Title: Windley Key Villas from CA $754 | Expedia.ca [Windley Key Travel Guide](https://expedia.ca/Windley-Key.dx553248635976197663)[Hotels in Windley Key](https://expedia.ca/Windley-Key-Hotels.d553248635976197663.Travel-Guide-Hotels)[Vacation Rentals in Windley Key](https://expedia.ca/Windley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Flights to Windley Key](https://expedia.ca/Cheap-Flights-To-Windley-Key.d553248635976197663.Travel-Guide-Flights)[Things to do in Windley Key](https://expedia.ca/Things-To-Do-In-Windley-Key.d553248635976197663.Travel-Guide-Activities)[Windley Key Car Rentals](https://expedia.ca/Car-Rentals-In-Windley-Key.d553248635976197663.Car-Rental-Guide)[Windley Key Vacation Packages](https://expedia.ca/Windley-Key.d553248635976197663.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/340000/340299-Windley-Key-Fossil-Reef-Geological-State-Park.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Windley Key Villa Rentals from CA $754 ![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 In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2026-01-23&endDate=2026-01-25&adults=2&lodging=VILLA&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Windley Key Villas ![2 outdoor pools, open 8:00 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/61575cce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/5be55ff2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a93dc7d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fireplace](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/531fe0b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada Matecumbe 9.8/10 Exceptional (66) "Absolutely outstanding resort. Legitimate 5 star property. " CA $602 CA $754 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/58000000/57570000/57563600/57563548/fc38c333.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57570000/57563600/57563548/76784526.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/58000000/57570000/57563600/57563548/cd933cb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/58000000/57570000/57563600/57563548/e3e74b6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Our place overlooks the Atlantic. Our marina is less than 50 ft from our patio Key Largo 9.8/10 Exceptional (51) "Great location Vivian was very responsive to any questions we had" [](https://www.expedia.ca/Key-Largo-Hotels-Oceanfront-Villa-Overlooking-The-Atlantic-And-Molasses-Reef-Marina.h57563548.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/35000000/34330000/34330000/34329991/ae5ac449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/35000000/34330000/34330000/34329991/393a7a7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, stereo](https://images.trvl-media.com/lodging/35000000/34330000/34330000/34329991/28c11c01.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/35000000/34330000/34330000/34329991/9ff6e220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Newly upgraded Key Largo Villa W/Boat Slip Key Largo 10/10 Exceptional (81) "Excellent location Great value" [](https://www.expedia.ca/Key-Largo-Hotels-Newly-Upgraded-Key-Largo-Villa-WBoat-Slip.h34329991.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/107000000/106100000/106096400/106096317/w8062h4529x0y9-3a7dc75c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/107000000/106100000/106096400/106096317/b997f05d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106100000/106096400/106096317/3b67e9e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/107000000/106100000/106096400/106096317/08363cd0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Isla Honeydew: 3 En-Suite Bedrooms! FREE boat dockage Sept-Oct only Matecumbe 10/10 Exceptional (4) "The home was just as it was described on the website! Beautiful, comfortable and clean. Plenty of cooking items. Location was wonderful-we could walk to several restaurants and store. Would stay again!" [](https://www.expedia.ca/Islamorada-Hotels-Isla-Honeydew-3-En-Suite-Bedrooms-Waterfront-Resort.h106096317.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/691ffb10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Staircase](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/cc96c50e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Egyptian cotton sheets, premium bedding, memory foam beds](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/478c87a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![75-inch Smart TV with digital channels, Netflix, streaming services](https://images.trvl-media.com/lodging/110000000/109730000/109724500/109724487/e85faba6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront House with Boat Dock Hammer Point 6.0/10 (1) "Covered porch was nice for time outside. Inside was in need of work. Closets unfinished, no place to put any luggage, advertises a king bed and a queen bed, but only had a king and a full, no tp, or tissue products when we arrived. None of the above were deal breakers but just allot of small things that add up to frustration." [](https://www.expedia.ca/Tavernier-Hotels-Waterfront-House-With-Boat-Dock.h109724487.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231680/88239648.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231680/9a5daf5e_edited_a9ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231680/32954482_edited_faa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231680/f0369f04_edited_8437.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Full Ocean View Luxury Villa | Gym & Beach Club Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-The-Lookout-With-Resort-Privileges.h98231680.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/120000000/119330000/119330000/119329985/a3c8cb42.