Key West Vacations from ¥427,690

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The Latest Key West Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Marker Key West Harbor Resort
The Key West Hotel
Coconut Beach Resort
Hyatt Vacation Club at Beach House, Key West
Hyatt Vacation Club at Windward Pointe, Key West

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

Find the Best Key West Vacation Packages

Things to do in and around Key West

Shopping

In Key West, visit The Kite House for unique gifts and souvenirs. We Cycle Key West offers biking gear and accessories. If you're up for a drive, check out the Big Pine Key Flea Market, 46.7km away, for a vibrant experience with local vendors and eclectic finds.

Recreation

Experience tranquility at Key West Golf Club, where you can enjoy a round of golf surrounded by lush landscapes. For a cultural touch, visit Red Barn Theater for entertaining performances that captivate the whole family. Cool off at the MLK Community Pool, perfect for outdoor fun and relaxation with loved ones.

Adventure

Explore the vibrant coral reefs while snorkeling or diving in the waters around Key West, offering an incredible chance to see diverse marine life. For thrill-seekers, jet skiing through the turquoise waters provides an exhilarating adventure with stunning ocean views.

Nightlife

In Key West, experience vibrant nightlife at Duval Street, packed with lively bars, live music, and late-night dining. Check out the Sunset Celebration at Mallory Square for street performers and local vendors, and enjoy a laid-back atmosphere at local favorites like Sloppy Joe's and Captain Tony's.

*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 vacations and offers a blend of beach, cultural, and outdoor experiences. Explore beautiful beaches, visit historic houses, and enjoy local state parks. Whether you're after relaxation or adventure, Key West has something for everyone. Don't miss out on the vibrant local culture and stunning natural scenery during your visit.

  • Duval Street: Experience the vibrant heart of Key West along Duval Street, where lively bars, unique shops, and eclectic restaurants create an unforgettable atmosphere. This bustling street is perfect for strolling, people-watching, and enjoying the local nightlife.
  • Mallory Square: At Mallory Square, witness the iconic sunset celebrations that bring together street performers, local artisans, and food vendors. The lively ambiance and stunning views of the Gulf of Mexico make this a must-visit destination for both relaxation and entertainment.
  • Southernmost Point: Stand at the Southernmost Point buoy, a symbolic landmark that marks the southern tip of the continental United States. This spot is rich in local culture and offers a great photo opportunity, showcasing the spirit of Key West.

Best time to go to Key West

None

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 kilometers 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 25,800 inches 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.

Key West Hotel Deals

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 ¥22,792 per night from Jun 7 to Jun 8
¥22,792
¥34,599 total
Jun 7 - Jun 8
includes taxes & fees
8.4/10 Very Good! (2,315 reviews)
"Enjoying fun outdoor games, lounging in a mini cabana by the sparkling pool, with a refreshing frozen Miami Vice in hand, and you all set to relax in Key West. We enjoyed this as a staycation and will definitely do so again. Thanks for the memories!"

Reviewed on May 31, 2026

Blue Flamingo Resort Key West
Southernmost Beach Resort and Guesthouses

Southernmost Beach Resort and Guesthouses

4 out of 5
1319 Duval Street Key West FL
Fully refundableReserve now, pay when you stay
The price is ¥32,133 per night from Jun 8 to Jun 9
¥32,133
¥47,796 total
Jun 8 - Jun 9
includes taxes & fees
8.8/10 Excellent! (3,341 reviews)
"The property we stayed at was nice. They got us into the room right away and it was conveniently located to Duvall Street. However, the room attendant did not come every day and our shower door would not close all the way which we told them the first day we got there and they never came to fix it. ..."

Reviewed on May 30, 2026

Southernmost Beach Resort and Guesthouses
Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection

3.5 out of 5
3850 N Roosevelt Blvd Key West FL
Fully refundableReserve now, pay when you stay
The price is ¥20,171 per night from Jun 21 to Jun 22
¥20,171
¥27,173 total
Jun 21 - Jun 22
includes taxes & fees
8/10 Very Good! (1,231 reviews)
"Amazing service and Amazing location."

Reviewed on May 30, 2026

Hilton Garden Inn Key West / The Keys Collection
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.