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
Smathers Beach showing a bay or harbor, tropical scenes and windsurfing

Beachside

1 out of top 10 points of interest in this area

If you're spending some time in Beachside, Smathers Beach and Florida Keys Beaches are top sights worth seeing.

Find hotels in Beachside

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 ₩255,073 per night from Nov 30 to Dec 1
₩255,073
₩392,427 total
Nov 30 - Dec 1
includes taxes & fees
8.6/10 Excellent! (2,840 reviews)
Billed me for parking when I didn’t have a car. Took several calls to try and resolve. Still haven’t received a refund. They were quick to take my money when I paid for the room but not so responsive in processing my refund.

Reviewed on Nov 1, 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 ₩366,543 per night from Dec 1 to Dec 2
₩366,543
₩498,896 total
Dec 1 - Dec 2
includes taxes & fees
8.2/10 Very Good! (417 reviews)
Been staying at the casa for over 40 years always amazing

Reviewed on Nov 2, 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 ₩366,543 per night from Nov 17 to Nov 18
₩366,543
₩498,895 total
Nov 17 - Nov 18
includes taxes & fees
8.4/10 Very Good! (1,014 reviews)
Great beach view!

Reviewed on Nov 1, 2025

The Reach Key West, Curio Collection by Hilton
See all 1,340 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

Harry S. Truman Little White House showing a house

Harry S. Truman Little White House

4.5/5(834 reviews)

Visit the winter home of President Harry S. Truman to see where some of America’s most important post-war decisions were made.

Harry S. Truman Little White House

Simonton Beach

Why not spend a carefree afternoon at Simonton Beach during your travels in Key West? While you're in the area, stroll along the seaside.

Simonton Beach
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.