Who We Are

Falling in love with Anna Maria Island was the easy part—building a business here was the real adventure.

In 2016, Nicole set out with determination, grit, and a dream. She launched Once Upon A Beach from the ground up—personally managing everything from guest communication and accounting to maintenance and marketing. What started as a one-woman operation quickly grew as word spread about her boutique, hands-on approach to vacation rental management.

Our Approach

From the beginning, Nicole shaped Once Upon A Beach around values inspired by the island itself:
→ Care for every property with the same dedication as her own
→ Create meaningful, memorable guest experiences
→ Build trust with homeowners through consistency and transparency

This personalized approach stood apart from the one-size-fits-all model of larger companies and resonated with both guests and property owners. Growth came naturally—through referrals, community connections, and genuine relationships.

Who We Are Today

Today, Once Upon A Beach remains a locally owned, community-driven business with an office in the heart of downtown Anna Maria on charming Pine Avenue.

Our small but highly skilled team specializes in every aspect of short-term rental management, including:

City compliance and licensing
Property care and maintenance
Guest services and hospitality
Marketing, social media, and storytelling

We’ve grown in size and sophistication, but our commitment to personalized, detail-driven service has never changed.

Rooted in Community

We’re honored to welcome travelers discovering Anna Maria Island for the first time, longtime visitors who return year after year, and families celebrating life’s milestones. Just as importantly, we partner with local homeowners who value a management style grounded in professionalism, local insight, and genuine care for the island community.

For us, this isn’t just a place to work. It’s where our kids learn, where our neighbors live, and where the community’s heartbeat is felt most strongly. That involvement shapes the way we care for our homes, our guests, and our owners, with the same level of pride and responsibility we bring to supporting our local school and the families who call Anna Maria home.

More Than Rentals

At Once Upon A Beach, we go beyond simply managing properties. We act as a bridge between guests, homeowners, and Anna Maria Island itself. From insider recommendations to thoughtfully curated stays, our goal is to connect people with the authentic spirit of island living.

As the sole point of contact for our guests, we provide a seamless, stress-free experience from booking to departure—ensuring every stay reflects the warmth, charm, and beauty of the island we call home.

Once Upon A Beach Books & Gift Shop

Step off the sand and into our cozy corner on Pine Avenue. The Once Upon A Beach Bookstore & Gift Shop is more than a storefront—it’s a place to browse island-inspired books, unique gifts, and beach-chic treasures you won’t find anywhere else.

Whether you’re looking for a vacation read, a keepsake to remember your trip, or just want to say hello, we’d love to see you. Our team is always happy to answer questions about Anna Maria Island or your stay.

Explore the Bookstore & Gift Shop