Key West Historic District Vacations from $295
Book a Hotel + Flight or Car together to unlock savings
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
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Perfectly located on Ocean Drive with an old-school Art Deco vibe that feels both historic and fresh. The room was spotless, the A/C was ice cold, and the bed was genuinely comfortable. Staff was friendly and helpful. You’re across from the beach, but it still feels like a quiet escape. Would absolutely stay here again.
Reviewed on Jul 1, 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 refundable
$259 nightly
The price is $291 total per night from Aug 4 to Aug 5
$291 total
Aug 4 - Aug 5
Total includes taxes and fees
8.6/10 Excellent! (2,589 reviews)
"My girlfriend and I had a nice stay. It’s a decent place. The pool gets extremely crowded and there is not much seating options out by the pool area. Beds are not the most comfortable. Bar out by the pool was a great amenity. Lounge pool is nice for adults only who are looking to relax. Everything ..."
Reviewed on Jul 5, 2025
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
$281 nightly
The price is $316 total per night from Aug 4 to Aug 5
$316 total
Aug 4 - Aug 5
Total includes taxes and fees
8.2/10 Very Good! (1,001 reviews)
"Oceanfront"
Reviewed on Jul 3, 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Fully refundableReserve now, pay when you stay
$291 nightly
The price is $328 total per night from Aug 4 to Aug 5
$328 total
Aug 4 - Aug 5
Total includes taxes and fees
8.2/10 Very Good! (213 reviews)
"Lovely hotel, rooms clean and spacious, staff very friendly. We would stay again."
Reviewed on Jul 4, 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
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.
Southernmost Point
4.5/5(3,182 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$50
per adult
92% of travellers recommend
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
$99
per adult
74% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per adult
92% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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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.