Anna Maria Island has no lack of waterfront activities. Boating, fishing, swimming, relaxing, lots of "salty" activities on and off Anna Maria Island. Review our list of waterfront vacation rentals. Bradenton Beach offers the Bay and Gulf all within a few blocks while Holmes Beach and Anna Maria City provides more private single family homes right on the water. Want to bring your boat? No Problem! You are just a few clicks away from finding your perfect Anna Maria Island Bayfront, Intercoastal, Gulf Front or Canal vacation rental below.