Downtown Key West Vacations
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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.
Price found within the past 48 hours. Click for updated prices.
- The Perry Hotel & Marina Key West
Aug 1 - Aug 6The Perry Hotel & Marina Key West + Flight
Stock Island5 nights9.4/10 - Exceptional (1,271 reviews)"Hi. Love this place. Great location. Shuttle bus to Downtown Key West. So know need to drive. Pool is awesome. They have a good restaurant and happy hour. Fighter jets have their 'sorties' . Its pretty cool. Thanks"Reviewed May 18, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Hyatt Vacation Club at Windward Pointe, Key West
Jul 11 - Jul 18Hyatt Vacation Club at Windward Pointe, Key West + Flight
Key West7 nights9.4/10 - Exceptional (1,091 reviews)"Beautiful rooms. It has to be one of the nicest in the Keys."Reviewed May 19, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • 1 stop EYW - ATL • 1 stop - Hyatt Vacation Club at Beach House, Key West
Jul 11 - Jul 18Hyatt Vacation Club at Beach House, Key West + Flight
Key West7 nights9.4/10 - Exceptional (1,062 reviews)"Nice clean room. one smoking area is not enough. no on site restaurant or snack bar of vending for snacks. "Reviewed May 19, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • 1 stop EYW - ATL • 1 stop - The Key West Hotel
Aug 1 - Aug 6The Key West Hotel + Flight
Key West Historic District5 nights9.2/10 - Wonderful (555 reviews)Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Amelia Home by Avantstay In Historic Old Town w/ Pool
Jul 5 - Jul 10Amelia Home by Avantstay In Historic Old Town w/ Pool + Flight
Old Town Key West5 nights10/10 - Exceptional (3 reviews)"Loved it"Reviewed March 20, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop
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
3 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.
Downtown Key West Hotel Deals
Heron House - Adult Only
512 Simonton St Key West FL
$159 nightly
The price is $179 total per night from May 21 to May 22
$179 total
May 21 - May 22
Total with taxes and fees
9.2/10 Wonderful! (1,153 reviews)
"This is a gem of a property that is reasonably priced, has the Key West charm, nice pool area, and amazing staff! I can't say enough about Trent and Greg up front as well as the wonderful lady in charge of the breakfast (I'm so sorry I didn't get her name but she was absolutely the sweetest!). Highly ..."
Reviewed on May 19, 2026
The Cabana Inn Key West - Adults Only
413 Applerouth Lane Key West FL
Fully refundableReserve now, pay when you stay
$210 nightly
The price is $236 total per night from May 21 to May 22
$236 total
May 21 - May 22
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
"Steps from Duval, quiet, wonderful people & very attentive. Breakfast included, wine & cheese from 5-7 great way to mingle & meet other guests. Several people stayed here before & continue to return. They let us stay & use all amenities before & after checkout."
Reviewed on May 18, 2026
Pegasus International Hotel
501 Southard Street Key West FL
$195 nightly
The price is $219 total per night from May 21 to May 22
$219 total
May 21 - May 22
Total with taxes and fees
8.2/10 Very Good! (1,025 reviews)
"Breakfast fresh nice clean room"
Reviewed on May 19, 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(1,744 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
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 beautiful beaches or experience its lively festivals.
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 seaside or discover the area's beautiful sunsets.
Things to do
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Shipwreck Treasure Museum Tickets
$19
per adult
78% of travellers recommend
Explore a world of travel with Expedia
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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.