Plan your trip
Group guides
Traveling with 9 or more?
🏡 Sleeping arrangements
In the City of Anna Maria, a vacation rental can hold no more than 8 people, day guests included, and never more than two per bedroom. That cap applies per lot, even when there are two houses on it. Bigger groups usually split across neighboring rentals or look in Holmes Beach and Bradenton Beach. City of Anna Maria, Sec. 108-53
In Holmes Beach, homes in the R-2 to R-4 zones rent by the week (7 night minimum), while R-1 homes need a 30 day stay. Always check the maximum occupancy printed on the listing. City of Holmes Beach rental rules
Compare the towns🍽️ Eating together
Call ahead for big tables and go early, since several island favorites don't take reservations. These do:
- Sandbar Seafood & Spirits
- Mademoiselle Paris
- Harry's Grill
- Beach Bistro
- The Feast Restaurant
- Beach House Waterfront Restaurant
- Blue Marlin Seafood
- Bridge Street Bistro
- The Doctor's Office
- Swordfish Grill & Tiki Bar
- Mar Vista Dockside
- Shore
Or skip the wait: private chefs who cook at your rental.
🚎 Getting around
The island trolley is free and runs 6:00 a.m. to 10:30 p.m., so nobody has to be the driver. For carts, read the golf cart rules before you rent a fleet, and park legally: parking rules.
⛵ Boats that fit the whole crew
- Shore Thing Tiki Cruises1 to 44 guests; every boat has a bathroom
- SeaEO Luxury Boat ChartersUp to 13 passengers
- Anna Maria Island Dolphin ToursPrivate tours up to 12 guests
- Passage Key Dolphin ToursUp to 6 per private boat (a second boat takes groups up to 12)
- Sea Rocket Gulf Coast ParasailFly solo, tandem or triple; party boat up to 12