An aerial view of a coastal town with a long pier extending into turquoise waters.

Anna Maria Island Vacations from $377

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Top destinations in Anna Maria Island

The Latest Anna Maria Island Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Sep 26 - Sep 29

    Hibiscus Suites - Gateway to Siesta Key + Flight

    Sarasota
    3 nights
    2.5 star property
    8.6/10 - Excellent (2,388 reviews)
    "The best"
    Reviewed July 30, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - RSW1 stop RSW - BOSNonstop
    $557
    $377
    per traveler
    found 1 day ago
    Hibiscus Suites - Gateway to Siesta Key
  • Sep 3 - Sep 8

    The Fold Hotels Indian Shores + Flight

    Indian Shores
    5 nights
    3.0 star property
    9.2/10 - Wonderful (1,004 reviews)
    "Such a great location. Not even a 5 minute walk to the beach. And there is free covered parking on site."
    Reviewed July 27, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPA1 stop TPA - BOS1 stop
    Save 100% on your flight
    $1,018
    $639
    per traveler
    found 1 day ago
    The Fold Hotels Indian Shores
  • Oct 8 - Oct 11

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    3 nights
    3.0 star property
    9.2/10 - Wonderful (563 reviews)
    "Everything was amazing from the moment I walked in to the office for check in, the staff was friendly, helpful and informative! This was a home away from home! I will definitely be back next year!"
    Reviewed July 26, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - SRQNonstop SRQ - BOSNonstop
    $1,192
    $787
    per traveler
    found 2 days ago
    Cedar Cove Resort and Cottages
  • Sep 3 - Sep 8

    The Hotel Zamora + Flight

    St. Pete Beach
    5 nights
    4.0 star property
    8.8/10 - Excellent (376 reviews)
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPA1 stop TPA - BOS1 stop
    Save 100% on your flight
    $1,054
    $703
    per traveler
    found 1 day ago
    The Hotel Zamora
  • Sep 3 - Sep 8

    Wyndham Grand Clearwater Beach + Flight

    Clearwater Beach
    5 nights
    4.0 star property
    9.4/10 - Exceptional (3,619 reviews)
    "All.pwrfect"
    Reviewed July 30, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPA1 stop TPA - BOS1 stop
    Save 100% on your flight
    $1,318
    $884
    per traveler
    found 1 day ago
    Wyndham Grand Clearwater Beach

Discover the most popular places to visit in Anna Maria Island

What to do in Anna Maria Island

Anna Maria Island Hotel Deals

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Things to do near Anna Maria Island

Anna Maria Island is perfect for beach and outdoor family vacations, offering a variety of activities. Enjoy stunning beach vacations, take a day trip to explore the area, play tennis at local courts, or visit nearby theme parks. For a unique experience, don't miss the hour-long dolphin cruise to see these playful creatures up close. With options for relaxation and recreation, Anna Maria Island is an ideal getaway for everyone.

Shopping

Visit West Coast Surf Shop, just 0.6 miles from Anna Maria Island, for surf gear and beachwear. Explore Bridge Street, 3 miles away, for a charming shopping area with a mix of local businesses. For a larger selection, check out Ellenton Premium Outlets, 13 miles from the island.

Recreation

At Aluna Wellness Center & Spa, indulge in rejuvenating treatments that promote relaxation and well-being, just 2 miles from the island. For family fun, visit Fish Hole Adventure Golf, a lively mini-golf venue offering sports and adventure vibes, located 3 miles away.

Adventure

Experience the thrill of paddleboarding with AMI Paddleboard Adventures, located 0.6 miles from Anna Maria Island. Dive into underwater exploration with Blue Water Explorers, situated 3 miles away. For family fun, visit the Astro Skate and Fun Center, found 10 miles from the island.

Nightlife

Experience the laid-back nightlife of Anna Maria Island with a visit to The Sandbar, where you can enjoy beachfront dining and live music. For a more casual vibe, check out the Island Pub for great drinks and friendly locals, perfect for unwinding after a day in the sun.

Find the best attractions near Anna Maria Island

Anna Maria Island is a perfect destination for beach and outdoor family vacations, offering attractions like pristine beaches, historical museums, and cultural experiences. Visitors can enjoy the beautiful Anna Maria Beach and explore local points of interest that highlight the island's charm. Whether you're seeking relaxation or adventure, Anna Maria Island provides a delightful mix of activities for every traveler looking for the best beach getaway.

  • Anna Maria Beach: Experience the quintessential beach vibes at Anna Maria Beach, located a short 3 miles from Anna Maria Island. With its soft white sands and gentle waves, it's perfect for sunbathing, swimming, and enjoying picturesque sunsets.
  • Bean Point Beach: Just 3 miles from Anna Maria Island, Bean Point Beach offers stunning scenery and a tranquil atmosphere. This cape is ideal for beachcombing, picnicking, and taking in breathtaking views of the Gulf of Mexico.
  • IMG Academy: Situated 8 miles from Anna Maria Island, IMG Academy is a premier sports training facility. While it's more focused on sports education, visitors can appreciate the impressive campus and various athletic events held throughout the year.

Best time to go to Anna Maria Island

The best time to visit Anna Maria Island 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 light rain.

Tips to save on your trip to Anna Maria Island

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Anna Maria Island during the low season (September to November) for more affordable options.
  • 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.