Seasonal guide
Early summer
S
May Pre-Summer Weeks in Holmes Beach (Anna Maria Island)
May delivers warm days and a calmer beach scene before peak summer.
Sandbox Beach House keeps the plan easy: private pool, beach access, and a cozy layout for small groups.
Best for
Best for early summer trips with lighter crowds.
Highlights
- *Warm water, sunny days, and an early-summer vibe.
- *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 may pre-summer weeks travel, start watching open dates about 6 to 9 weeks out.
If you can shift arrival by a day or two, a Sunday arrival can open more options.
Sample stay rhythm
- -Arrival day: groceries, quick beach walk, and pool time.
- -Midweek: slow mornings, beach time, and an easy dinner out.
- -One day: trolley ride to Bridge Street or Anna Maria City.
- -Last day: sunrise stroll and a final pool dip.
Local tips
Plan a Pine Avenue afternoon for shopping and snacks.
Keep evenings flexible with pool time and a simple meal.
Plan by month
Helpful links
Lock in a May pre-summer week. Check open dates.