Holiday planning
Romantic
❤️
Valentine's Weekend Stays in Holmes Beach (Anna Maria Island)
Valentine's Weekend works best when the plan is slow and beach-forward.
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 couples who want a simple, romantic beach getaway.
Highlights
- *Sunsets, a private pool, and a relaxed couples vibe.
- *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 Valentine's Weekend, start watching open dates about 6 to 9 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, beach walk, and a quiet dinner nearby.
- -Day 2: slow morning, pool reset, sunset on the Gulf.
- -Day 3: coffee on Pine Avenue, last swim, checkout.
Local tips
Plan a sunset walk, then dinner around Bridge Street.
Sleep in and make the pool your afternoon reset.
Plan by month
Helpful links
Book a calm Valentine's Weekend on the island. Check open dates.