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Bourbon City Rentals

Bourbon City Rentals

Anna Maria Island travel guide

The island, our way

Anna Maria Island sits just off Bradenton on the Gulf of Mexico. It has three small towns: Anna Maria, Holmes Beach, and Bradenton Beach. The Gulf sunsets here are famous for a reason. This Anna Maria Island travel guide collects the tips we give our own guests. These are the places we go ourselves.

Coming in February, March or April? Our Anna Maria Island spring break guide covers the weather, nonstop flights and big homes for families. Coming in June, July or August? See our Anna Maria Island summer vacation rentals guide.

Anna Maria Island travel guide: beachfront restaurant busy with diners at sunset

Beach Days

Bean Point beach at the north tip of Anna Maria Island

Our Favorite Places to Eat on the Water

The full list, with who takes reservations and who is cash only, is in our guide to where to eat on Anna Maria Island. The short version:

  • Sandbar Seafood & Spirits (Anna Maria): the best atmosphere and seafood on the island, right on the beach. Reserve, or expect a long wait.
  • Beach House Waterfront Restaurant (Bradenton Beach): tables in the sand, perfect at sunset.
  • Star Fish Company (Cortez): very casual dockside seafood. Bring cash; they don’t take cards.
  • Tide Tables (Cortez): small, casual, and very good seafood. It fills up fast.
  • Mar Vista (Longboat Key): old Florida charm under buttonwood trees strung with lights. Reserve.
  • The Ugly Grouper (Holmes Beach): outdoors, live music daily, and kid and dog friendly.

Off the Water

  • Peach’s on Manatee Ave: the best breakfast near the island.
  • Joey D’s: great Chicago-style pizza.
  • Olympic Cafe: great gyros, right next door to Joey D’s.
  • Oak & Stone in downtown Bradenton: a rooftop bar over the Manatee River.

Sunset Drinks

Swordfish Grill & Tiki Bar in the old Cortez fishing village, the Bridge Tender Inn on Bridge Street, and Daiquiri Deck’s rooftop in Bradenton Beach.

Traveling with a team? Families visiting IMG Academy stay with us often. See rentals near IMG Academy.

Anna Maria Island Travel Guide: When to Visit

February through April is peak season. Spring afternoons in Bradenton typically reach about 80°F, and the Gulf warms into the low 70s. Our Anna Maria Island spring break guide has the details. Summer brings the warmest water and afternoon thunderstorms, so plan beach time for the morning.

Getting Here

Sarasota-Bradenton International (SRQ) is about 20 minutes from our homes. Tampa (TPA) and St. Pete-Clearwater (PIE) are each about 50 to 55 minutes away. Walt Disney World is about 2 hours by car, so a park day fits into a beach week.

Getting Around the Island

Historic Bridge Street sign and palm trees in Bradenton Beach on Anna Maria Island

A free trolley runs the length of Anna Maria Island from 6 a.m. to 10:30 p.m., so you can park once and hop between beaches, restaurants and Bridge Street. The island keeps its Old Florida feel, with no high-rises. From our Bradenton homes, the drive to the beach takes about 10 to 15 minutes. Every stop in this Anna Maria Island travel guide is an easy trolley ride or short drive away.

Where to Stay

Bringing 40 or more? See our family reunion rentals near Anna Maria Island, two homes a quarter mile apart.

Heading to Kentucky too? See our Louisville travel guide, or browse all of our travel guides.

Book Direct and Save

Booking on our site means no platform fees, and you deal directly with the hosts. Questions about your trip? Reach out and we will help you plan.