Holiday planning
School break
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Winter Break Stays in Holmes Beach (Anna Maria Island)
Winter Break is ideal for a warm-weather reset without a packed schedule.
A heated pool, walkable dining pockets, and a laid-back neighborhood keep holiday trips simple.
Best for
Best for families traveling during school break weeks.
Highlights
- *A warm break from winter with easy beach days.
- *Private heated pool for off-beach time.
- *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 Winter Break, start watching open dates about 12 to 16 weeks out.
If you can shift arrival by a day or two, a Saturday arrival can unlock more options.
Sample holiday rhythm
- -Arrival day: stock the kitchen, then unwind by the pool.
- -Midweek: beach mornings, easy lunches, and sunset walks.
- -One day: trolley ride to Bridge Street for dinner and dessert.
- -Departure day: early beach stroll and a final pool dip.
Local tips
Keep afternoons flexible with pool time and naps.
Plan one outing to Bridge Street for dinner.
Plan by month
Helpful links
Plan Winter Break early. Browse open dates now.