Seasonal guide
Longer stays
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Extended Monthly Stays in Holmes Beach (Anna Maria Island)
Monthly stays let you settle in and enjoy a true island routine.
The Sandbox is a relaxed, dog-friendly home base with a heated pool and walk-to-beach access.
Best for
Best for travelers who want a longer, slower island rhythm.
Highlights
- *A relaxed pace with time to explore the island.
- *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 extended monthly stays travel, start watching open dates about 12 to 20 weeks out.
If you can shift arrival by a day or two, a midweek arrival can open more options.
Sample stay rhythm
- -Week 1: settle into a beach-pool rhythm and stock the kitchen.
- -Week 2: add Pine Avenue afternoons and a Bridge Street dinner.
- -Week 3: explore different beaches and keep evenings simple.
- -Final stretch: slow mornings, pool resets, and sunset walks.
Local tips
Build in one day each week for a new neighborhood or beach.
Use the pool and patio for quiet afternoons.
Plan by month
Helpful links
Plan a longer stay and settle in. Check open dates.