Old Town Key West, FL
Key West
Visit Old Town Key West
Stay near popular Old Town Key West attractions
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
￥7,175
per adult
94% of travellers recommend
Key West Sunset Cruise & Glass Bottom Eco Tour
￥11,165
per adult
76% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
￥8,874
per adult
88% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
￥12,609
per adult
94% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
￥11,485
per traveler
92% of travellers recommend
Old Town Key West Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
The price is ￥23,212 per night from Sep 9 to Sep 10
￥23,212
￥37,798 total
Sep 9 - Sep 10
includes taxes & fees
Book a stay at this spa hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
8.6/10 Excellent! (3,561 reviews)
"The resort fee is very expensive for what the resort has to offer for the guests. I will not rebook this resort the next time we are in Keywest. No shuttle services are offered. Nothing complimentary but two welcome drinks."
Reviewed on Sep 1, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
The price is ￥33,820 per night from Sep 13 to Sep 14
￥33,820
￥48,833 total
Sep 13 - Sep 14
includes taxes & fees
Book a stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa, and a private beach. Popular attractions Duval Street and Southernmost ...
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Fully refundable
The price is ￥31,457 per night from Sep 28 to Sep 29
￥31,457
￥46,203 total
Sep 28 - Sep 29
includes taxes & fees
Book a stay at this beach resort in Key West. Enjoy a full-service spa, a private beach, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Southwinds Motel
1321 Simonton Street Key West FL
The price is ￥19,493 per night from Sep 7 to Sep 8
￥19,493
￥27,337 total
Sep 7 - Sep 8
includes taxes & fees
Stay at this hotel in Key West. Enjoy free breakfast, 2 outdoor pools, and parking (surcharge). Our guests praise the breakfast and the pool in our reviews. ...
8.6/10 Excellent! (1,372 reviews)
"Perfect spot"
Reviewed on Sep 2, 2026
Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue Key West FL
The price is ￥34,355 per night from Sep 13 to Sep 14
￥34,355
￥46,739 total
Sep 13 - Sep 14
includes taxes & fees
Stay at this hotel in Key West. Enjoy free WiFi, 3 outdoor pools, and breakfast (surcharge). Our guests praise the breakfast and the pool in our reviews. Popular ...
9.2/10 Wonderful! (1,400 reviews)
"Two concerns: 1) TV issue was not addressed by staff in a timely fashion. Note; the amenity fee was reduced as a result. 2) concern may be equal parts Winslow’s Bungalows and Expedia. There should be transparent pricing that includes the TOTAL AMOUNT. It’s distasteful to a customer amenity fees, ..."
Reviewed on Sep 1, 2026
Douglas House - Adults Only
419 Amelia St Key West FL
The price is ￥16,346 per night from Sep 9 to Sep 10
￥16,346
￥20,229 total
Sep 9 - Sep 10
includes taxes & fees
Stay at this guesthouse in Key West. Enjoy free WiFi, daily housekeeping, and a garden. Popular attractions Duval Street and Ernest Hemingway Home and Museum ...
9.6/10 Exceptional! (511 reviews)
"Great location and clean!"
Reviewed on Sep 1, 2026
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.
Check Old Town Key West hotel availability
Where to stay in Old Town Key West
Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most.
Downtown Key West
If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.
Key West Historic District
Travelers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to make a stop by Duval Street and Florida Keys Beaches.
New Town
Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
