Your Perfect Anna Maria Island Getaway Awaits

Write Your Next Vacation Story ✨🌺 🌴

We noticed you’ve been exploring vacation options on Anna Maria Island, and we’d love to help make your getaway a reality! ✨

At Once Upon a Beach Vacation Rentals, we specialize in boutique, handpicked homes that combine comfort, style, and proximity to everything you love about the island. Each home is thoughtfully prepared with the details that make a big difference — fresh linens, fully stocked kitchens, and those little extras that make island living easy, like credit for beach chairs, umbrellas, and insider tips on the best dining and hidden gems.

Whether you’re dreaming of:

• 🐚 A charming cottage just steps from the beach

• 🌴 A spacious family home with room for everyone

• 🌅 A luxury retreat to truly unwind

…we have something for you.

Your vacation story deserves the perfect setting — and we’re here to make sure every detail is seamless. From the moment you arrive, we want you to feel at home, knowing everything you need to relax is already taken care of. All that’s left is for you to enjoy the sun, sand, and the special memories you’ll make with the people who matter most.

📅 Ready to check dates or see what fits your budget best? Click below and let’s start planning your perfect Anna Maria Island stay.

We’d be honored to host you and can’t wait to welcome you to your happy place. 🌴✨