Key West Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to €185 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Where to stay in Key West

Find the best Key West areas and neighborhoods for the activities you enjoy most. Learn more about Key West
Default Image

Key West Historic District

4 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 Saint Mary Star of the Sea.

Find hotels in Key West Historic District

Top hotels in Key West

Ibis Bay Beach Resort
Ibis Bay Beach Resort
2.5 out of 5
3101 N. Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is €340 per night from 3 Feb to 4 Feb
€340
includes taxes & fees
3 Feb - 4 Feb
8/10 Very Good! (1,740 reviews)
"This place i nice and quiet. Rooms are small with small pillows but altogether its nice and by the Gulf."

Reviewed on 31 Jan 2025

Ibis Bay Beach Resort
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West
4 out of 5
7001 Shrimp Road, Key West, FL
Fully refundableReserve now, pay when you stay
The price is €333 per night from 3 Feb to 4 Feb
€333
includes taxes & fees
3 Feb - 4 Feb
9.4/10 Exceptional! (1,007 reviews)
"Very nice."

Reviewed on 31 Jan 2025

The Perry Hotel & Marina 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 €553 per night from 3 Feb to 4 Feb
€553
includes taxes & fees
3 Feb - 4 Feb
8.6/10 Excellent! (2,246 reviews)
"Loved the tranquility pool and the beach cafe and access. Hotel has so much to offer. Will definitely be back."

Reviewed on 1 Feb 2025

Southernmost Beach Resort
See all 2,889 properties in 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 a Key West holiday package cost?
Offering excellent value package deals on Expedia, you’ll be pleasantly surprised at how much a holiday to Key West costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Key West?
August, September and October are the best times to search for cheap Key West holiday packages. Choosing to travel in quieter periods means you can usually find reduced prices on hotels and flights.
How many days is enough for Key West?
Key West holidays come in all shapes and sizes, but to really sink your teeth into this place, we’d say 3 days is a good ballpark. This will mean you can visit top sights like Key West Aquarium and Harry S. Truman Little White House along with underrated spots. Don’t miss out on neighbourhoods such as Key West Historic District and Old Town Key West either. If you’re clever with your time, you may even be able to take a day trip from Key West too.
Is it worth booking a holiday package to Key West?
Key West offers everything you need for an amazing trip. Begin your Key West holiday on a high note by visiting popular attractions like Smathers Beach.
How to find the best Key West package deals?
Bagging a cheap Key West package deal is a breeze with Expedia. Once you’ve entered your preferred dates and destination under our “Packages” tab, set your budget, add a couple of filters and browse what’s available. You can personalise your search by “Area,” “Amenities,” “Property type” and more. Sort the results by “Price: low to high” to view the most wallet-friendly Key West package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Key West holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You’ll usually land a better deal than booking each component separately. And you’ll still have the freedom to create a personalised Key West holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday package to Key West?
If you’re considering a spur-of-the-moment Key West trip, browse our last-minute deals that can be booked up to one week before you take off. Don’t want to leave things to the last minute? You can score terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Key West?

  1. Choose your travel dates: What you’d like to do in Key West and your favourite season will help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to cover everything from meals and transportation to activities and airfares. Your hotel will probably be the biggest expense during your trip to Key West.
  3. Decide how long to go for: Now that you’re more familiar with Key West, you can figure out the right length of your holiday. Pull together a rough itinerary and give yourself enough time to cover everything you want to see.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a personalised Key West holiday package.

Popular places to visit

Duval Street

Duval Street

4.5/5(47 reviews)

Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.

Duval Street
Mallory Square

Mallory Square

4/5(36 reviews)

Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.

Mallory Square
Smathers Beach featuring tropical scenes, a beach and a luxury hotel or resort

Smathers Beach

4/5(10 reviews)

Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.

Smathers Beach

What to do in Key West

12 hours Day at Key West With Boat Tour and Snorkeling

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

€157
per adult
80% of travellers recommend
Day trip to Paradise from Miami: Key West Tour with Snorkeling, Open bar
MIAMI: Key West Day Trip with Boating Options

MIAMI: Key West Day Trip with Boating Options

€94
per adult
MIAMI: Key West Day Trip with Boating Options
12-Hours Day Trip in Key West from Miami

Full Day Trip in Key West from Miami

€75
per adult
Full Day Trip in Key West from Miami
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.