Seasonal guide
Car-free
S
Trolley Season in Holmes Beach (Anna Maria Island)
Trolley season is about hopping between island neighborhoods with ease.
Sandbox Beach House keeps the plan easy: private pool, beach access, and a cozy layout for small groups.
Best for
Best for travelers who want to explore the island without driving.
Highlights
- *Easy island access without the car.
- *Private heated pool for a calm reset between outings.
- *Walk to the Gulf without crossing busy roads.
- *Central Holmes Beach base near Pine Avenue and Bridge Street.
- *Dog friendly for well-behaved pups 35 lbs or less.
Timing and open dates
For trolley season travel, start watching open dates about 4 to 8 weeks out.
If you can shift arrival by a day or two, a Sunday arrival can open more options.
Sample stay rhythm
- -Day 1: arrive, beach walk, and a relaxed dinner nearby.
- -Day 2: beach morning, pool reset, and sunset on the Gulf.
- -Day 3: coffee on Pine Avenue, last swim, checkout.
Local tips
Ride the trolley to Bridge Street for dinner.
Keep beach mornings close and simple.
Plan by month
Helpful links
Plan a trolley-friendly stay. Check open dates.