Key West Packages (Flight + Hotel)

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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 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

Shopping

In Key West, you can 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, located 46.7km away, offers a vibrant public market experience with a variety of local goods.

Recreation

Experience the scenic beauty at Key West Golf Club, where you can enjoy a round of golf amidst stunning landscapes. Unwind with captivating performances at Red Barn Theater, perfect for family and culture enthusiasts. For a refreshing swim, visit MLK Community Pool & Community Center, ideal for outdoor fun and sports activities.

Adventure

Experience the thrill of snorkeling at the vibrant coral reefs of Dry Tortugas National Park, accessible by ferry. Alternatively, embark on a kayaking adventure through the mangroves, where you can discover diverse wildlife and enjoy the tranquil beauty of the Florida Keys ecosystem.

Nightlife

In Key West, the nightlife is vibrant and eclectic, with lively bars like Sloppy Joe's and the Green Parrot, where you can enjoy live music and dancing. Duval Street buzzes with energy, offering a mix of casual pubs and upscale lounges, perfect for a memorable evening out.

*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-themed, and business-themed vacations. Visitors can explore captivating beaches, historic houses, and the stunning national parks, perfect for those seeking cultural and outdoor experiences. With attractions like Key West Getaway and various Florida Keys highlights, there's something for everyone to enjoy in this vibrant destination.

  • Duval Street: Experience the vibrant atmosphere of Duval Street, the heart of Key West, bustling with lively bars, eclectic shops, and delicious eateries. It's a perfect place to soak up the local culture and nightlife while enjoying street performances and art displays.
  • Smathers Beach: Relax on the golden sands of Smathers Beach, a picturesque stretch ideal for sunbathing, swimming, and water sports. The palm-lined shore offers a tranquil escape, with plenty of space to unwind and enjoy the stunning sunsets over the ocean.
  • Harry S. Truman Little White House: Step into history at the Harry S. Truman Little White House, where the 33rd U.S. President often retreated for respite. Explore the beautifully preserved rooms and learn about Truman's significant role in American history amidst the serene gardens.

Best time to go to Key West

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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 during the off-peak season (typically August to October) for more affordable package holidays to Key West.
  • 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
฿4,810
฿7,833 total
8 Sept - 9 Sept
includes taxes & fees
8.6/10 Excellent! (3,548 reviews)
"Everything was wonderful except the private beer area. We could not use it because of the sargassum and I wish they would have sent a message so we could have planned better. It was one of the reasons I booked there. If we could have used the beach it would have been a 10/10. Cleaning took a while ..."

Reviewed on 30 Aug 2026

Southernmost Beach Resort and Guesthouses
Beachside Resort & Residences

Beachside Resort & Residences

3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
฿3,196
฿6,762 total
31 Aug - 1 Sept
includes taxes & fees
8.6/10 Excellent! (2,482 reviews)
"I loved the ocean view from the pool and the shuttle service. Bob the bartender was amazing, great personality!"

Reviewed on 30 Aug 2026

Beachside Resort & Residences
Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
฿3,556
฿5,069 total
31 Aug - 1 Sept
includes taxes & fees
8.2/10 Very good! (2,362 reviews)
"Todo Super bien; el personal que trabaja en la instalación te hacen sentir como en casa muy acogedor; tranquilo y un servicio increíble"

Reviewed on 30 Aug 2026

Ibis Bay Beach Resort
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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 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

฿1,488
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Key West Parasailing Downtown

Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides

฿2,646
per traveller
92% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Aboard the trolley in Key West

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

฿1,840
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 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.