There’s something about a beach vacation and live performances that just seems to go hand in hand. There are plenty of opportunities to catch some live music on Anna Maria Island, in many cases not far from our Anna Maria Island, Florida vacation rentals. In the upcoming spring and summer months, you can put catching a show on the top of your list of things to do on Anna Maria Island, along with many other adventures and activities. Some major acts that have played or have upcoming concerts on Anna Maria Island include The Marshall Tucker Band, Richard Marx, Lou Gramm, and the Beach Boys. Local artists perform in various venues, mainly at several Anna Maria Island bars and restaurants.
Let’s take a look at some of the venues where you can enjoy Anna Maria Island live music during your stay in an Anna Maria Island vacation rental with Florida Dreams!
The Music Scene on Anna Maria Island
The music scene on Anna Maria Island is vibrant and diverse, adding a melodic backdrop to the island’s laid-back atmosphere. From quaint bars to beachside restaurants, live music permeates the air, offering an eclectic mix of genres to suit every taste. Local artists showcase their talents throughout the week, with performances ranging from blues and reggae to rock and country. Whether you’re enjoying a sunset cocktail by the shore or exploring the island’s charming streets, you’re sure to encounter the soulful sounds of Anna Maria Island’s thriving music scene, creating unforgettable memories for visitors and locals alike.
Where to See Live Music
For those seeking the rhythmic heartbeat of Anna Maria Island, discovering where to experience live music becomes a delightful adventure awaiting exploration. From beachside bars to historic venues, there’s a diverse array of spots to catch captivating live performances on the island.
Island Time Bar and Grill
Found at 111 Gulf Drive South in Bradenton Beach, Island Time Bar and Grill offers homemade dishes and great margaritas. Menu items include crab cakes, shrimp skewers, lobster mac n’ cheese, and sirloin. You can also order classics like tacos, seafood baskets, salads, burgers, and sandwiches. Vegan and gluten-free options are available, so everyone can have a delicious meal!
Live music is featured every night from 7 p.m. to 10 p.m., with a new artist each night. Some musicians play multiple times throughout the month.
This is a 100% outdoor setting, so live music shows are weather permitting.

The Ugly Grouper
Another location with an every-night music lineup is The Ugly Grouper at 5704 Marina Drive in Holmes Beach. You’ll find freshly caught fish, shrimp dinners, seafood pasta, and sandwiches on the menu. Drinks include cocktails, beers, and wines. They also have lots of outdoor seating, so you can enjoy the view while you dine!
Seven days a week, The Ugly Grouper brings you live music, sometimes twice a day: noon to 3 p.m. and 5 p.m. to 8 p.m. Once-per-day shows are 5 to 8 p.m.
The Blue Marlin
Housed in a blue 1920s cottage and operating in the heart of historic Bridge Street since 2011, The Blue Marlin has daily local fish dishes along with steaks, sandwiches, soups, and desserts.
Live music entertainment is typically every Thursday through Saturday night from 7 p.m. to 10 p.m., though some weeks it’s Friday only. Past artists have performed bluegrass, jazz, rock, and country.
Freckled Finn
Solo artists, duos, and bands can be found at the Freckled Finn, an Irish pub, most days of the week.
You are not likely to get the same type of music back to back at the Freckled Finn, located at 5337 Gulf Drive North in Holmes Beach, which is great for those who love a variety of genres. One night might be reggae; another, a steel drum performance; the next, pop rock or acoustic tunes.
Every Monday is karaoke night, from 7:30 to 11:30, and trivia is held on Wednesdays. All other nights of the week are for live music. Music start times vary from mid-afternoon through the evening.
Plan Your Visit
Ready to plan your next island escape? Browse our full rental catalog to find your new home away from home, and book your Anna Maria Island vacation rental today to get started!
Harry’s Bar and Grill
Serving “AMI’s Favorite Burger” since 2017, Harry’s Bar and Grill is a popular Anna Maria Island restaurant located at 9303 Gulf Drive in Anna Maria. Lunch and dinner menus include scrumptious chicken, burgers, sandwiches, soups, and salads. There’s even an outdoor patio where you can bring your dog to dine as a whole family.
Harry’s has beer on tap and live music seven days a week! Blues, folk, classic covers, and country are just some of the genres you could hear at Harry’s! They also host worship singing at every Sunday brunch from 10 a.m. to 11:30 a.m.
Book Your Anna Maria Island Rentals with Florida Dreams
At Florida Dreams, we pride ourselves on offering the ultimate Anna Maria Island experience through our exceptional vacation rentals. Our accommodations provide a perfect blend of comfort and convenience, ensuring that your stay on the island is nothing short of extraordinary. Enjoy the convenience of fully equipped kitchens, private patios, and luxurious amenities, all just steps away from the island’s pristine beaches and vibrant attractions. With personalized attention and unmatched customer service, booking with Florida Dreams guarantees a memorable and hassle-free vacation on Anna Maria Island.