Key West Historic District Vacations from $761
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 $1,672, price is now $761 per person
$761
per person
May 15 - May 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
7.8/10 Good! (1,027 reviews)
Hotel is 2 separate buildings, one down the street which we were in but not notified about prior. This building appears to be under renovation without a pool or water view. All rooms are along busy, loud A1A. AC barely work and water pressure is minimal.
Reviewed on Mar 25, 2026
Casablanca Miami Beach
North Beach
Price was $5,459, price is now $2,393 per person
$2,393
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Miami (MIA)
5.8/10 (321 reviews)
Room was clean and great location beside the beach. Room had kitchette and big fridge, microwave etc. so was great.
It was dated and internet didn't work in our room but worked well in the lobby. Great value for money :) happy with it.
Reviewed on Feb 22, 2026
Pelican Hotel
South Beach
Save 100% on your flight
Price was $1,578, price is now $855 per person
$855
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
9.2/10 Wonderful! (435 reviews)
We had a great stay overall. The breakfast was tasty and more than enough to start the day. The hotel’s restaurant was also consistently good, making dining convenient. Our room was clean and well-maintained, and the resort fee included 2 beach chairs and beach towels. Though, the resort fee is almost same as renting the chairs on the spot.
The location on Ocean Drive is excellent—perfect for enjoying the oceanfront atmosphere. The staff were friendly and helpful throughout our stay.
Reviewed on Mar 23, 2026
Cavalier Hotel South Beach
South Beach
Save 100% on your flight
Price was $1,698, price is now $938 per person
$938
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.6/10 Excellent! (1,007 reviews)
Everything was perfect . I would stay there again
Reviewed on Mar 16, 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(229 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
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$544 nightly
The price is $612 total per night from Apr 5 to Apr 6
$612 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (589 reviews)
what a disappointment to stay in a hotel with such great potential but obvious neglect. From the cold, unwelcoming staff to the dirty, dated rooms to the old ugly dining areas with big heavy curtains and dark scratched floors-the hotel is clearly mismanaged. The entire place needs a good scrubbing, ...
Reviewed on Mar 25, 2026
Pier House Resort & Spa
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$572 nightly
The price is $644 total per night from Mar 29 to Mar 30
$644 total
Mar 29 - Mar 30
Total with taxes and fees
9/10 Wonderful! (1,069 reviews)
Beach was small, overcrowded, no beds available around pool but resort fees still charged although we didn't use any of them
Reviewed on Mar 28, 2026
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
$384 nightly
The price is $432 total per night from Apr 19 to Apr 20
$432 total
Apr 19 - Apr 20
Total with taxes and fees
9.2/10 Wonderful! (1,075 reviews)
Great location. The price is too much since the waterfront views are often blocked by massive cruise ships docked right in front of the hotel.
Reviewed on Mar 27, 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(3,518 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(3,144 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(1,738 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 Rum & Reggae: Snorkel & Sunset Sail Combo
$55
per adult
88% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
82% of travellers recommend
Key West: Shark and Wildlife Viewing Catamaran Tour
$99
per adult
100% 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.