Holiday planning
Winter escape
🌬️
Midwinter Break Stays in Holmes Beach (Anna Maria Island)
Midwinter is a great time to trade cold days for beach sun.
Holmes Beach is central on the island, so day trips to Anna Maria City and Bradenton Beach stay easy.
Best for
Best for quick winter escapes and long-weekend travelers.
Highlights
- *A quick winter escape with warm afternoons.
- *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 Midwinter Break, start watching open dates about 6 to 9 weeks out.
If you can shift arrival by a day or two, a Thursday arrival can unlock more options.
Sample holiday rhythm
- -Day 1: arrive, settle in, and take a sunset walk on the beach.
- -Day 2: beach morning, pool reset, then dinner around Bridge Street.
- -Day 3: coffee on Pine Avenue, one more swim, easy checkout.
Local tips
Plan a morning beach walk, then reset by the pool.
End the day with a sunset stroll.
Plan by month
Helpful links
Plan a midwinter beach break. Browse open dates.