The Premier Boutique Vacation Rental Agency On Anna Maria Island
As a boutique luxury vacation rental & property management company, it is our privilege and honor, in collaboration with our owners, to make every one of our guests feel special and at home. Our unique, pristine, meticulously designed, and luxurious accommodations are maintained with the highest standards in quality and care. We are a locally owned and operated professional agency with a genuine team who love the island. We are passionate about providing personalized, comprehensive services that guarantee outstanding return on investment, exceptional guest experiences, all while preserving your home for you to enjoy.

If just purchased a home and can’t wait to get renting, or interested in what it means to have a vacation rental on the island and just want to answers to your questions on what it means to own a vacation rental. Feel free to reach out… we are here to help!
Perhaps you have owned a vacation rental home for years and feel very comfortable with the process but are looking for a change and not quite sure where to start. We understand, and we know that can seem stressful. No worries at all, we have successfully transitioned homes from other agencies on the island with professionalism, flexibility, and fairness and can easily navigate, streamline, and make the process as stress-free as possible.
We strategically select to partner with homes and owners that feel we are the best fit for what they are looking to accomplish with their home and that they feel comfortable with our approach and processes. We do not just add homes to our portfolio to get ‘bigger’, we prioritize how we can be ‘better’ for all our homes, owners, and guests.
Please send us a message or contact us at 941-584-5844 for additional information and no obligation vacation rental assessment.
Need to help stocking or REVIVING your Rental? Check out our Rental Revitalization Services page for more information!
Who Are We and Why We Do We Love What We Do?
Check out our About Us page!

What Our Owners Have to Say…
“We just completed a little over a year with Nicole from Once Upon A Beach managing the rental of our brand new vacation home. This experience was all brand new for us, as this was a new adventure in the vacation rental business. Nicole made what could have been a very intimidating process for us into something very easy and simplified. She is a hard worker and basically takes care of everything for us. She is especially good with handling persnickety guests and smoothing over any issues, minor or otherwise. Another attribute she has is her attention to details. This is especially important on all of the documents she provides for taxes, bookings, and others that are needed. We are highly satisfied and pleased that we selected Once Upon A Beach to manage our vacation rental..”
“We are so thankful to have found Mike and Nikki Kaleta “Owners of Once Upon A Beach” to manage our beach house on AMI! We bought our home with the intention of putting it in a rental program and also getting to use/share it with our family and friends. So it was very important to find the “RIGHT” management company. We like to say that Mike and Nikki have been a God send to us with this whole process of owning a beach rental. We were looking for a small boutique style rental company that would take care of the rental bookings, day to day operations with the renters, and most importantly to us was someone that would take care of our home as if it were there own. From our very first meeting with Mike and Nikki, we knew they were the ones! They took a lot of stress off of us right away and were a tremendous asset with getting everything in order for us to get the house in a rental program and have been phenomenal with marketing the home to prospective renters. We feel very blessed to have “Once Upon A Beach”, Mike and Nikki managing our home on AMI!
“Nikki and Mike are THE BEST! …hardworking, reliable, prompt, and kind. They are easy to get in contact with and respond ASAP. We interviewed several companies and knew right away that they were the best fit for us. Their attention to detail and personal care is unlike anyone else on the island. They do it all! We know that our new home is in good hands with them”
“I highly recommend Once Upon a Beach. They are the perfect boutique property management company. Owners, Michael and Nikki, manage my AMI properties Salty Pirate, and Seaswept Mermaid. They have been managing them for about two and a half years, and they run them like five star resorts. They are professional, pleasant and very responsive to both guests and owners. They handled the craziness of Covid in 2020 with compassion and concern, and quickly pivoted to the boom year of 2021, which is translating to a solid ROI this year. Nikki does accounting and licensing, but more importantly, she is a top tier marketer. She knows how social media works and has an active presence online. She continually monitors the pulse of the market for premium pricing, bookings, and solid occupancy rates. She crushed it this year! Michael handles owner and guest relations with care and concern about peoples needs. He visits each property the morning/afternoon before every guest arrives to make sure all is in proper order. He also keeps track of maintenance, handles contractors, and is sensitive to budgetary concerns. They have a terrific team around them. From Brittany in the office, to Bong and Ollie and their immaculate cleaning crew, to their hand picked local contractors if needed. Most have been working on the island for years. They are responsible and do an outstanding job. What do the guests think? I like 5 Star reviews and they get them. It is just about all they ever get! Again, I highly recommend Once upon a Beach. Give Michael and Nikki a call. If you are just getting set-up, contact them early as they have a lot of ideas to share about what works and what doesn’t. You will be happy!”
What sets us apart from the rest?
2. We are a husband and wife team that is the sole and direct contact & concierge for every guest 24/7… from first booking inquiry, to meeting and greeting them, to follow-up following their departure.
while keeping them to up-to-date on their home and taking the stress and all the details & logistics completely off their hands.
5. We have no hidden fees or costs. We base our fee off your base rental rate only and limit our fees for guests. Limiting traveler fees promotes competitive pricing and happy guests. Keeping expense costs low helps optimizes revenue for our owners. Optimizing revenue for owners optimizes revenue for us.
with in-depth listings, inventory and stocking of the home, incredible photos, and understanding the importance of positive reviews.
We built our website from the ground up, have a strong social media presence, and personally oversee our daily marketing!
We utilize Expanded Distribution platforms, Google Ads, Yelp & more for increased exposure of our homes.

DYNAMIC MARKETING
In addition to personally tailored listings and being featured on our mobile responsive website, we increase exposure through websites such as VRBO (Premier Partner), Homeaway, Trip Advisor, FlaRBO, Expedia & Airbnb (Superhost) as well as business partnerships with third parties. We also provide a personalized social media presence through Facebook & Instagram that market home specials and provide an insider’s view of island life.

OPTIMAL RETURN ON INVESTMENT
We offer a competitive fee for our comprehensive services. We meticulously research to provide fair but optimal rates with no hidden fees to guests or owners. We continually adjust rates for fluctuating supply and demand while properly pairing the right guests with the right home. We maintain homes with a proactively thorough maintenance schedule and serve as a liaison/manager of contractors and service providers.

PERSONALIZED MANAGEMENT
Whether you prefer to be completely hands-off or more intimately involved, we provide flexible, transparent, and comprehensive management options that allow your vacation rental to be stress-free for you. We hold the highest of quality and standards for management and maintenance of your home. Maintaining the quality of your home for you to enjoy while protecting the sanctity of the island.

EXCEPTIONAL SERVICE
By being the sole contact and personal concierge for all our guests we provide an intimate, boutique-style, exceptional, five star and stress-free experience from booking to departure for all of our guests. We have a vigorous cleaning and inspection process prior to all guest arrivals. We do our best to communicate effectively, personally interact, accommodate special requests, and gracefully handle any issues 24/7.