Key West Trips (flight + hotel)
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Where to stay in Key West
Old Town Key West
Old Town Key West captures the essence of island history with its pastel Victorian "Conch Houses" and lively atmosphere. Stroll past Ernest Hemingway's home where six-toed cats roam freely. The charming district buzzes with activity from Duval Street to Mallory Square's famous sunset celebrations. Explore this walkable neighborhood to discover hidden treasures like the Truman Little White House and Key West Butterfly Conservatory. Live music spills from open-air bars while local galleries showcase island artists. Rent a bicycle to navigate the narrow streets or simply wander among the bougainvillea-draped fences.
New Town
Key West's New Town neighborhood offers a refreshing glimpse into local island living. Here residential streets create a peaceful retreat from tourist crowds. Find budget-friendly hotels and everyday conveniences like shopping plazas and grocery stores. Smathers Beach is just a short drive away for sun seekers. The area's suburban character makes it perfect for travelers who want authentic experiences with practical amenities. Most locals choose New Town for its relaxed pace and affordable dining options.
Downtown Key West
Historic Downtown Key West captivates with its colorful charm and rich maritime legacy. Stroll along iconic Duval Street where Victorian architecture meets lively bars and shops. Ernest Hemingway's former home welcomes visitors with its famous six-toed cats and literary history. Join the nightly Sunset Celebration at Mallory Square where street performers entertain against breathtaking Gulf views. The Historic Seaport offers boat tours and waterfront dining options. Most attractions sit within easy walking distance, making Downtown Key West perfect for exploring on foot.
Key West Historic District
Step into a vibrant slice of history in Key West's Historic District. This charming neighborhood blends Victorian architecture with tropical flair along its narrow brick streets. The area boasts Hemingway's former home, the Truman Little White House, and sunset celebrations at Mallory Square. Duval Street forms the lively backbone of this walkable district. Visitors can explore art galleries by day and enjoy live music venues by night. Fort Zachary Taylor offers swimming and Civil War history just steps from the six-toed cats at the Hemingway House.
Uptown - Upper Duval
If you're spending some time in Uptown - Upper Duval, Duval Street and Florida Keys Beaches are top sights worth seeing.
Discover the most popular places to visit in Key West
What to do in Key West
Key West Rum & Reggae: Snorkel & Sunset Sail Combo
Champagne and Sunsets: A Key West Catamaran Adventure
Half-Day Key West's Ultimate Sandbar Adventure with Mangrove Kayak Tour
Key West Hotel Deals
DoubleTree Resort by Hilton Grand Key - Key West
DoubleTree Resort by Hilton Grand Key - Key West"Enjoyable"
The Perry Hotel & Marina Key West
The Perry Hotel & Marina Key West"All good."
Alexander's Guesthouse - Adult Exclusive
Alexander's Guesthouse - Adult Exclusive"Loved the amenities provided at Alexander’s! Awesome spot. All guests we encountered were extremely friendly."
Hilton Garden Inn Key West / The Keys Collection
Hilton Garden Inn Key West / The Keys Collection"Clean room"
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
Fairfield by Marriott Inn & Suites Key West at The Keys Collection"."
Hyatt Vacation Club at Windward Pointe, Key West
Hyatt Vacation Club at Windward Pointe, Key West"We had a great time at this property - booked it through Expedia so we didn't know it was a Vacation Club. View was gorgeous. Room was spacious and clean. Front desk staff was kind and offered lots of coupons for us to use on the vacation. Room was fantastic for what we needed - somewhere private, where we could sleep well, and just enjoy being in paradise. Unfortunately the shower had a smell of sulfur (it wasn't the water itself, so unsure what it was). The walls are also not soundproofed...
"Great stay! Would visit again."
Find out more about Key West
Things to do in and around Key West
Shopping
In Key West, you can shop at We Cycle Key West and The Kite House for unique gifts and souvenirs. If you're up for a drive, visit the Big Pine Key Flea Market, located 46.7km away, where you'll find a lively atmosphere and a variety of local goods.
Recreation
Relax at the MLK Community Pool, enjoying family-friendly outdoor swimming in a vibrant atmosphere. Unwind at Key West Golf Club, where you can play a round of golf amidst beautiful landscapes. Experience culture and entertainment at the Red Barn Theater, perfect for a romantic evening or family outing.
Adventure
Experience the thrill of snorkelling in the vibrant coral reefs of Dry Tortugas, paddleboarding through the mangroves, and exploring the underwater world on a scuba diving adventure. For land activities, try a sunset kayak tour or cycle along the scenic shoreline of the island.
Nightlife
Key West's nightlife buzzes with vibrant energy. Visit the iconic Duval Street for lively bars like Sloppy Joe's, where you can enjoy live music and fruity cocktails. For a more laid-back vibe, head to the Sunset Pier, offering stunning views and a relaxed atmosphere by the water.
Find the best attractions in Key West
Key West is an ideal destination for family vacations and business trips, offering a blend of culture, outdoor experiences, and beautiful beaches. Visitors can explore historic houses, indulge in the local beach scene, and enjoy the natural beauty of nearby national parks. With a range of attractions catering to diverse interests, Key West promises an enriching experience for all types of travellers seeking relaxation and adventure.
- Smathers Beach: Experience the quintessential beach vibes at Smathers Beach, where golden sands meet the crystal-clear waters of the Atlantic. This expansive beach is perfect for sunbathing, swimming, or enjoying water sports, with ample space to unwind or engage in beach activities.
- Key West Historic Seaport: Immerse yourself in adventure at the Key West Historic Seaport. This vibrant marina offers outdoor activities, including boat tours and fishing excursions, all set against a backdrop of charming shops and restaurants, perfect for a leisurely day by the water.
- USCGC Ingham Maritime Museum: Delve into the rich maritime culture at the USCGC Ingham Maritime Museum. Explore this historic cutter and learn about its fascinating naval history through exhibits that highlight its significant role in maritime service.
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.
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?
- Choose your travel dates: What you'd like to do in Key West and your favorite season will help you decide when to travel.
- 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.
- 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.
- 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.