The Premier Boutique Vacation Rental Agency On Anna Maria Island
AND OFFERING REDUCED COMMISSION FOR FIRST 6 MONTHS of AGREEMENT
CONTACT, NICOLE NATIELLO, OWNER OF ONCE UPON A BEACH
OR SUBMIT YOUR INQUIRY BELOW
TO RECEIVE YOUR FREE NO OBLIGATION RENTAL ASSESSMENT
The Once Upon A Beach Difference
As a boutique luxury vacation rental and property management company, we consider it both a privilege and an honor to collaborate with our owners in creating experiences that make every guest feel special, welcomed, and at home. Our unique, pristine, and thoughtfully designed accommodations are maintained to the highest standards of quality and care, ensuring your property always leaves a lasting impression.
What Sets Us Apart:
Locally Owned & Operated – A passionate team that lives, works, and loves Anna Maria Island.
Luxury Standards of Care – Pristine, meticulously designed homes maintained to the highest quality.
- Personalized Owner Collaboration – Tailored services designed around your goals and vision.
Revenue Optimization – Strategies that protect your investment and maximize your returns.
Exceptional Guest Experience – Welcoming, seamless stays that drive repeat bookings and glowing reviews.
If you’ve just purchased a home and are eager to begin renting—or you’re simply exploring what it means to own a vacation rental on the island—we’re here to help. Our team is happy to answer your questions, share our expertise, and guide you through every step of the process.
For long-time property owners seeking a change, we understand how overwhelming a transition can feel. Rest assured, we have successfully transitioned numerous homes from other agencies on Anna Maria Island with professionalism, fairness, and flexibility. Our approach ensures the process is smooth, efficient, and stress-free.
Our Expertise, Experience & Advocacy 🌴
FULL-Service Property Management — From repair and maintenance to guest relations, communications, bill pay, licensing, tax requirements, and preventative maintenance, OUAB delivers a truly comprehensive management experience designed to protect your investment and preserve your peace of mind.
10+ Years of Proven Leadership — Recognized as one of Anna Maria Island’s foremost authorities in the luxury vacation rental market, OUAB is trusted by other agencies, real estate professionals, investors, and homeowners alike for guidance on best practices, market trends, and revenue optimization strategies that consistently outperform island averages.
Island Life & Community Advocate — Deeply rooted in the island community, we’ve been among the first boots on the ground after hurricanes, providing real-time updates, videos, and support to guests and owners—demonstrating our ongoing commitment to both service and stewardship.
Vacation Rental Advocate — We champion a balanced approach that honors the integrity of island living while safeguarding the long-term value, reputation, and performance of every owner’s property.
Expansive Distribution & Partnerships — As a VRBO Premier Partner, Airbnb Superhost, and Marriott Homes & Villas (invitation-only) affiliate, OUAB offers unmatched visibility, credibility, and reach across top global booking platforms.
The Vacation Island Experience — Every stay is elevated with thoughtful details and VIP touches—from starter sets of premium amenities and beach gear to golf cart discounts and celebratory champagne for special occasions.
Revenue Management Excellence — Through innovative, data-driven pricing and cutting-edge trend analysis, we continuously adapt, adjust, and outperform, ensuring our properties achieve superior ADRs and occupancy rates across all seasons.
Higher Average Occupancy
Higher Average Daily Rate (ADR)
Higher Average ADR 2024 to 2025
Average 5 Star Review Rating
Positive Reviews
Of Bookings Are Return Guests
24/7 Guest Support – Emergency line available around the clock, with rapid response for off-hour needs.
Local Presence – Staffed office Monday–Saturday, 9 AM to 5 PM, right here on Anna Maria Island.
Award-Winning Service – Consistently 5-star reviews and recognized for our signature personal touch.
Special Welcome – Curated baskets and celebratory amenities that make every arrival memorable.
Trusted & Established – Loyal domestic and international clientele built through years of excellence.
