Old Town Key West Vacations from $695
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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
Price was $1,078, price is now $695 per person
$695
per person
Mar 6 - Mar 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
Oceans Edge Resort was a dream place to stay. I was shocked at the size of our room. It spanned from one side of the building to the other with a living room, coffee bar & sink, huge bathroom, massive bedroom, balcony overlooking the pools and marina & even fluffy robes. It couldn't have been any better. We were just steps from the restaurant and coffee bar. We loved being just a little removed from Key West but able to get their in just a few minutes. There were numerous pools which was both beautiful and made me feel like we had our own private pool. We loved sitting on our balcony and reading. This resort definitely enhanced our trip.
Reviewed on Jan 30, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,568, price is now $1,765 per person
$1,765
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Everything was great. I couldn’t complain about anything if I wanted to. Thanks for a great stay!
Reviewed on Jan 28, 2026
Bishop Hotel Key West
Old Town Key West
Save 100% on your flight
Price was $2,913, price is now $2,115 per person
$2,115
per person
Mar 14 - Mar 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.8/10 Exceptional! (291 reviews)
Room was great. Plenty of room. Cleaned perfectly every day. Front desk was super nice and helpful. Pool was warm and beautiful. Breakfast was delicious, pastries, fruit and yogurt. Water and coffee always available. Location is great if you want to be near the wharf.
Reviewed on Jan 26, 2026
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,496, price is now $1,100 per person
$1,100
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,002 reviews)
Very nice resort, and clean
Reviewed on Jan 27, 2026
Southernmost Beach Resort and Guesthouses
Old Town Key West
Save 100% on your flight
Price was $1,626, price is now $1,198 per person
$1,198
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
Perfect stay and location!
Reviewed on Jan 30, 2026
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
$530 nightly
The price is $596 total per night from Feb 2 to Feb 3
$596 total
Feb 2 - Feb 3
Total with taxes and fees
8.6/10 Excellent! (3,034 reviews)
Nice clean resort! Great fun time!
Reviewed on Jan 26, 2026
Winslow's Bungalows - Key West Historic Inns
725 Truman Avenue Key West FL
Fully refundableReserve now, pay when you stay
$534 nightly
The price is $601 total per night from Feb 1 to Feb 2
$601 total
Feb 1 - Feb 2
Total with taxes and fees
9.2/10 Wonderful! (1,138 reviews)
Beautiful place, clean, friendly and good location to everywhere!!
Reviewed on Jan 26, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$624 nightly
The price is $702 total per night from Jan 31 to Feb 1
$702 total
Jan 31 - Feb 1
Total with taxes and fees
8.2/10 Very Good! (517 reviews)
Beautiful historic hotel, room was spacious, lots of amenities, friendly staff, terrific views, can walk to town.
Reviewed on Jan 20, 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
Snap a memorable photograph from the edge of North America at this monumental landmark.
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.
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.
Things to do
Shipwreck Treasure Museum Tickets
$19
per adult
78% of travellers recommend
Sunset Sail in Key West with Beverages Included
$79
per adult
98% 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.