Title: Book the Best Downtown Key West WINERY Hotels in 2026 | 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)

![Ernest Hemingway Home and Museum featuring heritage elements and a house](https://images.trvl-media.com/place/501376/3b4c31fa-338d-424b-aa0f-482ad359d16a.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Find Winery Hotels in Downtown Key West, FL from CA $487

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## Check availability on Downtown Key West Winery Hotels

Tonight

[Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-05&endDate=2025-12-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 6 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-06&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=553248635976470405&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Downtown Key West Winery Hotels

![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/22000000/21700000/21690900/21690843/8dc353de.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

(236)

"Great location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carmel M.

CA $378

CA $694 total

includes taxes & fees

Jan 1 - Jan 2, 2026

[](https://www.expedia.ca/Key-West-Hotels-Downtown-Dog-Friendly-Cottage-Like-Studio-With-Patio.h21690843.Hotel-Information)

![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

(1000)

"The poolside seating was very nice. It was very comfortable. It was a nice being able to grab extra items if needed beside the washer and dryer. Our room even came with Tide Laundry Detergent and extra pool towels. We would definitely stay here again! It was so convenient to everything on Duval Street. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Mary

CA $308

CA $487 total

includes taxes & fees

Dec 16 - Dec 17

[](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)

![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)

![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/f7bd180e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/4dc70db6.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

(115)

"Great location, close to everything family had a great time."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

rafael m.

CA $377

CA $827 total

includes taxes & fees

Dec 8 - Dec 9

[](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.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=2025-12-19&endDate=2025-12-20&regionId=553248635976470405&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Downtown Key West Hotel Reviews

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