Holiday planning
School break
Presidents' Week Stays in Holmes Beach (Anna Maria Island)
Presidents' Week is ideal for families who want warm weather without peak summer crowds.
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 traveling during school break weeks.
Live calendar
Presidents' Week: Monday, February 15, 2027
Booked: the week of Presidents' 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.
In this rate period, the online booking needs a Saturday check-in; check-out can be any day, as long as the stay is at least 7 nights. For another arrival day, call the BeachRentals.Mobi office at 941-778-1979.
Highlights
- *A full week of sun and simple family routines.
- *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 Presidents' Week, start watching open dates about 10 to 14 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 matches your school's February break.
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
Build in pool breaks between beach time to keep the week easy.
Plan one afternoon at Bridge Street for dinner and dessert.
Plan by month
Helpful links
More holiday weeks
Other holidays on the island, or every holiday week.
Plan Presidents' Week early. Check open dates now.