Title: Windley Key Cottages | 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 Cottage 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 In two weeks [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-02-06&endDate=2026-02-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-03-06&endDate=2026-03-08&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windley Key Cottages No exact matches found, but these alternatives could be just right ## Recommended hotels in Windley Key ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/7c261d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, individually decorated](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9e08c794.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher Inn Resort & Marina Islamorada 8.2/10 Very good (1003) "Very nice hotel. Rooms totally remodeled. Ocean view rooms are amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Gretel CA $142 CA $206 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![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) ![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 | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/42d378ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/d0b4fd2b.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 $176 CA $247 total includes taxes & fees Nov 16 - Nov 17 [](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) ![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) ![Outdoor pool](https://images.trvl-media.com/lodging/111000000/110690000/110683500/110683445/01400ad0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ocean View Inn & Pub Islamorada 9.6/10 Exceptional (7) "The highlight was the fun outside bar and restaurant, we had a blast!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) MARY CA $220 CA $248 total includes taxes & fees Dec 11 - Dec 12 [](https://www.expedia.ca/Islamorada-Hotels-The-Ocean-View-Inn-Pub.h110683445.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/be3c8b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/8147c88b.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) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Cove Resort and Marina Islamorada 9.0/10 Wonderful (139) "Really great facility, very relaxing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) ken CA $213 CA $240 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/eab03112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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/1000000/20000/11900/11864/4dfe75fc.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 (109) "Our view of the beach was beautiful " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) William CA $309 CA $440 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/c052003d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, open 8 AM to 10 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/c604580a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/d369153c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 1 King Bed, Bay View | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/10000/5800/5731/68e30233.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Key Largo Manatee Bay Key Largo 8.8/10 Excellent (1007) "Great resort" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) david CA $158 CA $178 total includes taxes & fees Dec 1 - Dec 2 [](https://www.expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Premier Cottage, Bay View | Terrace/patio](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/0c81ecd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Cabin, 1 King Bed, Bay View](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/w1498h1001x2y0-11d0c529.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) ![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 (1057) "Everything clean, friendly staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Arlene CA $158 CA $178 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/1508fc00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Kitchenette](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/5746e378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, snorkeling, kayaking](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/f3e504e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, coffee/tea maker](https://images.trvl-media.com/lodging/14000000/13210000/13209600/13209518/0065f64e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drift Hotel Key Largo 9.0/10 Wonderful (1003) "The rooms are very nice, staff is friendly. The back is absolutely breathtaking. My boyfriend and I will be back here for sure. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Andrea [](https://www.expedia.ca/Key-Largo-Hotels-Drift-Hotel.h13209518.Hotel-Information) ![Deluxe Studio Suite | Balcony](https://images.trvl-media.com/lodging/1000000/20000/13800/13719/5d36f90b.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) ![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) ![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) ### Waterside Suites & Marina Key Largo 9.0/10 Wonderful (1121) "Came for the weekend and loved the room we stayed in super spacious and clean! It had everything we needed and got to enjoy the view of the marina. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudia CA $163 CA $223 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ![Dock](https://images.trvl-media.com/lodging/112000000/111560000/111555900/111555855/cc89f8fb.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) ![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/112000000/111560000/111555900/111555855/9aaf0d80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seafarer Key Largo Rock Harbor 9.4/10 Exceptional (123) "Rooms are remodeled and staff was great. Would stay here again " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jeff CA $118 CA $152 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Key-Largo-Hotels-Seafarer-Key-Largo.h111555855.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/4ac8a422.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/eec761cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sun loungers, beach umbrellas, beach towels, kayaking](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/ac9979c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/340e7f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dove Creek Resort & Marina, Trademark Collection by Wyndham Key Largo 7.6/10 Good (1003) "clean room nice balcony view nice staff nice breakfast" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Manuel CA $142 CA $204 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.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) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/46aade65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/ad31d180.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) ### Bayside Inn Key Largo Key Largo 8.6/10 Excellent (1605) "Great location and helpful staff !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nikki CA $123 CA $173 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3920000/3911700/3911616/ee3314c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aquamarina Deluxe Sea View Suite | Living area](https://images.trvl-media.com/lodging/4000000/3920000/3911700/3911616/9f59701c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Celeste Deluxe Sea View Suite | Living area](https://images.trvl-media.com/lodging/4000000/3920000/3911700/3911616/b9dfb26d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![La Palma Tropical Garden Suite | Private kitchen](https://images.trvl-media.com/lodging/4000000/3920000/3911700/3911616/5d87a0b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Azul del Mar Key Largo 9.0/10 Wonderful (781) "Room was spotless and staff was more than accommodating!