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

[Key West Travel Guide](https://expedia.ca/Key-West.dx1187)[Hotels in Key West](https://expedia.ca/Key-West-Hotels.d1187.Travel-Guide-Hotels)[Vacation Rentals in Key West](https://expedia.ca/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals)[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)[Key West Car Rentals](https://expedia.ca/Car-Rentals-In-Key-West.d1187.Car-Rental-Guide)[Key West Vacation Packages](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides)

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# Find Winery Hotels in Key West, FL from CA $499

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## Check availability on Key West Winery Hotels

Tonight

[Dec 27 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=1187&startDate=2025-12-27&endDate=2025-12-28&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 28 - Dec 29](https://www.expedia.ca/Hotel-Search?regionId=1187&startDate=2025-12-28&endDate=2025-12-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=1187&startDate=2026-01-02&endDate=2026-01-04&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=1187&startDate=2026-01-09&endDate=2026-01-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Key West hotels with winery

![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)

![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)

![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)

![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)

### Amsterdam's Curry Mansion Inn

[](https://www.expedia.ca/Key-West-Hotels-Amsterdams-Curry-Mansion-Inn.h217.Hotel-Information)

Key West Historic District

8.4/10

Very good

(1001)

"Great location "

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

Ronald

CA $320

CA $499 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](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)

![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)

![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

[](https://www.expedia.ca/Key-West-Hotels-Luxury-22-12-AVAILABLE-APRIL-2024.h31892617.Hotel-Information)

Stock Island

9.8/10

Exceptional

(116)

"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 $585

CA $1,080 total

includes taxes & fees

Jan 2 - Jan 3, 2026

[](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=2026-01-10&endDate=2026-01-11&regionId=1187&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true)

## Top Key West Hotel Reviews

## Frequently asked questions

### How much does a winery hotel in Key West cost?

### Which winery hotels in Key West offer wine tastings?

> The 4-star Gardens Hotel boasts an impressive review rating of 9.8, making it a top choice for travellers. It features an on-site tasting room where guests can indulge in wine tastings, along with beautiful gardens that create a tranquil atmosphere. The hotel also offers luxurious amenities like Egyptian cotton sheets, rainfall showerheads, and a poolside bar, superb for unwinding after a day of exploration.
> 
>   
> Paradise Inn Key West - Adults Only is a charming 3.5-star hotel rated 9.2 by our customers. It also includes a tasting room and provides complimentary breakfast, ensuring a delightful start to your day. The hotel's comfortable suites and beautiful pool area contribute to a relaxing getaway, while the friendly staff are always on hand to offer assistance and recommendations.

### Which are the top Key West winery hotels for couples?

> The 4-star Gardens Hotel, rated 9.8 by our travellers, provides a romantic oasis with stunning garden views and a tranquil atmosphere. It boasts an on-site tasting room where you can indulge in local wines, as well as comfortable rooms featuring premium bedding and designer toiletries. Couples can enjoy a lovely dining experience with garden views, relax by the private pool, or unwind by the fireplace with champagne service.
> 
>   
> For a charming and affordable option, the 3.5-star Paradise Inn Key West, with a rating of 9.2, is great for couples seeking a quieter getaway. This adults-only hotel features a delightful tasting room and offers complimentary breakfast. The comfortable, premium suites provide a peaceful retreat after a day of exploring the area's vineyards.

### What winery activities should we do in Key West?

> For couples seeking a romantic experience, consider a sunset wine tasting at a waterfront venue. Imagine sipping a glass of chilled white wine as the sun dips below the horizon, painting the sky in hues of orange and pink. This picturesque setting creates an intimate atmosphere, ideal for making cherished memories together.
> 
>   
> Families can enjoy educational vineyard tours that provide insights into the winemaking process. Many wineries offer activities for children, such as grape stomping during harvest season, ensuring that everyone has fun while learning about the art of winemaking.
> 
>   
> Additionally, don't miss the chance to visit the local wine bars and shops in Old Town, where you can sample a variety of wines and perhaps pick up a bottle or two as a special souvenir of your adventure.

### Does Key West host any wine festivals or events?

> For couples seeking a romantic escape, this festival offers a superb blend of intimate tastings and paired dinners, providing an opportunity to enjoy each other's company while indulging in the rich flavours of both wine and food. Picture yourselves sipping fine wines at sunset, surrounded by the charm of this beautiful island.
> 
>   
> Families can also enjoy wine-related events, as many local vineyards offer family-friendly activities and tours. While the adults sample wines, children can enjoy fun activities, ensuring a memorable experience for everyone.
> 
>   
> Key West's laid-back atmosphere combined with its thriving wine culture makes it an ideal destination for those seeking adventure, quality, and convenience in their travels.

### How can I save on a winery hotel in Key West with Expedia?

### Is it cheaper to book flights and a winery hotel in Key West as a package deal?

### Can I cancel my winery hotel reservation on Expedia?

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- [Duval Street ](https://www.expedia.ca/Duval-Street-Key-West-Historic-District.d6068616.Vacation-Attraction)
- [Visit Downtown Key West ](https://www.expedia.ca/Key-West-Downtown-Key-West.dx553248635976470405)

- [Book Winery Hotels in Key West on Expedia.com ](https://www.expedia.com/Key-West-Hotels-Winery-Hotel.0-0-d1187-tWineryHotel.Travel-Guide-Filter-Hotels)