Old Town Key West Vacations
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Your Old Town Key West Vacation
Organizing your next exciting getaway just got a whole lot easier with a vacation package to Old Town Key West. Take in the best this neighborhood has to offer while making precious memories you'll replay for years. Some leading nearby attractions to check out during your trip to Old Town Key West include Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Expedia will help put your plans into action. Book your ideal Old Town Key West vacation now.
Price found within the past 48 hours. Click for updated prices.
- The Perry Hotel & Marina Key West
Aug 13 - Aug 20The Perry Hotel & Marina Key West + Flight
Stock Island7 nights9.4/10 - Exceptional (1,275 reviews)"Nice room. Nice hotel. Shuttle was great. Active happy hour. Nice pool area. Don't arrive on a Sunday evening and expect to eat on site. But Matt's had great breakfast."Reviewed May 31, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Hyatt Vacation Club at Windward Pointe, Key West
Aug 13 - Aug 20Hyatt Vacation Club at Windward Pointe, Key West + Flight
Key West7 nights9.4/10 - Exceptional (1,100 reviews)"The room and balcony were fantastic. The pool, grounds, and view of the ocean were lovely. The staff was super welcoming and friendly when we arrived. We enjoyed the close restaurant and walking path right across the street."Reviewed May 28, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - The Key West Hotel
Aug 13 - Aug 20The Key West Hotel + Flight
Key West Historic District7 nights9.2/10 - Wonderful (556 reviews)Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Hyatt Vacation Club at Beach House, Key West
Jul 16 - Jul 23Hyatt Vacation Club at Beach House, Key West + Flight
Key West7 nights9.4/10 - Exceptional (1,074 reviews)"Booked the hotel for my bachelorette ~10 girls two rooms, a little far from duval so Ubers were annoying and too many main roads for a good bike ride experience but the pool was gorgeous, boat dock left right behind property, plenty of getting ready space, staff was sooo accommodating letting us check in early and holding our bags before/after the airport arrival and departure. Very clean room, fresh towels every morning, spacious room and bathroom."Reviewed May 31, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Lighthouse Hotel - Key West Historic Inns
Jul 16 - Jul 23Lighthouse Hotel - Key West Historic Inns + Flight
Old Town Key West7 nights9.0/10 - Wonderful (948 reviews)"Great service and clean space"Reviewed May 24, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop
Where to stay in Old Town Key West
Find the best Old Town Key West areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Key West
Key West Historic District
2 out of top 10 points of interest in this area
4.5/5(4,090 area reviews)
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.
Old Town Key West Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$257 nightly
The price is $290 total per night from Jun 8 to Jun 9
$290 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (3,345 reviews)
"Overall, we were very happy with our stay. The staff were extremely responsive to text requests and the food and bar beverages were very good and fairly priced. My only feedback is 1 - I purposely booked this hotel because it was one of the only ones with private beach access. Unfortunately, the ..."
Reviewed on May 31, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$297 nightly
The price is $334 total per night from Jun 28 to Jun 29
$334 total
Jun 28 - Jun 29
Total with taxes and fees
8.4/10 Very Good! (686 reviews)
"We were really disappointed by the beach. It’s rocky and was covered in seaweed (during our visit). The pools are beautiful, staff was lovely. The room was enormous and well maintained. I just wish we had more transparency regarding the condition of the beach."
Reviewed on May 30, 2026
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $331 total per night from Jun 11 to Jun 12
$331 total
Jun 11 - Jun 12
Total with taxes and fees
9.2/10 Wonderful! (1,120 reviews)
"Our first time at the opal and our first time at Key West enjoyed the service and the location would go again"
Reviewed on May 31, 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 Old Town Key West
Southernmost Point
4.5/5(3,246 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
South Beach
4/5(999 reviews)
Head to the southernmost beach of the continental United States to relax and swim in the waters where famous writer Tennessee Williams once took his daily swim.
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.
Things to do
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
Key West Dolphin & Snorkeling Tour - Small Group
$135
per adult
100% of travellers recommend
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- Key West Vacations
- All inclusive Vacation Packages Key West
- Ernest Hemingway Home and Museum
- Duval Street
- Saint Mary Star of the Sea
- South Beach
- Tennessee Williams Key West Exhibit
- Key West Lighthouse and Keeper's Quarters Museum
- Key West Cemetery
- City Zoo Gallery
- Key West Butterfly and Nature Conservatory
- Southernmost Point
- Key West Historic District Vacations
- The Kite House
- Visit Key West
- Simonton Beach
- Mlk Community Pool & Community Center
- Fort Zachary Taylor Historic State Park
- Bahama Village Vacations
- San Carlos Institute - Casa Cuba
- Visit Downtown Key West
- Jackson Square
- Donkey Milk House
- Key West Burlesque Theater
- Oldest House Museum and Garden
- Red Barn Theater
- Curry Mansion Museum
- Florida Keys Eco - Discovery Center
- Harry S. Truman Little White House
- Visit Uptown - Upper Duval
- Visit Key West Historic District
- Sails To Rails Museum at Flagler Station
- Romantic Vacation Packages Key West
- Schooner Western Union
- Florida Keys National Marine Sanctuary
- Mel Fisher Maritime Museum
- 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.