Vacation rentals in Anna Maria Island
Anna Maria Island is the Gulf coast as it used to be: a seven-mile barrier island of pastel cottages, two piers, sea grapes, and strict height limits that keep the skyline to palm-tree level — with some of Florida's finest white-sand beaches.
Best time to book
March through May and October–November; the island's free trolley makes a car-free stay easy year-round.
Common rental types
Beach cottages · Canal homes with pools · Gulf-view condos · Weekly island duplexes
Getting there
Fly into Sarasota–Bradenton (SRQ), 30 minutes away, or Tampa (TPA), about an hour. Two drawbridges connect the island to Bradenton; a free trolley runs the whole island.
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Vacation rentals in Anna Maria Island
Real, bookable homes in Anna Maria Island — compare space, amenities, and nightly budget, then open a listing for photos and booking options.
Where to stay in Anna Maria Island
Anna Maria (north end)
The historic village — Pine Avenue's shops and cafés, the City Pier, and Bean Point's wild tip.
Holmes Beach
The island's center — the main public beach, groceries, and most cottage courts.
Bradenton Beach (south end)
Historic Bridge Street, the Rod & Reel Pier, and Coquina Beach's Australian pines.
Canal neighborhoods
Key West–style canals with pool homes and docks, a short trolley ride from the sand.
Learn Anna Maria Island before you book
Neighborhoods, seasons, and booking tips — the full destination guide.
Read the Anna Maria Island guide