Key West Historic District Vacations from $504
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.
Creekside Inn
Price was $1,224, price is now $553 per person
$553
per person
May 14 - May 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,004 reviews)
This was our second time staying here and it’s wonderful. Everyone was super nice. We will definitely be back.
Reviewed on Feb 20, 2026
Hotel Riu Plaza Miami Beach
Mid Beach
Price was $1,569, price is now $766 per person
$766
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
8/10 Very Good! (1,120 reviews)
Staff are great but the bed and pillows were uncomfortable. Especially the pillows they are horrible. I had to use a towel as my pillow. Other hotels have feather pillows that are far more comfortable. It would be nice to have a choice. For this reason we won’t return. It’s too bad because everything else was nice.
Reviewed on Feb 19, 2026
Pelican Hotel
South Beach
Price was $1,254, price is now $631 per person
$631
per person
Apr 25 - Apr 30
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (394 reviews)
Staff was top notch!! They were helpful and kind and always happy to interact with us.
Reviewed on Feb 18, 2026
Casablanca Miami Beach
North Beach
Price was $1,152, price is now $590 per person
$590
per person
Apr 9 - Apr 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (311 reviews)
The sheets had stains on the when we arrived. The room was outdated but for the price we did kind of expect that. I was told we would have to pay extra for any additional sheets however when I told them they had already started out looking dirty they finally gave us new, but that was several nights into the stay. Most staff didn't speak english so there wasn't great communication or friendliness. It was nice to have the pool and beach within walking distance. Windows would open but no screens which was disappointing because if you wanted fresh air there was a fear of birds flying in. We also had a decent leak from our AC unit running down through the drywall causing it to bubble up and pool on the floor which caused me to slip and fall.
Reviewed on Feb 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
Fully refundable
$504 nightly
The price is $567 total per night from Mar 25 to Mar 26
$567 total
Mar 25 - Mar 26
Total with taxes and fees
8.6/10 Excellent! (3,098 reviews)
Staff very helpful and friendly. You do have wait for your room if you get there before 4 pm checkin!
Reviewed on Feb 21, 2026
Hyatt Centric Key West Resort and Spa
601 Front St Key West FL
Fully refundableReserve now, pay when you stay
$488 nightly
The price is $549 total per night from Mar 22 to Mar 23
$549 total
Mar 22 - Mar 23
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Great room and staff was great
Reviewed on Feb 15, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$609 nightly
The price is $685 total per night from Mar 3 to Mar 4
$685 total
Mar 3 - Mar 4
Total with taxes and fees
8.2/10 Very Good! (547 reviews)
Wouldn’t stay anywhere ekset absolutely love the beach and Dan and Sambita the beach staff
Reviewed on Feb 14, 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
Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Tour
$126
per adult
96% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
80% of travellers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
78% 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.