Anna Maria Island Vacations from $658
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top destinations in Anna Maria Island
Holmes Beach
Anna Maria
The Latest Anna Maria Island Vacation Packages
- BeachTrail Lodging
Sep 30 - Oct 6BeachTrail Lodging + Flight
Indian Rocks Beach6 nights3.0 star property9.8/10 - Exceptional (101 reviews)"The cottage was well stocked with a snack basket and a super dog basket. The kitchen was stocked with all needed essentials and the parking also worked out well."Reviewed April 14, 2026Roundtrip • New York (NYC) - Tampa (TPA)LGA - TPA • Nonstop TPA - LGA • Nonstop - Cedar Cove Resort and Cottages
Sep 3 - Sep 8Cedar Cove Resort and Cottages + Flight
Holmes Beach5 nights3.0 star property9.2/10 - Wonderful (561 reviews)Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • 1 stop - CW Hotel
Sep 24 - Sep 28CW Hotel + Flight
Clearwater Beach4 nights4.0 star property9.8/10 - Exceptional (20 reviews)"I thoroughly enjoyed my stay at CW Clearwater. It's newly renovated so if you're looking it up right now, you may end up viewing the old, previous property. We had Suite #601 - 2 bedrooms, 2 full baths, full kitchen, and small living room with dining table and balcony facing the street (ocean view across the street). I could've spent an entire week at this location. It felt like a cozy condo. The staff is wonderful. Drinks/food waa also great."Reviewed July 22, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • 1 stop - Ocean Club Treasure Island Hotel
Sep 25 - Sep 28Ocean Club Treasure Island Hotel + Flight
Sunshine Beach3 nights4.0 star property9.6/10 - Exceptional (1,099 reviews)Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • 1 stop - Wyndham Grand Clearwater Beach
Sep 3 - Sep 8Wyndham Grand Clearwater Beach + Flight
Clearwater Beach5 nights4.0 star property9.4/10 - Exceptional (3,564 reviews)"We stayed at the Wyndham Grand Clearwater in July 2026. The hotel was well maintained and very clean for a property so close to the beach. While the hotel did many things well, we had a few issues that arose. We booked two nights in a double queen with a balcony (partial gulf view); however, the room wasn’t available at check in (4:00PM). The gentleman at the front desk stated we’d need to wait another hour for the room we booked. We took a double queen without any view or balcony instead of..."Reviewed July 22, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • 1 stop TPA - BOS • 1 stop
Discover the most popular places to visit in Anna Maria Island
What to do in Anna Maria Island
Anna Maria Island & Bradenton Beach Parasailing Tour
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
Manatee Discovery Anna Maria Island
Anna Maria Island Hotel Deals
Cedar Cove Resort and Cottages
Cedar Cove Resort and Cottages
Tropic Isle at Anna Maria Island Inn
Tropic Isle at Anna Maria Island Inn
Silver Surf Gulf Beach Resort
Silver Surf Gulf Beach Resort
The Retreat at Anna Maria Island Inn
The Retreat at Anna Maria Island Inn
Driftwood at Anna Maria Island Inn
Driftwood at Anna Maria Island Inn
Waterline Villas & Marina, Autograph Collection
Waterline Villas & Marina, Autograph CollectionBook with confidence
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.