Anna Maria's housing stock is low-rise and beach-oriented, reflecting the island's strict building-height limits and its charter protections against high-rise development. The market consists of single-family homes, cottages, and small-scale vacation rentals and local resorts rather than large hotels or condominium towers. Properties are sought after for their proximity to the Gulf and the island's quiet, Old Florida character. The absence of high-rises is a defining — and deliberately preserved — feature of the community's real estate.

Life in Anna Maria is defined by the beach and a deliberately unhurried, Old Florida pace. The island's charter restricts building heights, so the city has no high-rises or large hotels, and a 35 mph speed limit keeps traffic gentle. Residents and visitors move between the sand, the water, and the walkable blocks of Pine Avenue, where small shops and restaurants set the tone. The lifestyle is casual and outdoors-oriented, centered on sunsets, boating, fishing, and Gulf Coast relaxation rather than large-scale development.

Anna Maria is part of Manatee County, whose public school district serves the island and the surrounding mainland. Anna Maria Elementary School, located on the island, provides a close-to-home option for younger students, while older students attend district middle and high schools on the mainland. The island's small scale keeps the school community intimate, with families connected through local institutions and island life.

Anna Maria Island is reached from the mainland by bridge from Bradenton, linking the city to the Sarasota-Bradenton region. The nearest airports are Sarasota–Bradenton International Airport and Tampa International Airport, both on the mainland and within driving distance. Once on the island, the 35 mph speed limit and compact, flat geography make walking, biking, and short car trips the norm, with the island's bridges serving as the primary connection to mainland services and employment.

Anna Maria's recreation centers on the Gulf of Mexico, with about seven miles of white-sand beaches along the island for swimming, shelling, and sunsets. Bean Point at the northern tip is prized for its wide, unobstructed views, while boating, kayaking, paddleboarding, and fishing are woven into daily life. The island's flat, low-traffic streets and 35 mph speed limit make walking and cycling pleasant ways to get around, reinforcing the easy, outdoors-oriented pace of the community.