch of luxury, the Key Largo Anglers Club provides exclusive amenities in a picturesque setting. Meanwhile, the New Mahogany Hammock State Botanical Site invites you to relax amidst beautiful flora and tranquil surroundings. **Adventure** The [Florida Keys Dive Center](https://www.expedia.ca/Florida-Keys-Dive-Center-Hotels.0-l553248621532652358-0.Travel-Guide-Filter-Hotels) offers thrilling underwater sports, located 8.0km from Windley Key, where you can explore vibrant marine life. For adrenaline junkies, [Keys Cable Park](https://www.expedia.ca/Keys-Cable-Park-Hotels.0-l901232018711719936-0.Travel-Guide-Filter-Hotels), 28.0km away, provides an exhilarating adventure activity. Meanwhile, the [Pa-hay-okee Trail](https://www.expedia.ca/Pa-Hay-Okee-Trail-Hotels.0-l553248621532652363-0.Travel-Guide-Filter-Hotels), also 28.0km away, invites you to hike amidst stunning scenery. **Nightlife** In Windley Key, the nightlife buzzes with excitement at [Jimmy Johnson's Big Chill](https://www.expedia.ca/Jimmy-Johnsons-Big-Chill-Hotels.0-l553248621563219632-0.Travel-Guide-Filter-Hotels), only 20.9km away, where you can enjoy vibrant entertainment in a romantic setting. The [Caribbean Club Bar](https://www.expedia.ca/Caribbean-Club-Bar-Hotels.0-l553248621533115829-0.Travel-Guide-Filter-Hotels), located 29.0km away, offers a similar atmosphere, perfect for unwinding with friends and drinks. ### Booking tips and Expedia advantages for Windley Key When planning your visit to Windley Key, consider travelling during the off-peak months from September to November for lower accommodation prices. Booking your hotel about a month in advance can help secure great deals, especially if you choose to stay on a Tuesday, the cheapest day. Explore nearby free attractions like Islamorada County Park and Florida Keys Brewing Co. To maximise savings, use Expedia to find package deals that combine flights, accommodations, and activities, and sort options by price to find the best value for your trip. - **The most and least expensive months on average to stay in a hotel:** The cheapest months to stay around Windley Key are September to November, where the prices are slightly lower. This is in comparison to February to April, where prices are slightly higher. - **The best time to book a hotel:** Book your hotel around Windley Key about 1 month out to secure some of the cheapest prices. If you're the spontaneous type, Expedia's last minute deals and discounts are indicated via the green label below the price. - **The most and least expensive days on average to stay in a hotel:** The least expensive day to stay around Windley Key is Tuesday. The most expensive day to stay around Windley Key is Saturday. - **Find cheap hotels on Expedia:** Utilize Expedia's search tool to refine your choices based on your budget, desired location, and the type of accommodation you prefer. For the best value, be sure to sort the price filter from lowest to highest to uncover the most affordable options and deals available. - **Consider bundling your trip:** You can save some money by combining your Windley Key hotel reservation with your flights and activities through an Expedia package deal. ### Find the best attractions near Windley Key Windley Key is perfect for outdoor enthusiasts and adventure seekers, offering attractions such as Windley Key State Park and the Windley Key Fossil Reef. Visitors can explore notable landmarks and enjoy the natural beauty of urban parks and marinas. With a rich cultural experience awaiting, Windley Key promises an exciting getaway filled with activities that highlight its unique landscape and history. - **[Windley Key Fossil Reef Geological State Park:](https://www.expedia.ca/Windley-Key-Fossil-Reef-Geological-State-Park-Hotels.0-l6282211-0.Travel-Guide-Filter-Hotels)** Experience the incredible geological history of Florida at this unique state park, where you can explore ancient fossilized coral reefs. Enjoy scenic trails surrounded by lush vegetation and discover the rich outdoor vibes that make it perfect for adventurers and nature lovers alike. - **[Founders Park:](https://www.expedia.ca/Founders-Park-Hotels.0-l6277602-0.Travel-Guide-Filter-Hotels)** This vibrant marina offers a beautiful beach and ample opportunities for outdoor adventure. With its stunning views and recreational activities, Founders Park is ideal for those looking to relax by the water or engage in exciting water sports. - **[Islamorada County Park:](https://www.expedia.ca/Islamorada-County-Park-Hotels.0-l553248621532652353-0.Travel-Guide-Filter-Hotels)** A fantastic urban park for families, Islamorada County Park features playgrounds, picnic areas, and walking trails. Enjoy the blend of city and outdoor vibes, making it a great spot to unwind and connect with loved ones amidst nature. ### Best time to go to Windley Key, Islamorada The best time to visit Windley Key, Islamorada can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Windley Key, Islamorada falls in August, when visitor numbers are moderately low and weather is mostly sunny with light rain. The coolest average temperature around Windley Key, Islamorada falls in January, visitor numbers are average and weather is mostly sunny with no rain. | **![calendar icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/calendar.png)Calendar Month** | **![temperature icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__hot.png)Temperature** | **![rain icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/03/04/weather__rain.png)Precipitation** | **![mostly cloudy icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/weather__day_mostly_cloudy.png)Cloudiness** | **![occupation rate icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/peoplebex.png)Occupancy** | **![price icon](https://forever.travel-assets.com/flex/flexmanager/images/2024/10/29/currency_dollar.png)Pricing** | | --- | --- | --- | --- | --- | --- | | January | 70.0°F (21.1°C) | No Rain (Dry) | Mostly Sunny | Average | Average | | February | 71.8°F (22.1°C) | No Rain (Dry) | Mostly Sunny | Average | Slightly High | | March | 72.9°F (22.7°C) | No Rain (Dry) | Mostly Sunny | Moderately High | Slightly High | | April | 76.6°F (24.8°C) | No Rain (Dry) | Mostly Sunny | Average | Slightly High | | May | 79.3°F (26.3°C) | Light Rain | Mostly