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.

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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 Fort East Martello Museum and Gallery.

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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

Shopping

For a delightful shopping experience in Key West, visit The Kite House and We Cycle Key West for unique gifts and souvenirs. If you're up for a drive, the Big Pine Key Flea Market offers a lively atmosphere, located 46.7km away, perfect for treasure hunting.

Recreation

Experience a round of golf at Key West Golf Club, where you can enjoy the lush landscape and outdoor atmosphere. For a cultural evening, catch a performance at Red Barn Theater, offering engaging entertainment for all ages. Alternatively, unwind at MLK Community Pool, perfect for family fun and relaxation.

Adventure

Explore the vibrant coral reefs while snorkelling or diving in the Florida Keys National Marine Sanctuary, teeming with marine life. For an adrenaline rush, try parasailing above the azure waters, offering stunning views of the island and the Gulf of Mexico.

Nightlife

Key West's nightlife is vibrant and eclectic. Enjoy live music at Sloppy Joe's, a historic bar on Duval Street, and sip cocktails at the Green Parrot, known for its laid-back atmosphere. For a unique experience, visit The Roof Top Café for stunning views and delicious dining under the stars.

*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 blend of family-friendly, city, and business-themed vacations, with attractions such as beautiful beaches, vibrant national parks, and historic houses. Visitors can immerse themselves in culture and outdoor experiences while exploring local highlights like the Key West Aquarium and the stunning Florida Keys. Whether you're seeking relaxation by the beach or engaging in cultural pursuits, Key West promises a memorable getaway for all types of travellers.

  • Smathers Beach: Experience the quintessential beach vibes at Smathers Beach, where you can relax on soft sands, swim in the turquoise waters, and partake in various water sports. This lively beach is perfect for sunbathing or enjoying a picnic with friends and family.
  • Key West Butterfly and Nature Conservatory: Immerse yourself in a tranquil paradise at this conservatory, where hundreds of butterflies flutter freely among lush plants. It's a delightful outing for families, offering educational exhibits and a serene atmosphere that connects visitors with nature.
  • Florida Keys Eco - Discovery Center: Discover the rich culture and ecology of the Florida Keys at this interactive museum. With engaging displays and hands-on experiences, it's an ideal spot for families to learn about the region's unique ecosystems and conservation efforts.

Best time to go to Key West

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Tips to save on your trip to Key West

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Key West.
  • 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

Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
HK$927
HK$1,484 total
1 Oct - 2 Oct
includes taxes & fees
8.6/10 Excellent! (2,681 reviews)
"Wish there were more options as far as eating, the staff was helpful in some ways, I think they were training a lot of them which is fine, I get it. Room was very clean. Would have been nice if there was an indoor eating area not just the outdoor bar areas but it was fine. Never were able to locate ..."

Reviewed on 23 Sept 2026

Blue Flamingo Resort 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
HK$1,254
HK$1,984 total
30 Sept - 1 Oct
includes taxes & fees
Southernmost Beach Resort and Guesthouses
Margaritaville Beach House Key West

Margaritaville Beach House Key West

2001 South Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
HK$1,396
HK$2,063 total
15 Oct - 16 Oct
includes taxes & fees
8.8/10 Excellent! (1,798 reviews)
"The room was fantastic, the staff excellent , the frozen drinks weak. We had lots of fun at the pool feeding the iguanas…would definitely recommend"

Reviewed on 23 Sept 2026

Margaritaville Beach House Key West
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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 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 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 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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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 vintage typewriter on a wooden table with a notebook and pen beside it.

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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A coastal fortification with a staircase leading to a higher platform, overlooking the sea.

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 beachside resort with palm trees, a large white building, and a checkered pattern on the sand.

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

Aboard the trolley in Key West

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

HK$436
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

HK$619
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

HK$333
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
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.

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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.