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.
- Hyatt Vacation Club at Sunset Harbor, Key West
Aug 11 - Aug 15Hyatt Vacation Club at Sunset Harbor, Key West + Flight
Old Town Key West4 nights8.6/10 - Excellent (380 reviews)"A/ C was amazing ! Clean very cute rooms. Loved the brewing coffee maker and the cleaning stuff they left for us. Made the stay comfortable like home ."Reviewed June 7, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Hyatt Vacation Club at Beach House, Key West
Jul 26 - Aug 2Hyatt Vacation Club at Beach House, Key West + Flight
Key West7 nights9.4/10 - Exceptional (1,094 reviews)"Property well very clean and maintained. Staff was very friendly and accommodating. Rooms had everything you would need and very clean. Great place to stay!"Reviewed June 8, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Hyatt Vacation Club at Windward Pointe, Key West
Jul 26 - Aug 2Hyatt Vacation Club at Windward Pointe, Key West + Flight
Key West7 nights9.4/10 - Exceptional (1,124 reviews)"Excellent stay! Walkable to the Smathers beach... rooms were very clean. Pool has great ocean view. Amenities were good!"Reviewed June 9, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - The Key West Hotel
Jul 26 - Aug 2The Key West Hotel + Flight
Key West Historic District7 nights9.2/10 - Wonderful (558 reviews)"We loved staying here and highly recommended it. Only thing that people might not like is the solo musicians play till 11pm every night. We didn’t mind it since we are not early birds."Reviewed June 7, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Oceans Edge Key West Resort, Hotel & Marina
Jul 26 - Aug 2Oceans Edge Key West Resort, Hotel & Marina + Flight
Stock Island7 nights9.0/10 - Wonderful (1,875 reviews)"Great place for a family reunion"Reviewed June 9, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop
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
$261 nightly
The price is $294 total per night from Jun 29 to Jun 30
$294 total
Jun 29 - Jun 30
Total with taxes and fees
8.8/10 Excellent! (3,375 reviews)
"Espectacular"
Reviewed on Jun 8, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$283 nightly
The price is $319 total per night from Jun 23 to Jun 24
$319 total
Jun 23 - Jun 24
Total with taxes and fees
8.4/10 Very Good! (698 reviews)
"The room was clean the first day. But everyone was complaining about their rooms not being cleaned the whole day and they didn't clean up the next day. Even more we had to call every day. And housekeeping half clean everytime they came We were asked to pay for the daybed. Things that should have ..."
Reviewed on Jun 9, 2026
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
$249 nightly
The price is $280 total per night from Jun 17 to Jun 18
$280 total
Jun 17 - Jun 18
Total with taxes and fees
8.6/10 Excellent! (1,013 reviews)
"Wonderful stay! Highly recommend."
Reviewed on Jun 7, 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.
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.
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.
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.