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Old Town Key West Hotel Guide

Don’t keep your travel plans on repeat year after year. The same city with the same hotel every season will bore you and give you an itch to go looking for something new. Expand your geographical horizons to more than just those five blocks around your usual haunt.

Nowhere else can you find better deals on Old Town Key West area hotels. You’ll find the best prices on the quirky, the haunted, the old, the new, and the legendary. If you’re wondering what side of the pricing scale some of these hotels fall on, you need not to worry. Compare cheap hotels near Old Town Key West to find the perfect one to will fit your budget.

Leave the ordinary routine you’re set on behind and go. Go anywhere you want. Anywhere that makes you think, “I wonder what that’s like?” Part of Travelocity’s mission is to get you off-the-beaten path and the hotels near Old Town Key West are perfect for that. Find your new favorite watering hole on a quiet street. Discover a place to escape for the weekend with tasty local fare and unique sights. We want you to consider the places outside your normal comfort zone. Browse our selection and find the ideal hotel, in a place you’d like to explore.

Recent Old Town Key West hotel reviews by fellow wanderers

Winslow's Bungalows - Key West Historic Inns

5 out of 5

Posted 3 hours ago

Travelocity Verified Review

"My stay at Winslow Bungalows was truly one of a kind. Celebrating my 50th birthday here was unforgettable, thanks in large part to the exceptional customer service from the front desk team. I felt thoroughly taken care of throughout my entire 4-night, 4-day stay. In particular, Ms. Sonya, the front office administrator, was exceptionally friendly, helpful, and generous in ensuring my visit was memorable. The atmosphere at the property is calming, peaceful, and breathtaking all at once—a true tropical vibe that feels like a private island surrounded by lush trees and plants. It was such a nice treat to have a bungalow with a private patio, making it a wonderful spot for scenic pictures. The entire property was spotlessly clean and exceptionally well-maintained by the staff. Every morning, Winslow Bungalows offers a light, fresh breakfast from 8:00 to 10:00 AM, which was the perfect start to fuel a day of exploring Key West. Additionally, the location is extremely convenient, situated just a short walk from Duval Street. I fully plan on returning to Winslow Bungalows on my next trip back to the Florida Keys!"

A verified traveler stayed at Winslow's Bungalows - Key West Historic Inns

The Southernmost Inn - Adults Only

4 out of 5

Posted 4 hours ago

Travelocity Verified Review

"First of all Anthony at the front desk was very helpful and kind. We needed to book into another room at the end of our stay because we had a late flight and needed more than just a “late check out”, he found us a great room for the day at a good rate. The rooms are no frills but beds are comfy ( although the poly cotton sheets and poly fill comforter are a NO GO!). And the room and resort are very clean. The wine and cheese at 5 is great and the breakfast is fabulous ( make your own waffles is a winner!) my only complaint was there are huge iguanas that come out every day at 5 for happy hour ( yes, I’m serious). Some fools have obvious been feeding them and they are a nuisance and frequently poop in the pool. It’s cleaned up right away but the big pool is a no go for me after 5. Frenchies Nextdoor is awesome for wonderful croissants and quiche and the Banana cafe around the corner delivers. All in all a good stay. They do need to do something about those sheets though!"

A verified traveler stayed at The Southernmost Inn - Adults Only