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
A white building with shutters, palm trees, and a lawn.

Old Town Key West

4 out of top 10 points of interest in this area

While visiting Old Town Key West, you might make a stop by sights like Duval Street and Florida Keys Beaches.

Find hotels in Old Town Key West

Key West Beach Holiday

Unwind on the shore while you watch the sunlight glistening across the water during your Key West holiday. If you're hoping for an unforgettable beach experience, a trip to Key West will definitely deliver. There's a good chance you've heard of Smathers Beach (3 kilometres away). We suggest staying in accommodation close by. However, many sightseers also opt for Key West packages that are closer to South Beach or Boca Chica Nude Beach, two other excellent nearby options.

Things You Should Know About Key West

  • Escape the daily grind at one of our Key West beach hotels. The sweet sound of lapping water and seagulls cawing far above are just a couple of clicks away.
  • If you're searching for lots of room to spread out and relax, Key West private holiday homes are a great choice. After a much-needed family getaway or a few nights escape with that special someone? Grand Maloney Hotel and The Capitana Key West will fit the bill.
  • With a population of approximately 25,800 inches Key West, you're sure to find some friendly locals who are happy to share their sightseeing tips. For more handy hints, check out our Key West things to do page.

Top hotels in Key West

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is Rp4.164.136 per night from 15 Nov to 16 Nov
Rp4.164.136
Rp5.836.178 total
15 Nov - 16 Nov
includes taxes & fees
8.8/10 Excellent! (1,800 reviews)
"Perfect beach view from the room."

Reviewed on 29 Oct 2026

Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is Rp2.618.496 per night from 19 Nov to 20 Nov
Rp2.618.496
Rp4.100.493 total
19 Nov - 20 Nov
includes taxes & fees
Havana Cabana at Key West
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 Rp2.111.162 per night from 1 Nov to 2 Nov
Rp2.111.162
Rp3.397.907 total
1 Nov - 2 Nov
includes taxes & fees
8.6/10 Excellent! (2,757 reviews)
"I went to the desk to check in. They said your room is ready. They said you can wait to check in or pay $35 to check in now. It was 3:00 so they wanted me to pay $35 to check in an hour early. It’s bad enough the fees were $80 but now they charge you to check in your room"

Reviewed on 29 Oct 2026

Blue Flamingo Resort Key West
See all 2,662 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.

Stay near popular Key West attractions

A street with a pharmacy, a theater, and a yellow building.

Duval Street

9.2/10 (20,928 reviews)
Stroll the vibrant heart of Key West where historic architecture meets lively entertainment. Evening visits offer the full experience of Duval Street's renowned music scene and spirited local culture.
See properties

What to do in Key West

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

Rp807.662
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

Rp998.910
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Photographing a landmark in Miami

Key West Express Day Trip from Miami

Rp1.300.900
per adult
88% of travellers recommend
Key West Express Day Trip from Miami
See all activities in Key West

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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.