Old Town Key West Vacations from $756
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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.
Hyatt Vacation Club at Beach House, Key West
Save 100% on your flight
Price was $1,207, price is now $756 per person
$756
per person
Dec 7 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,025 reviews)
The stunning coastline of Key West is the perfect destination for a fun-filled family getaway! This vibrant paradise offers something for everyone, making it an unforgettable spot to create lasting memories together.
Reviewed on Sep 15, 2025
Southernmost House
Old Town Key West
Save 100% on your flight
Price was $2,800, price is now $1,776 per person
$1,776
per person
Oct 18 - Oct 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,009 reviews)
Very enjoyable stay. Thank you.
Reviewed on Sep 10, 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $2,295, price is now $1,485 per person
$1,485
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (369 reviews)
This was a wonderful experience. It was everything we could ask for her rest and relaxation. We were celebrating our 25th and wedding anniversary and it did not disappoint.
Reviewed on Sep 12, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,588, price is now $1,052 per person
$1,052
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (781 reviews)
Great location and friendly staff.
Reviewed on Sep 13, 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
Beachside
1 out of top 10 points of interest in this area
If you're spending some time in Beachside, Smathers Beach and Florida Keys Beaches are top sights worth seeing.
Old Town Key West Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$207 nightly
The price is $233 total per night from Sep 30 to Oct 1
$233 total
Sep 30 - Oct 1
Total with taxes and fees
8.6/10 Excellent! (2,733 reviews)
"Wonderful!"
Reviewed on Sep 10, 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Fully refundableReserve now, pay when you stay
$207 nightly
The price is $232 total per night from Sep 25 to Sep 26
$232 total
Sep 25 - Sep 26
Total with taxes and fees
8.2/10 Very Good! (334 reviews)
"beautiful hotel with hidden expenses"
Reviewed on Sep 9, 2025
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
$250 nightly
The price is $282 total per night from Sep 25 to Sep 26
$282 total
Sep 25 - Sep 26
Total with taxes and fees
8.4/10 Very Good! (1,006 reviews)
"."
Reviewed on Sep 9, 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
Miami to Key West Day Trip with Activity Options
$39
per adult
82% of travellers recommend
The Dark Side of Key West Adults Only Walking Tour
$35
per adult
80% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Key West Hotels
- All-inclusive Resorts in Key West
- Cheap Hotels in Key West
- Oceanfront Hotels in Key West
- Hotels near Duval Street
- Beach Hotels in Key West
- Hotels near Key West Historic District
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- Condo Rentals in Key West
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- 4 Star Hotels in Key West
- Hotels near Tennessee Williams Key West Exhibit
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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.
