Title: Windley Key Vacation Rentals from CA $193: Short-Term Rentals for 2025 | 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)[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) # Windley Key Vacation Rentals ![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&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976197663&startDate=2025-10-31&endDate=2025-11-02&adults=2&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&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&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Windley Key ![Property grounds](https://images.trvl-media.com/lodging/35000000/34530000/34520800/34520723/b6691c8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/35000000/34530000/34520800/34520723/4af3e774.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/35000000/34530000/34520800/34520723/677b25ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/35000000/34530000/34520800/34520723/62cb2b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Paradise in Venetian Shores Pool / SPA - Heater / Chiller & Commercial Ice Maker Venetian Shores 10/10 Exceptional (38) "Was a nice property and pleasant enough for our stay." [](https://www.expedia.ca/Islamorada-Hotels-Paradise-In-Venetian-Shores-Pool-SPA-Heater-Chiller-Commercial-Ice-Maker.h34520723.Hotel-Information) ![A heated pool](https://images.trvl-media.com/lodging/26000000/25090000/25088000/25087966/a399288a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Children's area](https://images.trvl-media.com/lodging/26000000/25090000/25088000/25087966/5266da3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/26000000/25090000/25088000/25087966/5c0cbd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/26000000/25090000/25088000/25087966/1ab96f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### OCEANFRONT ANGLERS REEF in ISLAMORADA -Pool, Dock, Beach, Kayaks, Paddle Boards Islamorada 10/10 Exceptional (185) "Great property. Very clean and had everything we needed. The whole complex is very nice and loved our stay. Owners very good with communication and friendly." [](https://www.expedia.ca/Islamorada-Hotels-OCEANFRONT-ANGLERS-REEF-ISLAMORADA-HOME-Pool.h25087966.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/118000000/117370000/117360600/117360591/41466dc5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, video games, table tennis, stereo](https://images.trvl-media.com/lodging/118000000/117370000/117360600/117360591/f60fb0cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117370000/117360600/117360591/c86711e4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/118000000/117370000/117360600/117360591/e906dcf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW - Oceanfront FL Keys Home w/Pool, Free Dockage, Gameroom, Private Balcony Islamorada 10/10 Exceptional (1) "This property was amazing basically brand new definitely recommend " [](https://www.expedia.ca/Islamorada-Hotels-NEW-Oceanfront-FL-Keys-Home-WPool.h117360591.Hotel-Information) ![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/92a650b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/ee0752b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/1641bbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treasure Harbor Islamorada 8.8/10 Excellent (106) "If you are looking for a laid back vibe with no hassle here is the place. Friendly staff. Aqualodge was cute and comfortable. Easily rented a boat for the day...found great snorkeling and beautiful views. " CA $138 CA $352 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 1 Bedroom, Kitchen, Pool View | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/5e728c12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cottage | Living area](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/7a0bffa6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Cottage](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/b8fa0acc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezy Palms Resort Matecumbe 8.8/10 Excellent (541) "Spacious rooms and location was great for what we needed. " CA $107 CA $193 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![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) ![Fireplace](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/531fe0b4.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) ### The Islands of Islamorada Matecumbe 9.8/10 Exceptional (66) "Absolutely outstanding resort. Legitimate 5 star property. " CA $768 CA $941 total includes taxes & fees Oct 5 - Oct 6 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) ![Boating](https://images.trvl-media.com/lodging/24000000/23710000/23709100/23709068/461bf404.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, free beach cabanas, beach towels, scuba diving](https://images.trvl-media.com/lodging/24000000/23710000/23709100/23709068/cbfe047c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/24000000/23710000/23709100/23709068/6c9e5462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/24000000/23710000/23709100/23709068/a4a9e792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo Cottages Key Largo 9.6/10 Exceptional (24) "Beautiful and peaceful place " [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Cottages.h23709068.Hotel-Information) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/7f2e2269.