Key West Historic District Vacations from $592
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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.
Solé Miami, A Noble House Resort
Ocean Four
Price was $1,333, price is now $592 per person
$592
per person
Feb 25 - Mar 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,935 reviews)
The room was very clean. The restaurant had the best tuna tacos
Reviewed on Jan 16, 2026
Cavalier Hotel South Beach
South Beach
Price was $1,601, price is now $686 per person
$686
per person
Mar 26 - Mar 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
AC - do not work or air movement-
Only 1 channel for TV -
Checking was long and felt distracting to do.
Reviewed on Jan 16, 2026
The Penguin Hotel
South Beach
Price was $1,406, price is now $660 per person
$660
per person
Feb 25 - Mar 2
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,491 reviews)
The woman working at the front desk was amazing. She so kind and helpful with everything. We arrived early from a disembarked cruise and she was able to store all of our luggage. Give us nice recommendations for the area and introduce us to the pool in the adjacent property.
Reviewed on Jan 19, 2026
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
4 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
$530 nightly
The price is $596 total per night from Jan 26 to Jan 27
$596 total
Jan 26 - Jan 27
Total with taxes and fees
8.6/10 Excellent! (3,002 reviews)
The location, room, and amenities were all very good. An area for improvement would be the friendliness of the staff. Some were very good, but there were staff that seemed bothered by us ordering food and drinks. We showed up a the cafe bar 20 minutes before 9 and a lady (seemed like a manager) didn't ...
Reviewed on Jan 18, 2026
Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue Key West FL
Fully refundableReserve now, pay when you stay
$429 nightly
The price is $482 total per night from Jan 20 to Jan 21
$482 total
Jan 20 - Jan 21
Total with taxes and fees
9.2/10 Wonderful! (1,119 reviews)
The place and staff were amazing!!!!
Reviewed on Jan 13, 2026
La Concha Key West, Autograph Collection
430 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$399 nightly
The price is $449 total per night from Jan 25 to Jan 26
$449 total
Jan 25 - Jan 26
Total with taxes and fees
9/10 Wonderful! (315 reviews)
Clean, super comfortable, close to everything
Reviewed on Jan 9, 2026
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
4.5/5(3,475 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.
Mallory Square
4.5/5(3,096 reviews)
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
4.5/5(1,707 reviews)
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
Shipwreck Treasure Museum Tickets
$19
per adult
78% of travellers recommend
Sunset Sail in Key West with Beverages Included
$79
per adult
98% of travellers recommend
Key West Half-Day Fishing Charter
$95
per adult
90% 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.