Anna Maria Island Homes for Sale & Living Guide

Anna Maria Island has an Old Florida feel: low-rise beach cottages, a free trolley, piers and sunsets over the Gulf. Whether you're buying a vacation home, an investment rental, a full-time residence or selling, we're Eric and Traci Bolen of Sand + Sea Homes with eXp Realty, and we'd love to help.

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Life on Anna Maria Island

Anna Maria Island is a barrier island in Manatee County, west of Bradenton, with three cities: Anna Maria to the north, Holmes Beach in the middle and Bradenton Beach to the south. Island life revolves around the beach, fishing piers, local restaurants and shops, and getting around by bike or the free island trolley. It's busy with visitors in season and calmer the rest of the year.

The Three Island Cities

Anna Maria. Quiet residential streets, the Anna Maria City Pier and the shops along Pine Avenue. Its vacation rentals are registered with the city.
Holmes Beach. The island's largest city (nearly 4,000 residents), with homes, condos, canals and Manatee Public Beach.
Bradenton Beach. Bridge Street's shops and restaurants, its own historic City Pier, and Coquina Beach.

Each city has its own rules on rentals, building and parking, so we'll check the details for any property you're considering.

Home Types and Prices

You'll find beach cottages, elevated single-family homes, duplexes, condos and luxury Gulf-front homes. Many are used as vacation rentals.

Anna Maria Island FL housing market, September 2026, by island city: median sale price $1,704,188 in Anna Maria, $1,324,369 in Holmes Beach and $964,541 in Bradenton Beach, with 15, 63 and 15 sales. Source: Redfin.

Redfin reports market data separately for each island city. In September 2026, the median sale price was $1,704,188 in Anna Maria (up 0.5% year over year, 15 sales), $1,324,369 in Holmes Beach (up 52.2%, 63 sales) and $964,541 in Bradenton Beach (up 22.5%, 15 sales). With this few sales, medians swing a lot from month to month, so ask us for current comps on the specific street or building.

Selling? See our selling page or get a home value estimate.

Flood Zones, Insurance and Vacation Rental Rules

Flood zones. Much of the island is in FEMA flood zones. Check each property's flood zone, elevation certificate and claims history, and get flood quotes early.
Insurance. See whether Florida home insurance rates are coming down.
Vacation rentals. Short-term rentals are a big part of the island economy, but each city has its own rules. The City of Anna Maria requires annual vacation rental registration, with fees based on permitted occupancy. Holmes Beach requires a city Vacation Rental Certificate, issued after an inspection and valid for two years. Bradenton Beach has its own licensing rules, so check with that city directly. Confirm the current rules with the city before you buy for rental income, and read buying a second home or investment property.
Condos. Review milestone inspections and reserves: what to know before buying a Florida condo.
Full cost picture. See the hidden costs of buying a home in Sarasota, Manatee and Charlotte County.

Schools

The island is served by the School District of Manatee County. Anna Maria Elementary is on the island, and older students attend mainland schools. Confirm the assignment for any specific address with the district.

Getting Around

Manatee County's free Anna Maria Island Trolley runs daily from about 6 a.m. to 10:30 p.m. between the Anna Maria City Pier and Coquina Beach, and bikes and golf carts are popular for short trips. Bridges connect the island to Bradenton on the mainland, and Longboat Key is just to the south. Expect heavy traffic and tight beach parking in season.

Why Work With Sand + Sea Homes

We're Eric and Traci Bolen, a husband-and-wife team of REALTORS with eXp Realty. We help island buyers weigh rental rules, insurance and flood risk alongside the beach-cottage charm, and we help sellers market island homes to the right buyers. If you're new to the area, our buying page walks you through the process, and our step-by-step buying timeline shows what to expect.

Ready to explore Anna Maria Island? Call or text Eric & Traci at (941) 352-2121, search the homes above, or get your home's value.

Anna Maria Island FAQ

What cities are on Anna Maria Island?
There are three: Anna Maria at the north end, Holmes Beach in the middle and Bradenton Beach at the south end. Each has its own city government and rules.

Can I use an Anna Maria Island home as a vacation rental?
Often yes, but rules vary by city. Anna Maria requires annual vacation rental registration, and Holmes Beach requires a Vacation Rental Certificate with an inspection. Check each city's current rules, and any association limits, before you buy.

How much do homes cost on Anna Maria Island?
In September 2026, Redfin reported median sale prices of $1,704,188 in Anna Maria, $1,324,369 in Holmes Beach and $964,541 in Bradenton Beach. These are small markets, so medians can swing month to month.

Is there free transportation on Anna Maria Island?
Yes. Manatee County's free Anna Maria Island Trolley runs daily between the Anna Maria City Pier and Coquina Beach, and bikes and golf carts are popular for short trips.

Do I need flood insurance on Anna Maria Island?
Many island properties are in FEMA flood zones, and lenders typically require flood insurance in high-risk zones. Check the flood zone and get quotes before you make an offer.