Key West Holidays

Book a Hotel + Flight or Car together to unlock savings

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
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Old Town Key West

4 out of top 10 points of interest in this area
5/5(6 area reviews)

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Saint Mary Star of the Sea.

Find hotels in Old Town Key West

Top hotels in Key West

Beachside Resort & Residences
Beachside Resort & Residences
3.5 out of 5
3841 N Roosevelt Blvd, Key West, FL
Fully refundableReserve now, pay when you stay
The price is 5.781.332 ₫ per night from 29 Apr to 30 Apr
5.781.332 ₫
7.810.345 ₫ total
includes taxes & fees
29 Apr - 30 Apr
8.4/10 Very Good! (1,017 reviews)
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Reviewed on 4 Apr 2025

Beachside Resort & Residences
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
The price is 11.283.284 ₫ per night from 6 Apr to 7 Apr
11.283.284 ₫
14.424.260 ₫ total
includes taxes & fees
6 Apr - 7 Apr
8.6/10 Excellent! (2,373 reviews)
"Beautiful resort! We want to come back when we can spend more time here. Just ate at the restaurant and it was delicious!"

Reviewed on 2 Apr 2025

Southernmost Beach Resort
Margaritaville Beach House Key West
Margaritaville Beach House Key West
4 out of 5
2001 South Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is 7.352.430 ₫ per night from 4 May to 5 May
7.352.430 ₫
9.921.427 ₫ total
includes taxes & fees
4 May - 5 May
8.6/10 Excellent! (1,715 reviews)
"Stay was great. Staff very nice, helpful. Shuttle to/from airport so convenient. Hotel very close to airport. Shuttle into town and back great as well. Exterior grounds well maintained. Rented 2bd room suite with 1.5 bath. Would be nice if had another shower/tub esp with 5 ppl. Rooms clean, modernized ..."

Reviewed on 31 Mar 2025

Margaritaville Beach House Key West
See all 2,798 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)

With a visit to Duval Street, a favourite shopping spot in Key West, you can find the perfect gifts to bring home. Wander the seaside or discover the area's beautiful sunsets.

Duval Street
Mallory Square

Mallory Square

4/5(36 reviews)

You can find out about the history of Key West with a trip to Mallory Square. Stroll along the area's seaside or experience its lively festivals.

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

Smathers Beach

4/5(10 reviews)

If a restful holiday is part of your travel plans, Smathers Beach might be the perfect place to visit during your trip to Key West. Stroll along the seaside or discover the area's sunrises.

Smathers Beach