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Book your Anna Maria Island beach vacation for October 2026. Private pool, steps to the beach, and dog-friendly accommodations at Sandbox Beach House.
Fall offers the best of both worlds: warm beach weather without the summer heat, fewer crowds, and still-warm Gulf waters. Perfect for a peaceful, relaxing getaway.
Perfect 75-85°F with lower humidity
Perfect 75-85°F with lower humidity - ideal for beach activities and outdoor relaxation.
Walk directly to the Gulf of Mexico without crossing busy roads. Your beach paradise awaits.
Heated pool in your own backyard - perfect for morning swims or evening relaxation.
Choose from 1 available week above, or view our full calendar to find the perfect dates for your Anna Maria Island vacation.