Find Winery Hotels in Old Town Key West, FL

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Check availability on Old Town Key West Winery Hotels

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Dec 6 - Dec 7
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Dec 7 - Dec 8
Next weekend
Dec 12 - Dec 14
In two weeks
Dec 19 - Dec 21

Top Old Town Key West Winery Hotels

Fridge, microwave, oven, stovetop
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC

Old Town Key West
8.8 out of 10, Excellent, (236)
"Great location"
United States
Carmel M.
$425 nightly
The price is $472
Jan 1 - Jan 2, 2026
Total with taxes and fees
Downtown dog-friendly cottage-like studio with patio, full kitchen, cable, & AC
Front of property
Amsterdam's Curry Mansion Inn

Amsterdam's Curry Mansion Inn

3.0 star property
Key West Historic District
8.4 out of 10, Very Good, (1004)
"The pool loungers were awesome and it was great having towels for the pool and rooom self service. You are right downtown in the middle of everything so yes there's going to be noise but we had no problem sleeping and felt very safe in the area! We will definitely be back!"
United States
Karla
$318 nightly
The price is $358
Dec 17 - Dec 18
Total with taxes and fees
Amsterdam's Curry Mansion Inn
Property grounds
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED

Stock Island
9.8 out of 10, Exceptional, (115)
"Great location, close to everything family had a great time."
United States
rafael m.
$530 nightly
The price is $589
Dec 7 - Dec 8
Total with taxes and fees
Luxury 2/2 1/2 - FREE PARKING, WIFI, BIKES, BIG POOL, NEWLY RENOVATED
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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Price trends for hotels in Old Town Key West

Less expensive
More expensive
This month
Next month
September
March
$408
$522
Month
Price
January
$522
February
$597
March
$624
April
$581
May
$495
June
$373
July
$376
August
$358
September
$326
October
$445
November
$510
December
$408
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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