Once Upon A Beach Vacation Rentals

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Once Upon A Beach Vacation Rentals Come write the next chapter of your vacation story with Once Upon a Beach Vacation Rentals.

As frequent visitors to Anna Maria Island, Florida, we quickly fell in love with the small town feel of this beach island paradise. We relocated here for the purpose of being able to enjoy this gem full time and make a business of our passion to share the island with others. It is our utmost goal to make every one of our guests instantly feel at home as a ‘true local’ in one of our unique, pristine, meticulously designed and luxurious accommodations. From two bedroom beach bungalows to a premier waterfront homes to sprawling multi-story single family homes. We take great pride in ensuring our homes are maintained with the highest standards in quality and care. We know planning a vacation can be stressful so we are dedicated to providing a personalized and stress free rental experience from booking to departure for all of our guests. As a boutique short term vacation rental & property management company, our guests experiences are everything and we look forward to helping you write the next chapter of your vacation story with us and welcome you back for years and years to come.

🌴🎶 BAYFEST IS BACK & WE'RE CELEBRATING 25 YEARS OF ISLAND FUN! 🎉One of Anna Maria Island's favorite traditions returns T...
10/16/2026

🌴🎶 BAYFEST IS BACK & WE'RE CELEBRATING 25 YEARS OF ISLAND FUN! 🎉

One of Anna Maria Island's favorite traditions returns THIS SATURDAY! The 25th Annual BayFest is taking over Pine Avenue for a full day of live music, delicious food, local vendors, arts & crafts, classic cars, and all the island vibes we love! ☀️🌊

💙 COME SAY HELLO TO ONCE UPON A BEACH!

We'll be set up right in front of our office on Pine Avenue, and we'd love for you to stop by! We're celebrating with a special raffle featuring TWO fun prizes:

🛺 A FREE 3-Day Golf Cart Rental!

🎁 A Once Upon A Beach Swag Bag!

Stop by, say hello, and enter for your chance to win!

🎸 LIVE MUSIC LINEUP
🎤 Hosted by Mike Sales

🎶 11:00 AM – 1:30 PM | Sycamore Shade

🥁 2:00 PM – 4:00 PM | Memphis Rub

🎸 4:30 PM – 6:30 PM | Jack'D Up

🎤 7:00 PM – 9:00 PM | The Karen & Jimmy Band

📅 EVENT DETAILS
📆 Saturday, October 17, 2026
⏰ 10 AM – 9 PM
📍 Pine Avenue | City of Anna Maria
🎟️ FREE Admission!

🚧 IMPORTANT TRAFFIC REMINDER: Pine Avenue will be closed to vehicle traffic for the festivities! If you're staying on the north end of the island or planning to visit the area, please plan your travels accordingly and allow extra time for traffic and parking.

Whether you're visiting for the weekend or lucky enough to call this island home, BayFest is the perfect way to experience the community spirit that makes Anna Maria Island so special. 💙

25 years of BayFest, endless island memories! 🌴

We can't wait to see you on Pine Avenue!

🌊 Learn more: annamariaislandchamber.org

10/05/2026

TRAPS ARE HITTING THE WATER! 🦀🌊

If you’re from Cortez, you know what October 5th means.

Today marks the beginning of the soak period for Florida stone crab season. Our commercial crabbers can officially start setting and baiting their traps, kicking off the 10-day countdown to opening day on October 15.

So today, we’re wishing all of our local crabbers safe days on the water, full traps and one heck of a stone crab season. 🦀

This is the kind of tradition that makes Cortez special. Generations of commercial fishermen have worked these waters, and more than a century later, we’re still proud to be part of a real working fishing village.

Now we wait…

🦀 10 DAYS UNTIL STONE CRAB SEASON 🦀

Keep an eye on the Cortez Retail Market page. As soon as fresh local stone crab claws start hitting the dock, you’ll be the first to know.

09/15/2026

🌴 Out of office, but never out of touch.

The Once Upon A Beach team is working remotely Tuesday, September 15 through Friday, September 18 while we attend our annual team training and industry conference. 💻✨

We’re taking a few days to learn, grow, connect and bring home new ideas to make the experience even better for our homeowners and guests.

Our physical office will be closed, but our team is still available remotely for anything you need.

📲 Call or text 941-584-5844
📧 [email protected]

Back soon—smarter, inspired, and ready for what’s next. 🌊🤍

AlwaysLearning

09/15/2026

📞 Anna Maria Island is calling…

And yes, you should probably answer. 🌅🌴

Trade the notifications, deadlines and real life for salty air, bare feet and sunsets that make you stop whatever you’re doing just to watch.

And right now, there’s an even better reason to answer the call. 🤍

🥂 We’re celebrating 10 years with 10% OFF!

Use promo code 10CHAPTERS to save 10% on qualifying stays booked now through the end of September. Exclusions apply.

🏡 Browse our collection of Anna Maria Island vacation homes, book direct with Once Upon A Beach, and start planning your next beach story.

The island is calling. Your sunset is waiting. 🌅

OnceUponABeach BookDirect IslandLife AnnaMariaIslandVacation

09/15/2026

🎉🌴 BAYFEST IS COMING TO ANNA MARIA ISLAND! 🌴🎉

Get ready for one of the island’s biggest days of the year! The Anna Maria Island Chamber of Commerce is celebrating the 25th Annual Bayfest! 🎂🎶

📅 Saturday, October 17, 2026
⏰ 10:00 AM – 9:00 PM
📍 Pine Avenue, Anna Maria Island

Come spend the day with us and enjoy:

🎶 Live Music
🚘 Classic Car Show
🛍️ Local Vendors
🌮 Food Trucks & Delicious Eats
🍺 B**r, W**e & Adult Beverages
🌴 Island Fun All Day Long!

