Old Town Key West Vacations from $1,536
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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.
The Latest Old Town Key West Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- The Key West Hotel
Jan 20 - Jan 23The Key West Hotel + Flight
Key West Historic District3 nights3.0 star property9.2/10 - Wonderful (565 reviews)"Clean, clean, clean. Hidden! Elite Backyard Oasis. Top Tier bar and fantastic nightly entertainment. If your traveling with anyone under 25, choose different. Will be back, no doubt!"Reviewed October 29, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • Nonstop EYW - BOS • Nonstop - The Gardens Hotel
Jan 20 - Jan 23The Gardens Hotel + Flight
Old Town Key West3 nights4.0 star property9.8/10 - Exceptional (1,001 reviews)"Wonderful location, great room, cozy property. Check in and out was very easy. Would definitely stay here again the next time Im in Key West"Reviewed November 8, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - EYW • Nonstop EYW - BOS • Nonstop - Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
Jan 11 - Jan 16Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay + Flight
Beachside5 nights3.0 star propertyRoundtrip • New York (NYC) - Key West (EYW)LGA - EYW • Nonstop EYW - EWR • 1 stop - Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays
Jan 28 - Feb 1Duval Breeze by Avantstay Great Location Close to Beach & Nightlife Shared Pool! Week Long Stays + Flight
Old Town Key West4 nights3.0 star property10/10 - Exceptional (1 review)"Location, comfort and great customer service! A great place for a family to stay and share in some fun together!!"Reviewed July 26, 2026Roundtrip • Boston (BOS) - Key West (EYW)BOS - FLL • Nonstop MIA - BOS • Nonstop$2,378$1,790found 1 day agoper traveler - Amelia Home by Avantstay In Historic Old Town w/ Pool
Jan 9 - Jan 13Amelia Home by Avantstay In Historic Old Town w/ Pool + Flight
Old Town Key West4 nights3.0 star property10/10 - Exceptional (3 reviews)"Loved it"Reviewed March 20, 2026Roundtrip • Minneapolis (MSP) - Key West (EYW)MSP - EYW • 1 stop EYW - MSP • 1 stop$3,454$2,615found 1 day agoper traveler
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
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
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.
Photo by Ronaldo Esteves
Open Photo by Ronaldo Esteves
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 Fort East Martello Museum and Gallery.
Photo by David Lindsey
Open Photo by David Lindsey
Photo by Monica Ferro
Open Photo by Monica Ferro
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Discover the most popular places to visit in Old Town Key West
What to do near Old Town Key West
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
94% of travelers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
$59
per adult
94% of travelers recommend
Old Town Key West Hotel Deals
Silver Palms Inn & Historic Homes
Silver Palms Inn & Historic Homes3.5 star property
Old Town Key West
9.4 out of 10, Exceptional, (1,037 reviews)
9.4/10
Exceptional
(1,037 reviews)
$229 nightly
The price is $258
$258 total
Nov 10 - Nov 11
Total with taxes and fees
Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns4.0 star property
Old Town Key West
9.2 out of 10, Wonderful, (1,484 reviews)
9.2/10
Wonderful
(1,484 reviews)
$225 nightly
The price is $253
$253 total
Nov 17 - Nov 18
Total with taxes and fees
9.6 out of 10, Exceptional, (1,138 reviews)
9.6/10
Exceptional
(1,138 reviews)
$200 nightly
The price is $222
$222 total
Nov 18 - Nov 19
Total with taxes and fees
9.0 out of 10, Wonderful, (39 reviews)
9.0/10
Wonderful
(39 reviews)
"While check in was a little confusing, everything after that was fantastic. Room was great, spacious, and clean. The location is fabulous. A short walk to the center of Duval st, giving easy access to everything you'd want to do. The staff was super friendly. I needed to let someone know the battery was low on our lock and it was immediately handled, with a very friendly follow up call to make sure everything was all set and if we needed anything. Also nice 2nd floor porch, great for a morning...
$238 nightly
The price is $268
$268 total
Nov 24 - Nov 25
Total with taxes and fees
Lighthouse Hotel - Key West Historic Inns
Lighthouse Hotel - Key West Historic Inns3.5 star property
Old Town Key West
9.0 out of 10, Wonderful, (1,004 reviews)
9.0/10
Wonderful
(1,004 reviews)
"A Motel 6 is nicer than this place. At $550 per night, I expected a place that didn’t smell or look discussing. My King room was barely larger than the bed making it hard to walk around the end without hitting the TV on the wall. The bathroom floor tile was crushed and sunken in, no bathroom fan and the shower leaks. After 4 minutes the tiny old shower finally got barely warm water. Nice grounds and great location, but the rooms are a joke! I had to wait at the front desk, with the phone...
$245 nightly
The price is $276
$276 total
Nov 11 - Nov 12
Total with taxes and fees
9.6 out of 10, Exceptional, (456 reviews)
9.6/10
Exceptional
(456 reviews)
$215 nightly
The price is $238
$238 total
Nov 15 - Nov 16
Total with taxes and fees
8.6 out of 10, Excellent, (1,401 reviews)
8.6/10
Excellent
(1,401 reviews)
"Rude staff. They charge you for things after you leave that aren’t explained. Charged an extra $130 after we checked out for taxes and amenity fees."
$184 nightly
The price is $207
$207 total
Dec 1 - Dec 2
Total with taxes and fees
Southernmost Beach Resort and Guesthouses
Southernmost Beach Resort and Guesthouses4.0 star property
Old Town Key West
8.6 out of 10, Excellent, (3,653 reviews)
8.6/10
Excellent
(3,653 reviews)
$268 nightly
The price is $302
$302 total
Nov 30 - Dec 1
Total with taxes and fees
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.
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.