Anna Maria Island

Living on Anna Maria Island

Anna Maria Island is a roughly seven-mile barrier island off the Manatee County coast, reached by bridges from Bradenton and Cortez and connected to Longboat Key at its south end. It is not one town. The island is split into three cities, Anna Maria, Holmes Beach and Bradenton Beach, and each one sets its own zoning, building and rental rules. That matters more here than almost anywhere else on the Gulf Coast.

What draws people is what the island doesn't have: no high-rises, no big resorts, and no chain-store strips. Buildings stay low, the beaches stay open to the sky, and a free island trolley runs the length of the island, so many visitors and residents park the car for the week.

The Three Cities

Anna Maria, at the north end, is the quietest and most expensive of the three. It is mostly single-family homes on a street grid that runs to the Gulf and the bay. Pine Avenue is the small main street, and Bean Point at the northern tip is one of the least crowded beaches in the region.

Holmes Beach, in the middle, is the largest city and has the widest mix: single-family homes, duplexes, condos, and the canal-front homes of Key Royale, where many lots have boat docks with bay access. Manatee Public Beach and most of the island's everyday shopping are here.

Bradenton Beach, at the south end, has the most condos and the busiest nightlife. It is anchored by historic Bridge Street and its pier, with Cortez Beach and Coquina Beach running south toward Longboat Pass.

What You Can Buy Here

Inventory ranges from original ground-level Old Florida cottages to newer homes raised on pilings, plus duplexes, townhomes and low-rise condos. Since the 2024 hurricanes, the streetscape has been changing fast. Many older ground-level homes were damaged, and a large share of what is being built now is elevated new construction, often designed around rental income.

What Buyers Should Know Before Making an Offer

Hurricanes Helene and Milton hit the island hard in 2024. Storm surge flooded large parts of all three cities. Ask what the property went through, what was repaired, and whether permits were pulled and closed.

Understand the 50% rule. In flood zones, if repairs or improvements exceed half of a structure's value, the building has to be brought up to current flood elevation standards. For an older ground-level home, that can mean elevating it or tearing it down. Price the lot and the house separately.

Get flood and wind insurance quotes early. Premiums vary widely depending on elevation, construction year and roof age. Request the elevation certificate before you're under contract.

Rental rules depend on which city you buy in. Each city has its own vacation rental registration, inspection and occupancy limits, and in Holmes Beach minimum stays depend on the zoning district. If a property's value depends on rental income, verify the rules with that city before you write an offer. Don't rely on the seller's rental history.

Plan around bridge construction. The state is replacing the 1956 Cortez drawbridge with a taller fixed-span bridge, a project of about $123 million that is getting underway now. Expect construction traffic on the south-end approach for several years.

Some landmarks are still being rebuilt. The Anna Maria City Pier was heavily damaged in 2024 and is being rebuilt with deeper, stronger pilings.

Who Anna Maria Island Fits

The island fits buyers who want a slower, low-rise beach town rather than a condo tower, investors who are ready to do the homework on rental rules and flood costs, and boaters who want canal access in Holmes Beach. If you want a walkable city with restaurants and culture across the bridge, compare it with Lido Key and St. Armands. If you want a quieter luxury island, look at Longboat Key.

Buying or Selling on Anna Maria Island

The LaMaida Group has sold Gulf Coast real estate since 2008. We help buyers sort out which city's rules apply, what a property actually earns as a rental, and what it will cost to insure and maintain. Call us at 941.416.5654 to talk through current listings or what your island property would sell for today.