How much does a Key West vacation package cost?

You can pick up a vacation package to this popular destination from CA $1,431 on Expedia. But how much your vacation to Key West costs will depend on your hotel choice, length of stay and season.

What are the cheapest months to go to Key West?

August, September and October are the best times to look for cheap Key West vacation packages. Travelling in quieter months means you can usually find reduced prices on accommodations and flights.

How many days is enough for Key West?

With about 3 days, you'll have plenty of time to enjoy popular neighbourhoods such as Key West Historic District and Old Town Key West during your Key West vacation. Be sure to also add Southernmost Point and Ernest Hemingway Home and Museum to your list of must-sees. Up for some more adventures? Consider venturing outside of Key West on day trips and tours.

Is it worth booking a vacation package to Key West?

Key West is a good vacation destination with attractions like Smathers Beach among the many things to keep you busy. Whether you're travelling with the family or getting away with friends, a Key West vacation promises fun for everyone.

How to find the best Key West package deals?

Use Expedia's filters to help you find some fabulous Key West package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or search for Key West package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to lock in your vacation package as early as possible.

Is it cheaper to book a Key West vacation as a package?

An Expedia vacation package could land you considerable savings when compared to arranging flights and stays individually. Better still, you can tailor your Key West getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.

When to book a vacation package to Key West?

If you're planning an impromptu Key West getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can find sensational deals on your flights and hotels by booking ahead.

How to plan a trip to Key West?

Pick your travel dates: The things you want to do in Key West and your preferred season will help you decide when to get away. Budget wisely: As well as the price of your accommodations, you should consider other expenses. These include transportation, flights and food. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Key West. Work out your trip length: Consider how much time you'd like to spend discovering Key West. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace. Bundle your airfare and accommodations: Once you've nailed down your dates and duration, book the ideal Key West vacation package for you.

Key West Vacation Packages & Trips 2025 from $494

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.

Top Key West Vacation Deals

Price found within the past 48 hours. Click for updated prices.

Oceans Edge Key West Resort, Hotel & Marina

per person

Sep 13 - Sep 20

found 23 hours ago

Roundtrip flight included

Montreal (YUL) to Key West (EYW)

8.8/10 Excellent! (1,668 reviews)

Very clean, lovely room with friendly and helpful staff! We really liked the convenience of the shuttle downtown and appreciated the concierge’s help with booking activities.

Reviewed on Aug. 3, 2025

Almond Tree Inn Hotel - Adults Only

Old Town Key West

per person

Sep 13 - Sep 20

found 23 hours ago

Roundtrip flight included

Montreal (YUL) to Key West (EYW)

10/10 Exceptional! (1,002 reviews)

Wonderful little hotel that was relaxing with great breakfast.

Reviewed on Aug. 2, 2025

Hyatt Vacation Club at Windward Pointe, Key West

per person

Sep 13 - Sep 20

found 23 hours ago

Roundtrip flight included

Montreal (YUL) to Key West (EYW)

9.6/10 Exceptional! (1,024 reviews)

This property is fantastic a little drive from old Key West and all the shops in water activities but so beautiful. The little pool shack named Abby Road really has good food and the area is just so pretty to sit and take your food and watch the ocean or the pool or the iguanas. The staff was amazing. We would absolutely go back if we are going to visit Key West again.

Reviewed on Aug. 1, 2025

Hyatt Vacation Club at Beach House, Key West

per person

Sep 13 - Sep 20

found 23 hours ago

Roundtrip flight included

Montreal (YUL) to Key West (EYW)

9.2/10 Wonderful! (1,003 reviews)

Like the rooms and the convenien location

Reviewed on Aug. 1, 2025

Orchid Key Inn - Adults Only

Old Town Key West

per person

Sep 13 - Sep 20

found 23 hours ago

Roundtrip flight included

Montreal (YUL) to Key West (EYW)

9.8/10 Exceptional! (1,005 reviews)

Beautiful surroundings. Clean and quiet. Bed was comfy.

