Seasonal guide
Extended winter
S
Snowbird Stays in Holmes Beach (Anna Maria Island)
Settle into a snowbird rhythm with beach mornings and easy routines.
Stay in central Holmes Beach with a private pool, a calm neighborhood feel, and easy access to Pine Avenue and Bridge Street.
Best for
Best for longer winter stays and seasonal escapes.
Highlights
- *A comfortable home base for longer winter stays.
- *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 snowbird 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
Plan a weekly Pine Avenue afternoon for a change of pace.
Use the pool as a daily reset.
Plan by month
Helpful links
Secure a snowbird stay early. Browse open dates.