Key West Historic District Vacations from $248
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.
The Shelborne By Proper, a Member of Design Hotels
South Beach
Price was $3,708, price is now $1,664 per person
$1,664
per person
Dec 29 - Jan 2
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.8/10 Exceptional! (39 reviews)
Amenities are really clean, excellent quality ingredients, nice quality decor
Reviewed on Nov 9, 2025
Flow Miami Hotel
Downtown Miami
Price was $1,637, price is now $748 per person
$748
per person
Jan 10 - Jan 17
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9/10 Wonderful! (160 reviews)
The room was awesome. Nice space, everything you could need. Gym was fab as was pool. Location spot on. All round win.
Reviewed on Nov 1, 2025
Cavalier Hotel South Beach
South Beach
Price was $1,054, price is now $484 per person
$484
per person
Jan 10 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,004 reviews)
Room was clean. Staff was friendly beach, restaurants and shops nearby. Also a convenient parking garage within walking distance.
Reviewed on Nov 4, 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
$242 nightly
The price is $272 total per night from Nov 30 to Dec 1
$272 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (2,859 reviews)
Wonderful place to stay. Uber pickup was easy. Trolly available across the street for trolly. We had great dining options.
Reviewed on Nov 6, 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Fully refundableReserve now, pay when you stay
$307 nightly
The price is $346 total per night from Dec 1 to Dec 2
$346 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (426 reviews)
Clean spacious room, friendly & helpful staff, food & beverages top notch, security & privacy of property
Reviewed on Nov 8, 2025
La Concha Key West, Autograph Collection
430 Duval St, Key West, FL
Fully refundableReserve now, pay when you stay
$225 nightly
The price is $253 total per night from Nov 30 to Dec 1
$253 total
Nov 30 - Dec 1
Total with taxes and fees
9/10 Wonderful! (254 reviews)
Outstanding service from every employee we encountered.
Reviewed on Nov 3, 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.
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
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
Explore a world of travel with Expedia
- Key West Hotels
- All-inclusive Resorts in Key West
- Cheap Hotels in Key West
- Oceanfront Hotels in Key West
- Hotels near Duval Street
- Beach Hotels in Key West
- Adults Only Resorts & in Key West
- Houseboats in Key West
- Pet-friendly Hotels in Key West
- Condo Rentals in Key West
- Romantic Hotels in Key West
- Family Hotels in Key West
- 4 Star Hotels in Key West
- Hilton Hotels in Key West
- 5 Star Hotels in Key West
- Honeymoon Resorts & in Key West
- Hotels near The Kite House
- Resorts in Key West
- Hotels near Key West Cemetery
- Boutique Hotels in Key West
- Kimpton Hotels in Key West
- Cabin Rentals in Key West
- Cottages in Key West
- B&B in Key West
- Luxury Hotels in Key West
- Gay friendly Hotels in Key West
- Historic Hotels in Key West
- Hotels with Kitchenettes in Key West
- Hotels with Free Airport Shuttle in Key West
- Guest Houses in Key West
- Best Western Hotels in Key West
- Wyndham Hotels in Key West
- Hotels with smoking rooms in Key West
- Golf Hotels in Key West
- Vacation Homes in Key West
- Hotels with Hot Tubs in Key West
- Hotels with Free Breakfast in Key West
- Villas in Key West
- Hotels with Free Parking in Key West
- Hyatt Hotels in Key West
- Hostels in Key West
- Hotels with a Pool in Key West
- Fishing Resorts & in Key West
- Hotel Wedding Venues Hotels in Key West
- Resorts & Hotels with Spas in Key West
- Apartments in Key West
- Hotels with Early Check-in in Key West
- Hotels with Childcare in Key West
- 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.