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room | View from room](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/3c8c13d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Comfort Room](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/29275608.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/14000000/13280000/13279700/13279636/0514aa55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Bay Resort Tavernier 10/10 Exceptional (132) "Clean, friendly, has its own beach" [](https://www.expedia.ca/Tavernier-Hotels-Island-Bay-Resort.h13279636.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/103000000/102250000/102242200/102242195/430a28a4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102250000/102242200/102242195/3f852982.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/103000000/102250000/102242200/102242195/9573e9d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/103000000/102250000/102242200/102242195/16a93c35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Relax in your one bedroom Oceanfront Suite in Tavernier FL. Florida Keys. Tavernier 9.8/10 Exceptional (57) "Great unit, nicely renovated and a good weekend! " [](https://www.expedia.ca/Tavernier-Hotels-Relax-In-Your-One-Bedroom-Oceanfront-Suite-In-Tavernier-FL-Florida-Keys.h102242195.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44080000/44079000/44078971/172890e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/45000000/44080000/44079000/44078971/97d27293.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/45000000/44080000/44079000/44078971/eebfd124.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/45000000/44080000/44079000/44078971/ddcabe47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Two Panoramic Ocean Views from the Living room and Master Bedroom in this Condo Tavernier 9.8/10 Exceptional (224) "We found the condo very nicely located to Key Largo, Islamorada, and Tavernier. Enjoyed restaurants with sunset bayside, snorkeling excursion off John Pennecamp state park, and the pool and tiki hut on resortPremises! Would return here if back in the area. " [](https://www.expedia.ca/Tavernier-Hotels-Two-Panoramic-Ocean-Views-From-The-Living-Room-And-Master-Bedroom-In-This-Condo.h44078971.Hotel-Information) ![Fishing](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/b43053cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Cabin | Living area](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/1ac6888f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Apartment | Private kitchen](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/8d608263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers](https://images.trvl-media.com/lodging/79000000/78330000/78323400/78323367/96315701.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kings Kamp Key Largo 8.8/10 Excellent (23) "The property is beautiful, nicely renovated and clean. A true gem is a covered patio with grill and a small beach right outside the door. There is plenty of local attractions to choose from near by. We had a fantastic stay and would highly recommend this property. We hope to come back again some day. Thank you!" CA $225 CA $254 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Key-Largo-Hotels-Kings-Kamp.h78323367.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/115000000/114470000/114469100/114469045/a4739b6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/115000000/114470000/114469100/114469045/4beca01b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, in-room safe, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/115000000/114470000/114469100/114469045/aa42431b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/115000000/114470000/114469100/114469045/9e703d6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 5 Star Coastal Luxury: Key Largo 2BR Condo w/Lagoon, Golf Cart, Pools& Amenities Key Largo 10/10 Exceptional (16) "Great vacation spot , only thing missing is a good saltwater beach." [](https://www.expedia.ca/Key-Largo-Hotels-Coastal-Luxury-Key-Largo-2BR-Condo-W-Lagoon.h114469045.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/34000000/33570000/33568800/33568760/b543b616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/34000000/33570000/33568800/33568760/3d4f6280.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/34000000/33570000/33568800/33568760/be2db90c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bar (on property)](https://images.trvl-media.com/lodging/34000000/33570000/33568800/33568760/5f289790.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Front Private Beach, Pool/Hot Tub, Pool Bar, Marina with Cafe Tavernier 9.8/10 Exceptional (186) "The property was exactly as described. Great view nice amenities and friendly employees. Great location everything is close by. Already planning on coming back again " [](https://www.expedia.ca/Tavernier-Hotels-Ocean-Front-Private-Beach.h33568760.