A beach with palm trees, people relaxing on chairs, and colorful kayaks.

Florida Keys Vacations from ¥105,455

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The Latest Florida Keys Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 19 - Dec 25

    President Hotel Villa + Flight

    South Beach
    5 nights
    3.5 star property
    8.2/10 - Very good (1,002 reviews)
    "Good stay for a night"
    Reviewed November 3, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    ¥154,308
    ¥105,455
    per traveler
    found 1 day ago
    President Hotel Villa
  • Dec 19 - Dec 25

    Cavalier Hotel South Beach + Flight

    South Beach
    5 nights
    3.5 star property
    8.6/10 - Excellent (1,000 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    ¥192,465
    ¥121,867
    per traveler
    found 1 day ago
    Cavalier Hotel South Beach
  • Dec 19 - Dec 25

    President Hotel + Flight

    South Beach
    5 nights
    3.5 star property
    8.4/10 - Very good (2,927 reviews)
    "I would definitely stay here again. Close to everything. Should have added breakfast."
    Reviewed November 4, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    ¥156,706
    ¥106,566
    per traveler
    found 1 day ago
    President Hotel
  • Dec 19 - Dec 25

    Isla Bella Beach Resort & Spa + Flight

    Marathon
    4 nights
    5.0 star property
    9.2/10 - Wonderful (1,307 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    ¥423,219
    ¥294,650
    per traveler
    found 1 day ago
    Isla Bella Beach Resort & Spa
  • Dec 19 - Dec 25

    Essex House By Clevelander + Flight

    South Beach
    6 nights
    4.0 star property
    7.6/10 - Good (1,248 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • Nonstop MIA - BOS • Nonstop
    ¥168,917
    ¥119,660
    per traveler
    found 1 day ago
    Essex House By Clevelander

Discover the most popular places to visit in Florida Keys

What to do in Florida Keys

Florida Keys Hotel Deals

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.

Find out more about Florida Keys

Things to do near Florida Keys

Shopping

The Kite House offers a unique selection of gifts and souvenirs just 11.3km from Florida Keys, while We Cycle Key West, located 9.7km away, provides fun cycling gear and local memorabilia. Both stores promise a delightful shopping experience during your visit.

Recreation

At Key West Golf Club, enjoy a round of golf surrounded by lush landscapes and a vibrant outdoor atmosphere. The Red Barn Theater offers captivating performances, perfect for a romantic night out or family entertainment. For relaxation, the MLK Community Pool provides a refreshing swim in a family-friendly setting.

Adventure

Explore John Pennekamp Coral Reef State Park, where you can snorkel or dive among vibrant coral reefs teeming with marine life. For a thrilling experience, try parasailing over the clear waters of Key West, offering panoramic views of the beautiful coastline and surrounding islands.

Nightlife

The nightlife in the Florida Keys is vibrant and diverse. Enjoy a sunset cocktail at the iconic Sloppy Joe's in Key West, then dance at the Green Parrot Bar. Don't miss the live music at the Hog's Breath Saloon for an unforgettable experience.

Find the best attractions near Florida Keys

The Florida Keys offer a perfect blend of beach, outdoor, and family vacation experiences, featuring attractions such as modern squares, state parks, and historic government buildings. Whether you're seeking culture, adventure, or a city vibe, there's something for everyone. Be sure to explore the beautiful Florida Keys beaches and consider a Key West vacation for a truly memorable getaway.

  • Mallory Square: Experience the vibrant atmosphere of Mallory Square, a bustling modern square located 9.7km from Florida Keys. Known for its lively sunset celebrations, street performers, and local artisans, it’s a perfect spot to soak in the city vibes and enjoy breathtaking views of the Gulf of Mexico.
  • Fort Zachary Taylor Historic State Park: This national state park, also 9.7km away, offers stunning scenery and outdoor adventure. Explore the historic fort, relax on the beach, or hike the nature trails, making it an ideal destination for nature lovers and history buffs alike.
  • Harry S. Truman Little White House: Located 9.7km from Florida Keys, this historic civic government building provides a glimpse into American history. Tour the beautifully preserved rooms and learn about its significance as a winter retreat for President Truman, all while enjoying the rich cultural vibes of Key West.

Best time to go to Florida Keys

The best time to visit Florida Keys is dependent on what kind of holiday you are seeking. August is its hottest month on average. At this time, visitor numbers are average and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are average and weather is mostly sunny with no rain.

Tips to save on your trip to Florida Keys

  • 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 Florida Keys.
  • 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.