Title: Book the Best Downtown Key West WINERY Hotels in 2025 | Expedia.ca [Downtown Key West Travel Guide](https://expedia.ca/Key-West-Downtown-Key-West.dx553248635976470405)[Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights)[Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities)[Downtown Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Downtown-Key-West.d553248635976470405.Car-Rental-Guide)[Downtown Key West Vacations](https://expedia.ca/Downtown-Key-West.d553248635976470405.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/63000/63795-Florida-Keys.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Winery Hotels in Downtown Key West, FL from CA $291 ![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 availability on Downtown Key West Winery Hotels Tonight [Oct 6 - Oct 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-10-06&endDate=2025-10-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 7 - Oct 8](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-10-07&endDate=2025-10-08&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Downtown Key West Winery Hotels ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/300/217/c6778dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/300/217/dc75eb36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/300/217/b191a829.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/10000/300/217/8e70662e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amsterdam's Curry Mansion Inn Key West Historic District 8.4/10 Very good (1001) "Right in the middle of everything yet quiet at night. Beautiful room and helpful staff via text. " CA $194 CA $360 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Key-West-Hotels-Amsterdams-Curry-Mansion-Inn.h217.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/9d11031b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/f7bd180e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/156e79e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/d6954c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED Stock Island 9.8/10 Exceptional (113) "Great location. Clean and beautifully decorated. " CA $314 CA $749 total includes taxes & fees Oct 10 - Oct 11 [](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/81510f43.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Iron/ironing board, free internet, bed sheets](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/13c903c5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/ee58575e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hair dryer, towels](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/3927e1be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC Old Town Key West 8.8/10 Excellent (231) "Property was cute and in a great location! " CA $89 CA $291 total includes taxes & fees Oct 7 - Oct 8 [](https://www.expedia.ca/Key-West-Hotels-Downtown-Dog-Friendly-Cottage-Like-Studio-With-Patio.h21690843.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=2025-10-20&endDate=2025-10-21®ionId=553248635976470405&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Downtown Key West Hotel Reviews ## Explore a world of travel with Expedia - Lodging - More ways to book - [Adults Only Resorts & in Bahama Village](https://www.expedia.ca/Bahama-Village-Key-West-Hotels-Adults-Only-Resorts.0-n553248621533115696-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - [All Inclusive Resorts and in Bahama Village](https://www.expedia.ca/Bahama-Village-Key-West-Hotels-All-Inclusive-Hotel.0-n553248621533115696-0-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Bahama Village](https://www.expedia.ca/Bahama-Village-Key-West-Hotels-Beach-Hotel.0-n553248621533115696-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Bahama Village](https://www.expedia.ca/Bahama-Village-Key-West-Hotels-Boutique-Hotel.0-n553248621533115696-0-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - 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