Old Town Key West Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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.
Price found within the past 48 hours. Click for updated prices.
- The Perry Hotel & Marina Key West
Jul 17 - Jul 21The Perry Hotel & Marina Key West + Flight
Stock Island4 nights9.4/10 - Exceptional (1,276 reviews)"The hotel itself is decent in appearance, it is well cleaned and staffed I do feel like the food is way overpriced for the quality of the food and portion size, also the fees are absolutely absurd. Instead of just paying for the hotel stay, they tack on a resort fee, resort sales tax, resort county tax, destination fee, community impact fee, parking fee…..and yes parking fee is per day. why not just include these fees into the initial price so people actually see what they are paying for when..."Reviewed June 6, 2026Roundtrip • Boston (BOS) - Miami (MIA)BOS - MIA • Nonstop MIA - BOS • Nonstop$799$593found 2 days agoper traveler - Southernmost House - Adult Exclusive
Jul 12 - Jul 15Southernmost House - Adult Exclusive + Flight
Old Town Key West3 nights9.4/10 - Exceptional (1,001 reviews)"This is a wonderful old mansion. I love that they did NOT modernize it to the point it’s lost its charm and character. The staff were amazing. The room was nice, clean and cool with a nice view. I would highly recommend staying here. The only negatives experienced is the noise level. Be prepared to hear propane trucks at 6 in the morning stopping at the cafe and the smell of the seaweed can get pretty rough. So if you’re a light sleeper (which unfortunately I am) or if your sense of smell is..."Reviewed May 30, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - The Key West Hotel
Aug 10 - Aug 14The Key West Hotel + Flight
Key West Historic District4 nights9.2/10 - Wonderful (557 reviews)Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Hyatt Vacation Club at Sunset Harbor, Key West
Jul 13 - Jul 17Hyatt Vacation Club at Sunset Harbor, Key West + Flight
Old Town Key West4 nights8.6/10 - Excellent (378 reviews)"Like almost everywhere in the Keys, you start off by paying to park. Pool was great with a nice hot tub and swings and barbecue grills to use. We were asked to do the vacation club tour and at first I agree but then the $200 visa gift card turned into vouchers, etc. Since we only stayed a few days, it wasn’t worth our while, and we had already done all the tours. I mainly didn’t like that. I kept hearing anywhere from 100, 150 and 200 at different times from different people and it went from a..."Reviewed June 2, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop - Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!
Jul 14 - Jul 19Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool! + Flight
Old Town Key West5 nights10/10 - Exceptional (1 review)"Loved the closeness to Duval st and the privacy "Reviewed October 17, 2025Roundtrip • Philadelphia (PHL) - Key West (EYW)PHL - EYW • Nonstop EYW - PHL • Nonstop
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(4,090 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 refundableReserve now, pay when you stay
$261 nightly
The price is $294 total per night from Jun 29 to Jun 30
$294 total
Jun 29 - Jun 30
Total with taxes and fees
8.8/10 Excellent! (3,366 reviews)
"Property was beautiful! Booked 2 queen partial ocean view. Room was clean, some things needed a little updating but understandable being right on the water. Staff were pleasant, text notifications about activities of the day. I stayed with a friend in the Atlantic building, in the 6300s (3rd floor), ..."
Reviewed on Jun 6, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$316 nightly
The price is $355 total per night from Jun 22 to Jun 23
$355 total
Jun 22 - Jun 23
Total with taxes and fees
8.6/10 Excellent! (694 reviews)
"Historic hotel away from the noise and crowds on Duval St. Two private beaches, Beach dining, and friendly staff. The breakfast buffet is to die for! You get what you pay for and well worth the little extra cost. In my opinion by far the best hotel / resort on the island. Will stay at the Casa Marina ..."
Reviewed on Jun 6, 2026
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
$294 nightly
The price is $331 total per night from Jun 11 to Jun 12
$331 total
Jun 11 - Jun 12
Total with taxes and fees
9.2/10 Wonderful! (1,123 reviews)
"Cleanness and helpfulness of staff members alongside with the location makes it a very pleasurable and worry free stay in Key West."
Reviewed on Jun 5, 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
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
Key West Half-Day Fishing Charter
$95
per adult
92% of travellers recommend
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
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.