Old Town Key West Vacations from $817
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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.
The Latest Old Town Key West Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (1,668 reviews)
I really loved the whole experience from beginning to end! The receptionist are awesome and very pleasant to speak to all the staff are very pleasant and we really really enjoyed our stay
Reviewed on Jul 29, 2025
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,003 reviews)
Great place, huge rooms, 2 bathrooms, washer and dryer, screened in porch. Covered parking. Pool and games for lids. We had a great time.
Reviewed on Jul 29, 2025
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (1,002 reviews)
Stayed with my husband and 3 kids. The room was very spacious. The balcony was gorgeous overlooking the pool and the ocean. We all agreed for our next family trip we will stay here again. It was very close to the marina where we rented our boat. The island is fairly small so we didn’t feel we missed out by not staying on Duval street, especially with kids. I really appreciated the washer and dryer so we didn’t have to bring home wet bathing suits. The pool area has a volleyball area and outdoor games. Totally worth it to stay here with family.
Reviewed on Jul 27, 2025
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
per person
Aug 29 - Sep 5
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,611 reviews)
Great view from the room and quiet location on the property.
Reviewed on Jul 29, 2025
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(4,033 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 refundable
$244 nightly
The price is $275 total per night from Aug 25 to Aug 26
$275 total
Aug 25 - Aug 26
Total includes taxes and fees
8.6/10 Excellent! (2,656 reviews)
"Everything was perfect, except the washed up seaweed. They said a net broke, and it would be fixed eventually! Cannot wait to go back and utilize the beach area as well."
Reviewed on Jul 28, 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
$258 nightly
The price is $290 total per night from Aug 13 to Aug 14
$290 total
Aug 13 - Aug 14
Total includes taxes and fees
8.4/10 Very Good! (252 reviews)
"Only issue was the $200 per night hold on card"
Reviewed on Jul 23, 2025
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
$295 nightly
The price is $332 total per night from Aug 24 to Aug 25
$332 total
Aug 24 - Aug 25
Total includes taxes and fees
8.4/10 Very Good! (1,024 reviews)
"Nice and clean hotel!"
Reviewed on Jul 29, 2025
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
Snap a memorable photograph from the edge of North America at this monumental landmark.
South Beach
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
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
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
$99
per adult
74% of travellers recommend
The Dark Side of Key West Adults Only Walking Tour
$35
per adult
Guided Night Kayak Adventure Tour in Luminous Lagoon
$85
per adult
74% of travellers recommend
Explore a world of travel with Expedia
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
- 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.