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Windy CA $121 CA $136 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Key-Largo-Hotels-Azul-Del-Mar.h3911616.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/9a9545cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/5200/5114/19311fed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### Marina Del Mar Resort and Marina Key Largo 8.4/10 Very good (1629) "This was our 5th year staying there love the 1bdrm suite" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Roberta CA $132 CA $189 total includes taxes & fees Dec 15 - Dec 16 [](https://www.expedia.ca/Key-Largo-Hotels-Marina-Del-Mar-Resort-And-Marina.h5114.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/b5cef261.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) ![Private beach, kayaking, rowing, fishing](https://images.trvl-media.com/lodging/7000000/6840000/6839400/6839376/a2a4b9c8.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) ### The Pelican Key Largo Cottages Key Largo 8.8/10 Excellent (1002) "Great cottages very clean n quiet place right on waterfront " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ms Maria CA $140 CA $158 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Key-Largo-Hotels-The-Pelican-Key-Largo-Cottages.h6839376.Hotel-Information) ![Studio Suite | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/38a88171.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Oceanfront | Terrace/patio](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/e0609cf0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, open 9 AM to 9 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/b15145a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite | Private kitchen](https://images.trvl-media.com/lodging/6000000/5320000/5311400/5311313/af2541bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amoray Dive Resort Key Largo 9.2/10 Wonderful (1001) "Room and grounds were spotless and the location, directly on the water and with several restaurants within a short walking distance, was ideal. Staff were polite and helpful, also." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alan CA $133 CA $150 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Key-Largo-Hotels-Amoray-Resort.h5311313.Hotel-Information) ![Superior Bungalow, Multiple Beds, Beachfront (Ground Level Sleeps 6) | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/6747175b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/31d6a642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 2 Queen Beds, Kitchenette, Bay View](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/c0d44f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Jolla Resort Matecumbe 9.0/10 Wonderful (1003) "Great place to stay lovely staff Easy to find " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) diane [](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/fa9b6bdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ![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) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort Matecumbe 9.2/10 Wonderful (1574) "Great breakfast very well kept grounds" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) James CA $198 CA $302 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Gazebo](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/fe271bae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/484a28a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage 3 Not Pet-Friendly](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/9ba18998.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/6000000/5030000/5027500/5027403/28719020.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sunset Cove Beach Resort Key Largo 9.0/10 Wonderful (1000) "Always a great stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Richard CA $212 CA $239 total includes taxes & fees Nov 17 - Nov 18 [](https://www.expedia.ca/Key-Largo-Hotels-Sunset-Cove-Beach-Resort.h5027403.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/76d0e123.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/b41300e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, in-room safe, blackout drapes](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/43b1d1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/7300/7230/759ada7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Key Largo by IHG Key Largo 8.6/10 Excellent (1005) "Excellent place to stay for a weekend " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carlos CA $222 CA $249 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.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=2025-11-29&endDate=2025-11-30®ionId=553248635976197663&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=APART_HOTEL) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=APARTMENT) Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=VACATION_HOME) Condos [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=VILLA) Houseboats [](https://www.expedia.ca/Hotel-Search?destination=Windley+Key%2C+Florida%2C+United+States+of+America®ionId=553248635976197663&latLong=24.954588%2C-80.592445&adults=2&startDate=2026-02-13&d1=2026-02-13&endDate=2026-02-16&d2=2026-02-16&lodging=HOUSE_BOAT) ![](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-Cottages.d553248635976197663-aaCottages.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Cottages.d553248635976197663-aaCottages.Travel-Guide-Accommodation) ## Top Windley Key Hotel Reviews ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Rooms were clean big and had a great view. The staff was amazing. " [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ### Cheeca Lodge & Spa 10/10 Excellent "Amazing!" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ### Chesapeake Beach Resort 10/10 Excellent "Room was clean, breakfast and staff were good " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Rock Reef Resort](//images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "This place was awesome. Friendly staff. Would definitely stay again if in the area." [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.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 , coconut beach was wonderful, the other beach too. Nice rooms with nice views " [](https://expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ### Coconut Cove Resort and Marina 10/10 Excellent "Really really enjoyed the laid back style at this resort and what a beautiful property. Will be back soon!" [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.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. Great staff" [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.Hotel-Information) ### Amara Cay Resort 10/10 Excellent "Very nice resort! Nice pool and the tiki bar was amazing. Great service and so close to Bud and Mary’s since we were fishing a few days. Definitely will return." [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ### Lime Tree Bay Resort 10/10 Excellent "Room was spotless the view was to die for and the staff absolutely amazing " [](https://expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ## Find out more about Windley Key ## Windley Key Cottages information | Number of reviews | | | --- | --- | | Accommodation | Cottages | | 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) - 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