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.
Hyatt Vacation Club at Beach House, Key West
The Key West Hotel
Hyatt Vacation Club at Windward Pointe, Key West
Beachfront 2bdr Condo, Pool & Hot Tub w/ Ocean Views Papaya Place by Avantstay
The Gardens Hotel

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

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?

 

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Key West Hotel Deals

Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundable
The price is CA $635 per night from Feb 8 to Feb 9
CA $635
CA $815 total
Feb 8 - Feb 9
includes taxes & fees
8.6/10 Excellent! (3,045 reviews)
Room was nice. The sink was clogged.

Reviewed on Jan 31, 2026

Southernmost Beach Resort and Guesthouses
Ibis Bay Beach Resort

Ibis Bay Beach Resort

2.5 out of 5
3101 N. Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $388 per night from Feb 8 to Feb 9
CA $388
CA $473 total
Feb 8 - Feb 9
includes taxes & fees
8/10 Very Good! (2,066 reviews)
Everything was fantastic

Reviewed on Feb 1, 2026

Ibis Bay Beach Resort
Oceans Edge Key West Resort, Hotel & Marina

Oceans Edge Key West Resort, Hotel & Marina

4 out of 5
5950 Peninsular Avenue Key West FL
Fully refundableReserve now, pay when you stay
The price is CA $437 per night from Feb 9 to Feb 10
CA $437
CA $576 total
Feb 9 - Feb 10
includes taxes & fees
8.8/10 Excellent! (1,801 reviews)
The room was very nice and homey feeling. The staff was very nice. We enjoyed breakfast lunch and diner at the restaurant the Waite staff was very friendly and food was good. We enjoyed the shuttle that is offered the drivers were knowledgeable about the island and history. Jeffery was the best. ...

Reviewed on Feb 3, 2026

Oceans Edge Key West Resort, Hotel & Marina
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.

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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.