Key West Historic District Vacations from $434

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Your Key West Historic District Vacation

Experience all the wonderful things this neighborhood has to offer with a tailor-made Key West Historic District vacation package. However you imagine spending your time here, you'll find endless opportunities for relaxation, fun and adventure. Can't wait to explore the sights during your trip to Key West Historic District? Be sure to check out nearby attractions such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Stop dreaming and start doing. When it's time to lock in your ideal vacation to Key West Historic District, Expedia will help you get there.

The Latest Key West Historic District Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Bay Breeze Premium Apartments By Eskape Collection
Cavalier Hotel South Beach
The Club at Brickell Bay by Palermo Home
Hawks Cay Resort
Iberostar Waves Miami Beach

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.

Where to stay in Key West Historic District

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

Key West Historic District Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$227 nightly
The price is $255 total per night from Dec 2 to Dec 3
$255 total
Dec 2 - Dec 3
Total with taxes and fees
8.6/10 Excellent! (2,881 reviews)
A1

Reviewed on Nov 24, 2025

Southernmost Beach Resort and Guesthouses
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
Fully refundableReserve now, pay when you stay
$214 nightly
The price is $241 total per night from Dec 16 to Dec 17
$241 total
Dec 16 - Dec 17
Total with taxes and fees
9.2/10 Wonderful! (1,057 reviews)
Great staff, beautiful grounds, clean.

Reviewed on Nov 27, 2025

Winslow's Bungalows - Key West Historic Inns
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$299 nightly
The price is $336 total per night from Dec 17 to Dec 18
$336 total
Dec 17 - Dec 18
Total with taxes and fees
8.2/10 Very Good! (443 reviews)
The hotel is in good state, clean and fresh; the rooms offer plenty of comfort and beach front balcony is a pleasing extra!

Reviewed on Nov 23, 2025

Casa Marina Key West, Curio Collection by Hilton
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.