Write the Next Chapter of your Vacation Story...

Experience the ultimate Anna Maria Island getaway with Once Upon A Beach, where world-class luxury meets laid-back island living. Our handpicked collection of premium vacation rentals on Anna Maria Island offers everything from charming beach cottages perfect for a romantic escape to sprawling luxury homes with private pools designed for unforgettable family gatherings. Each of our meticulously maintained vacation homes is thoughtfully appointed with high-end amenities, stylish furnishings, and unique touches that enhance your stay, ensuring an unparalleled vacation experience from booking to departure.

At Once Upon A Beach, our local team is dedicated to providing personalized concierge services and insider island tips, helping you make the most of your time in this enchanting beach destination. From the moment you arrive, you’ll find yourself just steps away from the powder-soft white sand and crystal-clear waters that make Anna Maria Island a true paradise. Whether you’re sunbathing, enjoying water activities, or exploring the charming local shops and eateries, our rentals place you right at the heart of island life.

As a boutique vacation rental and property management company, we take pride in delivering five-star service and an intimate island experience that goes beyond expectations. Nestled in one of Florida’s most picturesque and serene coastal communities, Once Upon A Beach ensures that every guest enjoys a seamless stay and creates lifelong memories.

Discover your perfect vacation home with us and start writing the next chapter of your Anna Maria Island story. Let us make your stay extraordinary – where your dream island getaway becomes a reality.