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

Florida Keys Vacations from ¥173,751

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The Latest Florida Keys Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 18 - Dec 25

    Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort + Flight

    Marathon
    6 nights
    2.5 star property
    9.2/10 - Wonderful (147 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • 1 stop MIA - BOS • Nonstop
    ¥269,278
    ¥173,751
    per traveler
    found 1 day ago
    Bluegreen Vacations Hammocks at Marathon, Ascend Collection Resort
  • Dec 18 - Dec 25

    Isla Bella Beach Resort & Spa + Flight

    Marathon
    6 nights
    5.0 star property
    9.2/10 - Wonderful (1,303 reviews)
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • 1 stop MIA - BOS • Nonstop
    ¥569,783
    ¥361,687
    per traveler
    found 1 day ago
    Isla Bella Beach Resort & Spa
  • Dec 18 - Dec 25

    Cheeca Lodge & Spa + Flight

    Matecumbe
    6 nights
    5.0 star property
    9.2/10 - Wonderful (1,515 reviews)
    "Lovely"
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • 1 stop MIA - BOS • Nonstop
    ¥445,782
    ¥296,462
    per traveler
    found 1 day ago
    Cheeca Lodge & Spa
  • Dec 18 - Dec 25

    Skipjack Resort & Marina + Flight

    Marathon
    6 nights
    3.0 star property
    8.6/10 - Excellent (1,298 reviews)
    "Nice place"
    Reviewed November 8, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • 1 stop MIA - BOS • Nonstop
    ¥265,710
    ¥191,259
    per traveler
    found 1 day ago
    Skipjack Resort & Marina
  • Dec 18 - Dec 25

    Lime Tree Bay Resort + Flight

    Long Key
    6 nights
    3.5 star property
    9.4/10 - Exceptional (1,588 reviews)
    "Very pretty waterfront property with outdoor activities available for guests. We reserved two rooms and at check-in was told they were identical. Room 131 was excellent. Room 128-B was clean and the beds comfortable but the room was smaller, the sheets felt damp, and there was no ceiling fan."
    Reviewed November 10, 2026
    Roundtrip • Boston (BOS) - Miami (MIA)
    BOS - MIA • 1 stop MIA - BOS • Nonstop
    ¥309,625
    ¥228,673
    per traveler
    found 1 day ago
    Lime Tree Bay Resort

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.