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/36000000/35140000/35132500/35132443/382a8bcb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35140000/35132500/35132443/194b23b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/36000000/35140000/35132500/35132443/4f978649.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![A heated pool](https://images.trvl-media.com/lodging/36000000/35140000/35132500/35132443/460eff2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### VOTED BEST KEY LARGO VACATION RENTAL Key Largo 10/10 Exceptional (82) "Wonderful property! Very clean, plenty of space, and updated interior. Access to many amenities across the whole property with multiple pools, a swimming lagoon, fishing equipment, bikes, kayaks, and more. Great location to everything in Key Largo and southern Florida activities. Would highly recommend. " [](https://www.expedia.ca/Key-Largo-Hotels-VOTED-BEST-KEY-LARGO-VACATION-RENTAL.h35132443.Hotel-Information) ![On the beach, sun loungers, beach towels](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/2b862fb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/6717e112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/69382ece.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, DVD player, table tennis, books](https://images.trvl-media.com/lodging/35000000/34020000/34015800/34015770/ee947f8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly Islamorada 9.4/10 Exceptional (98) "Oceans views for miles! Great pool. " [](https://www.expedia.ca/Tavernier-Hotels-Oceanfront-Estate-With-Private-350-Foot-Pier.h34015770.Hotel-Information) ![Marina](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/88377e50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/9f308d75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/a381fdfe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/56000000/55190000/55186000/55185936/f3ee7112.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Waterfront Tiny House w Pool, Beach, and Boat Dock Key Largo 9.6/10 Exceptional (61) "Excelent place " CA $163 CA $508 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-Largo-Hotels-Tiny-House-On-The-Water-Pool.h55185936.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/94241dd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/006a1068.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shower, hair dryer, towels, soap](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/95c54ed2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/100000000/99970000/99961500/99961430/b3fdbd21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Home in Key Largo Key Largo 9.8/10 Exceptional (25) "Great location. Very clean very nice, stay there again" CA $188 CA $599 total includes taxes & fees Oct 17 - Oct 18 [](https://www.expedia.ca/Key-Largo-Hotels-Charming-Home-In-Key-Largo.h99961430.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/97000000/96940000/96937900/96937889/749b2e71.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/97000000/96940000/96937900/96937889/ebe28741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/97000000/96940000/96937900/96937889/4f4e00aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96940000/96937900/96937889/4aed51c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amazing Ocean view at Ocean Pointe w/Heated Pool Tavernier 9.6/10 Exceptional (39) "We enjoyed our time at Ocean Point. " [](https://www.expedia.ca/Tavernier-Hotels-Amazing-Ocean-View-At-Ocean-Pointe-WHeated-Pool.h96937889.Hotel-Information) ![Beach nearby, sun loungers, beach towels](https://images.trvl-media.com/lodging/56000000/55190000/55183800/55183749/9d06b7de.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/56000000/55190000/55183800/55183749/03594f35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/56000000/55190000/55183800/55183749/7fbea524.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/56000000/55190000/55183800/55183749/0c6f892e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Beachside Retreat w/ Pool, Boat Ramp Dock for Rent Key Largo 9.6/10 Exceptional (39) "Beautiful place. Our stay was quiet and wonderful. Very clean and comfortable. " CA $107 CA $387 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Key-Largo-Hotels-Cozy-Home-Beach.h55183749.Hotel-Information) ![Sun loungers](https://images.trvl-media.com/lodging/114000000/113320000/113313700/113313657/362909f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113320000/113313700/113313657/660dcd95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, dishwasher, coffee/tea maker](https://images.trvl-media.com/lodging/114000000/113320000/113313700/113313657/2eebfb00.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/114000000/113320000/113313700/113313657/19e63d0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### BeachFront Paradise/By The Glam Homes Matecumbe [](https://www.expedia.ca/Islamorada-Hotels-BeachFront-ParadiseBy-The-Glam-Homes.h113313657.