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.
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $4,935, price is now CA $3,552 per person
CA $3,552
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
8.6/10 Excellent! (3,636 reviews)
Wonderful stay all around!

Reviewed on Oct 27, 2026

The Key West Hotel

The Key West Hotel

3 out of 5
Key West Historic District
Save 100% on your flight
Price was CA $7,115, price is now CA $4,561 per person
CA $4,561
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (564 reviews)
Property was everything as described, clean, in the heart of the excitement that is Key West Pool was refreshing and close to tiki bar and local entertainment. The room was spacious, clean and comfy beds. There were issues and there was really no staff to address. Most impactive was the fire alarm. First started going off rang for a min or two, then reset. Happened a dozen times, each causing us to avoid sleep, leave room to make sure nothing was wrong. It wasn't. Then around 10 PM it went off and would not stop. Tried to call office, but nobody there after 6pm. Freaking insane, no emergency contact, maintenance number, nothing. We sent email in hopes it w May have been monitored... nope. Been 2 days and heard nothing back at all. Found the bartender at on site tici bar and though he abd is barback wete busy they found a ladder, called someone who told them to remove the devise. Eureka after almost 3 hours problem solved. Safety device removed and left peace and quite, perhaps fo fire warning, buy fine Also internet and this TV / entertainment no work. No maintenance, no visible router to reboot, be gave up and ended the insanity Maintenance guy was at the door early morning to properly troubleshoot or replace fire annunciator We only were booked for a night so when we checked out in morning front desk girl simply apologized and was actually sort of blowing us off as she was leaving the desk empty the service a near $600 o/n should offer

Reviewed on Oct 6, 2026

The Gardens Hotel

The Gardens Hotel

4 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $7,209, price is now CA $5,101 per person
CA $5,101
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.8/10 Exceptional! (1,006 reviews)
Un hotel hermoso , limpio , con una localización insuperable . El servio de primera , volveré pronto

Reviewed on Oct 20, 2026

The Marker Key West Harbor Resort

The Marker Key West Harbor Resort

4 out of 5
Key West Historic District
Save 100% on your flight
Price was CA $5,403, price is now CA $3,857 per person
CA $3,857
per person
Jan 11 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Key West (EYW)
9.2/10 Wonderful! (1,033 reviews)
Love this place!!!

Reviewed on Oct 24, 2026

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

Tropical Dreaming by Avantstay 4 Blks to Beach! Private Pool!

3 out of 5
Old Town Key West
Save 100% on your flight
Price was CA $9,837, price is now CA $7,052 per person
CA $7,052
per person
Jan 10 - Jan 17
found 20 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Key West (EYW)
10/10 Exceptional! (1 review)
Loved the closeness to Duval st and the privacy

Reviewed on Oct 17, 2025

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.

Find hotels in Old Town Key West

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

Margaritaville Beach House Key West

Margaritaville Beach House Key West

4 out of 5
2001 South Roosevelt Blvd Key West FL
The price is CA $298 per night from Oct 28 to Oct 29
CA $298
CA $423 total
Oct 28 - Oct 29
includes taxes & fees
8.8/10 Excellent! (1,808 reviews)
"Great property."

Reviewed on Oct 24, 2026

Margaritaville Beach House Key West
Havana Cabana at Key West

Havana Cabana at Key West

4 out of 5
3420 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Nov 16 to Nov 17
CA $213
CA $329 total
Nov 16 - Nov 17
includes taxes & fees
9/10 Wonderful! (1,897 reviews)
"Great hotel, not crowded, great staff. Enjoyed the breakfast and drinks that came with the package. Would recommend."

Reviewed on Oct 27, 2026

Havana Cabana at Key West
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
The price is CA $163 per night from Nov 1 to Nov 2
CA $163
CA $262 total
Nov 1 - Nov 2
includes taxes & fees
8.6/10 Excellent! (2,762 reviews)
"It was a very nice, well-kept place. The staff was very friendly and knowledgeable. I would NOT recommend buying essentials from this hotel, as they wanted $50 for a beach towel that you can get for $10 off Duval. The elevator was also hit or miss; we got stuck in it twice."

Reviewed on Oct 27, 2026

Blue Flamingo Resort Key West
See all 2,659 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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.
See properties

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 $79
per adult
88% of travellers recommend
Historic Key West Old Town Trolley Hop-On Hop-Off Tour
Key West Champagne Sunset Sail

Champagne and Sunsets: A Key West Catamaran Adventure

CA $83
per adult
94% of travellers recommend
Champagne and Sunsets: A Key West Catamaran Adventure
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 $3,552 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.