Title: Book the Best Old Town Key West WINERY Hotels in 2026 | Expedia.ca

[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)[Old Town Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Old-Town-Key-West.d553248635976481920.Car-Rental-Guide)[Old Town Key West Vacations](https://expedia.ca/Old-Town-Key-West.d553248635976481920.Destination-Travel-Guides)

![Key West Lighthouse and Keeper\'s Quarters Museum featuring a lighthouse](https://images.trvl-media.com/place/501383/0a79f1bb-7c8b-43da-830f-8c77ccf8ffbb.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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

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## Check availability on Old Town Key West Winery Hotels

Tonight

[Dec 5 - Dec 6](https://www.expedia.ca/Hotel-Search?regionId=553248635976481920&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=553248635976481920&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=553248635976481920&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=553248635976481920&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Top Old Town 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)

![Exterior](https://images.trvl-media.com/lodging/22000000/21700000/21690900/21690843/8dc353de.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)

![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)

![Classic King Balcony](https://images.trvl-media.com/lodging/1000000/10000/300/217/af12ee69.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)

### 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)

![Terrace/patio](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/f7bd180e.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)

![Exterior](https://images.trvl-media.com/lodging/32000000/31900000/31892700/31892617/156e79e7.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=553248635976481920&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Price trends for hotels in Old Town Key West

| Less expensive | More expensive | This month | Next month |
| -------------- | -------------- | ---------- | ---------- |
| September      | February       | CA $406    | CA $534    |

| Month     | Price   |
| --------- | ------- |
| January   | CA $534 |
| February  | CA $631 |
| March     | CA $593 |
| April     | CA $537 |
| May       | CA $455 |
| June      | CA $393 |
| July      | CA $392 |
| August    | CA $331 |
| September | CA $323 |
| October   | CA $427 |
| November  | CA $432 |
| December  | CA $406 |

Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed hotels in Old Town Key West. Select dates and complete search for nightly totals inclusive of taxes and fees.

## Top Old Town Key West Hotel Reviews

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