Key West Holidays

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Top Flight + Hotel Deals in Key West

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
Northside Resort
Save 100% on your flight
per person
27 Feb - 6 Mar
found 20 hours ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
8/10 Very Good! (1,675 reviews)
Clean and consistent

Reviewed on 22 Dec 2024

Havana Cabana at Key West - Adults Only

Havana Cabana at Key West - Adults Only

4 out of 5
New Town
Save 100% on your flight
per person
27 Feb - 6 Mar
found 20 hours ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
8.8/10 Excellent! (1,611 reviews)
The area around the pool had an amazing tropical atmosphere. Great music and beautiful palm trees.

Reviewed on 21 Dec 2024

Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
Save 100% on your flight
per person
27 Feb - 6 Mar
found 20 hours ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
8.8/10 Excellent! (1,525 reviews)
Clean, lovely resort! Poor quality bed pillows and extremely high food/drink prices kept this review from being 5 stars.

Reviewed on 15 Dec 2024

Douglas House

Douglas House

3 out of 5
Key West Historic District
Save 100% on your flight
per person
27 Feb - 6 Mar
found 20 hours ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
10/10 Exceptional! (2 reviews)
This is clearly a property where management is making excellent decisions on what travellers are looking for with respect to cleanliness, safety, convenience, privacy and key amenities (parking, pool, relaxing environment). Well done. Mark W.

Reviewed on 13 Dec 2024

Paradise Inn Key West - Adults Only

Paradise Inn Key West - Adults Only

3.5 out of 5
Key West Historic District
Save 100% on your flight
per person
27 Feb - 6 Mar
found 20 hours ago
Return direct flight included
Dublin (DUB) to Key West (EYW)
9.2/10 Wonderful! (1,002 reviews)
Overall fantastic experience

Reviewed on 20 Dec 2024

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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Key West Historic District

4 out of top 10 points of interest in this area

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 Ernest Hemingway Home and Museum.

Find hotels in Key West Historic District

Top hotels in Key West

Oceans Edge Key West Resort, Hotel & Marina
Oceans Edge Key West Resort, Hotel & Marina
4 out of 5
5950 Peninsular Avenue, Key West, FL
Fully refundableReserve now, pay when you stay
The price is €367 per night from 8 Jan to 9 Jan
€367
includes taxes & fees
8 Jan - 9 Jan 2025
8.8/10 Excellent! (1,522 reviews)
"Great place to stay"

Reviewed on 18 Dec 2024

Oceans Edge Key West Resort, Hotel & Marina
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 €250 per night from 7 Jan to 8 Jan
€250
includes taxes & fees
7 Jan - 8 Jan 2025
8.4/10 Very Good! (1,010 reviews)
"Thank you"

Reviewed on 21 Dec 2024

Beachside Resort & Residences
Southernmost Beach Resort
Southernmost Beach Resort
4 out of 5
1319 Duval Street, Key West, FL
Fully refundable
The price is €450 per night from 15 Jan to 16 Jan
€450
includes taxes & fees
15 Jan - 16 Jan 2025
8.4/10 Very Good! (2,196 reviews)
"Different types of accommodations, walking distance many things. Right on the beach. Activities daily at the resort. Super friendly staff, very welcoming!"

Reviewed on 20 Dec 2024

Southernmost Beach Resort
See all 2,825 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 from €1,439 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

€31
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

€114
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

€31
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.