Key West Vacation Packages

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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.

Top Key West Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Ibis Bay Beach Resort

Ibis Bay Beach Resort

Northside Resort
CA $822
per person
Sep 18 - Sep 21
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Key West (EYW)
8.2/10 Very good! (2,319 reviews)
Nice property. Didn't love that it was on a busy street but overall a great place to stay. Not close to downtown but if you rent a golf cart it's no problem.

Reviewed on Aug 10, 2026

Lighthouse Hotel - Key West Historic Inns

Lighthouse Hotel - Key West Historic Inns

Old Town Key West
CA $932
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9/10 Wonderful! (971 reviews)
Winslow's Bungalows - Key West Historic Inns

Winslow's Bungalows - Key West Historic Inns

Old Town Key West
CA $924
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.2/10 Wonderful! (1,371 reviews)
The Key West Hotel

The Key West Hotel

Key West Historic District
CA $3,463
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Key West (EYW)
9.2/10 Wonderful! (561 reviews)
This is the best place to stay in Key West! It is a hotel but it has the quaint B&B vibes. The tiki bar by the pool is amazing and they are adding food soon which makes it literally perfect. Close to everything you’d want to do- walk or scooter. 10/10 recommend!

Reviewed on Jul 27, 2026

Hyatt Vacation Club at Windward Pointe, Key West

Hyatt Vacation Club at Windward Pointe, Key West

CA $1,447
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Key West (EYW)
9.4/10 Exceptional! (1,219 reviews)
Beautiful resort! Well kept, great staff! Only downfall of the on resort restaurant….. service fees are STEEP!

Reviewed on Aug 9, 2026

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.

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.

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.

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.

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.

Things to do in and around Key West

Key West offers a delightful blend of activities for families and business travellers alike. Visitors can enjoy shopping at local boutiques and mall centers, while also indulging in beach experiences perfect for vacations. Key West is known for its exciting attractions and day trips, making it an ideal spot to soak up the sun and explore the area's unique charm.

Shopping

In Key West, you can shop at local stores like We Cycle Key West and The Kite House for unique gifts. If you're up for a drive, the Big Pine Key Flea Market, 46.7km away, offers a vibrant market experience with various vendors and local goods.

Recreation

Key West Golf Club offers a picturesque outdoor setting for golf enthusiasts, surrounded by lush landscapes. Enjoy a round while soaking in the warm Florida sun. For family fun, the MLK Community Pool & Community Center is perfect for swimming and recreational activities, promoting a vibrant community atmosphere.

The Waterfront Playhouse presents a delightful cultural experience, showcasing engaging performances that evoke romance and entertainment. It's an ideal spot for families looking to immerse themselves in the local arts scene while enjoying a memorable evening out.

Adventure

Experience the thrill of snorkeling in the vibrant coral reefs, kayaking through mangroves, or paddleboarding at sunset. For an adrenaline rush, try parasailing high above the turquoise waters or embark on a fishing charter for a chance to catch a big one in the Gulf Stream.

Nightlife

Key West's nightlife is vibrant and eclectic. Visit the Green Parrot Bar for live music and a lively atmosphere. For a laid-back vibe, head to Sloppy Joe's, known for its fun crowds and refreshing drinks. Don't miss sunset celebrations at Mallory Square for street performers and local artisans.

*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, city, and business vacations, offering a variety of attractions like beautiful beaches, national parks, and historic houses. Visitors can immerse themselves in the rich culture while enjoying outdoor activities and the stunning beach experience. Don't miss exploring Key West and the Florida Keys for a memorable getaway filled with diverse experiences and local charm.

  • Duval Street: Experience the vibrant atmosphere of Duval Street, the heart of Key West. Lined with eclectic shops, lively bars, and delightful restaurants, this iconic street is perfect for strolling and soaking up the city's unique culture.
  • Southernmost Point: Visit the Southernmost Point buoy, a symbolic landmark marking the southern tip of the continental U.S. This spot is rich in history and offers a perfect photo opportunity, embodying the cultural essence of Key West.
  • Mallory Square: Enjoy the bustling ambiance of Mallory Square, where you can witness the stunning sunset celebrations. This modern square hosts street performers and vendors, making it a lively gathering place for visitors and locals alike.

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 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

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
CA $192
CA $318 total
Sep 1 - Sep 2
includes taxes & fees
8.8/10 Excellent! (3,500 reviews)
"Phenomenal stay! Gorgeous views and amenities. Staff was so attentive and went above and beyond for everything. Will absolutely be coming back!"

Reviewed on Aug 10, 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
CA $149
CA $301 total
Aug 11 - Aug 12
includes taxes & fees
8.6/10 Excellent! (2,419 reviews)
"No housekeeping, the room is not clean and they said that they will charge for housekeeping services. So bad. No private beach as advertised"

Reviewed on Aug 10, 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
CA $168
CA $268 total
Sep 9 - Sep 10
includes taxes & fees
Blue Flamingo Resort Key West
See all 2,641 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)
Along one of the southernmost streets in the continental U.S., enjoy a lively area filled with shops, pubs, restaurants and lots of sidewalk acts and vendors.
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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)
Arrive at this square at day’s end to find street performers, food carts and one of the most beautiful sunsets in the United States.
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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)
Snap a memorable photograph from the edge of North America at this monumental landmark.
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A beach with white sand, palm trees, and a building in the background.

Smathers Beach

8.4/10 (8,320 reviews)
Key West’s popular party beach has an electric atmosphere on the weekends and is a destination for water sports lovers.
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Fort Jefferson, a brick fort with arched windows and a flagpole.

Dry Tortugas National Park

8.8/10 (2,184 reviews)
Separated from the mainland and encased by golden beaches and colorful coral reefs, this is a national park of fascinating ocean scenery.
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A brick corridor with arched ceilings and benches.

Fort Zachary Taylor Historic State Park

9.0/10 (4,544 reviews)
The displays of old weapons and interpretive panels in a fort at the heart of the southernmost state park in the continental U.S. provide information about the Civil War.
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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)
Meet six-toed cats and watch as the life of one America’s great writers unfolds before your eyes at his former home.
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A beach with people sunbathing, palm trees, and a multi-story building in the background.

South Beach

8.4/10 (5,461 reviews)
The southernmost beach in the continental United States is a convenient sandy enclave, just minutes from the center of town.
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What to do in Key West

Aerial view of people snorkeling in Key West

Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast

CA $63
per adult
94% of travellers recommend
Key West Morning Snorkel Adventure with Bottomless Mimosas & Breakfast
Aboard the trolley in Key West

Historic Key West Old Town Trolley Hop-On Hop-Off Tour

CA $78
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Snorkler waving underwater in Key West

Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch

CA $85
per adult
86% of travellers recommend
Key West Coral Reef Snorkel with Mimosas, Margaritas or Rum Punch
See all activities in Key West

Frequently asked questions

How much does a Key West vacation package cost?
You can pick up a vacation package to this popular destination from CA $822 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?
  1. 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.
  2. 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.
  3. 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.
  4. Bundle your airfare and accommodations: Once you've nailed down your dates and duration, book the ideal Key West vacation package for you.

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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.