Seasonal guide
Winter sun
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Winter Sun Escapes in Holmes Beach (Anna Maria Island)
Winter sun on AMI is all about simple beach days and warm afternoons.
Sandbox Beach House is a boutique 2BR/1.5BA in Holmes Beach with a heated pool and a short walk to the Gulf.
Best for
Best for winter travelers who want warmth and a calm pace.
Highlights
- *Sunlit days and a calm, uncrowded feel.
- *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 winter sun escapes travel, start watching open dates about 6 to 10 weeks out.
If you can shift arrival by a day or two, a midweek 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
Use the pool for a mid-afternoon reset.
Plan an easy dinner on Bridge Street.
Plan by month
Helpful links
Chase winter sun on AMI. Check open dates now.