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.
Sea Life Happy 4 Bedroom | Sleeps 8Overview Sprawling Canal-front Home with Private Heated Pool & Spa, Dock, Indoor/Outdoor Bar 4 Bedroom, 3 Bath in Anna Maria, FL Sea Life Happy Anna Maria, FL 34216 Highlights Open Layout Kitchen, Dining Area, Living Room w/...
A Wave From It All 3 Bedroom | Sleeps 10 Overview Gorgeous Luxury Home with Heated Pool, Outdoor Pavilion, Hammock, and 6-8 Min Walk to Beach! 3 Bedroom, 3 Bath in Anna Maria, FL A Wave From It All Anna Maria, FL 34216 This home is brand new to rental market and has...
Salty Pirate 4 Bedroom | Sleeps 11 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 rented in conjunction...
Come write ✍🏼 your vacation story 📚 with us. A boutique luxury vacation rental company on Anna Maria Island, FL 🏝 941-584-5844 #writeyourvacationstory
“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.”