Sunny | Average | Average | | June | 82.4°F (28.0°C) | Light Rain | Mostly Sunny | Average | Average | | July | 83.8°F (28.8°C) | Light Rain | Mostly Sunny | Moderately High | Average | | August | 84.4°F (29.1°C) | Light Rain | Mostly Sunny | Moderately Low | Average | | September | 83.3°F (28.5°C) | Light Rain | Mostly Sunny | Moderately High | Slightly Low | | October | 80.2°F (26.8°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | November | 75.9°F (24.4°C) | Light Rain | Mostly Sunny | Moderately Low | Slightly Low | | December | 72.9°F (22.7°C) | No Rain (Dry) | Mostly Sunny | Average | Average | ### The nearest major airports for your trip to Windley Key To reach Windley Key, you can fly into Marathon, FL ([MTH](https://www.expedia.ca/Florida-Keys-Marathon-Airport-Hotels.0-aMTH-0.Travel-Guide-Filter-Hotels)\-Florida Keys Marathon), situated 53.1km away. Recommended hotels nearby include the [Isla Bella Beach Resort & Spa](https://www.expedia.ca/Marathon-Hotels-Isla-Bella-Beach-Resort-Spa.h24101706.Hotel-Information), a 4.5-star property located 6.4km from the airport, and both the Tranquility Bay Beachfront Hotel and [Faro Blanco Resort & Yacht Club Marathon](https://www.expedia.ca/Marathon-Hotels-Faro-Blanco-Resort-Yacht-Club.h1169583.Hotel-Information), both rated 4 stars and just 4.8km from MTH. These hotels offer convenient access to the airport, ensuring a smooth transition from your flight to your accommodation. Enjoy the beautiful surroundings of the Florida Keys while staying at these comfortable options. ## Recent reviews of Windley Key hotels ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 5/5 Excellent "Beautiful room, stunning views " A verified traveller stayed at Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort Posted 2 days ago [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg) ### Coconut Cove Resort and Marina 5/5 Excellent "Quiet and relaxing. Great place" A verified traveller stayed at Coconut Cove Resort and Marina Posted 2 days ago [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 5/5 Excellent "Rooms were clean, landscape was beautiful, staff was friendly. Access to the (2) other resorts were a plus. Would stay again." A verified traveller stayed at Amara Cay Resort Posted 3 days ago [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 5/5 Excellent "Beautiful resort with lots of included activities & water sports. Friendly staff. Clean rooms. " A verified traveller stayed at Chesapeake Beach Resort Posted 3 days ago [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 5/5 Excellent "Beautiful facility and grounds, wonderful location for quiet get away. The room was very clean. We really enjoyed sitting by the pool and also lounging on our private patio. Would definitely stay here again if we were in the area. A broom on the patio would be helpful to sweep away any insects." A verified traveller stayed at Islander Resort Posted 3 days ago [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Marina Del Mar Resort and Marina](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/d42f8885_y.jpg) ### Marina Del Mar Resort and Marina 5/5 Excellent "Enjoyed breakfast looking out over the water. " A verified traveller stayed at Marina Del Mar Resort and Marina Posted 5 days ago [](https://expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Reefhouse Resort & Marina](https://images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 5/5 Excellent "Rooms were clean big and had a great view. The staff was amazing. " A verified traveller stayed at Reefhouse Resort & Marina Posted 6 days ago [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 5/5 Excellent "Amazing!" A verified traveller stayed at Cheeca Lodge & Spa Posted 6 days ago [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Rock Reef Resort](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 5/5 Excellent "This place was awesome. Friendly staff. Would definitely stay again if in the area." A verified traveller stayed at Rock Reef Resort Posted 7 days ago [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ## Frequently asked questions ### When is the best time to go to Windley Key? > The most popular time to visit Windley Key is in the winter months, particularly from December to February. During this peak season, temperatures are pleasantly warm, averaging around 24 to 27 Celsius, providing ideal conditions for outdoor activities such as snorkeling, kayaking, and exploring the lush natural landscapes of the Florida Keys. > > > > As you plan your getaway, keep in mind that this period attracts many visitors, drawn by the fabulous weather and the vibrant atmosphere. The warm sunshine and gentle breezes create the superb setting for leisurely strolls along the scenic shores or engaging in water sports in the crystal-clear waters. Popular attractions, including the nearby John Pennekamp Coral Reef State Park, can be quite lively, adding to the vibrant energy of the region. > > > > For those seeking a more affordable option, consider visiting in September. While the weather is still warm, with temperatures around 28 Celsius, you may find lower accommodation rates and fewer crowds. This month also offers a fantastic opportunity to experience the natural beauty of Windley Key without the hustle and bustle of peak tourist season. ### Can I cancel my hotel reservation on Expedia? > Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline – this is often within 24-48 hours of your scheduled arrival. If you have a non-refundable booking, it might still be possible to receive a refund if you cancel it within 24 hours of booking. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use our "Fully refundable property" filter during your search to find the right Windley Key hotel for you. ### How can I save on a Windley Key hotel booking with Expedia? > With Expedia, you'll unlock our lowest prices by becoming a member. It's free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Windley Key hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings. ### How much is the nightly rate at a Windley Key hotel? > Prices for hotels in Windley Key often vary, but you can find a great deal from CA $144 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. 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