Old Town Key West Holidays

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Our guide on 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
Audubon House and Tropical Gardens featuring a house

Key West Historic District

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

Our pick of the best Old Town Key West Hotel Deals

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 NZ$984 per night from 26 Jan to 27 Jan
NZ$984
26 Jan - 27 Jan
includes taxes & fees
8.6/10 Excellent! (3,006 reviews)
The right location at the right price. They sent texts to update you on activities on-site.

Reviewed on 19 Jan 2026

Southernmost Beach Resort and Guesthouses
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
725 Truman Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is NZ$1,010 per night from 25 Jan to 26 Jan
NZ$1,010
25 Jan - 26 Jan
includes taxes & fees
9.2/10 Wonderful! (1,122 reviews)
Outstanding place. Great location minutes from Duval Street, walkable to everything. Room was safe, clean, updated, great shower and three pools all heated! Breakfast was a feast of so many options you have to limit yourself or you won't eat again that day. We didn't have a car but they had two big ...

Reviewed on 19 Jan 2026

Winslow's Bungalows - Key West Historic Inns
Duval House

Duval House

3 out of 5
815 Duval St Key West FL
The price is NZ$671 per night from 26 Jan to 27 Jan
NZ$671
26 Jan - 27 Jan
includes taxes & fees
9.4/10 Exceptional! (1,000 reviews)
This is a great property in a fantastic location, yet quiet within the property walls, great breakfast, staff and lovely gardens. I would have loved a hot tub and a little more sun at the pool area (even on sunny days) but I went in January when it’s a little cooler. Overall it was a great stay, ...

Reviewed on 16 Jan 2026

Duval House
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.

Discover the most popular places to visit in Old Town Key West

Southernmost Point featuring signage as well as a large group of people

Southernmost Point

Snap a memorable photograph from the edge of North America at this monumental landmark.

Southernmost Point
South Beach featuring a sandy beach and general coastal views as well as a small group of people

South Beach

The southernmost beach in the continental United States is a picturesque bay and a relaxing spot to spend the day for sun-loving visitors.

South Beach
Key West Butterfly and Nature Conservatory showing food, animals and zoo animals

Key West Butterfly and Nature Conservatory

This conservatory houses a flower-filled forest and a colourful butterfly population that attracts visitors from around the globe.

Key West Butterfly and Nature Conservatory

Activities

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

NZ$77
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
12 hours Day at Key West With Boat Tour and Snorkeling

Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar

NZ$47
per adult
90% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
Aboard the trolley in Key West

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

NZ$99
per adult
88% 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.