Old Town Key West Vacations
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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.
Price found within the past 48 hours. Click for updated prices.
- Hyatt Vacation Club at Windward Pointe, Key West
Aug 7 - Aug 10Hyatt Vacation Club at Windward Pointe, Key West + Flight
Key West3 nights9.4/10 - Exceptional (1,110 reviews)"loved our stay here!"Reviewed June 5, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Hyatt Vacation Club at Sunset Harbor, Key West
Aug 6 - Aug 12Hyatt Vacation Club at Sunset Harbor, Key West + Flight
Old Town Key West6 nights8.6/10 - Excellent (377 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 • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - The Key West Hotel
Jul 16 - Jul 23The Key West Hotel + Flight
Key West Historic District7 nights9.2/10 - Wonderful (556 reviews)Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Jul 5 - Jul 15Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front + Flight
Key West10 nights9.4/10 - Exceptional (3 reviews)"Key west is a vibe! My teenagers had a blast. No complaints. A lot of elders which is fine. I do have teens and they seems less than pleased while at he pool. We didn’t care though! We will be back, can not beat the location ."Reviewed March 26, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Lighthouse Hotel - Key West Historic Inns
Jul 16 - Jul 23Lighthouse Hotel - Key West Historic Inns + Flight
Old Town Key West7 nights9.0/10 - Wonderful (951 reviews)"Staff is friendly, attentive and helpful. Continental Breakfast is fresh and the perfect start for a day of adventure. We were there for a destination wedding at the Hemingway House that is right across the street. Location could not have been any better."Reviewed June 1, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • 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! (3,362 reviews)
"Look, we had a nice time. I put "OK" for your survey questions which may seem like we didn't enjoy. But, it would be hard to put "Good" for your survey answers. The beach was unusable due to dead, smelly seaweed that permeated the main pool, overall exterior (stairs, pool area, etc.) rooster poop, ..."
Reviewed on Jun 5, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$285 nightly
The price is $320 total per night from Jun 30 to Jul 1
$320 total
Jun 30 - Jul 1
Total with taxes and fees
8.4/10 Very Good! (691 reviews)
"Plan for rain! Don't forget sunscreen - the pool was amazing"
Reviewed on Jun 5, 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
4.5/5(3,246 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
Ernest Hemingway Home and Museum
4.5/5(1,744 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
4/5(999 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.
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
90% 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.