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/120000000/119330000/119330000/119329985/w1349h897x0y3-2ce0a7ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119330000/119329985/w1349h897x0y3-0d3b59fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/120000000/119330000/119330000/119329985/179208e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Luxe Pool, Hot Tub, Theater, Games and More! Buccaneer Point [](https://www.expedia.ca/Key-Largo-Hotels-Waterfront-Luxe-Pool.h119329985.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231662/30d6d9b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231662/b8a64e90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231662/e7ea0923_edited_b4fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231662/8f493072.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Key Largo – Gym, Pool + Beach Key Largo 10/10 Exceptional (3) "The house was great and so was the resort access. Enjoyable long weekend!" [](https://www.expedia.ca/Key-Largo-Hotels-Sandcastle-Luxury-Villa-In-Key-Largo-With-Resort-Privileges.h98231662.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/58000000/57190000/57185700/57185636/15c6915b_edited_d6bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/58000000/57190000/57185700/57185636/1d861020_edited_67c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/58000000/57190000/57185700/57185636/3015b27c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57190000/57185700/57185636/d7d72835_edited_1546.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Key Largo Villa w/ Beach & Marriott Perks Key Largo 9.6/10 Exceptional (25) "We all had fantastic time" [](https://www.expedia.ca/Key-Largo-Hotels-Gulls-Nest-With-Resort-Privileges.h57185636.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/19000000/18770000/18762500/18762434/a6567322.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/19000000/18770000/18762500/18762434/57f69904.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/19000000/18770000/18762500/18762434/2503f5e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/19000000/18770000/18762500/18762434/08dd61fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Serenity by the Sea!! Anglers Reef with Boat Slip Available!! Islamorada 10/10 Exceptional (116) "Great house and neighborhood!" [](https://www.expedia.ca/Islamorada-Hotels-Serenity-By-The-Sea-Anglers-Reef-With-Boat-Slip-Available.h18762434.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/105000000/104520000/104514700/104514629/w8062h4529x0y9-483ea7e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/105000000/104520000/104514700/104514629/7923061f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/105000000/104520000/104514700/104514629/5a858704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/105000000/104520000/104514700/104514629/0549e724.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only! Matecumbe 9.6/10 Exceptional (4) "Enjoyed my stay, plenty of room and amenities. May let people know you have a kareg coffee maker not a regular filter coffee maker. Very clean and comfortable." [](https://www.expedia.ca/Islamorada-Hotels-Isla-Key-Guava-Waterfront-Boutique-Resort.h104514629.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/58000000/57190000/57185700/57185641/8e910ddb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach](https://images.trvl-media.com/lodging/58000000/57190000/57185700/57185641/d7f66310_edited_8e20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/58000000/57190000/57185700/57185641/87de9ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/58000000/57190000/57185700/57185641/2f952b47_edited_d114.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Key Largo Stay – Pool, Parking + Beach Club Key Largo 9.6/10 Exceptional (14) "This is a fantastic place to stay. Home is beautiful, the pool overlooking the ocean is outstanding, and the Playa Largo resort has a large pool, and beautiful blue bay to swim in. The host Josie is wonderful, is very responsive and quick to answer your questions. Nobody wanted to go home so we stayed an extra day. Loved it and will definitely return." [](https://www.expedia.ca/Key-Largo-Hotels-Endless-Summer-With-Resort-Privileges.h57185641.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231678/c2bfc6f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231678/df14637e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231678/d4a972e4_edited_2b50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231678/7941fbe7_edited_11ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo 4BR Villa | Partial Ocean View + Marriott Key Largo 9.4/10 Exceptional (6) "Excellent in every way … clean , new and beautiful place !!" [](https://www.expedia.ca/Key-Largo-Hotels-Coastal-Oasis-With-Resort-Privileges.h98231678.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231677/ce23fbb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231677/cb9b220a_edited_5973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231677/80465bf7_edited_2a22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231677/ae5544a3_edited_7cba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo 4BR Villa – Partial Ocean View & Pool Key Largo 9.0/10 Wonderful (6) "Place was better than listed as pictures don’t show it allGreat location and service from the resort was awesome " [](https://www.expedia.ca/Key-Largo-Hotels-Coral-Breeze-With-Resort-Privileges.h98231677.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231683/c6575dcc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231683/3ac4b5a1_edited_cb22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231683/8138b73b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231683/3aba8639_edited_0bec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo 4BR Villa | Pool, Clubhouse & Gym Key Largo 10/10 Exceptional (1) "What a great option to have access to the hotel but come back each day and finish at the clubhouse pool for sunset! Really great house with plenty of room and great variety to get away from the hotel! " [](https://www.expedia.ca/Key-Largo-Hotels-Twilight-With-Resort-Privileges.h98231683.