New Town Vacations from $611
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
Your New Town Vacation
Our New Town vacation packages are a simple and practical way to arrange and book your next getaway. Uncover the true character of this unique neighborhood without the stress of planning everything yourself. Your trip to New Town wouldn't be complete without stopping by leading attractions nearby such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Stop dreaming and start doing. When you're ready to lock in your ideal vacation to New Town, Expedia is here to help.
The Latest New Town 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 $913, price is now $611 per person
$611
per person
Nov 16 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
Cleveland (CLE) to Key West (EYW)
9.6/10 Exceptional! (1,011 reviews)
We loved our stay here. Everything was clean, comfortable, and well appointed. The pool was gorgeous and spacious, and the food and drinks from the bar/cafe were tasty. The only complaint we had was how loud the carts rolling by outside of our room could be heard inside our room. I think a room that is not located right next to the offices would be quieter.
Reviewed on Aug 31, 2025
Lighthouse Hotel - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,731, price is now $887 per person
$887
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (779 reviews)
it’s a great location but quiet. Love the free breakfast, pool and rooms! staff was great too!
Reviewed on Aug 23, 2025
Oceans Edge Key West Resort, Hotel & Marina
Save 100% on your flight
Price was $1,380, price is now $878 per person
$878
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,729 reviews)
In general, I enjoyed my stay at Ocean Edge Resort. The room was clean and comfortable with a nice view of the ocean and the Marina. The property in general looks beautiful with an island vibe touch and it’s really pleasant to walk around. The staff at the front desk were friendly and polite. My only complaint is the restaurant. Extremely overpriced for the poor quality of the breakfast offered and the terrible customer service. The only thing I can save is the key lime pie. My advice, if you are looking for a nice place to stay in Key West, this is a lovely option, just don’t go to the restaurant.
Reviewed on Aug 31, 2025
Winslow's Bungalows - Key West Historic Inns
Old Town Key West
Save 100% on your flight
Price was $1,299, price is now $831 per person
$831
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.2/10 Wonderful! (1,006 reviews)
Was an amazing experience. The staff was lovely ......my only complaint was the roosters but thats a Key West thing lol strongly reccomend and will be returning
Reviewed on Aug 31, 2025
Douglas House
Old Town Key West
Save 100% on your flight
Price was $2,003, price is now $1,329 per person
$1,329
per person
Nov 14 - Nov 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Key West (EYW)
9.6/10 Exceptional! (157 reviews)
We were pleasantly surprised with a free upgrade. The suite was lovely. The staff were friendly and helpful. Highly recommend.
Reviewed on Aug 31, 2025
Where to stay in New Town
Find the best New Town areas and neighborhoods for the activities you enjoy most. Learn more about New Town
Old Town Key West
3 out of top 10 points of interest in this area
4.5/5(226 area reviews)
Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.
New Town Hotel Deals
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$126 nightly
The price is $142 total per night from Sep 7 to Sep 8
$142 total
Sep 7 - Sep 8
Total with taxes and fees
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $189 total per night from Sep 2 to Sep 3
$189 total
Sep 2 - Sep 3
Total with taxes and fees
Fairfield Inn and Suites by Marriott Key West
2400 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $151 total per night from Sep 14 to Sep 15
$151 total
Sep 14 - Sep 15
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.