Key West Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥109,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

Old Town, the historic heart of Key West, boasts a central business district and numerous tourist attractions. Explore the Key West Aquarium, Ernest Hemingway House, Mallory Square, and more in this vibrant area.

Find hotels in Old Town Key West
A coastal town with a prominent building featuring a blue awning, a chicken shack, and a store with colorful merchandise.

Downtown Key West

If you're spending some time in Downtown Key West, Duval Street and Ernest Hemingway Home and Museum are top sights worth seeing.

Find hotels in Downtown Key West
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

Old Town Key West boasts a rich history with 2485 historic buildings, and is home to popular attractions like Ernest Hemingway House and Mallory Square. Enjoy the lively atmosphere in the central business district.

Find hotels in Key West Historic District
A marina with yachts docked, a prominent red building, and a coastal cityscape in the background.

New Town

Though New Town might not have many top sights, you can venture to the surrounding area to see attractions like Smathers Beach and Key West Tropical Forest and Botanical Garden.

Find hotels in New Town
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.

Find hotels in Uptown - Upper Duval

Find the Best Key West Vacation Packages

Things to do in and around Key West

Shopping

In Key West, visit The Kite House for unique gifts and souvenirs. We Cycle Key West offers biking gear and accessories. If you're up for a drive, check out the Big Pine Key Flea Market, 46.7km away, for a vibrant experience with local vendors and eclectic finds.

Recreation

Experience tranquility at Key West Golf Club, where you can enjoy a round of golf surrounded by lush landscapes. For a cultural touch, visit Red Barn Theater for entertaining performances that captivate the whole family. Cool off at the MLK Community Pool, perfect for outdoor fun and relaxation with loved ones.

Adventure

Explore the vibrant coral reefs while snorkeling or diving in the waters around Key West, offering an incredible chance to see diverse marine life. For thrill-seekers, jet skiing through the turquoise waters provides an exhilarating adventure with stunning ocean views.

Nightlife

In Key West, experience vibrant nightlife at Duval Street, packed with lively bars, live music, and late-night dining. Check out the Sunset Celebration at Mallory Square for street performers and local vendors, and enjoy a laid-back atmosphere at local favorites like Sloppy Joe's and Captain Tony's.

*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 is perfect for family vacations and offers a blend of beach, cultural, and outdoor experiences. Explore beautiful beaches, visit historic houses, and enjoy local state parks. Whether you're after relaxation or adventure, Key West has something for everyone. Don't miss out on the vibrant local culture and stunning natural scenery during your visit.

  • Duval Street: Experience the vibrant heart of Key West along Duval Street, where lively bars, unique shops, and eclectic restaurants create an unforgettable atmosphere. This bustling street is perfect for strolling, people-watching, and enjoying the local nightlife.
  • Mallory Square: At Mallory Square, witness the iconic sunset celebrations that bring together street performers, local artisans, and food vendors. The lively ambiance and stunning views of the Gulf of Mexico make this a must-visit destination for both relaxation and entertainment.
  • Southernmost Point: Stand at the Southernmost Point buoy, a symbolic landmark that marks the southern tip of the continental United States. This spot is rich in local culture and offers a great photo opportunity, showcasing the spirit of Key West.

Best time to go to Key West

None

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 Vacation

Unwind on the shore while you watch the sunlight glistening across the water during your Key West vacation. 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 kilometers away). We suggest staying in accommodations 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 vacation 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.

Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
￥21,754
￥36,003 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (3,485 reviews)
"Loved this place. Friendly staff. Great views. Amenities were awesome! Highly recommend!"

Reviewed on Aug 6, 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
￥16,820
￥33,999 total
Aug 16 - Aug 17
includes taxes & fees
8.6/10 Excellent! (2,405 reviews)
"Clean. Balcony was very good, Beach access."

Reviewed on Aug 6, 2026

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
￥18,305
￥29,462 total
Aug 17 - Aug 18
includes taxes & fees
8.6/10 Excellent! (2,604 reviews)
"Everything is absolutely satisfied by me However you can still improve more better I really enjoyed myself"

Reviewed on Aug 6, 2026

Blue Flamingo Resort Key West
See all 2,639 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
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.
See properties
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 colorful 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.
See properties
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.
See properties
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.
See properties
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 favorite beach with crystal-clear waters perfect for snorkeling.
See properties
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.
See properties
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.
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

￥7,175
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

￥11,485
per traveler
92% of travellers recommend
Bucket-List Parasailing In Downtown Key West - Highest & Longest Rides
Key West Premium Sunset Sail with Champagne, Wine & Tapas

Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar

￥12,609
per adult
94% of travellers recommend
Dolphin Watch Catamaran Sunset Sail w/ Tapas and Open Bar
See all activities in Key West

Frequently asked questions

How much does a Key West vacation package cost?
Offering excellent value package deals on Expedia, you'll be pleasantly surprised at how much a vacation 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 vacation 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 vacations 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 neighborhoods 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 vacation package to Key West?
Key West offers everything you need for an amazing trip. Begin your Key West vacation 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 personalize 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 vacation as a package?
Expedia vacation 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 personalized Key West vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation 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 favorite 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 vacation. 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 personalized Key West vacation package.

Explore a world of travel with Expedia

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