Old Town Key West Holidays from NZ$2,741
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Top Holiday Package Deals in Old Town Key West
Price found within the past 48 hours. Click for updated prices.
Southernmost Beach Resort and Guesthouses
Old Town Key West
NZ$2,741
per person
24 Dec - 27 Dec
found 13 hours ago
Return direct flight included
Charlottesville (CHO) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
The resort was excellent. It was clean. The staff were very accommodating. The breakfast & dinners we had a The beach side Cafe were very good. The bars closed rather early on the resort by 9pm. We felt that one bar on the resort should open until 11pm to accommodate guests that want stay at the resort in the evening. Also a shuttle to and from the airport should be offered.
Reviewed on 13 Oct 2026
Southernmost House - Adult Exclusive
Old Town Key West
NZ$2,886
per person
24 Dec - 27 Dec
found 13 hours ago
Return direct flight included
Charlottesville (CHO) to Key West (EYW)
9.4/10 Exceptional! (1,001 reviews)
Great stay. Older locations like this face many challenges so there is certainly more work to be done but everything worked like new and the staff was super helpful even offering an upgrade at no charge due to availability.
Reviewed on 11 Oct 2026
Our guide on 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
Downtown Key West
While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.
Key West Historic District
2 out of top 10 points of interest in this area
Travellers to Key West Historic District praise its fantastic nightlife. If you've got some more time to explore, be sure to stop by Duval Street and Florida Keys Beaches.
New Town
While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Fort East Martello Museum and Gallery.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Historic Seaport
If you're spending some time in Historic Seaport, Duval Street and Florida Keys Beaches are top sights worth seeing.
Our pick of the best Old Town Key West Hotel Deals
Southernmost Beach Resort and Guesthouses
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
NZ$452
25 Oct - 26 Oct
includes taxes & fees
8.6/10 Excellent! (3,628 reviews)
"The resort was excellent. It was clean. The staff were very accommodating. The breakfast & dinners we had a The beach side Cafe were very good. The bars closed rather early on the resort by 9pm. We felt that one bar on the resort should open until 11pm to accommodate guests that want stay at the ..."
Reviewed on 13 Oct 2026
Casa Marina Key West, Curio Collection by Hilton
1500 Reynolds Street Key West FL
Fully refundableReserve now, pay when you stay
NZ$556
25 Oct - 26 Oct
includes taxes & fees
8.4/10 Very good! (969 reviews)
"The beach was not swimma"
Reviewed on 14 Oct 2026
The Southernmost Inn - Adults Only
525 United Street Key West FL
NZ$381
25 Oct - 26 Oct
includes taxes & 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.
Frequently asked questions
How much does an Old Town Key West holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Old Town Key West from just NZ$2,741. And the more you bundle, the more money you save. The holiday of your dreams has never been so affordable.
How do I get a cheap travel package to Old Town Key West?
One of the easiest ways to save money (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got everything you need. Select a combination that best suits you and watch your savings grow. Of course, a travel package is never one-size-fits-all. That's why we offer over 550 partner airlines and 1 000 000 hotel options around the globe, which lets you customize your Old Town Key West getaway.
Where should I stay in Old Town Key West?
A trip to Old Town Key West isn't complete without stopping by Ernest Hemingway Home and Museum and Audubon House and Tropical Gardens. Book a hotel as close as possible for quick access to these awesome attractions.
What are the top hotels in Old Town Key West?
Secure a room at Southernmost Retreat: 2 Blocks From Duval In Old Town. It's one of this area's most in-demand properties. Another top-rated option in Old Town Key West is Curry House.
How far in advance should I book my Old Town Key West holiday?
Smart travellers often book as early as possible. You can generally look up international fares on Expedia up to a year before your intended flight. If you're purchasing tickets last minute, don't despair. Budget prices occasionally become available just weeks prior to departure.
What does an Expedia Old Town Key West travel package include?
Hotels, car rentals and flights — we bring you the very best deals. All you have to do is pick and choose your favourite combination. After you've made your booking, you can add on the exciting stuff like experiences and tours. Our travel packages make it easy to create an awesome Old Town Key West holiday.
What should I know before booking an Old Town Key West travel package?
A package can be cheaper than separately booking everything you need for your trip. For example, bundle your hotels, flights and rental cars and save big. Whatever your holiday goals are, there's sure to be a package within your budget.
Can I choose my airline with an Old Town Key West Expedia holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines all over the world. Our packages give you the freedom to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Old Town Key West holiday package?
You can. We realise life doesn't always go to plan, so we're here to help if you have to make changes to your Old Town Key West holiday package. You may be able to amend or cancel your itinerary at no cost if you've booked in the last 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Take a look at our Customer Service Portal for more information. Also, be sure to check your itinerary for the finer details on change fees.
Stay near popular Old Town Key West attractions
Southernmost Point
8.8/10 (17,214 reviews)
Snap a memorable photograph from the edge of North America at this monumental landmark.
Ernest Hemingway Home and Museum
9.2/10 (8,543 reviews)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
South Beach
8.4/10 (5,461 reviews)
The southernmost beach in the continental United States is a picturesque bay and a relaxing spot to spend the day for sun-loving visitors.
Clarence S. Higgs Memorial Beach Park
8.4/10 (4,659 reviews)
Pay your respects at an impressive African burial site, explore landscaped gardens or snorkel with the family at this oceanfront beach park.
Key West Butterfly and Nature Conservatory
9.2/10 (1,711 reviews)
This conservatory houses a flower-filled forest and a colourful butterfly population that attracts visitors from around the globe.
Harry S. Truman Little White House
9.0/10 (995 reviews)
Discover the historic significance of this presidential home, where Harry S. Truman and his successors made decisions that shaped the world.
Key West Lighthouse and Keeper's Quarters Museum
8.6/10 (548 reviews)
Climb to the top of this historic lighthouse for unparalleled photo opportunities and then visit the former home of Key West’s lighthouse keepers.
Florida Keys Eco - Discovery Center
8.8/10 (128 reviews)
Learn about the area’s important marine ecology at this comprehensive attraction that addresses global environmental concerns, interesting for visitors of all ages.
Activities
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
NZ$74
per adult
94% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
NZ$57
per adult
82% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
NZ$97
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.