New Town Vacations from $627
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
The Perry Hotel & Marina Key West
Price was $839, price is now $627 per person
$627
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,282 reviews)
Was upgraded to the best room on property without asking, after they learned we had missed a flight and were arriving late. Our third stay this year, the staff and property is beyond excellent.
Reviewed on Jul 11, 2026
Southernmost House - Adult Exclusive
Old Town Key West
Save 100% on your flight
Price was $1,846, price is now $1,012 per person
$1,012
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
The room was amazing with a great kitchen, and very clean. The staff was very professional and friendly and the breakfast delicious.
Reviewed on Jul 10, 2026
Ibis Bay Beach Resort
Northside Resort
Price was $948, price is now $646 per person
$646
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
8.2/10 Very Good! (2,289 reviews)
Great property and excellent value. The place was clean and very nice. Really appreciated how clean and well kept everything was.
Reviewed on Jul 9, 2026
Pier House Resort & Spa
Key West Historic District
Save 100% on your flight
Price was $1,250, price is now $920 per person
$920
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (1,199 reviews)
The private beach was 1000% the best part of the resort
Reviewed on Jul 10, 2026
Caribbean House
Old Town Key West
Price was $991, price is now $744 per person
$744
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Key West (EYW)
9/10 Wonderful! (379 reviews)
I loved the hospitality of the young lady at the front desk. She was amazing and made our stay feel like home. Bikes were available to rent with the stay and that made ALL the difference of getting around key west.
Reviewed on Jul 10, 2026
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
4 out of top 10 points of interest in this area
4.5/5(229 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
Blue Flamingo Resort Key West
3820 North Roosevelt Boulevard Key West FL
$171 nightly
The price is $192 total per night from Aug 10 to Aug 11
$192 total
Aug 10 - Aug 11
Total with taxes and fees
8.4/10 Very Good! (2,519 reviews)
"The floor in our room was filthy dirty!! Shower and sink was clean. When I went to take a shower and closed the shower door the soap dispenser fell off the wall. You could tell it had fallen off before. Really disappointed that we were charged a resort fee for $50 per day. That is on top of your ..."
Reviewed on Jul 10, 2026
Hilton Garden Inn Key West / The Keys Collection
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $184 total per night from Aug 10 to Aug 11
$184 total
Aug 10 - Aug 11
Total with taxes and fees
8/10 Very Good! (1,273 reviews)
"The listing stated that there was a restaurant on site. There wasn’t! The listing stated that there were 2 bars open. There was only one. To us, that’s false advertisement!"
Reviewed on Jul 9, 2026
Havana Cabana at Key West
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$198 nightly
The price is $223 total per night from Jul 12 to Jul 13
$223 total
Jul 12 - Jul 13
Total with taxes and fees
9/10 Wonderful! (1,831 reviews)
"This is a vibrant and lively hotel with a cubano theme. It has enough entertainment on the property to keep you from wanting to ever leave. The pool is the best part"
Reviewed on Jul 10, 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.
Things to do
Shark and Wildlife Viewing Adventure in Key West
$93
per adult
100% of travellers recommend
Miami to Key West Day Trip with Activity Options
$39
per adult
84% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
$79
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.