Old Town Key West Vacations from $683
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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 Beach House, Key West
Save 100% on your flight
Price was $1,111, price is now $683 per person
$683
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,010 reviews)
This was a perfect location for our visit to Key West. The property was above and beyond what we expected!
Reviewed on Oct 30, 2025
The Key West Hotel
Key West Historic District
Save 100% on your flight
Price was $2,115, price is now $1,194 per person
$1,194
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (498 reviews)
Great location and friendly staff. They have remodeled a lot and are doing a super job. Nice decorations and LOVE the tiki bar and pool area. Key West Aloe products were a nice touch as well as the key lime cookies. The porch deck and handrail outside the Envy/Lust room needs a little attention. Overall, very comfortable and accommodating. I would definitely stay here again.
Reviewed on Oct 17, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,269, price is now $763 per person
$763
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,021 reviews)
Nice, walkable, safe
Reviewed on Oct 30, 2025
Ella's Cottages - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,147, price is now $691 per person
$691
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (378 reviews)
Loved it! Felt totally at home!!
Reviewed on Oct 30, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,170, price is now $752 per person
$752
per person
Jan 19 - Jan 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (803 reviews)
Laura at the desk very helpful/ clean rooms and great ambiance
Reviewed on Oct 30, 2025
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
Beachside
1 out of top 10 points of interest in this area
If you're spending some time in Beachside, Smathers Beach and Florida Keys Beaches are top sights worth seeing.
Old Town Key West Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street, Key West, FL
Fully refundable
$242 nightly
The price is $272 total per night from Nov 30 to Dec 1
$272 total
Nov 30 - Dec 1
Total with taxes and fees
8.6/10 Excellent! (2,833 reviews)
The room was clean, the staff so friendly.
Reviewed on Oct 30, 2025
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street, Key West, FL
Fully refundableReserve now, pay when you stay
$337 nightly
The price is $379 total per night from Dec 1 to Dec 2
$379 total
Dec 1 - Dec 2
Total with taxes and fees
8.2/10 Very Good! (409 reviews)
Yes property is in an excellent location and the rooms and common areas were very good.
Reviewed on Oct 22, 2025
The Reach Key West, Curio Collection by Hilton
1435 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
$312 nightly
The price is $351 total per night from Nov 3 to Nov 4
$351 total
Nov 3 - Nov 4
Total with taxes and fees
8.4/10 Very Good! (1,007 reviews)
Great job
Reviewed on Oct 27, 2025
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 Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
$50
per adult
92% of travellers recommend
Key West Sunset Sail with Live Music, Drinks and Appetizers!
$80
per adult
92% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
$27
per adult
80% of travellers recommend
Explore a world of travel with Expedia
- 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.