Holiday planning
Spooky season
Halloween Week Stays in Holmes Beach (Anna Maria Island)
Halloween Week on the island means beach mornings and cozy evenings.
The Sandbox is a 2-bedroom, 1.5-bath cottage in Holmes Beach for up to 6 guests, with a private saltwater pool and direct beach access one house off the beach.
Best for
Best for families who want a warm-weather Halloween week.
Live calendar
Halloween Week: Saturday, October 31, 2026
Booked: the week of Halloween Week 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
- *Warm days and easy nights during spooky season.
- *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 Week, 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 October 31.
Sample holiday rhythm
- -Arrival day: groceries, quick beach walk, and a calm pool dip.
- -Midweek: slow mornings, beach time, and a sunset dinner out.
- -One day: explore Anna Maria City or Bradenton Beach by trolley.
- -Last day: sunrise stroll, pack up, and head home refreshed.
Local tips
Keep afternoons free for pool time and easy dinners.
Plan one day for shopping and snacks on Pine Avenue.
Plan by month
Helpful links
More holiday weeks
Other holidays on the island, or every holiday week.
Plan a warm Halloween Week escape. Check open dates.