Holiday planning
Celebrate mom
A Week Around Mother's Day Weekend on Anna Maria Island (Holmes Beach)
Give mom a week that feels calm, sunny, and easy, with Mother's Day right in it.
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 family trips that feel special but low stress.
Live calendar
Mother's Day Weekend: Sunday, May 9, 2027
Booked: the week of Mother's Day Weekend is not open for a 7-night stay on the live calendar. The nearest open windows are Jul 12-24, 2027 and Aug 7-14, 2027.
Highlights
- *A gentle, beach-first week that feels like a gift.
- *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 Mother's Day 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 Mother's Day.
Sample holiday rhythm
- -Arrival day: check in at 4 PM, take a first swim, and keep dinner simple.
- -Most days: beach in the morning, a pool or nap break after lunch, and a sunset walk.
- -One day: ride the free island trolley to Anna Maria City or Bridge Street.
- -Last morning: pancakes, a final beach visit, and checkout by 10 AM.
Local tips
Plan a relaxed brunch, then head to the beach.
End the day with a poolside sunset moment.
Plan by month
Helpful links
More holiday weeks
Other holidays on the island, or every holiday week.
Plan a thoughtful Mother's Day week. Check open dates.