Seasonal guide
Explore
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Island Hopping Season in Holmes Beach (Anna Maria Island)
Island hopping is simple when you stay central in Holmes Beach.
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 travelers who want to explore multiple island neighborhoods.
Highlights
- *Central base for easy island exploration.
- *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 island hopping season travel, start watching open dates about 4 to 8 weeks out.
If you can shift arrival by a day or two, a Sunday or Monday 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
Take one day for Anna Maria City and another for Bridge Street.
Use the pool to rest between outings.
Plan by month
Helpful links
Explore the island with ease. Check open dates.