Key West Historic District Vacations from $596
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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.
Cavalier Hotel South Beach
South Beach
Price was $1,242, price is now $596 per person
$596
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
Fantastic service, great restaurant downstairs, super convenient for beach access, shopping and dining!
Reviewed on Oct 13, 2025
Flow Miami Hotel
Downtown Miami
Price was $1,853, price is now $851 per person
$851
per person
Jan 1 - Jan 8
found 2 days ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (160 reviews)
The hotel was clean, the location was ideal and the amenities were impressive
Reviewed on Oct 14, 2025
The Shelborne By Proper, a Member of Design Hotels
South Beach
Save 100% on your flight
Price was $1,824, price is now $876 per person
$876
per person
Jan 2 - Jan 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Really great stay, big thanks to Crispy and team! Hotel has a great atmosphere and location. I’ll be sure to visit again!
Reviewed on Oct 21, 2025
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
Old Town Key West
3 out of top 10 points of interest in this area
4.5/5(226 area reviews)
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
Key West Historic District Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $253 total per night from Oct 26 to Oct 27
$253 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (2,805 reviews)
A great place to stay!
Reviewed on Oct 18, 2025
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL
Fully refundableReserve now, pay when you stay
$242 nightly
The price is $272 total per night from Oct 27 to Oct 28
$272 total
Oct 27 - Oct 28
Total with taxes and fees
8.8/10 Excellent! (1,011 reviews)
👍
Reviewed on Oct 19, 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Fully refundableReserve now, pay when you stay
$287 nightly
The price is $323 total per night from Oct 26 to Oct 27
$323 total
Oct 26 - Oct 27
Total with taxes and fees
8.2/10 Very Good! (400 reviews)
This hotel is beautiful. Great view from the room. Staff is amazing
Reviewed on Oct 19, 2025
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.
Discover the most popular places to visit in Key West Historic District
Duval Street
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.
Mallory Square
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
Ernest Hemingway Home and Museum
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$50
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per adult
92% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
80% of travellers recommend
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- Key West Vacations
- All inclusive Vacation Packages Key West
- Ernest Hemingway Home and Museum
- Duval Street
- Key West Cemetery
- The Kite House
- Saint Mary Star of the Sea
- Donkey Milk House
- Visit Key West
- San Carlos Institute - Casa Cuba
- Old Town Key West Vacations
- Key West Lighthouse and Keeper's Quarters Museum
- Tennessee Williams Key West Exhibit
- Jackson Square
- Curry Mansion Museum
- Oldest House Museum and Garden
- Red Barn Theater
- Sails To Rails Museum at Flagler Station
- Key West Burlesque Theater
- South Beach
- Schooner Western Union
- Fort Zachary Taylor Historic State Park
- City Zoo Gallery
- Harry S. Truman Little White House
- Bahama Village Vacations
- Audubon House and Tropical Gardens
- Mel Fisher Maritime Museum
- Key West Butterfly and Nature Conservatory
- Southernmost Point
- Roy John-Karl Gallery
- Custom House Museum
- Visit Downtown Key West
- Romantic Vacation Packages Key West
- Key West Museum of Art and History
- Mallory Dock
- MLK Community Pool & Community Center
- Florida Keys Eco - Discovery Center
- Visit Old Town Key West
- Simonton Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.