Bring your family, bring your friends, and come celebrate 25 YEARS OF BAYFEST while supporting our local businesses and community. 💙

📣 SAVE THE DATE & SHARE WITH YOUR FRIENDS!

More Bayfest announcements, entertainment details, vendors, sponsors and event information are coming soon!

09/11/2026

25 years later, the weight of September 11th is still felt.

Today, we remember the lives taken far too soon, the families who carried unimaginable loss, the first responders and ordinary people who showed extraordinary courage, and a nation that came together in the face of heartbreak.

May we never forget their names, their stories, their sacrifice… or the way we stood together as Americans in the days that followed.

We remember. We honor. We will never forget. 🇺🇸

#911

Don’t take our word for it… ⭐️⭐️⭐️⭐️⭐️Take theirs. 🤍Thousands of nights hosted. Countless beach memories made. And five-...
09/10/2026

Don’t take our word for it… ⭐️⭐️⭐️⭐️⭐️

Take theirs. 🤍

Thousands of nights hosted. Countless beach memories made. And five-star experiences that keep our guests coming back to Anna Maria Island year after year.

🏆 Airbnb Superhost
🏆 Vrbo Premier Host
🏆 Marriott Homes & Villas partner
🏆 Airbnb Luxe portfolio
🌴 10 years of locally owned, boutique hospitality

Beautiful homes are only part of the story. It’s the experience—from booking to beach day to checkout… that makes the difference.

Swipe through to see what our guests have to say. ➡️

Once Upon A Beach… where every stay becomes part of the story. 🌊✨

AirbnbSuperhost VrboPremierHost AirbnbLuxe LuxuryVacationRental VisitAMI FloridaVacation

09/09/2026

✨ WELCOME TO VELA MAR ✨
Where Miami hotel vibes meet laid-back AMI style island luxury. 🌴🥂

This stunning 4-bedroom luxury smart home was designed for effortless vacation living… sprawling, open, completely ground level, and just 4 blocks from the beach in the heart of Anna Maria Island.

🌴 Private pool + spa
🛏️ TWO custom bunk rooms
✨ TWO luxurious primary suites
🐾 Pet friendly
⚡ EV charger
🚿 Outdoor shower
🏡 Spacious open-concept living
📍 Centrally located on the island
🏖️ Just 4 blocks to the Gulf

Sleek. Sophisticated. A little sexy. And made for the whole crew.

Vela Mar is island living… elevated. 🌊✨

🔗 Link in bio or comment miAMI for more info

LuxuryVacationRental FloridaVacation BeachHouse LuxuryTravel VisitAMI PoolHouse PetFriendlyVacation

10 YEARS. 5 NEW PARTNERSHIPS. 🏡🌴In honor of 10 years of Once Upon A Beach, we’re opening our boutique portfolio to five ...
09/08/2026

10 YEARS. 5 NEW PARTNERSHIPS. 🏡🌴

In honor of 10 years of Once Upon A Beach, we’re opening our boutique portfolio to five new qualifying homes with a very special anniversary offer:

✨ 15% management commission for your first 6 months.

And when we say full-service, we mean it.

No upfront costs. No nickel-and-diming.

Your management partnership includes:

• Basic maintenance visits
• A/C filters, batteries & lightbulbs
• All marketing costs
• All credit card processing fees
• Guest welcome starter amenities for every kitchen & bathroom
• Initial AND annual enrollment in our professional linen program — at our cost
• Exclusive golf cart discounts for guests
• Beach gear gift credit program for every stay
• Local guest services & hands-on property oversight
• Professional revenue management & distribution
• Industry-leading technology, marketing and expertise built over a decade specializing in Anna Maria Island
• Direct access to Nikki, the owner of Once Upon A Beach

You bring us your home. We take care of the rest.

For 10 years, we’ve believed vacation rental management should feel like a partnership… not a transaction. Our homeowners aren’t account numbers in a massive portfolio. They have a local team, a local office, and direct access to the person who owns the company.

To celebrate our next chapter, we’re looking for five exceptional homes and homeowners ready to write theirs with us.

15% for your first six months. First five qualifying new partnerships only.

Interested in learning what your home could do with Once Upon A Beach?

Contact Nikki, Owner & Founder, directly at [email protected]

Once Upon A Beach | Boutique Vacation Rental Management Since 2016

09/07/2026

✨ THE CURATED PALM ✨
Where elevated island living meets the laid-back magic of Anna Maria. 🌴

An Airbnb Luxe-qualified retreat, The Curated Palm is a stunning 4-bedroom canal-front home designed for guests who want a little more from their beach vacation.

🚤 Bring the boat.
👙 Bring the swimsuit.
🌊 Leave the rest behind.

Spend your days around the sprawling private pool and outdoor living spaces, then step inside to expansive, beautifully curated interiors featuring a chef-worthy kitchen with multiple islands, an incredible primary suite and bath, private office, three additional bedrooms, and an elevator connecting it all.

Tucked away on a quiet street yet close to everything—walk to the Bayside waterfront, Anna Maria City Pier & Pine Avenue shops, then hop on a bike or golf cart for the quick ride to the sugar-white Gulf beaches.

Luxury. Location. Waterfront living.
This is The Curated Palm. 🌴✨

Now welcoming guests exclusively with Once Upon A Beach.

🔗 onceuponabeachami.com/rentals/the-curated-palm
📞 941-584-5844

LuxuryVacationRental AnnaMariaIslandVacation AMI WaterfrontLiving CanalFront LuxuryTravel VisitAnnaMariaIsland FloridaVacation

Address

411A Pine Avenue
Anna Maria, FL
34216

Telephone

+19415845844

Website

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