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…

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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!

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Premier Property Management

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

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Anna Maria Island Insider's Guide

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


Featured Properties

Sunset Margarita

Sunset Margarita

Sunset Margarita 2 Bedroom  |  Sleeps 6Overview Luxury Condominium with Screened Lanai, Shared Heated Pool in One Particular Harbour 2 Bedroom, 2 Bath in Bradenton, FL 391 Aruba Circle #301 Less than 2 miles from the Anna Maria Public Beach in the highly desirable...

Bodacious Oasis

Bodacious Oasis

Bodacious Oasis 4 Bedroom  |  Sleeps 8Overview Elevated Upscale Spacious Home w/Large Heated Pool & Sunshelf, Steps to Pine Avenue! 4 Bedroom, 2 1/2 Bath in Anna Maria, FL (Anna Maria Island) 2120 sq. feetHighlights Kitchen, Dining Area, Living w/ TV 1 King...

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....

Award Winning Homes

Our Island and Homes are OPEN!

Click below for our COVID-19 Travel Information & Information on Our Updated Cancellation Policy which now includes Penalty-Free Cancellations*!

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“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.”