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 Beach House, Key West
Jul 5 - Jul 10Hyatt Vacation Club at Beach House, Key West + Flight
Key West5 nights9.4/10 - Exceptional (1,071 reviews)"Beautiful place! Had so much staying here for my sister’s bachelorette weekend. We very much enjoyed having a pool and beach to lounge around at. Guests and staff were very friendly during our stay"Reviewed May 30, 2026Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Amelia Home by Avantstay In Historic Old Town w/ Pool
Aug 8 - Aug 15Amelia Home by Avantstay In Historic Old Town w/ Pool + Flight
Old Town Key West7 nights10/10 - Exceptional (3 reviews)"Loved it"Reviewed March 20, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • 1 stop EYW - BOS • 1 stop$4,140$2,962found 12 hours agoper traveler - Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
Jul 20 - Jul 31Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front + Flight
Key West11 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 - Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub!
Aug 18 - Aug 25Casita de Catherine by Avantstay 1 Block to Duval St w/ Hot Tub! + Flight
Old Town Key West7 nights10/10 - Exceptional (6 reviews)"Although not on the beach you are a ten min bike ride from most. All restaurants Duval has to offer. The house is cute, clean and the back yard is awesome. We will stay again nextime!"Reviewed November 24, 2025Roundtrip • Atlanta (ATL) - Key West (EYW)ATL - EYW • Nonstop EYW - ATL • Nonstop - Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Aug 16 - Aug 22Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays + Flight
Old Town Key West6 nightsRoundtrip • 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 8 to Jun 9
$294 total
Jun 8 - Jun 9
Total with taxes and fees
8.8/10 Excellent! (3,341 reviews)
"The property we stayed at was nice. They got us into the room right away and it was conveniently located to Duvall Street. However, the room attendant did not come every day and our shower door would not close all the way which we told them the first day we got there and they never came to fix it. ..."
Reviewed on May 30, 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$297 nightly
The price is $334 total per night from Jun 27 to Jun 28
$334 total
Jun 27 - Jun 28
Total with taxes and fees
8.4/10 Very Good! (685 reviews)
"We were really disappointed by the beach. It’s rocky and was covered in seaweed (during our visit). The pools are beautiful, staff was lovely. The room was enormous and well maintained. I just wish we had more transparency regarding the condition of the beach."
Reviewed on May 30, 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! (1,116 reviews)
"The property was very nice the only complaint is that with paid for an ocean view room and on 2 of our 4 days a cruise ship docked and obscured the view from 8am to 5pm."
Reviewed on May 29, 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.
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.
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.
Things to do
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$45
per adult
94% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per traveler
92% of travellers recommend
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- Key West Hotels
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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.