Old Town Key West Packages (Flight + Hotel)

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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
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Key West Historic District

2 out of top 10 points of interest in this area
4.5/5(66 area reviews)

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 Ernest Hemingway Home and Museum.

Find hotels in Key West Historic District

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 ฿5,990 per night from 25 Aug to 26 Aug
฿5,990
฿8,933 total
25 Aug - 26 Aug
includes taxes & fees
8.6/10 Excellent! (2,667 reviews)
"Location was perfect."

Reviewed on 31 Jul 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 ฿7,330 per night from 2 Sept to 3 Sept
฿7,330
฿10,197 total
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (262 reviews)
"This property was one of the nicest I saw on the island. Technically wouldn’t have to leave if you didn’t want to."

Reviewed on 28 Jul 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 ฿7,870 per night from 24 Aug to 25 Aug
฿7,870
฿10,804 total
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Our room was not cleaned one day but it wasn’t a big deal. We requested more towels"

Reviewed on 30 Jul 2025

The Reach Key West, Curio Collection by Hilton
See all 1,348 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 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.

Popular places to visit

Harry S. Truman Little White House featuring a house

Harry S. Truman Little White House

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

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

฿3,212
per adult
74% of travellers recommend
Full-Day Key West Tour and Coral Reef Snorkeling with Open Bar
MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

฿2,498
per adult
MIAMI: Key West Day Trip with Boating Options
Lemon Sharks

Shark and Wildlife Viewing Adventure in Key West

฿3,212
per adult
100% of travellers recommend
Shark and Wildlife Viewing Adventure in Key West
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.