Write the next chapter of your vacation story with Once Upon a Beach

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.

Extra Fee Free Reservations

We never charge administrative, booking, pool heating, linen service, or any extra fees for guests or owners. Just rental rate for people & pets, damage policy, cleaning & taxes.

Secure Online Booking

We provide flexible online booking so you can quickly submit requests online and offer secured and simple online payment methods to reserve your next stay stress free.

Pristine & Inspected Homes

We work with an amazing team to ensure the homes & pools are sparking and spotless for all of our guests. Each home goes through rigorous cleaning and inspected prior to every arrival.

Personalized Service

As a husband & wife team, we are your primary contact & concierge from booking to departure and dedicated to making your stay perfect for whatever needs or questions may arise.

Trusted & Licensed Business

Our business and homes are licensed and insured. We have great business partnerships and are well-respected, trusted, and known for our integrity on the island.

About Us

Find out about who we are and why we love what we do!

Get To Know Us

Guest Testimonials

What people are saying about us and our homes…

Read Reviews

Rental Locations

Check out our rental map and their locations on the island.

View Map

Availability Calendar

Check out our availability calendar for weekly rentals at a glance!

View Calendar

Premier Property Management

Find out what sets our intimate boutique experience apart from the rest!

Learn More

Anna Maria Island Insider's Guide

Find out everything you need to know to make the most of your island stay!


Featured Properties

A Shore Thing

A Shore Thing

A Shore Thing 4 Bedroom  |  4-7 Night MinimumOverview Newly Constructed Waterfront Home with Pool, Spa, Private Dock on Canal & Gulf & Bay Rooftop Views 4 Bedroom, 5 Full & 2 1/2 Bath in Anna Maria, FL 108 Tern Drive Anna Maria, FL 34216 3875 sq. ft....

Sea Mist

Sea Mist

Sea Mist 3 Bedroom  |  Sleeps 6  |  3-7 Nights Overview Elevated 3 Bed, 2 Bath in Anna Maria, Florida just STEPS to Pine Avenue & Anna Maria City Pier 3 Bedroom, 2 Bath in Anna Maria, FL 1700 sq. feet  Highlights Kitchen, Dining Area, Living w/ TV 1 King...

Sol Mate

Sol Mate

785 Jacaranda 3 Bedroom  |  3-7 NightsOverview Elevated 3 Bed, 2 1/2 Bath with Pool/Spa within easy walking distance of Bean Point beaches 3 Bedroom, 2 1/2 Bath in Anna Maria, FL 1500 sq. feet Under new ownership & management. Currently undergoing renovations and...

Award Winning Homes

Our Island and Homes are OPEN!

Click below for our COVID-19 Travel Information

Contact Us

“All of our homes are licensed and meet the requirements of the Florida Department of Business and Professional Regulation Division of Hotels and Restaurants. The information provided online, though deemed accurate is not guaranteed. It is subject to errors, omissions, change of price or withdrawal without notice.”