Shift your focus, change your life.
Once Upon a Beach is a boutique luxury vacation rental and property management company that provides exceptional guest experiences on Anna Maria Island. We offer a curated selection of meticulously cared for homes, each with unique thoughtful amenities, carefully crafted concierge-style island information, and just steps away from the pristine sugary sand beaches and gin-clear waters of our island paradise. Our mission is to make your dream vacation come true by offering a world-class island getaway with locally-based experts dedicated to providing five-star care and attention to detail in one of the most beautifully quaint beach towns on earth, Anna Maria Island.
Luxury Vacation Rentals Tailored to You
At Once Upon a Beach, we offer premier vacation rentals that cater to various group sizes and preferences, from intimate escapes for two in our beach chic cottages to spacious luxury homes accommodating extended families or large groups. Our diverse portfolio includes one to eight-bedroom homes, pet-friendly rentals, heated pools, and waterfront rentals, with an array of properties that highlight the Anna Maria Island charm. We are committed to providing an intimate island experience with focus and care, delivered through our luxurious vacation homes uniquely designed to make your stay unforgettable.
Unrivaled Guest Services - Exceeding Expectations
Once Upon a Beach is committed to delivering the highest level of service, which starts from the moment you book your stay with us. Our dedicated guest services team is available to help with all aspects of your island vacation, from arranging baby equipment rentals, trip insurance, concierge services, and planning for your visit, ensuring a seamless and enjoyable experience. Our local expertise allows us to personalize each guest's visit, ensuring you feel the warm, laid-back Anna Maria Island vibe from the moment you arrive until your departure.
Property Management with a Distinct Difference
As a leading vacation rental management company on Anna Maria Island, Once Upon a Beach offers exceptional property management services that focus on maximizing revenue for homeowners while maintaining homes with the utmost care. Our Revive program emphasizes top-tier guest services, proactive maintenance, and intelligent pricing strategies, resulting in optimized occupancy and increased revenue for our valued homeowner partners.
Discover the Once Upon a Beach difference by exploring our exquisite portfolio of Anna Maria Island vacation rentals, and experience the ultimate in luxurious island living tailored to your unique needs.
Overall Experience
The reviewers had an extremely positive experience with Once Upon A Beach Vacation Rentals, with all of them giving a 5-star rating. They praised the company for providing excellent vacation rentals, with comfortable and well-appointed homes, beautiful views, and perfect locations.
Accommodations
The homes were described as "wonderful", "cozy", and "spacious", with "beautiful trees and flowers" surrounding them. The rentals were also well-stocked with essentials, including cooking utensils and beach bags.
Location
The location of the rentals was a major highlight, with many reviewers mentioning that they were just a short walk from the beach. The proximity to shopping, great restaurants, and other amenities was also appreciated.
Communication and Service
The reviewers praised the company for their excellent communication and service. They responded quickly to any issues that arose, and provided clear directions for check-in and check-out.
Return Customers
Many of the reviewers mentioned that they would definitely return to Once Upon A Beach Vacation Rentals for their future vacations, with some already having booked their next stay.

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