Old Town Key West Vacations

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Your Old Town Key West Vacation

Take the stress and hassle out of organizing your next adventure by booking an Old Town Key West vacation package. Take in the sights and sounds of this captivating neighborhood and enjoy what it has to offer. Wondering what to see and do during your trip to Old Town Key West? Nearby attractions such as Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square are good places to begin. No matter your travel plans or the size of your budget, booking your dream Old Town Key West vacation is quick and easy with Expedia.

The Latest Old Town Key West Vacation Packages

The Grand Guesthouse
Ibis Bay Beach Resort
Paradise Inn Key West - Adults Only
Casa Marina Key West, Curio Collection by Hilton
Westwinds Inn
Prices and availability subject to change. Additional terms may apply.

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

Old Town Key West Hotel Deals

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 $401 per night from Apr 29 to Apr 30
$401
$514 total
includes taxes & fees
Apr 29 - Apr 30
8/10 Very Good! (1,778 reviews)
"We arrived at the resort about 2.5 hours before check in and we extremely happy to be given our room. I sent a request to the resort asking for my poolside room to be located by the Pineapple Bar and they granted my request, which was greatly appreciated. It’s a beautiful resort and the accommodations ..."

Reviewed on Mar 27, 2024

Southernmost Beach Resort
Winslow's Bungalows
Winslow's Bungalows
4 out of 5
725 Truman Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $289 per night from Apr 29 to Apr 30
$289
$367 total
includes taxes & fees
Apr 29 - Apr 30
8.6/10 Excellent! (612 reviews)
"We really enjoyed our stay for 3 nights. The rooms are clean and pretty big. We liked having the first floor bungalow. The pools and outdoor bar are great. There was live music at the pool in the afternoon. The staff are friendly and accomodating. I would stay there again."

Reviewed on Mar 27, 2024

Winslow's Bungalows
Opal Key Resort & Marina, Key West
Opal Key Resort & Marina, Key West
4 out of 5
245 Front Street, Key West, FL
Fully refundableReserve now, pay when you stay
The price is $359 per night from Apr 1 to Apr 2
$359
$443 total
includes taxes & fees
Apr 1 - Apr 2
8.8/10 Excellent! (1,009 reviews)
"We will definitely come back! We love the Opal Key and Key West!!"

Reviewed on Mar 25, 2024

Opal Key Resort & Marina, 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.

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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 $662. 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

Things to do

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