Downtown Key West Vacations from $654
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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.
Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Old Town Key West
$2,365
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy
Reviewed on Oct 17, 2025
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
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
2 out of top 10 points of interest in this area
Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.
New Town
Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Historic Seaport
Many of the best parts of the southern portion of Florida are rolled into one location. Enjoy your time experiencing attractions in this historic area.
Downtown Key West Hotel Deals
Duval House
815 Duval St Key West FL
$109 nightly
$120 total
Sep 1 - Sep 2
Total with taxes and fees
9.6/10 Exceptional! (1,089 reviews)
"What an amazing experience. The Duval house is the perfect quiet respite from the wacky fun times of Key West!"
Reviewed on Aug 30, 2026
Heron House - Adult Only
512 Simonton St Key West FL
$136 nightly
$154 total
Sep 1 - Sep 2
Total with taxes and fees
9.2/10 Wonderful! (1,158 reviews)
"great location friendly staff. they do have poolside construction going on currently."
Reviewed on Aug 30, 2026
Wicker Guesthouse
913 Duval Street Key West FL
$169 nightly
$190 total
Sep 2 - Sep 3
Total with taxes and fees
8.6/10 Excellent! (1,006 reviews)
"Our room was VERY hot even with the A/C and the fans going full-blast day and night. The beds were on opposite sides of the room which made it hard to have a casual conversation. The room was large, which was nice, and had a little kitchen we did not use. The whole unit was beautifully decorated. ..."
Reviewed on Aug 29, 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.
Stay near popular Downtown Key West attractions
Ernest Hemingway Home and Museum
9.2/10 (8,543 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
8.8/10 (110 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
8.6/10 (34 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 beautiful beaches or experience its lively festivals.
Tennessee Williams Key West Exhibit
9.0/10 (2 reviews)
You can spend an afternoon studying the exhibits at Tennessee Williams Key West Exhibit during your travels in Key West. Wander the seaside and beautiful beaches in the area.
Things to do
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
$69
per adult
88% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
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- Fort East Martello Museum and Gallery
- Key West Historic District Vacations
- Custom House Museum
- Bahama Village Vacations
- Tennessee Williams Key West Exhibit
- Key West Cemetery
- Southernmost Point
- Sails To Rails Museum at Flagler Station
- Clarence S. Higgs Memorial Beach Park
- All inclusive Vacation Packages Key West
- Visit Downtown Key West
- Red Barn Theater
- Mallory Square
- Smathers Beach
- Visit Key West
- San Carlos Institute - Casa Cuba
- Key West Vacations
- Key West Shipwreck Museum
- Key West Firehouse Museum
- The Kite House
- Fort Zachary Taylor Historic State Park
- South Beach
- Museum of Art & History at the Custom House
- Mallory Dock
- Sunset Key Vacations
- Key West Burlesque Theater
- Old Town Key West Vacations
- Ernest Hemingway Home and Museum
- Robbie's
- Duval Street
- Key West Butterfly and Nature Conservatory
- Schooner Western Union
- Key West Lighthouse and Keeper's Quarters Museum
- Waterfront Playhouse
- Curry Mansion Museum
- Mel Fisher Maritime Museum
- Key West National Wildlife Refuge
- Donkey Milk House
- Saint Mary Star of the Sea
- Jackson Square
- Harry S. Truman Little White House
- Key West Museum of Art and History
- Florida Keys Eco - Discovery Center
- Boca Chica Nude Beach
- Audubon House and Tropical Gardens
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.