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 private pool and direct beach access, with no road to cross.
Best for
Best for travelers who want a full week to unwind at the end of summer.
Live calendar
Labor Day Week: Monday, September 6, 2027
Open: a 7-night stay that includes Labor Day Week fits in the open window Aug 21 - Oct 18, 2027. See the manager's itemised quote for Sep 4-11, 2027.
Highlights
- *An easy week of late-summer sunshine and beach time.
- *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 Labor Day Week, start watching open dates about 8 to 12 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 Labor Day.
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
More holiday weeks
Other holidays on the island, or every holiday week.
Reserve a Labor Day week early. Check open dates now.