Once Upon A Beach Vacation Rentals

09/02/2026

We know there are a lot of questions surrounding the new and upcoming parking changes in the City of Anna Maria… and we want our owners and guests to know that we’re here to help. 🌴

At Once Upon A Beach, being local means more than simply managing vacation homes. We’re committed to being an active partner in our community and a voice and resource for our residents, homeowners, and visitors.

Nikki, our owner, attended Monday’s community parking meeting, where we listened, learned, asked questions, and participated in the conversation surrounding the proposed changes including paid parking.

Most importantly: these changes will not keep our guests from enjoying your Anna Maria Island beach vacation. 🏖️

As details are finalized, we’re committed to helping our guests and owners understand exactly what the changes mean and how to navigate them. Parking maps will be available on our website as soon as available.

Have a question? Don’t hesitate to call or email us… we’re local, we’re paying attention, and we’re here to help. 💙

Are you in favor or opposed to paid parking in the City of Anna Maria?

09/01/2026

Want to add a seafood boil to your island vacation? Yes, please! 🙋🏼‍♀️ 🦀 🍻

We’re giving ONE lucky winner a FREE Shark Bite Signature Bay Bucket! 🦈🪣🔥

Ready to enter? Tell us your favorite seafood protein to throw in your seafood boil! 🦞🦀🦐

HOW TO ENTER:
❤️ Like this post
📲 Follow us on Instagram OR follow us on Facebook
🦞 Comment your favorite seafood protein — Lobster, Crab, Oysters, Shrimp or Scallops
🌴 Tell us what month you’re visiting AMI!
— No trip booked? Comment the month you’d love to visit
— AMI local? Comment LOCAL!

👯 BONUS ENTRY: Tag a friend! Each friend tagged = an additional entry!

That’s it! One lucky seafood lover will be taking home a Shark Bite Signature Bay Bucket! 🌴🦈

What protein are you picking?! 👇

Winner must like this post, follow us on Instagram or Facebook, and comment to qualify. Giveaway is not sponsored, endorsed, administered by, or associated with Instagram or Facebook.

09/01/2026

✨ 10 YEARS = 10% OFF ✨

We’re celebrating 10 years of Once Upon A Beach — and kicking off our 10th anniversary month with a little something for YOU. 🌴🥂

For the entire month of September, book a new Once Upon A Beach vacation and receive:

☀️ 10% OFF YOUR STAY
🏝️ Stays of 4–10 nights
✨ Use promo code 10CHAPTERS
🌴 Book direct at onceuponabeachami.com

For 10 years, you’ve trusted us with one of the best parts of your story — your vacation. From first trips to AMI to annual traditions, family celebrations, sunsets, sandy toes and “we’re never leaving” moments… you’ve helped write our story, too.

Here’s to 10 years, 10 chapters & the next vacation story waiting to be written. 🌴✨

New reservations booked during September only. Excludes holiday and spring break weeks. Cannot be combined with other discounts. Additional restrictions may apply.

FloridaVacation BeachVacation 10Years10Chapters

Find your Anna Maria Island beach rental today. We have a pristine collection of luxury Anna Maria Island vacation rentals curated by local stewards who treat every home like their own.

08/31/2026

🌴✨ JUST ADDED: Hidden Palms ✨🌴

Welcome Hidden Palms to the exclusive Once Upon A Beach portfolio! 🌊

This beautifully updated 3 bedroom, 2 bathroom Holmes Beach retreat brings all the tropical vacation vibes — a private pool surrounded by lush landscaping, gorgeous interiors, and the beach just minutes away. 🌺☀️👙

And because she’s brand new to our collection… the calendar is WIDE open. 👀

Be one of the first to make Hidden Palms part of your Anna Maria Island story. 🏝️

AnnaMariaIslandVacation FloridaVacation BeachHouse VacationRental VisitAMI BeachVacation

08/30/2026

Labor Day plans = handled. 🍺🌴☀️ In true Jimmy Buffett style!

There’s still time to trade the long weekend at home for island time on Anna Maria Island. We have a few last-minute openings and some specials too good to leave sitting empty. 👀

Pack the flip-flops, grab a cheeseburger in paradise, cold one at Skinny’s, and we’ll handle the beach house. 🏡🌊

Come live the parrot-heads life with us 🦜

📞 Call us directly for our Labor Day last-minute specials: 941-584-5844

See you on the island. 🌴 Fins up! 🤘🏼

08/29/2026

🌴 HOUSE HIGHLIGHT | THE PALM AT BEAN POINT 🌴

New to the Once Upon A Beach collection and bringing all the old Florida charm + modern island luxury. ✨

Welcome to The Palm at Bean Point, a beautifully updated 3-bedroom, 2-bath, single-story retreat tucked away at the tip-top of Anna Maria Island, just moments from the iconic Bean Point beach access. 🌊

Step inside and you’ll find thoughtful Florida designer touches throughout, but outside is where this home really shines. An enormous private pool, lush tropical surroundings and plenty of spaces to lounge, dine and unwind give The Palm its own little Royal Palm resort feel. 🌴🥂

No stairs. No high-rises. Just laid-back luxury in one of the most special corners of the island.

Your Bean Point vacation story starts here. 🤍

🌟 https://www.onceuponabeachami.com/rentals/the-palm-at-bean-point

08/28/2026

Your vacation story deserves a little encore. 🌴📸

Share your favorite Once Upon A Beach vacation memory with us for a chance to win a 3-Day Golf Cart Rental + OUAB Swag Bag! 🛺☀️

Here’s how to enter:
• Like this post + make sure you’re following Once Upon A Beach
• Tag us in OR email us a photo from your recent AMI vacation
• Submit by September 30th

Beach days, family moments, sunsets, golf cart adventures, first trips, tenth trips… we want to see the moments that became part of your Anna Maria Island story. 💙

Winner announced after 9/30. Good luck! 🌊

08/25/2026

As we reflect on the life and legacy of Dolly Parton, we’re reminded of the incredible impact she has made on children and families everywhere.

The Center of Anna Maria Island is honored to be an official partner of Dolly Parton's Imagination Library, bringing FREE books every month to children ages 0–5 living in our participating ZIP codes:

📍 34216 • 34217 • 34215 • 34209 • 34228

Thanks to Dolly and the generous support of donors to The Center, eligible children can have a new, age-appropriate book delivered right to their home every month. ❤️📖

👉 Sign your child up today:
https://centerami.org/youth/dolly-partons-imagination-library/

RIP Dolly, and thank you for a lifetime of making a difference. 💜