Anna Maria IslandA seven-mile Gulf-of-Mexico barrier island between Tampa Bay and Sarasota — three small towns (Anna Maria, Holmes Beach, Bradenton Beach), a strict 35-foot building height cap, and a free trolley running every twenty minutes

Anna Maria Island guards the mouth of Tampa Bay just south of the Sunshine Skyway — seven miles of barrier sand divided into three small towns: Anna Maria at the north tip with Pine Avenue's cottage-shopfront row and the rebuilt 1911 Anna Maria City Pier; Holmes Beach in the middle with Manatee Public Beach, the local-favorite Skinny's Place, and the Beach Bistro's chef-driven dining room; and Bradenton Beach at the south end with the historic Bridge Street walking district, Coquina Beach's pavilions, and the long-running Bridge Tender Inn under the Cortez Bridge. The 35-foot height cap (one of the strictest on the Gulf coast) keeps every building under three stories.

Our rentals run from elevated stilted beach cottages on Gulf Drive in Holmes Beach to canal-front bungalows with private docks on Bradenton Beach's bay side, century-old key-lime cottages on Pine Avenue, and three-bedroom homes a block from Manatee Public Beach. Sarasota International (SRQ) sits 30 minutes south and Tampa International (TPA) 75 minutes north — most weekly renters fly into one and out of the other.