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

Anna Maria Island Vacations from $602

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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

    ChartHouse Clearwater Beach Marina Hotel + Flight

    Clearwater Beach
    3 nights
    2.0 star property
    9.6/10 - Exceptional (1,323 reviews)
    "Every staff member was very friendly and accommodating. The entire facility and pool was clean and modern. No complaints other than $20/day parking."
    Reviewed July 30, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - MCONonstop MCO - BOS1 stop
    Save 100% on your flight
    $659
    $410
    per traveler
    found 2 days ago
    ChartHouse Clearwater Beach Marina Hotel
  • Sep 26 - Sep 29

    Cedar Cove Resort and Cottages + Flight

    Holmes Beach
    3 nights
    3.0 star property
    9.2/10 - Wonderful (564 reviews)
    "The central location on the island is perfect. We stayed in Wildflower cottage. Bed was comfortable. Kitchen was minimally equipped but functional. Western facing deck was amazing. Bikes and beach towels available for free."
    Reviewed July 30, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - MCONonstop MCO - BOS1 stop
    Save 100% on your flight
    $890
    $560
    per traveler
    found 2 days ago
    Cedar Cove Resort and Cottages
  • Sep 26 - Sep 29

    Ocean Club Treasure Island Hotel + Flight

    Sunshine Beach
    3 nights
    4.0 star property
    9.6/10 - Exceptional (1,122 reviews)
    "Great"
    Reviewed July 31, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - MCONonstop MCO - BOS1 stop
    Save 100% on your flight
    $822
    $543
    per traveler
    found 2 days ago
    Ocean Club Treasure Island Hotel
  • Oct 11 - Oct 16

    Hibiscus Suites - Gateway to Siesta Key + Flight

    Sarasota
    5 nights
    2.5 star property
    8.6/10 - Excellent (2,389 reviews)
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPANonstop TPA - BOS1 stop
    $902
    $602
    per traveler
    found 1 day ago
    Hibiscus Suites - Gateway to Siesta Key
  • Oct 11 - Oct 16

    The Westin Sarasota + Flight

    Central Sarasota
    5 nights
    4.0 star property
    9.0/10 - Wonderful (1,145 reviews)
    "tHEY CHARGE YOU CREDIT CARD WITHOUT AUTHORIZATION FOR BREAkfast / never used and still charged / staff not friendly to respond and assist / very rude / manager never called / i called x 5 / Receptionist did not want to connect to a manager / They were raising voice / I spend thousands of dollars for business transaction / I am very reputable businessman and do not deserve for such a treatment American Express helped to clarify and refunded money / It is not money it is principles . Management..."
    Reviewed July 30, 2026
    Roundtrip Boston (BOS) - Tampa (TPA)
    BOS - TPANonstop TPA - BOS1 stop
    Save 100% on your flight
    $1,089
    $743
    per traveler
    found 1 day ago
    The Westin Sarasota

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.