Seasonal guide
Longer stays
Extended Monthly Stays in Holmes Beach (Anna Maria Island)
Monthly stays let you settle in and enjoy a true island routine. They are priced at the seasonal weekly rate, with no monthly discount.
The Sandbox is a relaxed, dog-friendly home base with a private pool and walk-to-beach access.
Best for
Best for travelers who want a longer, slower island rhythm.
Highlights
- *A relaxed pace with time to explore the island.
- *Private saltwater pool for a calm reset between outings. 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.
- *Walk to the Gulf without crossing a road: the beach is one house away.
- *Central Holmes Beach base, a short drive or free trolley ride from Pine Avenue and Bridge Street.
- *Dog friendly for one well-behaved dog up to 35 lb, with approval. The $150 per week pet fee is charged at booking.
Timing and open dates
For extended monthly stays travel, start watching open dates about 12 to 20 weeks out.
If your dates are flexible, start from the open weeks on the live calendar. Every stay is at least seven nights, with check-in at 4 PM and check-out at 10 AM.
In many rate periods the online booking needs a Saturday check-in; for another arrival day, call the BeachRentals.Mobi office at 941-778-1979.
Sample stay rhythm
- -Week 1: settle into a beach-pool rhythm and stock the kitchen.
- -Week 2: add Pine Avenue afternoons and a Bridge Street dinner.
- -Week 3: explore different beaches and keep evenings simple.
- -Final stretch: slow mornings, pool resets, and sunset walks.
Local tips
Build in one day each week for a new neighborhood or beach.
Use the pool and patio for quiet afternoons.
Plan by month
Helpful links
Plan a longer stay and settle in. Check open dates.