Holiday planning
Summer finale
A Week Around Labor Day Weekend on Anna Maria Island (Holmes Beach)
Labor Day weekend is a great way to close out summer, and a full week gives it room to breathe.
Stay in central Holmes Beach with a private pool, a calm neighborhood feel, and easy access to Pine Avenue and Bridge Street.
Best for
Best for an end-of-summer week that takes in the holiday.
Live calendar
Labor Day Weekend: Monday, September 6, 2027
Open: a 7-night stay that includes Labor Day Weekend fits in the open window Aug 21 - Oct 19, 2027. See the manager's itemised quote for Sep 4-11, 2027.
Highlights
- *Late-summer beach days with a calm island pace.
- *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 Weekend, 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: check in at 4 PM, stock the kitchen, and walk to the beach for sunset.
- -Holiday days: you are already settled in, so skip the holiday traffic and spend them on the beach, by the pool, and at dinner out.
- -Quieter days: slow mornings, pool afternoons, and a trolley ride to Anna Maria City or Bridge Street.
- -Last morning: one more swim and a 10 AM checkout.
Local tips
Take a morning beach walk, then cool off in the pool.
Head to Pine Avenue for an easy dinner plan.
Plan by month
Helpful links
More holiday weeks
Other holidays on the island, or every holiday week.
Plan a Labor Day beach week. Browse open dates.