Explore top 2026 4 Star Hotels in Key West Historic District

Name: Winslow's Bungalows - Key West Historic Inns
Price range: $293 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

$210 nightly

$237 total

Sep 9 - Sep 10

Total with taxes and fees

A full-service spa, 3 outdoor pools, and a restaurant are all featured at this hotel. Traveling on business? Take advantage of the 2 conference rooms, along ...

8.6/10 Excellent! (3,562 reviews)

"From check in and check out everything in between this Hotel was everything and more during our weekend girls trip get away!! We will not hesitate to book again in a few months!!"

Reviewed on Sep 2, 2026

Hyatt Centric Key West Resort and Spa

601 Front St Key West FL

Fully refundableReserve now, pay when you stay

$263 nightly

$296 total

Sep 29 - Sep 30

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! (1,008 reviews)

"The staff were outstanding, especially Anna at the front desk. They all were so warm and welcoming. The rooms were spacious and clean. The pool was clean and mostly quiet (which was nice and relaxing)."

Reviewed on Sep 2, 2026

La Concha Key West, Autograph Collection

430 Duval St Key West FL

Fully refundableReserve now, pay when you stay

$199 nightly

$224 total

Sep 16 - Sep 17

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 ...

Casa Marina Key West, Curio Collection by Hilton

1500 Reynolds Street Key West FL

Fully refundableReserve now, pay when you stay

$272 nightly

$305 total

Sep 15 - Sep 16

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 ...

Pier House Resort & Spa

1 Duval St Key West FL

Fully refundableReserve now, pay when you stay

$316 nightly

$356 total

Sep 9 - Sep 10

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. ...

9/10 Wonderful! (1,309 reviews)

"Great location. Nice amenities. Overall, a great place to stay."

Reviewed on Sep 2, 2026

The Reach Key West, Curio Collection by Hilton

1435 Simonton Street Key West FL

Fully refundableReserve now, pay when you stay

$256 nightly

$288 total

Sep 28 - Sep 29

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, ...

The Marker Key West Harbor Resort

200 William Street Key West FL

Fully refundable

$238 nightly

$267 total

Sep 13 - Sep 14

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! (1,004 reviews)

"Clean friendly and relaxing!"

Reviewed on Sep 2, 2026

Opal Key Resort & Marina, Key West

245 Front Street Key West FL

Fully refundableReserve now, pay when you stay

$294 nightly

$331 total

Sep 3 - Sep 4

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 ...

Ocean Key Resort - A Noble House Resort

Zero Duval St. Key West FL

Fully refundableReserve now, pay when you stay

$323 nightly

$364 total

Sep 27 - Sep 28

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! (1,000 reviews)

"Expensive"

Reviewed on Sep 1, 2026

Winslow's Bungalows - Key West Historic Inns

725 Truman Avenue Key West FL

$260 nightly

$293 total

Sep 3 - Sep 4

Total with taxes and fees

This smoke-free hotel features 3 outdoor pools, a bar/lounge, and a poolside bar. WiFi in public areas is free. Self parking, a garden, and luggage storage are ...

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

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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.

Recent Key West Historic District hotel reviews by fellow wanderers

Douglas House - Adults Only

5 out of 5

Posted 3 hours ago

Travelocity Verified Review

"Loved this property. Have been coming to KW for last 40+ years and never stayed here? Great location. Our room was more like and apartment. We were down from Miami for rum festival and were close to all of the different events at Douglas. The property was meticulously kept. The staff was helpful. Plenty of parking on street and close to the moondog cafe and so many other places to eat and drink. Highly recommend this property. Will be back."

A verified traveler stayed at Douglas House - Adults Only