Let us manage your Anna Maria Island vacation rental!  

Owning a home on the island is a wise investment opportunity when managed correctly.  We are not a large rental company, but instead a boutique vacation rental management company that prides ourselves on exceptional service for our guests, meticulous care of our homes, and the utmost satisfaction and great relationships with our owners.  We love the fact that we are not just another rental company on the island.  We are genuine people who love this island and are passionate about providing unique, personalized, and comprehensive property management services that bring in excellent revenue while also preserving your home for you and your family to be able to enjoy.

Regardless of whether you have owned an island home for years, 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 not sure where to start…

Please send us a message or contact us at 941-584-5844 for additional information and no obligation vacation rental assessment.  

We are excited to work with you!

Need to help stocking or REVIVING your Rental?  Check out our Rental Revitalization Services page for more information!

What Our Owners Have to Say…

“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!

N.T. Cline

“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..” 

D.D. Schaefer

“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” 

W.N. Fish

What sets us apart from the rest?

1. We treat every home as if it were our own and every guest like family.

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.

3. We are excellent at communicating and working with our owners
while keeping them to up-to-date on their home and taking the stress and all the details & logistics completely off their hands.
4. We spend a great deal of time in the homes… inspecting, cleaning, and maintaining to ensure the home is kept in pristine condition so that you can continue to enjoy your home as if no one had ever stayed there.

5. We spend a great deal of time in the homes… inspecting, cleaning, and maintaining to ensure the home is kept in pristine condition so that you can continue to enjoy your home as if no one had ever stayed there.

6. We only keep a limited number of homes in our portfolio as we understand and appreciate the time and attention to detail that is needed for every home.
7. We have obtained Premier Partner status with VRBO, Superhost status with Airbnb, and Host of the Month on FlaRBO.com. These statuses directly correlate to improved listing presence and marketability of our homes.
8. We understand how best to prepare, showcase, and market the home
with in-depth listings, inventory and stocking of the home, incredible photos, and understanding the importance of positive reviews.
9. We are proud we have a great reputation of honesty & integrity on the island and have built business partnerships & relationships to best enhance our guests’ and owners’ experiences.
10. We conduct and manage our own personalized marketing!
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.
11. We have an incredible ‘team’ that works alongside us from our design team, cleaners, pool service, maintenance and more. We have an expansive contact list ready to get any job done!
12. In addition to providing pristine homes we provide an experience for our guests’ whether greeting them with a welcome basket or a gift to commemorate their special occasion. We also provide in-depth rental binders and an interactive website for insider tips and tricks to best explore the island.



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.

Press Coverage >




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.

Contact Us >



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. 

More About Us >



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.

What Our Guests Say >

"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."