Holiday planning
Fall week
A Week Around Halloween Weekend on Anna Maria Island (Holmes Beach)
A week at the beach around Halloween is a fun and easy reset.
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 fall trips that keep the plan simple.
Live calendar
Halloween Weekend: Saturday, October 31, 2026
Booked: the week of Halloween Weekend is not open for a 7-night stay on the live calendar. The nearest open windows are Nov 13-20, 2026 and Nov 30 - Dec 16, 2026.
Highlights
- *A light, beach-forward week with a hint of fall.
- *Private saltwater pool. Pool heat is added to online bookings by default ($150 for a one-week stay; the office adjusts it for longer stays). You can decline it - just ask the office.
- *Direct beach access one house off the beach, with no road to cross.
- *Central Holmes Beach base, with Pine Avenue and Bridge Street an easy trolley ride or drive away.
- *One dog up to 35 lb is welcome with approval. The $150 per week pet fee is charged at booking.
Timing and open dates
For Halloween Weekend, start watching open dates about 6 to 10 weeks out.
Every stay is at least 7 nights, with check-in at 4 PM and checkout at 10 AM, so choose a week that includes Halloween.
Sample holiday rhythm
- -Arrival day: check in at 4 PM, stock the kitchen, and walk to the beach for sunset.
- -Holiday days: you are already settled in, so skip the holiday traffic and spend them on the beach, by the pool, and at dinner out.
- -Quieter days: slow mornings, pool afternoons, and a trolley ride to Anna Maria City or Bridge Street.
- -Last morning: one more swim and a 10 AM checkout.
Local tips
Take a sunset walk, then keep dinner casual nearby.
Use the pool for a quiet afternoon break.
Plan by month
Helpful links
More holiday weeks
Other holidays on the island, or every holiday week.
Book a Halloween week at the beach. Browse open dates.