
Old Town Key West Vacations from $683
Book a Hotel + Flight or Car together to unlock savings
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

Hyatt Vacation Club at Beach House, Key West
Reviewed on Oct 30, 2025

The Key West Hotel
Reviewed on Oct 17, 2025

Winslow's Bungalows - Key West Historic Inns
Reviewed on Oct 30, 2025

Ella's Cottages - Key West Historic Inns
Reviewed on Oct 30, 2025

Lighthouse Hotel - Key West Historic Inns
Reviewed on Oct 30, 2025
Where to stay in Old Town Key West

Beachside
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
The room was clean, the staff so friendly.
Reviewed on Oct 30, 2025

Casa Marina Key West, Curio Collection by Hilton
Yes property is in an excellent location and the rooms and common areas were very good.
Reviewed on Oct 22, 2025

The Reach Key West, Curio Collection by Hilton
Great job
Reviewed on Oct 27, 2025
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

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Key West Sunset Sail with Live Music, Drinks and Appetizers!

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
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
- Adults Only Resorts & in Key West
- Houseboats in Key West
- Pet-friendly Hotels in Key West
- Condo Rentals in Key West
- Hotels near Saint Mary Star of the Sea
- Romantic Hotels in Key West
- Family Hotels in Key West
- 4 Star Hotels in Key West
- Hotels near Tennessee Williams Key West Exhibit
- Hilton Hotels in Key West
- Hotels near Uptown - Upper Duval
- Hotels near Ernest Hemingway Home and Museum
- 5 Star Hotels in Key West
- Honeymoon Resorts & in Key West
- Hotels near Key West Firehouse Museum
- Hotels near Downtown Key West
- Resorts in Key West
- Hotels near Key West Cemetery
- 4 Star Hotels in Key West Historic District
- Boutique Hotels in Key West
- Kimpton Hotels in Key West
- Family Hotels in Key West Historic District
- Oceanfront Hotels in Key West Historic District
- Historic Hotels in Key West Historic District
- Gay friendly Hotels in Key West Historic District
- Pet-friendly Hotels in Key West Historic District
- Hotel Wedding Venues Hotels in Key West Historic District
- Hotels with Connecting Rooms in Key West Historic District
- Cheap Hotels in Key West Historic District
- Hotels with Free Airport Shuttle in Key West Historic District
- Hotels with Laundry Facilities in Key West Historic District
- Hotels with a Pool in Key West Historic District
- Hotels with Suites in Key West Historic District
- Adults Only Resorts & in Key West Historic District
- Hotels with Free Parking in Key West Historic District
- Luxury Hotels in Key West Historic District
- Romantic Hotels in Key West Historic District
- Boutique Hotels in Key West Historic District
- Hotels with Balconies in Key West Historic District
- Honeymoon Resorts & in Key West Historic District
- Beach Hotels in Key West Historic District
- Resorts & Hotels with Spas in Key West Historic District
- Hotels with Kitchenettes in Key West Historic District
- Non-Smoking Hotels in Key West Historic District
- Hotels with Free Breakfast in Key West Historic District
- Hotels with Hot Tubs in Key West Historic District
- Hotels with Room Service in Key West Historic District
- Hotels with Bars in Key West Historic District
- Hotels with a View in Key West Historic District
- 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






















