Key West Historic District Vacations from $761
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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 Penguin Hotel
South Beach
Save 100% on your flight
Price was $1,440, price is now $761 per person
$761
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,725 reviews)
The people were really nice. I would have preferred to not be forced to do the valet thing but they said it was a spring break thing.
Reviewed on Mar 31, 2026
Casablanca Miami Beach
North Beach
Price was $9,920, price is now $3,805 per person
$3,805
per person
Jun 4 - Jun 11
found 4 hours 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
President Hotel
South Beach
Save 100% on your flight
Price was $1,669, price is now $810 per person
$810
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.4/10 Very Good! (2,145 reviews)
Room was nice and the staff was great. We got upgraded to a bigger room with a huge terrace. It was nice!
Reviewed on Apr 2, 2026
President Hotel Villa
South Beach
Save 100% on your flight
Price was $1,669, price is now $810 per person
$810
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Miami (MIA)
8.2/10 Very Good! (1,001 reviews)
The breakfast is worth the book, its nothing to fancy but definitely worth getting. The area is close to a bus stop and othet amenities nearby. If i was to come back to miami id definitely book again
Reviewed on Apr 1, 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
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$415 nightly
The price is $467 total per night from May 4 to May 5
$467 total
May 4 - May 5
Total with taxes and fees
8.8/10 Excellent! (3,177 reviews)
We stayed in the Adults ONLY Duval Gardens. We enjoyed the privacy and location on Duval Street. It was nice to have the option of the amenities at the resort for the different pools and beach access. Free breakfast too! We would stay here again. The room was clean, staff is friendly no beach view ...
Reviewed on Apr 2, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$413 nightly
The price is $465 total per night from Apr 15 to Apr 16
$465 total
Apr 15 - Apr 16
Total with taxes and fees
8.4/10 Very Good! (599 reviews)
We had an outstanding stay at Casa Marina in Key West. The property itself is absolutely beautiful — the grounds are meticulously maintained, everything is spotless, and the overall atmosphere just feels polished and relaxing from the moment you arrive. The pool setup is excellent, especially having ...
Reviewed on Apr 2, 2026
Pier House Resort & Spa
1 Duval St Key West FL
Fully refundableReserve now, pay when you stay
$581 nightly
The price is $654 total per night from Apr 6 to Apr 7
$654 total
Apr 6 - Apr 7
Total with taxes and fees
9/10 Wonderful! (1,070 reviews)
My husband and I had a spectacular time at this resort. Looking forward to coming back real soon! The food and location were perfect!
Reviewed on Apr 2, 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
Miami to Key West Day Trip with Activity Options
$39
per adult
82% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
$55
per adult
88% 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.