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Check availability on Key West Winery Hotels

Next weekend
13 Nov - 15 Nov
In two weeks
20 Nov - 22 Nov

Our top choices for Key West hotels with winery

A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
3.5 star property
Old Town Key West
10.0 out of 10, Exceptional, (1,003 reviews)
"We really enjoyed our stay! The staff were amazing and the room was perfect!"
United States
Teresa
The price is £245
includes taxes & fees
30 Nov - 1 Dec
Almond Tree Inn Hotel - Adults Only
A tropical outdoor area with palm trees, hanging plants, and string lights.

2. Douglas House - Adults Only

Douglas House - Adults Only
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (584 reviews)
"Loved our stay! I would definitely stay there again."
United States
Maricela
The price is £191
includes taxes & fees
30 Nov - 1 Dec
Douglas House - Adults Only
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.

3. H2O Suites - Adults Only

H2O Suites - Adults Only
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (674 reviews)
"Amazing stay! Loved the private pool!"
United States
Kimberly
The price is £353
includes taxes & fees
30 Nov - 1 Dec
H2O Suites - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.

4. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (1,003 reviews)
"Fantastic property. Love staying here 💗"
United States
Jessica
The price is £245
includes taxes & fees
30 Nov - 1 Dec
Orchid Key Inn - Adults Only
A porch with a white railing, a bench, and a flag.

5. The Conch House Heritage Inn

The Conch House Heritage Inn
3.5 star property
Old Town Key West
9.8 out of 10, Exceptional, (198 reviews)
"We really enjoyed getting to know the staff. The breakfast was excellent and everything was in walking distance."
United States
Jennifer
The price is £281
includes taxes & fees
24 Nov - 25 Nov
The Conch House Heritage Inn
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.

6. Duval House

Duval House
3.0 star property
Old Town Key West
9.6 out of 10, Exceptional, (1,135 reviews)
"Great stay!"
United States
Dennis
The price is £166
includes taxes & fees
18 Nov - 19 Nov
Duval House
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.

7. Island City House Hotel

Island City House Hotel
3.0 star property
Key West Historic District
9.6 out of 10, Exceptional, (999 reviews)
"Great place with lots of character and perfect location."
United States
Elise
The price is £168
includes taxes & fees
2 Dec - 3 Dec
Island City House Hotel
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.

8. The Grand Guesthouse

The Grand Guesthouse
2.5 star property
Old Town Key West
9.6 out of 10, Exceptional, (1,001 reviews)
"Fun apartment style living in Key West…fun little patio with coffee and continental breakfast. Make sure you look at the check in hours :) great spot makes you feel local"
United States
Justyn
The price is £181
includes taxes & fees
3 Dec - 4 Dec
The Grand Guesthouse
A green house with a white porch, a flag, and a sign advertising a property for sale.

9. L'Habitation Guest House - Adults Only

L'Habitation Guest House - Adults Only
2.5 star property
Key West Historic District
9.4 out of 10, Exceptional, (1,003 reviews)
"A very cute, cozy and comfortable place to stay especially for old Key West charm. Will definitely stay here again."
United States
Callie
The price is £142
includes taxes & fees
1 Dec - 2 Dec
L'Habitation Guest House - Adults Only
A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.

10. Westwinds Inn

Westwinds Inn
3.5 star property
Key West Historic District
9.4 out of 10, Exceptional, (1,006 reviews)
"Breakfast was great . Pools were great and easy walk or bike ride to Duval street"
United States
Shari
The price is £181
includes taxes & fees
29 Nov - 30 Nov
Westwinds Inn
A swimming pool with lounge chairs, a covered deck, and a view of lush greenery.

11. Coco Plum Inn

Coco Plum Inn
3.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (578 reviews)
"Location was perfect"
United States
August
The price is £222
includes taxes & fees
17 Nov - 18 Nov
Coco Plum Inn
A rectangular pool with a white deck, surrounded by lush greenery and a gazebo.

12. Ambrosia Key West

Ambrosia Key West
3.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,002 reviews)
"Great location beautiful property we enjoyed our stay !"
United States
daniela
The price is £159
includes taxes & fees
30 Nov - 1 Dec
Ambrosia Key West
A swimming pool with water splashing, surrounded by palm trees and a building in the background.

13. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
3.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,035 reviews)
"Great location Beautiful property very clean and quiet. Great omelet station w breakfast."
United States
Carleen
The price is £179
includes taxes & fees
1 Dec - 2 Dec
Silver Palms Inn & Historic Homes
A room with a door featuring horizontal blinds, a visible outdoor view through the window, and a patterned carpet.

14. Alexander Palms Court

Alexander Palms Court
2.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,004 reviews)
"We love staying at Alexander’s!!!"
United States
Brenda
The price is £166
includes taxes & fees
7 Dec - 8 Dec
Alexander Palms Court
A large, ornate hotel with a pool, palm trees, and a view of the ocean.

15. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
4.0 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,003 reviews)
"Such a wonderful peaceful place to stay! Great food close by and Duval Street"
United States
Edward Lance
The price is £269
includes taxes & fees
30 Nov - 1 Dec
Southernmost House - Adult Exclusive
A covered porch with white railings, wooden benches, and a hanging light fixture.

16. Marrero's Guest Mansion

Marrero's Guest Mansion
3.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (347 reviews)
"Very nice and central to Duval night life."
United States
Jeffrey
The price is £332
includes taxes & fees
22 Nov - 23 Nov
Marrero's Guest Mansion
Room

17. The Independent Inn

The Independent Inn
3.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (71 reviews)
"Dan and Emma own the property and they go out of their way to give you the best experience you can receive. They are continuously on the property, working trying to maintain and make improvements. Thoroughly enjoyed the stay."
United States
Malcolm
The price is £180
includes taxes & fees
8 Dec - 9 Dec
The Independent Inn
A hotel with a covered entrance, palm trees, and a brick pathway leading to the building.

18. Opal Key Resort & Marina, Key West

Opal Key Resort & Marina, Key West
5.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1,222 reviews)
"have stayed here many times. nice location in old Town."
United States
A
The price is £248
includes taxes & fees
29 Nov - 30 Nov
Opal Key Resort & Marina, Key West
A hotel with a swimming pool, balconies, and a view of the sea.

19. Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
4.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1,003 reviews)
"Wonderful property with wonderful staff"
United States
Michael Joseph
The price is £267
includes taxes & fees
1 Dec - 2 Dec
Hyatt Centric Key West Resort and Spa
A building with a white exterior, a large red awning, and a gated entrance.

20. Authors of Key West Guest House

Authors of Key West Guest House
3.0 star property
Key West Historic District
9.2 out of 10, Wonderful, (1,083 reviews)
"The check-in was smooth, breakfast was adequate, and the room was comfortable."
United States
Perry
The price is £121
includes taxes & fees
30 Nov - 1 Dec
Authors of Key West Guest House
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.
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Top Key West Hotel Reviews

Frequently asked questions

Which winery hotels in Key West offer wine tastings?
In Key West, The Gardens Hotel and Paradise Inn Key West - Adults Only both offer wine tastings for guests.

The 4-star Gardens Hotel, with an outstanding guest rating of 9.8, boasts its own on-site tasting room, making it super convenient for wine lovers. You'll also find lovely touches like premium bedding, designer toiletries, and a poolside bar, superb for unwinding after a tasting. Our customers often highlight its beautiful, clean rooms, friendly staff, and central, great location.

Paradise Inn Key West - Adults Only, a 3.5-star hotel rated 9.2 by our travellers, also provides a wine tasting room. It's an excellent choice if you're looking for a relaxing adults-only escape, offering free breakfast to get your day started right.
How much does a winery hotel in Key West cost?
Enjoy staying in a winery hotel in Key West, with plenty of hotels from £262 offering incredible amenities. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during the weekend or around public holidays.
Which are the top Key West winery hotels for couples?
For couples seeking a romantic winery experience in Key West, consider The Gardens Hotel and Paradise Inn Key West - Adults Only.

The 4-star Gardens Hotel, with an outstanding guest rating of 9.8, offers a unique blend of luxury and charm. While not a traditional vineyard, it features winery release events and a tasting room on-site, allowing you to enjoy fine wines in a beautiful garden setting. Couples will appreciate amenities like bathrobes, fireplaces, Egyptian cotton sheets, champagne service, designer toiletries, and private pools. Our customers consistently praise its beautiful, clean rooms, friendly staff, and central location.

Paradise Inn Key West - Adults Only is a 3.5-star hotel with a very good rating of 9.2, superb for a peaceful couples' retreat. This hotel also boasts a tasting room, making it easy to enjoy a glass of wine together. Guests benefit from free breakfast, comfortable suites, and complimentary toiletries.
Can I cancel my winery hotel reservation on Expedia?
Many Expedia hotel reservations are refundable, provided that you cancel before the hotel's cancellation deadline. This is often within 24-48 hours of your scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right winery hotel in Key West for you.
How can I save on a winery hotel in Key West with Expedia?
Find Key West hotel deals by joining One Key™, Expedia's free travel rewards programme. As a member, you can unlock instant savings with Member Prices and member perks when you're logged in. Booking your hotel in advance will typically help you save, but there are last-minute deals to explore too.
Is it cheaper to book flights and a winery hotel in Key West as a package deal?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Savings vary depending on factors like destination, travel dates, and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect travel package. *Savings vary and are not available on all flight and hotel bookings.