A large red brick building with arched windows and a prominent entrance.

Explore beach hotels in Old Town Key West, FL from $302

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Beach Condos in Old Town Key West

THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!

Key West FL

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9.8/10 Exceptional! (43 reviews)

Beach Villas in Old Town Key West

Secret Villa I @ Old Town with Private Pool, close to Duval!

Key West FL

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10/10 Exceptional! (189 reviews)

Popular Beach Stays in Old Town Key West

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Recent Old Town Key West Hotel Reviews By Fellow Wanderers

Southwinds Motel

4 out of 5

Posted 4 hours ago

Travelocity Verified Review

"We love staying at Southwinds. Since we have been traveling to Key West for the past 9 years, we have stayed at Southwinds 7 of the 9 times. We love the location. The rooms are always clean. Maybe a bit outdated, but for the little bit of time we spend in the room it's not an issue. I do wish the showers were a little larger but it's something I look past. We love the Tipsy Rooster being on location. It's a great added benefit. We usually go out to breakfast but being able to grab something from the lobby if needed for breakfast is also a nice bonus. In addition, being able to use the beach/towels/chairs at Southernmost Beach Resort is great also. We look forward to our stay at Southwinds each year!"

A verified traveler stayed at Southwinds Motel