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.
We live and work here locally on the island! We are dedicated to providing you all the best information on how to make the most of your AMI vacation!
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 led team, we are dedicated, from booking to departure, 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.
Oasis on Spring 4 Bedroom | 4-7 Night Minimum | Sleeps 8Overview Luxurious Updated Main Home Plus Secondary Guest Home w/Oversized Heated Pool & Spa in True Backyard Oasis 4 Bedroom, 3 Bath in Anna Maria, FL (Anna Maria Island) 1518 sq. ft Highlights Two homes...
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...
AMI Peppertree Paradise 3 Bedroom | 4-7 Night MinimumOverview Elevated Updated Home w/Large Heated Pool on Amazing Street on North End of Island, Just 2 Houses to Beach! 3 Bedroom, 2 Bath in Anna Maria, FL (Anna Maria Island) 1970 sq. ft Highlights Kitchen, Dining...
“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.”