Old Town Key West Holidays

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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 Key West Cemetery.

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 Rp4.690.133 per night from 13 Jan to 14 Jan
Rp4.690.133
Rp6.499.352 total
13 Jan - 14 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,934 reviews)
The room was very clean. The staff were very pleasant. Constantine, the bartender at the Pineapple pool was amazing!!!

Reviewed on 15 Dec 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
The price is Rp7.116.974 per night from 11 Jan to 12 Jan
Rp7.116.974
Rp9.009.976 total
11 Jan - 12 Jan 2026
includes taxes & fees
8.2/10 Very Good! (471 reviews)
Clean, great staff and location.

Reviewed on 13 Dec 2025

Casa Marina Key West, Curio Collection by Hilton
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 Rp4.838.756 per night from 22 Dec to 23 Dec
Rp4.838.756
Rp6.288.817 total
22 Dec - 23 Dec
includes taxes & fees
9.2/10 Wonderful! (1,078 reviews)
Grounds are beautiful, staff was Great! Room was a little moist smelling but besides that a great time.

Reviewed on 18 Dec 2025

Winslow's Bungalows - Key West Historic Inns
See all 1,353 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

Higgs Beach showing tropical scenes and a beach as well as a large group of people

Clarence S. Higgs Memorial Beach Park

Pay your respects at an impressive African burial site, explore landscaped gardens or snorkel with the family at this oceanfront beach park.

Clarence S. Higgs Memorial Beach Park

Things to do

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Rp749.625
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

Rp1.333.166
per traveller
92% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

Rp962.148
per adult
86% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
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.