Key West Holidays

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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

3 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 3.516.236 ₫ per night from 12 Aug to 13 Aug
3.516.236 ₫
5.283.531 ₫ total
12 Aug - 13 Aug
includes taxes & fees
8.4/10 Very Good! (1,436 reviews)
"It was very homely and comfortable ."

Reviewed on 6 Aug 2025

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard, Key West, FL
Fully refundableReserve now, pay when you stay
The price is 2.988.801 ₫ per night from 8 Sept to 9 Sept
2.988.801 ₫
4.837.333 ₫ total
8 Sept - 9 Sept
includes taxes & fees
7.6/10 Good! (1,535 reviews)
"It was worth money spent on it but not that luxurious if you want a 4 star resort"

Reviewed on 10 Aug 2025

Blue Flamingo Resort 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 4.637.446 ₫ per night from 24 Aug to 25 Aug
4.637.446 ₫
6.987.045 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (2,662 reviews)
"We really enjoyed our stay. We loved the location, as it was close to the action but also being at the end of the street, felt private still. There were a couple things broken in our room, like the blinds and a light in our room and the water pressure was awful, otherwise I would have given it 5 ..."

Reviewed on 8 Aug 2025

Southernmost Beach Resort and Guesthouses
See all 2,722 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.

Popular places to visit

Duval Street

Duval Street

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
Southernmost Point

Southernmost Point

You can find out about the history of Key West with a stop at Southernmost Point. Discover the area's lively bars and its lively festivals.

Southernmost Point
Mallory Square

Mallory Square

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

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.