Explore top 2026 4 Star Hotels in Key West Historic District

Name: Winslow's Bungalows - Key West Historic Inns
Price range: $223 total
Rating: 9.2

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Top Key West Historic District 4 Star hotels

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL

Fully refundableReserve now, pay when you stay

$225 nightly

$253 total

Aug 10 - Aug 11

Total with taxes and fees

This hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling ...

8.8/10 Excellent! (3,471 reviews)

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Reviewed on Jul 17, 2026

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL

Fully refundableReserve now, pay when you stay

$261 nightly

$294 total

Aug 11 - Aug 12

Total with taxes and fees

This smoke-free resort features a full-service spa, a marina, and a restaurant. Enjoy the outdoor pool and perks like free WiFi. Enjoy the 24-hour gym and unwind ...

9/10 Wonderful! (1,017 reviews)

"Highly recommend the Hyatt Centric. Perfect location to walk easily to the most popular tourist attractions, restaurants, and view the beautiful sunset. Staff was friendly, great amenities, beautiful resort, and large, clean rooms."

Reviewed on Jul 16, 2026

Pier House Resort & Spa

1 Duval St Key West FL

Fully refundableReserve now, pay when you stay

$382 nightly

$429 total

Aug 13 - Aug 14

Total with taxes and fees

This smoke-free resort features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. ...

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Fully refundableReserve now, pay when you stay

$279 nightly

$314 total

Aug 11 - Aug 12

Total with taxes and fees

A private beach, a full-service spa, and 2 outdoor pools are all featured at this smoke-free resort. Relax with sun loungers and beach umbrellas, and cool off ...

8.4/10 Very Good! (765 reviews)

"I really enjoyed my stay. The staff went out of their way to make you feel welcome and cared for. I want to make special mention of Ann - Marie at the front desk, Robert in the breakfast dining area, and Gabor from in he breakfast dining area, who went out of their way to make sure my stay was comfortable ..."

Reviewed on Jul 16, 2026

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Fully refundableReserve now, pay when you stay

$248 nightly

$279 total

Aug 17 - Aug 18

Total with taxes and fees

This resort features a private beach, a full-service spa, and a restaurant. Traveling on business? Take advantage of the express check-out, laundry service, ...

8.6/10 Excellent! (1,002 reviews)

"Beach View excellent"

Reviewed on Jul 16, 2026

La Concha Key West, Autograph Collection

430 Duval St Key West FL

Fully refundableReserve now, pay when you stay

$225 nightly

$253 total

Aug 2 - Aug 3

Total with taxes and fees

This smoke-free hotel includes 3 restaurants, an outdoor pool, and a 24-hour gym. Traveling on business? Take advantage of the free WiFi in public areas, express ...

9/10 Wonderful! (436 reviews)

"Our stay at La Concha Key West was amazing. The location is within walking distance to all of the major attractions. The hotel was exceptionally clean and well maintained. The entire staff was knowledgeable, accommodating, and went above and beyond to meet our requests and needs. We stayed three ..."

Reviewed on Jul 9, 2026

Opal Key Resort & Marina, Key West

245 Front Street Key West FL

Fully refundableReserve now, pay when you stay

$294 nightly

$331 total

Aug 16 - Aug 17

Total with taxes and fees

A marina, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Enjoy the outdoor pool and visit the 3 bars/lounges and poolside bar for ...

9.2/10 Wonderful! (1,165 reviews)

"Excellent location, friendly staff. Highly recommend!"

Reviewed on Jul 16, 2026

The Marker Key West Harbor Resort

200 William Street Key West FL

Fully refundable

$238 nightly

$267 total

Aug 11 - Aug 12

Total with taxes and fees

This smoke-free hotel features 3 outdoor pools, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in ...

9.2/10 Wonderful! (1,016 reviews)

"Very clean, AC was great in the 95 degree heat"

Reviewed on Jul 17, 2026

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

Fully refundableReserve now, pay when you stay

$198 nightly

$223 total

Aug 3 - Aug 4

Total with taxes and fees

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. Guests will appreciate free perks like continental breakfast and WiFi in public ...

9.2/10 Wonderful! (1,340 reviews)

"A stunning hotel with fairly spacious rooms and an excellent location. There was a small pool right below our rooms, making it feel just like a private pool. The breakfast was rather poor, and there were extra charges for everything. In my opinion, given the hotel's price point, they could have offered ..."

Reviewed on Jul 16, 2026

Ocean Key Resort - A Noble House Resort

Zero Duval St. Key West FL

Fully refundableReserve now, pay when you stay

$383 nightly

$430 total

Aug 16 - Aug 17

Total with taxes and fees

A full-service spa, 2 restaurants, and an outdoor pool are all featured at this smoke-free resort. Traveling on business? Take advantage of the free WiFi in ...

9.2/10 Wonderful! (1,001 reviews)

"Staff was exceptionally friendly and very helpful."

Reviewed on Jul 15, 2026

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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.