Old Town Key West Holidays

Book a Hotel + Flight or Car together to unlock savings

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 which includes a bay or harbour, tropical scenes and a sandy beach

Beachside

1 out of top 10 points of interest in this area

While there might not be top attractions in Beachside, you can explore the larger area and discover places like Duval Street and Smathers Beach.

Find hotels in Beachside

Top hotels in Old Town Key West

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 4.465.440 ₫ per night from 29 Oct to 30 Oct
4.465.440 ₫
6.802.313 ₫ total
29 Oct - 30 Oct
includes taxes & fees
8.6/10 Excellent! (2,775 reviews)
"We loved thi"

Reviewed on 7 Oct 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 5.770.869 ₫ per night from 13 Oct to 14 Oct
5.770.869 ₫
8.073.288 ₫ total
13 Oct - 14 Oct
includes taxes & fees
8.2/10 Very Good! (384 reviews)
"The property was very pretty. Loved that it is on the beach. There was an elevator that was down so we had to use another one that I think was the staff elevator. It wouldn’t open the one time we used it for several minutes. The inside was very hot as it was not air conditioned. It was kind of scary, ..."

Reviewed on 4 Oct 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 5.481.008 ₫ per night from 12 Oct to 13 Oct
5.481.008 ₫
7.747.194 ₫ total
12 Oct - 13 Oct
includes taxes & fees
8.4/10 Very Good! (1,004 reviews)
"Great property we really enjoyed everything. Staff was very helpful with anything that we needed great place highly recommended definitely will come back."

Reviewed on 5 Oct 2025

The Reach Key West, Curio Collection by Hilton
See all 1,332 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 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 . 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 1null000null000 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.

Popular places to visit

Southernmost Point

Southernmost Point

4/5(39 reviews)

You can find out about the history of Key West with a stop at Southernmost Point. Discover the area's lively bars and its lively festivals.

Southernmost Point
Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

4.5/5(23 reviews)

You can spend time studying the exhibits at Ernest Hemingway Home and Museum during your trip to Key West. Wander the area's seaside or simply enjoy one of its lively bars.

Ernest Hemingway Home and Museum
Higgs Beach showing tropical scenes and a beach as well as a large group of people

Clarence S. Higgs Memorial Beach Park

4/5(11 reviews)

Why not spend a care-free afternoon at Clarence S. Higgs Memorial Beach Park during your travels in Key West? Wander the seaside and gardens while you're in the area.

Clarence S. Higgs Memorial Beach Park