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.
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.
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 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...
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...
“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.”