Once Upon A Beach Vacation Rentals

06/19/2026

☀️🚤 OUAB Boat Day 🚤☀️

Some days the office looks a little different around here! 🌴

The Once Upon A Beach crew traded keyboards for boat keys and spent the day enjoying the waters that make Anna Maria Island such a special place. From sunshine and salt air to great company and island views, it was the perfect reminder of why we love sharing this slice of paradise with our guests.

Because sometimes the best way to experience island life is from the water. 🌊🐬☀️

ParadiseFound

Nicole / Nikki Natiello
Brittany Holley
Josh Haldeman
Heather Booth

06/17/2026

06/10/2026

🏝️🏄‍♀️ 🤟

06/09/2026

✨ NEW TO THE ONCE UPON A BEACH COLLECTION ✨

Introducing Vela Mar 🌴

Where coastal sophistication meets effortless island living.

Step inside a home designed for gathering, relaxing, and making memories. Inspired by modern luxury with subtle Miami and Latin influences, Vela Mar blends clean architectural lines, warm textures, and resort style outdoor spaces into one unforgettable Anna Maria Island escape.

☀️ Private pool and outdoor oasis
🌴 Elevated designer interiors
🍹 Spaces made for entertaining and reconnecting
🏖️ Minutes from the sugar sand beaches of Anna Maria Island
✨ Thoughtfully curated details throughout

From morning coffee by the pool to evenings spent under the palms, Vela Mar invites you to slow down, settle in, and experience island life in a whole new way.

Your next vacation story begins here.

📖 Book your stay:
Vela Mar⁠

🌐 www.onceuponabeachami.com
📞 Call or text: 941-584-5844
✉️ Email: [email protected]
🎵 tiktok.com/onceuponabeachami

🌊⛱☀️🌴
PROMO CODE: WRITEYOURSTORY

06/08/2026

🐦🌴 Three Little Birds 🌴🐦

Some places are designed for vacation.

Others are designed for connection.

At Three Little Birds, mornings begin with Gulf breezes and coffee on the porch, afternoons are spent splashing in the private heated pool and spa, and evenings bring everyone together for games, laughter, and unforgettable island sunsets. With Gulf views, a bonus outdoor entertainment space, and the beach just a short stroll away, this Anna Maria Island retreat was made for making memories.

✨ Gulf & Bay views
✨ Private heated pool & spa
✨ Outdoor bar, TV & ping pong area
✨ 4 bedrooms | Sleeps 8
✨ Just a 3-minute walk to the beach
✨ Thoughtfully designed for gathering and reconnecting

Because the best island stories aren’t about where you stayed.

They’re about who you shared it with.

Book your stay and start writing your vacation story.

🌊☀️🏝️🐚✨

🌐 www.onceuponabeachami.com
📞 Call or text: 941-584-5844
✉️ Email: [email protected]
🎵 tiktok.com/onceuponabeachami

🌊⛱☀️🌴
PROMO CODE: WRITEYOURSTORY

06/08/2026

🌴🐬 FINS UP, STRESS DOWN. 🐬🌴

Just two blocks from the sugar-white sands of Anna Maria Island, Fins Up is the kind of place where mornings start with coffee by the pool and afternoons drift effortlessly between the beach and island adventures. Featuring two private en-suite bedrooms, a heated pool with sun shelf, outdoor bar, and bright open living spaces, it’s the perfect escape for couples, small families, and anyone craving a little coastal reset.

✨ Private heated pool
✨ 2 bedrooms | 2 bathrooms | Sleeps 6
✨ Outdoor bar & covered seating
✨ Steps from the trolley
✨ Walkable to the beach
✨ Managed by a local Anna Maria Island team who knows the island best

The only thing missing is your flip-flops.

Book your island story today:
Fins Up⁠

🌐 www.onceuponabeachami.com
📞 Call or text: 941-584-5844
✉️ Email: [email protected]
🎵 tiktok.com/onceuponabeachami

🌊⛱☀️🌴
PROMO CODE: WRITEYOURSTORY

06/06/2026

Looking for something islandey to do today?!

🌊 The One Love AMI Skim Competition is almost here! 🌊

Get ready for a full day of skimboarding, beach vibes, and island energy on Anna Maria Island! Whether you’re competing or cheering from the sand, this is an event you won’t want to miss.

📅 Saturday, June 6th
⏰ 10:00 AM – 5:00 PM

🏄 Age Divisions:
• 7 & Under
• 8–12
• 13–17
• 18+

💲 $45 per participant
⚠️ Space is limited!

Competitor check-in starts at 8:30 AM.

For registration and event info visit https://centerami.org/events or call 📞 (941) 778-1908.

Presented by WEST COAST SURF SHOP, Tom Sanger Pool and Spa LLC,Slim's Place, GRub Tropical BBQ, Oneloveami.com, AMI Skim & Surf, and The Center 🌴

06/05/2026

FREE Public Turtle Walks will take place every Saturday during June and July.

Our first one is this Saturday, June 6th

Saturdays at 6:45 AM
Public Beach Access
4795 Gulf of Mexico Drive

Join our amazing volunteers for a morning walk on the beach while learning about the sea turtles and their nesting activities.

05/28/2026

✨ Welcome to Vela Mar ✨

Modern coastal luxury meets effortless island living at the newest addition to the Once Upon A Beach portfolio. 🌊☀️

Thoughtfully designed with elevated finishes, open gathering spaces, and a seamless indoor-outdoor flow, Vela Mar was created for the kind of vacation that feels both luxurious and easy. From sun-filled interiors and designer details to inviting outdoor living spaces made for pool days, evening cocktails, and slow mornings, every corner of this home was curated with intention.

Perfectly positioned on beautiful Anna Maria Island, Vela Mar offers the ideal balance of relaxation, connection, and upscale comfort, creating a backdrop for unforgettable family vacations, celebrations, and coastal escapes.

We are beyond excited to officially welcome Vela Mar to the Once Upon A Beach collection and cannot wait for guests to experience this incredible island retreat. 🐚✨

📍Anna Maria Island
🌴 Managed by Once Upon A Beach Vacation Rentals

🌐 www.onceuponabeachami.com
📞 Call or text: 941-584-5844
✉️ Email: [email protected]
🎵 tiktok.com/onceuponabeachami

🌊⛱☀️🌴
PROMO CODE: WRITEYOURSTORY