Old Town Key West Vacations from $1,026
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
Price found within the past 48 hours. Click for updated prices.
Parrot Key Hotel & Villas
Northside Resort
$1,026
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,460 reviews)
Wonderful stay with my family. Fantastic location. Friendly staff. Large, clean rooms.
Reviewed on Sep 11, 2026
Coconut Beach Resort
Old Town Key West
$1,055
per person
Oct 17 - Oct 20
found 23 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.8/10 Excellent! (219 reviews)
Maintenance people were so nice and helpful
Place was clean
Blanket on the bed was paper thin like a sheet
Could not get both TVs to work said no service
Room was on Third floor all stairs no elevator a bit difficult with luggage
Reviewed on Sep 11, 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
Downtown Key West
If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.
Key West Historic District
2 out of top 10 points of interest in this area
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.
New Town
Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Historic Seaport
Many of the best parts of the southern portion of Florida are rolled into one location. Enjoy your time experiencing attractions in this historic area.
Old Town Key West Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
$239 nightly
$269 total
Sep 27 - Sep 28
Total with taxes and fees
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$287 nightly
$323 total
Sep 22 - Sep 23
Total with taxes and fees
8.4/10 Very Good! (905 reviews)
"The location is fantastic, and the staff is wonderful. I’m already planning to return!"
Reviewed on Sep 10, 2026
Southwinds Motel
1321 Simonton Street Key West FL
$145 nightly
$163 total
Sep 20 - Sep 21
Total with taxes and fees
8.6/10 Excellent! (1,371 reviews)
"Great property and the staff very helpful and friendly."
Reviewed on Sep 11, 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.
Stay near popular Old Town Key West attractions
Southernmost Point
8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
Ernest Hemingway Home and Museum
9.2/10 (8,543 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
8.4/10 (5,461 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.
Clarence S. Higgs Memorial Beach Park
8.4/10 (4,659 reviews)
Pay your respects at an impressive African burial site, explore landscaped gardens or snorkel with the family at this oceanfront beach park.
Key West Butterfly and Nature Conservatory
9.2/10 (1,711 reviews)
With about 60 species of butterfly, an indoor waterfall and a tropical rainforest, this nature conservatory is one of the most popular attractions in Key West.
Harry S. Truman Little White House
9.0/10 (995 reviews)
Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.
Key West Lighthouse and Keeper's Quarters Museum
8.6/10 (548 reviews)
Climb to the top of this historic lighthouse for unparalleled photo opportunities and then visit the former home of Key West’s lighthouse keepers.
Florida Keys Eco - Discovery Center
8.8/10 (128 reviews)
Learn about the area’s important marine ecology at this comprehensive attraction that addresses global environmental concerns, interesting for visitors of all ages.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$42
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travellers recommend
Key West Afternoon At The Reef Snorkeling Adventure with Open Bar!
$45
per adult
92% of travellers recommend
Explore a world of travel with Expedia
- Key West Historic District Hotels
- Hotels near Duval Street
- Condo Rentals in Key West
- Adults Only Resorts & in Key West
- Houseboats in Key West
- Resorts in Key West
- Oceanfront Hotels in Key West
- Beach Hotels in Key West
- All-Inclusive Resorts in Key West
- Pet-Friendly Hotels in Key West
- Family Hotels in Key West
- Cheap Hotels in Key West
- Key West Hotels
- Flights to Key West
- Flights from Indianapolis (IND) to Key West (EYW)
- Flights from Dallas (DFW) to Key West (EYW)
- Flights from Tampa (TPA) to Key West (EYW)
- Flights from Richmond (RIC) to Key West (EYW)
- Flights from Pensacola (PNS) to Key West (EYW)
- Flights from Newark Liberty Intl. Airport (EWR) to Key West (EYW)
- Flights from Atlanta (ATL) to Key West (EYW)
- Flights from Cincinnati (CVG) to Key West (EYW)
- Flights from Minneapolis (MSP) to Key West (EYW)
- Flights from West Palm Beach (PBI) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights from Baltimore (BWI) to Key West (EYW)
- Flights from Sarasota (SRQ) to Key West (EYW)
- Flights from Key West Intl.
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Boston (BOS) to Key West (EYW)
- Flights from Fort Myers (RSW) to Key West (EYW)
- Flights from Columbus (CMH) to Key West (EYW)
- Flights from New Orleans (MSY) to Key West (EYW)
- Flights from Raleigh (RDU) to Key West (EYW)
- Flights from Orlando (MCO) to Key West (EYW)
- Flights from Philadelphia (PHL) to Key West (EYW)
- Flights from Kansas City (MCI) to Key West (EYW)
- Flights from Charlotte (CLT) to Key West (EYW)
- Flights from Cleveland (CLE) to Key West (EYW)
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Jacksonville (JAX) to Key West (EYW)
- Flights from Houston (IAH) to Key West (EYW)
- Flights from Hartford (BDL) to Key West (EYW)
- Flights from Denver (DEN) to Key West (EYW)
- Flights from Nashville (BNA) to Key West (EYW)
- Flights from Chicago (ORD) to Key West (EYW)
- Flights from Washington (DCA) to Key West (EYW)
- Flights from Pittsburgh (PIT) to Key West (EYW)
- Flights from New York (JFK) to Key West (EYW)
- Flights from St. Louis (STL) to Key West (EYW)
- Duval Street
- Fort Zachary Taylor Historic State Park
- Donkey Milk House
- Robbie's
- Visit Key West
- Key West National Wildlife Refuge
- Museum of Art & History at the Custom House
- Florida Keys Eco - Discovery Center
- Sunset Key Vacations
- Key West Cemetery
- Mel Fisher Maritime Museum
- Key West Vacations
- Tennessee Williams Key West Exhibit
- Key West Butterfly and Nature Conservatory
- Key West Lighthouse and Keeper's Quarters Museum
- San Carlos Institute - Casa Cuba
- Key West Tropical Forest and Botanical Garden
- Key West Burlesque Theater
- Visit Downtown Key West
- Saint Mary Star of the Sea
- Clarence S. Higgs Memorial Beach Park
- Key West Museum of Art and History
- Southernmost Point
- South Beach
- The Kite House
- Audubon House and Tropical Gardens
- Custom House Museum
- Simonton Beach
- Key West Historic District Vacations
- Key West Shipwreck Museum
- Schooner Western Union
- Red Barn Theater
- Smathers Beach
- Key West Firehouse Museum
- Bahama Village Vacations
- Mallory Dock
- All inclusive Vacation Packages Key West
- Mallory Square
- Ernest Hemingway Home and Museum
- Jackson Square
- Waterfront Playhouse
- Boca Chica Nude Beach
- Fort East Martello Museum and Gallery
- Sails To Rails Museum at Flagler Station
- Harry S. Truman Little White House
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.