Holiday planning
Romantic
A Week Around Valentine's Weekend on Anna Maria Island (Holmes Beach)
Valentine's weekend feels best as part of an unhurried week by the beach.
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 slow, romantic week at the beach.
Live calendar
Valentine's Weekend: Sunday, February 14, 2027
Booked: the week of Valentine's Weekend is not open for a 7-night stay on the live calendar. The nearest open windows are Nov 13-20, 2026 and Nov 30 - Dec 16, 2026.
In this rate period, the online booking needs a Saturday check-in; check-out can be any day, as long as the stay is at least 7 nights. For another arrival day, call the BeachRentals.Mobi office at 941-778-1979.
Highlights
- *Sunsets, a private pool, and a relaxed pace for two.
- *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 Valentine's 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 Valentine's Day.
Sample holiday rhythm
- -Arrival day: settle in, walk to the beach, and keep dinner close by.
- -Slow days: sleep in, swim, and watch the sunset from the side deck or on the sand one house away.
- -One evening: a dinner out on Bridge Street or Pine Avenue.
- -Last morning: coffee, one more swim, and a 10 AM 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
More holiday weeks
Other holidays on the island, or every holiday week.
Book a calm Valentine's week on the island. Check open dates.