Old Town Key West Vacations from $1,132
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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.
Hyatt Vacation Club at Windward Pointe, Key West
Save 100% on your flight
Price was $1,813, price is now $1,132 per person
$1,132
per person
May 17 - May 22
found 11 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,020 reviews)
Great location, wonderful room and resort.
Reviewed on Mar 12, 2026
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,040, price is now $1,263 per person
$1,263
per person
May 18 - May 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (534 reviews)
Excellent location on Duval st. Would definitely stay here again.
Reviewed on Mar 13, 2026
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Price was $6,142, price is now $4,257 per person
$4,257
per person
Apr 21 - Apr 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (907 reviews)
Always love seeing and talking to Eddie at the front desk when we visit the various historic inn's throughout Key West. He is always so warm and welcoming and has great stories. The Lighthouse Hotel didn't disappoint at all. Has everything you need and more. Definitely on our return list for sure.
Reviewed on Mar 16, 2026
Ridley House - Key West Historic Inns
Key West Historic District
Save 100% on your flight
Price was $1,922, price is now $1,348 per person
$1,348
per person
May 24 - May 29
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (886 reviews)
Very nice place! Very kind and helpful staff! Highly recommend!
Reviewed on Mar 15, 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
Key West Historic District
2 out of top 10 points of interest in this area
4.5/5(4,033 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
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
$547 nightly
The price is $615 total per night from Apr 5 to Apr 6
$615 total
Apr 5 - Apr 6
Total with taxes and fees
8.4/10 Very Good! (581 reviews)
A beautiful high end resort on an idyllic beach. Highway recommed!
Reviewed on Mar 15, 2026
Opal Key Resort & Marina, Key West
245 Front Street Key West FL
Fully refundableReserve now, pay when you stay
$534 nightly
The price is $601 total per night from Apr 5 to Apr 6
$601 total
Apr 5 - Apr 6
Total with taxes and fees
9.2/10 Wonderful! (1,069 reviews)
Clean, friendly, and great view from the balcony. Highly recommend.
Reviewed on Mar 16, 2026
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street Key West FL
Fully refundableReserve now, pay when you stay
$574 nightly
The price is $646 total per night from Mar 22 to Mar 23
$646 total
Mar 22 - Mar 23
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
Great property right on a private beach, perfect for families.
Reviewed on Mar 16, 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(3,182 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
South Beach
4/5(980 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(1,707 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 Rum & Reggae: Snorkel & Sunset Sail Combo
$55
per adult
88% of travellers recommend
Key West: Shark and Wildlife Viewing Catamaran Tour
$99
per adult
100% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
82% 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.