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


As frequent visitors to Anna Maria Island, 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 inspire others to visit as well. 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 one bedroom bungalows to a premier private beachside oasis 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 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 absolutely 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!

Explore

Featured Properties

Point’s Hideaway

Point’s Hideaway

Point's Hideaway 3 Bedroom  |  Sleeps 8  |  7 Night Minimum Overview Single Family Home with Private Heated Pool &Rooftop Deck w/stunning sunset Water Views 3 Bedroom, 3 Bath in Anna Maria, FL 2300 sq. ft. Highlights   Layout  Kitchen, Dining, Living w/ TV 1 King...

Decked Out

Decked Out

Decked Out 2 Bedroom  |  Sleeps 4  |  Max Occupancy 6Overview   Newly Renovated Single Family Elevated Home with HUGE Sunny Private Heated Pool    2 Bedroom, 2 Bath in Anna Maria, FL 1200 sq. ft. Highlights   Layout   Kitchen w/ Island seating for 2, Dining...

Cozy Cabana East

Cozy Cabana East

Cozy Cabana East 2 Bedroom  |  Sleeps 6  |  7 Night Minimum Overview Newly Renovated Ground Floor Home (Duplex) with Private Pool 2 Bedroom, 2 Bath on Holmes Beach, FL 205 82nd Street Holmes Beach, FL 34217 1132 sq. ft. Highlights Layout    Kitchen, Dining, Living w/...

Salty Pirate

Salty Pirate

Salty Pirate 4 Bedroom  |  Sleeps 8  |  7 Night Minimum Overview NEWLY LUXURIOUSLY RENOVATED with Heated Pool, Spa, Bay & Canal Views on Canal with Dock 4 Bedroom, 3 Bath on Anna Maria, FL Salty Pirate Anna Maria, FL 34216 2512 sq. ft. Need more room? Can be...

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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.”s.