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.
- Hyatt Vacation Club at Beach House, Key West
Aug 12 - Aug 15Hyatt Vacation Club at Beach House, Key West + Flight
Key West3 nights9.4/10 - Exceptional (1,061 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 • Nonstop EYW - ATL • Nonstop$1,134$814found 2 days agoper traveler - Hyatt Vacation Club at Windward Pointe, Key West
Aug 12 - Aug 15Hyatt Vacation Club at Windward Pointe, Key West + Flight
Key West3 nights9.4/10 - Exceptional (1,090 reviews)"Property was amazing. Room was clean, staff was very friendly. Has a great time at the pool. "Reviewed May 19, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - The Key West Hotel
Aug 6 - Aug 10The Key West Hotel + Flight
Key West Historic District4 nights9.2/10 - Wonderful (555 reviews)Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Hyatt Vacation Club at Sunset Harbor, Key West
Aug 12 - Aug 15Hyatt Vacation Club at Sunset Harbor, Key West + Flight
Old Town Key West3 nights8.6/10 - Excellent (371 reviews)"Wished we had paid more for a unit that at least had a window other than to a hallway. Room was clean but not spotless. Found at least 3 long hairs in the bathroom area. Staff at desk was quite abrupt and condescending. At check in AND check out. Gave 4 stars but 5 stars could easily be reached with just a little more attention to detail"Reviewed May 18, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Jul 11 - Jul 18Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front + Flight
Key West7 nights9.4/10 - Exceptional (3 reviews)"Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location ."Reviewed March 26, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • 1 stop EYW - ATL • 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 20 to May 21
$179 total
May 20 - May 21
Total with taxes and fees
9.2/10 Wonderful! (1,152 reviews)
"One of the best hotel beds I have ever slept on. I will be contacting management to ask for the brand so I can buy one. Excellent Hotel!! Great Location!!"
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
$208 nightly
The price is $234 total per night from May 26 to May 27
$234 total
May 26 - May 27
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 20 to May 21
$219 total
May 20 - May 21
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
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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.