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

Top hotels in Old Town Key West

Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is 12.408.640 ₫ per night from 3 Feb to 4 Feb
12.408.640 ₫
15.654.376 ₫ total
includes taxes & fees
3 Feb - 4 Feb
8.6/10 Excellent! (2,232 reviews)
"Safe and clean"

Reviewed on 22 Jan 2025

Southernmost Beach Resort
The Southernmost Inn - Adults Only
The Southernmost Inn - Adults Only
3 out of 5
525 United Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is 5.749.274 ₫ per night from 27 Jan to 28 Jan
5.749.274 ₫
7.597.452 ₫ total
includes taxes & fees
27 Jan - 28 Jan
7.8/10 Good! (1,000 reviews)
"There were bugs all over the bathroom and they didn’t even seem to care"

Reviewed on 4 May 2023

The Southernmost Inn - Adults Only
Winslow's Bungalows - Key West Historic Inns
Winslow's Bungalows - Key West Historic Inns
4 out of 5
725 Truman Avenue, Key West, FL
The price is 10.017.294 ₫ per night from 27 Jan to 28 Jan
10.017.294 ₫
12.314.619 ₫ total
includes taxes & fees
27 Jan - 28 Jan
9/10 Wonderful! (1,000 reviews)
"This is a very interesting property. We stayed in one of the bungalows though there are other types of rooms available. It is an old property, but recently refurbished/renovated. The room was small but well appointed and had a nice bathroom with a tiled walk-in shower. There is a nice full service ..."

Reviewed on 14 Jan 2025

Winslow's Bungalows - Key West Historic Inns
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