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231667/e59e1fae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231667/fb16f4f3_edited_d945.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231667/bd34dd06_edited_c9ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231667/20cc5d68_edited_b0c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Villa w/ Private Pool & Gym Access Key Largo 9.4/10 Exceptional (10) "Great property!" [](https://www.expedia.ca/Key-Largo-Hotels-Sea-Haven-With-Resort-Privileges.h98231667.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/105000000/104970000/104966900/104966897/c313d88e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104970000/104966900/104966897/3e7c013a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/105000000/104970000/104966900/104966897/1bcdc669.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/105000000/104970000/104966900/104966897/e0e0d5ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only! Matecumbe 10/10 Exceptional (2) "Great as always. Clean, well maintained, and the support staff always helpful!" [](https://www.expedia.ca/Islamorada-Hotels-Bayberry-Key-Waterfront-Boutique-Resort.h104966897.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231672/076ec94e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231672/a450d627_edited_3fa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231672/04daf6e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231672/6f3b4767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa in Key Largo – Pool & Beach Club Key Largo 10/10 Exceptional (8) "We had an amazing winter getaway . Clean , new , house in a wonderful location " [](https://www.expedia.ca/Key-Largo-Hotels-Sea-Esta-With-Resort-Privileges.h98231672.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231661/10150c09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231661/6a3c4600.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231661/5c67a019_edited_51e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/99000000/98240000/98231700/98231661/98282b0c_edited_40a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo 4BR Villa | Pool + Resort Access Key Largo 8.8/10 Excellent (3) "Family Men’s Bible study and “slow living” weekend. Perfect scene and stay! Thank you!" [](https://www.expedia.ca/Key-Largo-Hotels-Latitudes-With-Resort-Privileges.h98231661.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/113000000/112180000/112179700/112179681/fa8b844d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112180000/112179700/112179681/fed4de75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112180000/112179700/112179681/a095e8bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/113000000/112180000/112179700/112179681/a928b74c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl Matecumbe 10/10 Exceptional (2) "The house is clean, well decorated, and equipped with everything that you would need for a vacation. Quick response and good communication. The plunging pool was great at the house, and a larger pool - ocean side if you need more sun! Within walking distance to restaurants, and Cafe Moka next door. We would stay here again, in a heart beat." [](https://www.expedia.ca/Islamorada-Hotels-Villa-With-Private-Plunge-Pool.h112179681.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=2025-10-13&endDate=2025-10-14®ionId=553248635976197663&adults=2&lodging=VILLA&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Villas.d553248635976197663-aaVillas.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Villas.d553248635976197663-aaVillas.Travel-Guide-Accommodation) ## Top Windley Key Hotel Reviews ![Bayside Inn Key Largo](//images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787_y.jpg) ### Bayside Inn Key Largo 10/10 Excellent "Yes everything was just amazing i felt so safe It was just me and my sister and we would definitely come back " [](https://expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ![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 "Beautiful views, friendly staff. Great amenities " [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Drop Anchor](//images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "It was a perfect little cottage and peace and quiet. Lots of Palm trees and perfect boat launch" [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "We thoroughly enjoyed our stay at Reefhouse. Staff was friendly and helpful. Water and cookies at the front desk is a nice touch. Carlos, bartender at pool bar, went out of his way to make you feel welcome. When we saw him the following day he even remembered our drinks." [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Clean room, ocean view, friendly staff. Highly recommended!" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Waterside Suites & Marina](//images.trvl-media.com/lodging/1000000/20000/13800/13719/7b7ca43b_y.jpg) ### Waterside Suites & Marina 10/10 Excellent "Clean with friendly staff, right next to the marina and dive shop. Definitely will be staying again on next trip." [](https://expedia.ca/Key-Largo-Hotels-Waterside-Suites-Marina.h13719.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 "The location is very nice, with a small private beach and beautiful views. The rooms were clean and spacious. The hot/cold breakfast was delicious. The pool and gym were good. Nicole the bartender at the tiki bar was friendly and great." [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Everything was perfect and beautiful " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "The resort had free kayaking and paddle boarding which was a great addition. " [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ## Find out more about Windley Key ## Windley Key Villas information | Number of reviews | 349 | | --- | --- | | Accommodation | 53 Villas | | Lowest Price | CA $754 | | Highest Price | CA $754 | ## 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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