Holiday planning
Summer kickoff
Memorial Day Weekend Stays in Holmes Beach (Anna Maria Island)
Memorial Day Weekend marks the start of summer and pairs perfectly with beach time.
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 early summer escapes and long-weekend travelers.
Highlights
- *Beach days and a private pool to start summer right.
- *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 Memorial Day Weekend, start watching open dates about 6 to 10 weeks out.
If you can shift arrival by a day or two, a Thursday arrival can unlock more options.
Sample holiday rhythm
- -Day 1: arrive, settle in, and take a sunset walk on the beach.
- -Day 2: beach morning, pool reset, then dinner around Bridge Street.
- -Day 3: coffee on Pine Avenue, one more swim, easy checkout.
Local tips
Start with a beach morning, then use the pool to cool off.
Grab dinner on Bridge Street to end the day.
Plan by month
More holiday guides
Plan ahead with other holiday windows and island celebrations.
Memorial Day Week Stays in Holmes Beach (Anna Maria Island)
Plan a Memorial Day Week stay in Holmes Beach with a heated pool, walk-to-beach access, and a calm island routine.
See guide →
Father's Day Weekend Stays in Holmes Beach (Anna Maria Island)
Plan a Father's Day Weekend escape to Holmes Beach with a private heated pool, walkable dining, and easy beach access.
See guide →
Fourth of July Stays in Holmes Beach (Anna Maria Island)
Celebrate the Fourth of July on Anna Maria Island with walk-to-beach access, a private heated pool, and a Holmes Beach home base.
See guide →
Fourth of July Week Stays in Holmes Beach (Anna Maria Island)
Book a full Fourth of July Week on Anna Maria Island with a private heated pool, beach access, and a relaxed Holmes Beach base.
See guide →
Fourth of July Weekend Stays in Holmes Beach (Anna Maria Island)
Spend Fourth of July Weekend in Holmes Beach with walk-to-beach access, a private heated pool, and easy island dining.
See guide →
Labor Day Weekend Stays in Holmes Beach (Anna Maria Island)
Wrap up summer with Labor Day Weekend in Holmes Beach, featuring walk-to-beach access and a private heated pool.
See guide →
Helpful links
Start summer with a beach long weekend. Browse open dates.