Key West Historic District Travel Guide

Name: Southwinds Motel
Price range: £138
Rating: 8.6

Key West

Visit Key West Historic District

Hotels

Stay near popular Key West Historic District attractions

Duval Street

4.6/5 (20,928 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

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Top hotels in Key West Historic District

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

£227

per night

22 Jun - 23 Jun

Stay at this beach hotel in Key West. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...

8.8/10 Excellent! (3,386 reviews)

"The property is dated. The rooms were small and old. The so-called balconies were not in the rooms, they were common for all. The pool bar closed at 7, the main bar closed at 9. Sometimes there were no towels at the pool and the number of chairs were limited."

Reviewed on 12 Jun 2026

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

£284

per night

22 Jun - 23 Jun

Stay at this beach resort in Key West. Enjoy 2 outdoor pools, a full-service spa and a private beach. Popular attractions Southernmost Point and Duval Street ...

8.6/10 Excellent! (706 reviews)

"Very beautiful....feels like old money clasic vibes. Feels like you stepped back in time to an area when"

Reviewed on 12 Jun 2026

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL

£238

per night

28 Jun - 29 Jun

Stay at this beach resort in Key West. Enjoy free Wi-Fi, a full-service spa and a marina. Our guests praise the pool and the helpful staff in their reviews. ...

9/10 Wonderful! (1,008 reviews)

"Cleannroom"

Reviewed on 9 Jun 2026

Pier House Resort & Spa

1 Duval St Key West FL

£276

per night

24 Jun - 25 Jun

Stay at this beach resort in Key West. Enjoy a full-service spa, a private beach and 2 bars/lounges. Our guests praise the pool and the helpful staff in their ...

9/10 Wonderful! (1,177 reviews)

"Place is a hidden jem. We came by boat."

Reviewed on 11 Jun 2026

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

£211

per night

24 Jun - 25 Jun

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 property ...

8.6/10 Excellent! (1,019 reviews)

"Stayed the first week of June. Rooms were nice but property felt very dated. Not a lot of beaches in Key West so was excited to find a property with a man made one. Unfortunately there was a ton of seaweed and it was essentially not usable. The pool was small and underwhelming. Food and drink on ..."

Reviewed on 11 Jun 2026

Southwinds Motel

1321 Simonton Street Key West FL

£138

per night

15 Jun - 16 Jun

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 their reviews. ...

8.6/10 Excellent! (1,353 reviews)

"Plan on spending more for amenities! We were hit with an additional charge at checkin! Nowhere in our reservation were we told about the additional charge"

Reviewed on 12 Jun 2026

See all 1,687 properties in Key West Historic District

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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Where to stay in Key West Historic District

Find the best Key West Historic District areas for the activities you enjoy most. Learn more about Key West Historic District

Old Town Key West

While visiting Old Town Key West, you might make a stop by sights like Florida Keys Beaches and Duval Street.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

Key West Style Three Bay House is a common style on the Keys. Photo taken on Key West, Florida, USA

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Key West Tropical Forest and Botanical Garden.