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.
Kona Kai Oasis

Kona Kai Oasis

Old Town Key West
€716
per person
24 Sept - 28 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Key West (EYW)
8/10 Very good! (650 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
€1,251
per person
24 Sept - 28 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
Great place to stay - highly recommend.

Reviewed on 20 Aug 2026

Ibis Bay Beach Resort

Ibis Bay Beach Resort

Northside Resort
€725
per person
24 Sept - 28 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Key West (EYW)
8.2/10 Very good! (2,329 reviews)
Pier House Resort & Spa

Pier House Resort & Spa

Key West Historic District
€1,131
per person
24 Sept - 28 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Key West (EYW)
9/10 Wonderful! (1,258 reviews)
The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

Key West Historic District
€988
per person
24 Sept - 28 Sept
found 1 day ago
Return direct flight included
Chicago (ORD) to Key West (EYW)
9.2/10 Wonderful! (1,002 reviews)
The fact they have an EV charger in their garage was a HUGE PLUS! The property is really nice and the staff was awesome!

Reviewed on 18 Aug 2026

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.

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A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

While visiting Downtown Key West, you might make a stop by sights like Duval Street and Ernest Hemingway Home and Museum.

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A two-story house with green shutters and a wooden balcony.

Key West Historic District

2 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 Florida Keys Beaches.

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A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

While there might not be top attractions in New Town, you can explore the larger area and discover places like Smathers Beach and Key West Tropical Forest and Botanical Garden.

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A sunset over the ocean with scattered clouds.

Uptown - Upper Duval

If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.

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Things to do in and around Key West

Key West is an ideal destination for families and business travellers alike, offering a variety of attractions and activities. Visitors can enjoy shopping at local malls and explore vibrant resorts. Key highlights include exciting kayak trips, lively venues featuring live music, and numerous fun places to experience the local culture. With its charming atmosphere, Key West promises a memorable vacation filled with unique attractions and delightful experiences.

Shopping

In Key West, explore The Kite House for unique gifts and We Cycle Key West for bike rentals and accessories. If you're up for a drive, visit the Big Pine Key Flea Market, a vibrant public market offering a variety of local goods, located 46.7km away.

Recreation

Experience the serene atmosphere at Key West Golf Club, where you can enjoy a round of golf amidst lush landscapes. For a dose of culture, catch a performance at the Red Barn Theater, perfect for families. Alternatively, unwind at the MLK Community Pool, offering a refreshing escape for all ages.

Adventure

In Key West, dive into the vibrant underwater world with a snorkelling adventure at the Florida Keys National Marine Sanctuary. Explore the historic shipwrecks and colourful coral reefs. Alternatively, embark on a thrilling sunset sail, where you can enjoy breathtaking views while sailing across the sparkling waters of the Gulf of Mexico.

Nightlife

Key West's nightlife buzzes with energy, featuring lively bars like Sloppy Joe's and the laid-back vibe of the Green Parrot. For a unique experience, enjoy live music at the Sunset Pier, or sip cocktails while watching the sunset at Mallory Square.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Key West

Key West offers a delightful experience for families and business travellers alike, with its stunning beaches, national parks, and historic houses. Visitors can immerse themselves in local culture while enjoying outdoor activities. Notable attractions include the Key West Aquarium and various beautiful beaches, making it a perfect destination for those seeking both relaxation and adventure.

  • Duval Street: Experience the vibrant atmosphere of Duval Street, the heart of Key West. Lined with lively bars, eclectic shops, and delightful eateries, this bustling thoroughfare offers a perfect blend of city vibes and island charm, making it a must-visit for socialising and shopping.
  • Mallory Square: Known for its stunning sunset celebrations, Mallory Square is a lively gathering point where street performers showcase their talents. Enjoy the picturesque views of the Gulf of Mexico while sampling local delicacies from nearby vendors.
  • Smathers Beach: Unwind at Smathers Beach, a beautiful stretch of golden sand ideal for sunbathing and water sports. With its relaxed beach vibes, it's perfect for leisurely strolls or enjoying a refreshing swim in the azure waters.

Tips to save on your trip to Key West

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Key West during the low season (August to October) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
€196
1 Sept - 2 Sept
includes taxes & fees
8.8/10 Excellent! (3,549 reviews)
"Parking and resort fees expensive for what you get."

Reviewed on 21 Aug 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
€131
23 Aug - 24 Aug
includes taxes & fees
Ibis Bay Beach Resort
Havana Cabana at Key West

Havana Cabana at Key West

3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
€193
8 Sept - 9 Sept
includes taxes & fees
9/10 Wonderful! (1,859 reviews)
"Very good 😊"

Reviewed on 19 Aug 2026

Havana Cabana at Key West
See all 2,637 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.
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A sign reading "Welcome to Mallory Square" with an American flag, a red and white striped awning, and a statue of a man in a blue shirt and straw hat.

Mallory Square

9.2/10 (15,939 reviews)
Mallory Square hosts Key West's legendary Sunset Celebration, where street performers and artisans gather nightly. Arrive early to secure a prime viewing spot for the breathtaking Gulf of Mexico sunset.
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A colorful monument with text indicating it is the Southernmost Point of the Continental U.S.A. in Key West, Florida.

Southernmost Point

8.8/10 (17,214 reviews)
This colourful buoy marks the continental United States' southernmost point, just 90 miles from Cuba. Arrive early to capture your photo at this iconic Key West landmark without the typical crowds.
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A beach with white sand, palm trees, and a building in the background.

Smathers Beach

8.4/10 (8,320 reviews)
Key West's largest beach boasts half a mile of soft white sand and calm, shallow waters ideal for swimming. Rent paddleboards or jet skis, or simply relax under swaying palms with panoramic ocean views.
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A brick corridor with arched ceilings and benches.

Fort Zachary Taylor Historic State Park

9.0/10 (4,544 reviews)
Explore a Civil War-era fortress housing the nation's largest collection of seacoast cannons. After touring the historic corridors, cool off at Key West's favourite beach with crystal-clear waters perfect for snorkelling.
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A two-story colonial-style building with a balcony, surrounded by lush greenery and palm trees.

Ernest Hemingway Home and Museum

9.2/10 (8,543 reviews)
Step into the Spanish Colonial home where Hemingway wrote his classics, surrounded by descendants of his six-toed cats. Explore his writing studio and gardens for a glimpse into the legendary author's 1930s life.
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Fort Jefferson, a brick fort with arched windows and a flagpole.

Dry Tortugas National Park

8.8/10 (2,184 reviews)
This remote island fortress combines pristine coral reefs with Civil War history at Fort Jefferson. Snorkel in turquoise waters or explore the massive 19th-century brick structure, accessible only by ferry or seaplane.
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A beach with people sunbathing, palm trees, and a multi-story building in the background.

South Beach

8.4/10 (5,461 reviews)
This intimate shoreline at Key West's southern tip offers shallow waters perfect for wading near the iconic Southernmost Point. Enjoy ocean views and refreshments at the Beach Café.
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What to do in Key West

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

€39
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

€68
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Aboard the trolley in Key West

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

€48
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
See all activities in Key West

Frequently asked questions

How much does a Key West holiday package cost?
Offering excellent value package deals from €716 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.

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