Holiday planning
Late summer
🏝️
Labor Day Week Stays in Holmes Beach (Anna Maria Island)
A full Labor Day week gives you space to slow down and breathe.
The Sandbox is a relaxed, dog-friendly home base with a heated pool and walk-to-beach access.
Best for
Best for travelers who want a full week to unwind at the end of summer.
Highlights
- *An easy week of late-summer sunshine and beach time.
- *Private heated pool for off-beach time.
- *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 Labor Day Week, start watching open dates about 8 to 12 weeks out.
If you can shift arrival by a day or two, a Saturday arrival can unlock more options.
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
Build in a midweek Pine Avenue afternoon to change the pace.
Use the pool for a daily reset.
Plan by month
Helpful links
Reserve a Labor Day week early. Check open dates now.