Key West Historic District Vacations from $488
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $1,045 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $1,641, price is now $692 per person
$692
per person
Apr 8 - Apr 14
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (1,001 reviews)
I had a wondeful time at this hotel (1/20-1/24/2026). The staff was polite, friendly and always ready to help. Room was clean and stylish exacly like the photo. The location is perfect: quiet and peaceful. And the same time not far from popular places.
I really enjoyed my stay and would definitely recommend this hotel to others.
Reviewed on Jan 26, 2026
Bay Breeze Premium Apartments By Eskape Collection
Price was $1,200, price is now $557 per person
$557
per person
Apr 9 - Apr 14
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (189 reviews)
The staff was courteous and helpful. The apartment was equipped with basic essentials. The area was quiet. I would suggest adding oven mittens in the kitchen as there was nothing to use to take the pan out of the oven with.
Reviewed on Jan 21, 2026
Casablanca Miami Beach
North Beach
Price was $1,066, price is now $510 per person
$510
per person
Apr 8 - Apr 14
found 2 days ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (311 reviews)
I stood in the multiple bed 1 bedroom everything was good beach right there pool and security where very friendly
Reviewed on Nov 12, 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
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
Fully refundable
$530 nightly
The price is $596 total per night from Jan 28 to Jan 29
$596 total
Jan 28 - Jan 29
Total with taxes and fees
8.6/10 Excellent! (3,034 reviews)
Nice clean resort! Great fun time!
Reviewed on Jan 26, 2026
La Concha Key West, Autograph Collection
430 Duval St Key West FL
$499 nightly
The price is $561 total per night from Feb 1 to Feb 2
$561 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (315 reviews)
Clean, super comfortable, close to everything
Reviewed on Jan 9, 2026
Pier House Resort & Spa
1 Duval St Key West FL
$579 nightly
The price is $651 total per night from Jan 28 to Jan 29
$651 total
Jan 28 - Jan 29
Total with taxes and fees
9/10 Wonderful! (1,021 reviews)
Clean room, and amenities
Reviewed on Jan 22, 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
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
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
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.