Downtown Key West Vacations from $765
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Your Downtown Key West Vacation
Our Downtown Key West vacation packages are a time-saving and convenient way to arrange and book your next escape. Experience the magic of this unique neighborhood without the bother of planning everything yourself. Your trip to Downtown Key West wouldn't be complete without stopping by big-name attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Don't just imagine it — make it a reality! Book your ideal Downtown Key West vacation with Expedia and get to where you're going your way.
The Latest Downtown Key West Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,777, price is now $1,208 per person
$1,208
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
Great location with beautiful ocean views. Clean and comfortable rooms and friendly staff. 3 pools to choose from but we spent all of our time at the Shore pool right next to the beach. Can’t wait to visit them again!
Reviewed on Feb 2, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,700, price is now $1,923 per person
$1,923
per person
Apr 14 - Apr 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!
Reviewed on Jan 28, 2026
The Perry Hotel & Marina Key West
Save 100% on your flight
Price was $1,472, price is now $1,086 per person
$1,086
per person
Apr 8 - Apr 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
The Perry Hotel was a great experience. Traveled with a friend and stayed in a Mangrove room. Rooms were clean and well cared for. Pool and outside area is clean too. Although outside of downtown, there is a free shuttle that takes you downtown. If you are planning a specific time to go into town, you should ask if the shuttle is typically busy or not. It is first come first serve. Restaurants are great for breakfast or lunch when you arrive. It was a great quiet place to stay with the benefit of being on the water and being able to walk around the docks. Some excursions go out from the marinas as well.
Reviewed on Feb 1, 2026
Where to stay in Downtown Key West
Find the best Downtown Key West areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Key West
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.
Downtown Key West Hotel Deals
Duval House
815 Duval St Key West FL
$371 nightly
The price is $414 total per night from Feb 5 to Feb 6
$414 total
Feb 5 - Feb 6
Total with taxes and fees
9.4/10 Exceptional! (1,010 reviews)
Clean room
Reviewed on Jan 28, 2026
Heron House - Adult Only
512 Simonton St Key West FL
$323 nightly
The price is $363 total per night from Feb 8 to Feb 9
$363 total
Feb 8 - Feb 9
Total with taxes and fees
9/10 Wonderful! (1,137 reviews)
Such a lovely resort - room was clean and comfortable. Plenty of options around the resort to relax and get some sun [or shade].
Reviewed on Jan 29, 2026
Pegasus International Hotel
501 Southard Street Key West FL
$367 nightly
The price is $413 total per night from Feb 4 to Feb 5
$413 total
Feb 4 - Feb 5
Total with taxes and fees
8/10 Very Good! (1,009 reviews)
The room was clean, bathroom was very clean. Daily towel service was appreciated. Enjoyed the second floor outside area quite a bit. Bar vending machine on the second floor was broken, but wouldn't have used anyways. Other reviewers complained about street noise, but we didn't hear anything in room ...
Reviewed on Jan 28, 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 Downtown Key West
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.
Jackson Square
4.5/5(81 reviews)
You can learn about the history of Key West with a stop at Jackson Square. Stroll along the beautiful beaches or discover the area's beautiful sunsets.
San Carlos Institute - Casa Cuba
4.5/5(22 reviews)
You can spend an afternoon exploring the galleries in San Carlos Institute - Casa Cuba during your trip to Key West. Stroll along the area's seaside or experience its lively festivals.
Things to do
Shipwreck Treasure Museum Tickets
$19
per adult
78% of travellers recommend
Key West Half-Day Fishing Charter
$95
per adult
90% 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 Lighthouse and Keeper's Quarters Museum
- Tennessee Williams Key West Exhibit
- Fort Zachary Taylor Historic State Park
- Visit Key West
- Saint Mary Star of the Sea
- South Beach
- City Zoo Gallery
- Bahama Village Vacations
- Old Town Key West Vacations
- San Carlos Institute - Casa Cuba
- Southernmost Point
- Jackson Square
- Key West Cemetery
- Key West Historic District Vacations
- Key West Butterfly and Nature Conservatory
- MLK Community Pool & Community Center
- The Kite House
- Donkey Milk House
- Florida Keys Eco - Discovery Center
- Oldest House Museum and Garden
- Harry S. Truman Little White House
- Red Barn Theater
- Curry Mansion Museum
- Florida Keys National Marine Sanctuary
- Romantic Vacation Packages Key West
- Simonton Beach
- Mel Fisher Maritime Museum
- Audubon House and Tropical Gardens
- Roy John-Karl Gallery
- Custom House Museum
- Visit Bahama Village
- Key West Museum of Art and History
- Visit Old Town Key West
- Sails To Rails Museum at Flagler Station
- Schooner Western Union
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.