Key West Vacations from $769

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Your Key West Vacation

Lock in a Key West vacation package and focus on what counts — enjoying yourself. There's no more travel planning headaches, just a lot more free time to savor what's special about this captivating city, such as its beaches and relaxed vibe. If a sightseeing tour is on the agenda during your trip to Key West, look around well-known attractions like Ernest Hemingway Home and Museum, Audubon House and Tropical Gardens and Mallory Square. Whoever you're taking a break with and whatever you plan to spend, your dream Key West vacation is just clicks away with Expedia.

The Latest Key West vacation packages

Price found within the past 48 hours. Click for updated prices.
Hyatt Vacation Club at Windward Pointe, Key West
Oceans Edge Key West Resort, Hotel & Marina
The Key West Hotel
Havana Cabana at Key West
Brisa Del Mar by Avantstay Communal Pool Gated Community Ocean Front
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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

Discover the most popular places to visit in Key West

What to do in Key West

Key West Hotel Deals

Beachside Resort & Residences

Beachside Resort & Residences

3.5 out of 5
3841 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
$321 nightly
The price is $361 total per night from Jan 13 to Jan 14
$361 total
Jan 13 - Jan 14
Total with taxes and fees
8.6/10 Excellent! (1,871 reviews)
Very awesome and accommodating place!

Reviewed on Jan 5, 2026

Beachside Resort & Residences
Blue Flamingo Resort Key West

Blue Flamingo Resort Key West

4 out of 5
3820 North Roosevelt Boulevard Key West FL
Fully refundableReserve now, pay when you stay
$301 nightly
The price is $339 total per night from Jan 13 to Jan 14
$339 total
Jan 13 - Jan 14
Total with taxes and fees
8/10 Very Good! (1,831 reviews)
Room was clean. Amenities were great.

Reviewed on Jan 6, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
$435 nightly
The price is $489 total per night from Jan 13 to Jan 14
$489 total
Jan 13 - Jan 14
Total with taxes and fees
8.6/10 Excellent! (2,982 reviews)
Fun and safe

Reviewed on Jan 6, 2026

Southernmost Beach Resort and Guesthouses
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.

Find the Best Key West Vacation Packages

Things to do in and around Key West

Key West is an ideal destination for family vacations, offering a mix of city and business themes. Visitors can enjoy a variety of activities, including shopping at local malls and resorts, jet skiing, and exploring popular attractions. The vibrant Fantasy Fest and beautiful beach experiences add excitement to any trip, making Key West a perfect spot for unforgettable adventures and relaxation.

Shopping

In Key West, visit The Kite House for unique gifts and souvenirs, or We Cycle Key West for biking essentials. If you're up for a drive, check out the Big Pine Key Flea Market, 29 miles away, where you can find local crafts and enjoy a bustling atmosphere.

Recreation

Experience golfing at the Key West Golf Club, where lush greens and outdoor vibes enhance your game. For a touch of culture and entertainment, catch a show at the Waterfront Playhouse, perfect for a romantic evening. Dive into fun at the MLK Community Pool, ideal for family-friendly activities.

Adventure

In Key West, explore the vibrant coral reefs while snorkeling or diving in the Florida Keys National Marine Sanctuary. Experience thrilling water sports like parasailing and jet skiing, or embark on a sunset sailing cruise for breathtaking views and unforgettable memories.

Nightlife

In Key West, dive into the vibrant nightlife along Duval Street, filled with lively bars, open-air venues, and live music. Don't miss iconic spots like Sloppy Joe's and the Green Parrot for a laid-back atmosphere, or enjoy sunset celebrations at Mallory Square for a festive evening vibe.

*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 an ideal destination for family vacations, business trips, and city-themed getaways. Visitors can explore beautiful beaches, historic houses, and national parks, catering to those seeking culture, outdoor experiences, and relaxation. With its unique charm and diverse attractions, Key West offers something for everyone, making it a perfect choice for your next vacation adventure.

  • Duval Street: Experience the vibrant energy of Duval Street, the heart of Key West, lined with lively bars, eclectic shops, and art galleries. Stroll along this iconic street, soaking in the local culture and enjoying the unique atmosphere that captures the essence of island life.
  • Southernmost Point: Visit the Southernmost Point buoy, a must-see landmark that marks the southernmost point in the continental U.S. Snap a photo at this iconic spot while immersing yourself in the rich history and culture of Key West, surrounded by beautiful ocean views.
  • Mallory Square: End your day at Mallory Square, a bustling modern square famous for its sunset celebrations. Enjoy street performers, local artisans, and stunning views as the sun sets over the Gulf, creating a magical atmosphere that draws visitors from around the world.

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 (2 miles 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 in 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 Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Key West Intl. Airport (EYW)
Population
25,800
Max Temp Winter
75ºF
Max Temp Summer
85ºF
Top Sights
Smathers Beach, Fort Zachary Taylor Historic State Park and South Beach

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Frequently asked questions

How much does a Key West vacation package cost?
Offering excellent value package deals from $769 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?
You can typically find lower prices and greater availability in August, September and October. Check out our cheap Key West vacation packages and you could get some great off-season deals.
How many days is enough for Key West?
Key West vacations can be as short or long as you like, but to get a real feel for this place, we reckon 3 days is about right. In this timeframe, you can visit major attractions like South Beach and Clarence S. Higgs Memorial Beach Park and track down some underrated gems. Don't forget to visit cool neighborhoods such as Old Town Key West and Historic Seaport either. If you plan wisely, you can even take a day trip from Key West too.
Is it worth booking a vacation package to Key West?
It's easy to see why a Key West vacation is on the to-do list of many travelers. Leading attractions like Ernest Hemingway Home and Museum are just the beginning of what you can explore here.
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 when to get away: Check your calendar and get your bags packed. Your favorite time of year and the type of activities available will also help you decide when to visit Key West.
  2. Budget wisely: As well as the cost of your hotel, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected costs that could arise during your trip to Key West.
  3. Organize your Key West getaway with Expedia's trip planning tool: Look for and book hotels and things to do all in one place. You can also collaborate with your group to plan an unforgettable trip to Key West together.
  4. Determine how many days away: Start by compiling a list of the activities and attractions you'd like to experience in Key West. Then, estimate how long you'll need for each, as well as any travel time.
  5. Combine your airfare and accommodations: Once you've nailed down your trip dates and duration, book the right Key West vacation package for you.
  6. Book any activities or day trips: Now to the fun part — locking in everything you want to see and do. Check out some of the incredible things to do in Key West and reserve your tickets early to save time (and maybe some money too!).

Does Expedia offer Book Now, Pay Later Key West vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the total cost of your Key West trip across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.

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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.