How much does a Key West vacation package cost?

You can pick up a vacation package to this popular destination from CA $983 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 2025/2026 from CA $983

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.

Hyatt Vacation Club at Beach House, Key West

CA $983

per person

Nov 15 - Nov 19

found 23 hours ago

Roundtrip non-stop flight included

Toronto (YYZ) to Key West (EYW)

9.4/10 Exceptional! (1,008 reviews)

Nice resort, great location.

Reviewed on Aug. 25, 2025

Oceans Edge Key West Resort, Hotel & Marina

CA $1,376

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,722 reviews)

Fantastic staff, always smiling. Great amenities, super clean, fantastic location.

Reviewed on Aug. 25, 2025

Pier House Resort & Spa

Key West Historic District

CA $2,327

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9/10 Wonderful! (1,014 reviews)

It was fabulous. The staff was amazing and we enjoyed the pool, beach and restaurant. My only suggestion is they add a pet walking area with turf. There is no grass on the property for pet relief.

Reviewed on Aug. 24, 2025

Ella's Cottages - Key West Historic Inns

Old Town Key West

CA $2,237

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (366 reviews)

everything was easy and staff was very helpful!

Reviewed on Aug. 18, 2025

The Perry Hotel & Marina Key West

CA $1,649

per person

Nov 9 - Nov 16

found 1 day ago

Roundtrip non-stop flight included

Detroit (DTW) to Key West (EYW)

9.4/10 Exceptional! (1,068 reviews)

It's a really nice property next to a marina. Quiet at night much livelier during the day. There is a shuttle from property to get to down town if you don't have a rental car. Rental car is needed and necessary in my opinion. The pool was great and there are three places to eat in the immediate area. Our first time here and we will be returning in the future.

Reviewed on Aug. 25, 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 $173

CA $265 total

Aug 26 - Aug 27

includes taxes & fees

Oceans Edge Key West Resort, Hotel & Marina

5950 Peninsular Avenue, Key West, FL

Fully refundableReserve now, pay when you stay

CA $232

CA $341 total

Sep 2 - Sep 3

includes taxes & fees

Hilton Garden Inn Key West / The Keys Collection

3850 N Roosevelt Blvd, Key West, FL

Fully refundableReserve now, pay when you stay

CA $140

CA $196 total

Sep 1 - Sep 2

includes taxes & fees

See all 2,700 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.