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=2025-10-18&endDate=2025-10-19®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-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWindley-Key-Vacation-Rentals.d553248635976197663.Travel-Guide-VacationRentals) ## Top Windley Key Hotel Reviews ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Yes" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Holiday Inn Key Largo by IHG](//images.trvl-media.com/lodging/1000000/10000/7300/7230/160ba216_y.jpg) ### Holiday Inn Key Largo by IHG 10/10 Excellent "September is the quietest month and this has been exceptionally quiet apparently, still staff were very attentive, no reason to think it unusual ," [](https://expedia.ca/Key-Largo-Hotels-Holiday-Inn-Key-Largo.h7230.Hotel-Information) ![Rock Reef Resort](//images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999_y.jpg) ### Rock Reef Resort 10/10 Excellent "The staff were friendly and funny. The room was comfortable. I had fun. " [](https://expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Excellent recommendation for a small budget." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Playa Largo Resort & Spa, Autograph Collection](//images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/489feb58_y.jpg) ### Playa Largo Resort & Spa, Autograph Collection 10/10 Excellent "The entire environment " [](https://expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.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 "Truly enjoyed our visit to this property. Lots to do and great dining options! We will be back." [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "Loved the stay at Amara Cay! Will be back. Staff was amazing." [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Reefhouse Resort & Marina](//images.trvl-media.com/lodging/1000000/10000/3500/3427/af093823_y.jpg) ### Reefhouse Resort & Marina 10/10 Excellent "Great location. Very nice and quiet 🤐 " [](https://expedia.ca/Key-Largo-Hotels-Reefhouse-Resort-Marina.h3427.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 "There’s a small but cozy beach area with the best view for sunset during happy hour at the tiki bar. We saw other guests have easy access to kayaks and paddle boarding and pets were welcomed!" [](https://expedia.ca/Key-Largo-Hotels-Hampton-Inn-Key-Largo-Manatee-Bay.h5731.Hotel-Information) ## Find out more about Windley Key **Everything you need to know about** **Windley Key** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Windley Key vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windley Key vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Windley Key vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Windley Key. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windley Key vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Windley Key vacation rentals we have selected for you start as low as CA $193 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Windley Key rentals** At Expedia, we put the best Windley Key vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Windley Key rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windley Key vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windley Key. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Windley Key ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - 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[Visit Union Square](https://expedia.ca/San-Francisco-Union-Square.dx800129) - [Visit Honeymoon Island State Park](https://expedia.ca/Honeymoon-Island-State-Park.dx6160046) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAyAAAAMgAQAAAADzCzvFAAAFTElEQVR4Xu3aPXLcOBBAYbgUKNwjzFFwNPBoc5Q5gsMJVIud/gHQhGiVO/AG8nuJqB4AHzOKkkr/Hyr74E8EkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUgqkFQB+ShbtzH60fu9vL8Wv0baT5nW/iyv7Q+5bjaKtXUySAHZl4FYbZ0MUkD2ZSBWWyd/V6St7/TE5VYbPmx7RHzjT7mV2fksEBAQEAlEA9FAZr5We59Isw/vMvWFR/HHvo4e8sURHZ03SiAgIPIFBKSAgHhfI5pujx22psq1XYKASCCxw9ZUubZLEBAJJHbYmirXdgkSkZWPev83IG+2CkQDGUtBQEAKCMjvIquwVk98TslvpY6Vfnc/5tb9LBAQEBAJZI1mICAf8xTPEd1+L+/BvRxttXUyyMVoq62TQS5GW22dDHIx2mrrZJCL0VZbJ4NcjLbaOhnkYrTV1skBuUi36zPeu8n0KP+Ex74jXwUCchHIFgjIRSBb3xfxR/V7H0/v8jqxywO92D9zrV9na457NYyar5DJutRArBpGzVfIZF1qIFYNo+YrZLIuNRCrhlHzFTJZlxqIVcOo+QqZrEsNxKph1HyFTNalBmLVMGq+Qibrsoent/bYt/uoGXKXa3ePov9x3fvTRrpqBgLSQUA0XevFEYgH8jci+kD3/BnfbXtxZH4cb0WLdycL3sJnICAgFggISAHxdkTfp+ejWtd+euuWZ3yRE9cDPW6UQEA6CAgISAexjdJXiG+PJ0rr5Vk7Po+8u2ycdzcDAQEJgYDEQEAUWf/M5WsPe3rrdhnr9nUr80QdVXH97uQsDwQEBAQEBOQXiOZ/Ol4nOtJt+0TWqtvYOJruDAREAwEBAZFA+gmJz+WnrV1VmfqJR1mv2DL6sCVr5LcyAwEBAQEB8apMQXbEH9XvcqKv1Qd6PFFW6ejceDf3WwmBgICMQEC2T0BAujy99X36Lsh5tCNFHvvP+ZPA2X3Y3c1AQDoICIgFAqKdkW5rFZG9a+1dvp3bfZWO5kbt00YJBEQDAQEBAfEC8mHLBuLNx752s6GfWMzV4ioQ336zIQgICAgIyC8RTbdX/eR14oe8POvvrnUkJ/p2/XX2+VbGb7jdbfNDEBALBAQEBMQLSDzxKWu1o+hjP+aju53o6Vv3zM/yQEBALBANBGQEIukHvvYpB9xkVIq/PL8e6OfRXOXp3XVZVcZPAh6IBgLSQUBAQKxLRE+cxbfu2biVudGRdXcy8kBAQEBAQEC+QnytfLLWjpGvioivivX+kC+y0QMBAQHRT0BAQLyAXKSIPuNLeZfBw16e408C8cT5w4HfnQcCchEICIgEAvJhh61uMj2K/udW7c/TZwPxb+VWdOTprcxAQEAkEBANBKTvSFvf9TNS5ERJV8XHftw4kXI6CwQEBEQCAQEZ7cjaLoiPfqxFkriaPvZ11Uzdh1y1tQFEAwEZgYCsDSAayCekFH3GV11c/OXZVxX7a/LbdO+G+FkzEBAQEBAQkCSiVV38Gmm6qvanfaaI/tJ7PvbPgegIBKSAgICAWDuy8rWyPZ64qmHxMUYgcXushsXHGIHE7bEaFh9jBBK3x2pYfIwRSNweq2HxMUYgcXushsXHGIHE7bEaFh9j9BvIuZtM5eV5vWLPUZ/v0w9ZKj8cjGe8jN7kegbSQTYDBATEA+l/PfLnAkkFkgokFUgqkFQgqUBSgaQCSQWSCiQVSCqQVCCpQFKBpAJJBZIKJBVIKpBUIKlAUoGkAkkFkgokFUiq74P8BybPEgcNx3OaAAAAAElFTkSuQmCC)