Key West Historic District Vacations from $356
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.
Park Central South Beach
South Beach
Price was $797, price is now $356 per person
$356
per person
Oct 31 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (930 reviews)
I appreciated the close location to the beach. We were literally a walk across the street to the beach. Everything was walkable.
The staff were attentive & present. Very helpful and friendly & accommodating. The lobby area always was clean smelling. I liked they provided complimentary bikes to ride, beach chairs & bottled water.
What I did not like were the little bit of channels available on the tv. The stations they did have did not have service so it did not work.
Would also recommend a full length mirror.
Reviewed on Aug 23, 2025
Cavalier Hotel South Beach
South Beach
Price was $901, price is now $426 per person
$426
per person
Oct 29 - Nov 3
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,000 reviews)
Loved the Art Deco look of the rooms, lobby and hallway. Staff was very kind and helpful.
Reviewed on Aug 16, 2025
The Penguin Hotel
South Beach
Price was $1,011, price is now $488 per person
$488
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,414 reviews)
The only thing missing was breakfast. We were given drink vouchers, however we don’t drink.
Reviewed on Aug 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 refundable
$229 nightly
The price is $258 total per night from Sep 8 to Sep 9
$258 total
Sep 8 - Sep 9
Total with taxes and fees
8.6/10 Excellent! (2,701 reviews)
"Out dated."
Reviewed on Aug 24, 2025
Hyatt Centric Key West Resort and Spa
601 Front St, Key West, FL
Fully refundableReserve now, pay when you stay
$232 nightly
The price is $261 total per night from Sep 7 to Sep 8
$261 total
Sep 7 - Sep 8
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
"So close to everything! Great views and helpful staff"
Reviewed on Aug 22, 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Fully refundableReserve now, pay when you stay
$274 nightly
The price is $308 total per night from Sep 2 to Sep 3
$308 total
Sep 2 - Sep 3
Total with taxes and fees
8.2/10 Very Good! (308 reviews)
"Great Property and Staff. Rooms were very clean and housekeeping did a great job. Lot of rooms with actual view and beach access was amazing. Highly recommend."
Reviewed on Aug 22, 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.
Southernmost Point
Snap a memorable photograph from the edge of North America at this monumental landmark.
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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$40
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
Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Tour
$126
per adult
98% 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.