Old Town Key West Vacations

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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
Audubon House and Tropical Gardens featuring a house

Key West Historic District

2 out of top 10 points of interest in this area
4.5/5(4,033 area reviews)

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.

Find hotels in Key West Historic District

Old Town Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is ￥24,953 per night from Aug 27 to Aug 28
￥24,953
￥38,012 total
Aug 27 - Aug 28
includes taxes & fees
8.6/10 Excellent! (2,674 reviews)
"Best resort!! My boyfriend just said “ I would say there 100 more times”. The staff was great, upgraded our rooms since it was a big family trip. Walkable distance to everything. Special shoutout the the restaurant chef on the property who cooked us the most unforgettable meal after we brought her ..."

Reviewed on Aug 12, 2025

Southernmost Beach Resort and Guesthouses
Casa Marina Key West, Curio Collection by Hilton

Casa Marina Key West, Curio Collection by Hilton

4 out of 5
1500 Reynolds Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is ￥31,273 per night from Aug 25 to Aug 26
￥31,273
￥44,017 total
Aug 25 - Aug 26
includes taxes & fees
8.4/10 Very Good! (287 reviews)
"The property was beautiful. The only downside was they are updating and a few things were closed that we were expexring. And the elevator closest to our room was broken tbe whole time. The room was super clean and view was amazing!"

Reviewed on Aug 10, 2025

Casa Marina Key West, Curio Collection by Hilton
The Reach Key West, Curio Collection by Hilton

The Reach Key West, Curio Collection by Hilton

4 out of 5
1435 Simonton Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is ￥34,987 per night from Aug 24 to Aug 25
￥34,987
￥48,195 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (1,007 reviews)
Tropical paradise within your Reach
"Staff friendly and so accommodating! My wife somewhat particular about view from room; Phiwe and her colleague guided us to the perfect room overlooking pool and, a few feet beyond, the sandy beach. Lots of extras and you are able to walk over to sister property Casa Marina and hang out there too. ..."

Reviewed on Aug 10, 2025

The Reach Key West, Curio Collection by Hilton
See all 1,326 properties in Old Town Key West
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 vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Old Town Key West from just . And the more you bundle, the more money you save. The vacation 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 vacation?
Smart travelers 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 favorite 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 vacation.
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 vacation goals are, there's sure to be a package within your budget.
Can I choose my airline with an Old Town Key West Expedia vacation 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 vacation package?
You can. We realize 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 vacation 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.

Discover the most popular places to visit in Old Town Key West

Southernmost Point featuring signage as well as a large group of people

Southernmost Point

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
South Beach featuring a sandy beach and general coastal views as well as a small group of people

South Beach

The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.

South Beach
Ernest Hemingway Home and Museum featuring heritage elements and a house

Ernest Hemingway Home and Museum

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Ernest Hemingway Home and Museum

Things to do

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar

￥14,621
per adult
74% of travellers recommend
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

￥8,116
per adult
84% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
The Dark Side of Key West Adults Only Walking Tour

The Dark Side of Key West Adults Only Walking Tour

￥5,168
per adult
80% of travellers recommend
The Dark Side of Key West Adults Only Walking Tour
See all activities in Key West
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.