Location guide
From Holmes Beach
Anna Maria Island: Towns, Beaches and Getting Around
Anna Maria Island blends sugar-sand beaches with pastel cottages and a small-town rhythm that feels unhurried. It is best for travelers who want easy beach days, local dining, and a low-key island pace, with three small towns and the free trolley to tie them together. Our Holmes Beach cottage sits mid-island, so every town on the island is an easy ride on the free island trolley.
Travelling with a dog? The Sandbox takes one dog up to 35 lb with approval: see our dog-friendly rental in Holmes Beach.
Local highlights
Beach type
Wide Gulf beaches with soft white sand and calm surf.
Restaurants
Casual seafood spots, ice cream stops, and waterfront patios.
Walkability
Bikeable neighborhoods plus the free island trolley.
Vibe
Old-Florida, easygoing, family-friendly.
Annual events here: Fourth of July parade, Christmas parade. See also the holiday weeks, each with its live calendar.
The island's three towns
North end
Anna Maria
Quiet streets, Pine Avenue's shops and cafes, the City Pier, and Bean Point at the island's northern tip.
Mid-island
Holmes Beach
The central town, with Manatee Public Beach, everyday shops and cafes, and The Sandbox cottage one house off the beach.
South end
Bradenton Beach
Historic Bridge Street, its fishing pier and waterfront dining, with Coquina Beach's wide sands just to the south.
Getting around
The free island trolley runs the length of the island every 20 minutes, so you can reach all three towns without moving the car. Two bridges, on Manatee Avenue and Cortez Road, connect the island to mainland Bradenton, and Sarasota Bradenton (SRQ) is the closest airport. See the best beaches on Anna Maria Island and where to stay on the island.
Where to stay: Sandbox Beach House in Holmes Beach
Sandbox Beach House is a relaxed, family-friendly 2-bedroom cottage in Holmes Beach for up to 6 guests, one house off the beach, with a private saltwater pool and a 7-night minimum stay. One dog up to 35 lb is welcome with approval ($150 per week pet fee, charged at booking). Anna Maria Island is an easy ride on the free island trolley from our Holmes Beach base, so day trips feel effortless.
Bringing a dog?
Dogs are not allowed on the island's beaches, so plan walks, patios and off-island outings with these guides.
Explore nearby
Also explore Holmes Beach, Bradenton Beach. See our walk-to-beach location, review the Pet policy (one dog up to 35 lb), and peek at pool and family spaces.
Ready to plan your Anna Maria Island week?
Confirm your dates, then build your beach + pool rhythm around the part of Anna Maria Island you like most.
Check availability at Sandbox Beach House in Holmes Beach, your base for Anna Maria Island.