Key West Vacations

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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
Key West Historic District

Old Town Key West

4 out of top 10 points of interest in this area
4.5/5(226 area reviews)

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West

Find the Best Key West Vacation Packages

Key West Hotel Deals

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 AED 948 per night from Apr 21 to Apr 22
AED 948
AED 1,252 total
includes taxes & fees
21 Apr - 22 Apr
8.4/10 Very Good! (1,010 reviews)
"Property was great and the food and drinks were great as well"

Reviewed on 2 April 2025

Beachside Resort & Residences
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
The price is AED 1,616 per night from Apr 6 to Apr 7
AED 1,616
AED 2,066 total
includes taxes & fees
6 Apr - 7 Apr
8.6/10 Excellent! (2,380 reviews)
"I really enjoyed my long weekend at the Southernmost Beach Resort. There are several pools, beaches, bars and a restaurant. My room was clean and spacious. All the staff I encountered were super friendly. Great location and easy walking distance to Duval."

Reviewed on 1 April 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 AED 1,047 per night from May 4 to May 5
AED 1,047
AED 1,413 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 March 2025

Margaritaville Beach House Key West
See all 2,779 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 vacation package cost?
Offering excellent value package deals on Expedia, you’ll be pleasantly surprised at how much a vacation 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 vacation packages. Choosing to travel in quieter periods means you can usually find reduced prices on hotels and flights.
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 personalize 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 vacation as a package?
Expedia vacation 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 personalized Key West vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation 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 favorite 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 vacation. 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 personalized Key West vacation package.

Discover the most popular places to visit in Key West

Duval Street featuring signage

Duval Street

4.5/5(3,475 reviews)

With a visit to Duval Street, a favorite shopping spot in Key West, you can search for that perfect souvenir. Wander the seaside or discover the area's beautiful sunsets.

Duval Street
Mallory Square which includes a sunset and a bay or harbor as well as a large group of people

Mallory Square

4.5/5(3,096 reviews)

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

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

Smathers Beach

4/5(1,151 reviews)

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

Smathers Beach