Reviewed on Aug. 2, 2025

Things to do in and around Key West

Key West is an ideal destination for family getaways and business trips alike, offering a mix of attractions and activities. Visitors can enjoy beach vacations and unique beach experiences, explore vibrant shopping areas and malls, and discover local attractions. Day trips are also a popular option to fully experience the charm of Key West. This tropical paradise promises a memorable vacation for everyone.

Shopping

Experience shopping in Key West at We Cycle Key West and The Kite House, both offering unique local products. If you're up for a drive, visit the Big Pine Key Flea Market, 46.7km away, where you can find a vibrant mix of goods in a bustling atmosphere.

Recreation

Experience serene golfing at the Key West Golf Club, surrounded by lush landscapes. Enjoy cultural performances at the Waterfront Playhouse, perfect for a romantic night out. For family fun, relax at the MLK Community Pool & Community Center, where outdoor activities await. Embrace wellness in a vibrant setting.

Adventure

In Key West, explore the vibrant underwater world while snorkelling at the stunning John Pennekamp Coral Reef State Park. Experience thrilling parasailing over the crystal-clear waters, or embark on a sunset sailing adventure to witness breathtaking views of the horizon as the sun dips below the sea.

Nightlife

Key West's nightlife is vibrant, with lively bars like Sloppy Joe's, where live music and fun cocktails abound. For a relaxed vibe, check out the Sunset Pier, perfect for enjoying stunning sunsets and refreshing drinks. Don’t miss the unique performances at the Red Barn Theatre for a cultural touch.

*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, Florida, offers a diverse range of attractions perfect for families and business travellers alike. Explore its stunning beaches, the nearby national parks, and historic houses that reflect the area's rich culture. Whether you seek outdoor adventures or a relaxing beach experience, Key West and the Florida Keys have something for everyone. Don't miss the chance to discover the charm of this vibrant town during your visit.

Duval Street: Experience the vibrant heart of Key West along Duval Street, a bustling thoroughfare brimming with lively bars, unique shops, and delicious eateries. The city's lively atmosphere invites you to explore art galleries and indulge in local cuisine, all while soaking in the lively street performances.
Southernmost Point: Visit the iconic Southernmost Point buoy, a colourful landmark that marks the southernmost tip of the continental U.S. Immerse yourself in the rich history and culture of the area as you capture memorable photos against this symbolic backdrop.
Mallory Square: Enjoy the vibrant energy of Mallory Square, where you can take in stunning sunset views while surrounded by street performers, local artisans, and food vendors. This modern square is the perfect place to unwind and soak up the lively atmosphere of Key West.

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 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 kilometres 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 65,532 cm 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.

Ready to book your vacation to Key West?

Choose your dates

Key West Hotel Deals

Beachside Resort & Residences

3841 N Roosevelt Blvd, Key West, FL

Fully refundableReserve now, pay when you stay

CA $177

CA $269 total

Aug 24 - Aug 25

includes taxes & fees

8.4/10 Very Good! (1,410 reviews)

"Staff was very helpful, room was clean, shuttle to downtown was awesome. We loved the Tavern and Town restaurant on site. Great food and priced right at happy hour!"

Reviewed on Aug. 1, 2025

Southernmost Beach Resort and Guesthouses

1319 Duval Street, Key West, FL

Fully refundable

CA $254

CA $379 total

Aug 25 - Aug 26

includes taxes & fees

8.6/10 Excellent! (2,647 reviews)

"Loved it!"

Reviewed on Aug. 2, 2025

Blue Flamingo Resort Key West

3820 North Roosevelt Boulevard, Key West, FL

Fully refundableReserve now, pay when you stay

CA $168

CA $266 total

Sep 2 - Sep 3

includes taxes & fees

7.6/10 Good! (1,511 reviews)

"Nice pool and courtyard with games, good A/C, quiet rooms, and a great location. However, breakfast was a big disappointment: waited 20–30 minutes just to order, then another 20+ for food, all while workers were using loud tools just a meter away. Shower water was only lukewarm, not hot. At 2 PM, ..."

Reviewed on Aug. 1, 2025

See all 2,725 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.