Old Town Key West Holidays

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Price found within the past 48 hours. Click for updated prices.
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Price was €1,957, price is now €1,368 per person
€1,368
per person
22 Mar - 28 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
9/10 Wonderful! (1,736 reviews)
The entire resort was absolutely beautiful. It was also very welcoming. Not just in appearance but the staff were all so friendly and wonderful to work with!

Reviewed on 16 Jan 2026

The Key West Hotel

The Key West Hotel

2.5 out of 5
Key West Historic District
Price was €3,602, price is now €2,210 per person
€2,210
per person
22 Mar - 28 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
9.2/10 Wonderful! (505 reviews)
Being right on Duval Street if city noise bothers you you might want to stay a block or two off Duval. But if you want all the action then this place is fantastic. Staff is great and the room was nicely appointed and very comfortable.

Reviewed on 12 Dec 2025

The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West

4 out of 5
Price was €2,356, price is now €1,675 per person
€1,675
per person
22 Mar - 28 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
9.4/10 Exceptional! (1,151 reviews)
Rooms need to be quieter lots of noise from hall and next door food menu needs more options and lower prices

Reviewed on 15 Jan 2026

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Price was €2,602, price is now €1,935 per person
€1,935
per person
22 Mar - 28 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
8.6/10 Excellent! (2,844 reviews)
Excellent location and outstanding service

Reviewed on 15 Jan 2026

Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

4 out of 5
Old Town Key West
Price was €2,126, price is now €1,599 per person
€1,599
per person
22 Mar - 28 Mar
found 1 day ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
9.2/10 Wonderful! (1,044 reviews)
Amazing!! Clean, cozy and the continental breakfast including was really good. I highly recommend!

Reviewed on 16 Jan 2026

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 €513 per night from 26 Jan to 27 Jan
€513
26 Jan - 27 Jan
includes taxes & fees
8.6/10 Excellent! (3,015 reviews)
Perfect location

Reviewed on 13 Jan 2026

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 €605 per night from 25 Jan to 26 Jan
€605
25 Jan - 26 Jan
includes taxes & fees
8.2/10 Very Good! (505 reviews)
The resort was very beautiful and clean. Beach access and staff were amazing.

Reviewed on 11 Jan 2026

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
Fully refundableReserve now, pay when you stay
The price is €465 per night from 19 Jan to 20 Jan
€465
19 Jan - 20 Jan
includes taxes & fees
9.2/10 Wonderful! (1,115 reviews)
Cool resort. Loved all the lush greenery on the grounds. Very comfy bed. Very clean room!

Reviewed on 10 Jan 2026

Winslow's Bungalows - Key West Historic Inns
See all 1,359 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 €1,368. 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

Ernest Hemingway Home and Museum

Ernest Hemingway Home and Museum

4.5/5(23 reviews)

Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.

Ernest Hemingway Home and Museum
Key West Butterfly and Nature Conservatory showing food, animals and zoo animals

Key West Butterfly and Nature Conservatory

4.5/5(10 reviews)

With about 60 species of butterfly, an indoor waterfall and a tropical rainforest, this nature conservatory is one of the most popular attractions in Key West.

Key West Butterfly and Nature Conservatory
Harry S. Truman Little White House showing a house

Harry S. Truman Little White House

4.5/5(12 reviews)

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

Aboard the trolley in Key West

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

€52
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

€38
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

€23
per adult
92% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
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.