New Town Vacation Packages 2026 from $1,071

Plan, book, travel with confidence
Better together
Save up to $2,000 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.

Kona Kai Oasis

Old Town Key West

Save 100% on your flight

$1,071

per person

Nov 16 - Nov 23

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8/10 Very Good! (666 reviews)

The Key West Hotel

Key West Historic District

$3,099

per person

Dec 21 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.2/10 Wonderful! (563 reviews)

The Gardens Hotel

Old Town Key West

$2,971

per person

Dec 21 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,000 reviews)

Hyatt Vacation Club at Sunset Harbor, Key West

Old Town Key West

$2,500

per person

Dec 21 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

8.6/10 Excellent! (433 reviews)

Orchid Key Inn - Adults Only

Old Town Key West

$2,219

per person

Dec 21 - Dec 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Key West (EYW)

9.8/10 Exceptional! (1,001 reviews)

We stayed for five days and we thoroughly enjoyed the property would highly recommend and would love to come back Kim and Maili from Seattle

Reviewed on Oct 1, 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

A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 out of top 10 points of interest in this area

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.

A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

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.

A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 out of top 10 points of interest in this area

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.

A sunset over the ocean with scattered clouds.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

A pier with people dining under umbrellas, a sailboat in the distance, and a sunset over the water.

Historic Seaport

Many of the best parts of the southern portion of Florida are rolled into one location. Enjoy your time experiencing attractions in this historic area.

New Town Hotel Deals

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL

Fully refundableReserve now, pay when you stay

$168 nightly

$189 total

Oct 4 - Oct 5

Total with taxes and fees

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$184 nightly

$207 total

Nov 2 - Nov 3

Total with taxes and fees

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd Key West FL

Fully refundableReserve now, pay when you stay

$137 nightly

$154 total

Oct 8 - Oct 9

Total with taxes and fees

8.2/10 Very Good! (1,328 reviews)

"Staff was very nice. Pool was great as well as the hot tub."

Reviewed on Oct 3, 2026

See all 3,046 properties in New Town

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.