Island Experts – Local concierge team enhancing each stay with insider recommendations and tailored experiences.
Clear & Consistent Communication – Prompt, frequent, and transparent updates every step of the way.
Licensed & Insured – Full compliance with all industry regulations and professional standards.
Paperwork Made Simple – We manage all tax filings, licensing, and inspection requirements for you.
Real-Time Technology – Reservation software with secure online owner portal for instant access.
Comprehensive Management – Full-service utility oversight, bill payments, and detailed accounting.
Stay Connected – Owner newsletters featuring recent area updates, market insights, and property news.
Pre-Arrival Inspections – Thorough home checks before every guest’s stay.
Impeccable Standards – Rigorous cleaning practices and strict safety protocols.
Professional Linen Service – Fresh, hotel-quality linens with optional program enrollment.
Preventative Maintenance – Comprehensive care to protect and extend your home’s value.
Trusted Network – Reliable contacts for upkeep, repairs, or renovations.
Smart Home Security – E-locks and integrated technology keep homes safe, secure, and efficient.
Powerful Online Presence – Exceptional website, advanced SEO, and comprehensive marketing campaigns.
Transparent Practices – No hidden fees for owners or guests, ensuring optimized revenue.
Smart Pricing – Innovative, data-driven dynamic supply and demand strategies.
Active Promotion – Direct outreach, proactive campaigns, and strong social media presence.
Recognized Performance – VRBO Premier Partner, Airbnb Superhost, and FlaRBO Host of the Month.
Luxury Visuals – Premiere photography, videography, and drone imagery to showcase homes at their best.
Why Partner With Us
When you choose to work with us, you gain more than just a management company—you gain a dedicated partner invested in your property’s success. Here’s what sets our approach apart:
Guidance for New Owners – Step-by-step education, support, and a clear path to making your property rental-ready.Seamless Transitions – Proven systems to smoothly transition homes from other agencies with ease.
Fair & Flexible Process – Transparent communication and owner-first solutions tailored to your needs.
Selective Partnerships – We collaborate with homes and owners who align with our values and standards.
Quality Over Quantity – Our focus is not on being the biggest, but on being the best for every home, every owner, and every guest.
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 - Owner Since 2017We 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 - Owner Since 2018Nikki 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 - Owner Since 2018I 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!
D. Panella - Owner Since 2019Over the past several years, Once Upon a Beach have done an outstanding job of managing two of our vacation rental properties on AMI. In one year alone, they more than doubled the revenue yr/yr achieved by the previous property management company on one of the properties. They also do a fantastic job with property maintenance and property remodeling projects. If you are a remote owner, you can have the piece of mind in knowing they are managing your property like they are the owner. I highly recommend Once Upon a Beach for your property management needs.
Nodler1. We treat every home as if it were our own and every guest like family.
We are island locals. We live here. We work here. We love our island.
2. We are a dedicated, expert team serving as the sole, direct point of contact and concierge for every guest — available 24/7 from the very first booking inquiry, to personally welcoming them upon arrival, and continuing with attentive follow-up after their departure.
3. We excel at clear, consistent communication with our owners, keeping them fully informed about their property while seamlessly managing all the details and logistics. Our goal is to take the stress completely off their hands, allowing them to enjoy peace of mind knowing their home is expertly cared for.
4. We dedicate significant time and attention to every home, personally cleaning, inspecting, and preparing each property before every single guest arrival. This includes checking appliances, refreshing linens, testing internet connectivity, tidying landscaping, and ensuring pools are spotless. Our goal is to maintain each home in pristine condition, so every guest — and every owner — can arrive with complete comfort and confidence.
5. We operate with complete transparency — no hidden fees or surprise costs. Our management fee is based solely on your base nightly rate, and we intentionally limit guest fees. By keeping traveler costs low, we promote competitive pricing and deliver a better guest experience, which in turn drives higher occupancy and repeat bookings. This approach not only maximizes revenue for our owners but also ensures mutual success, as your growth is directly aligned with ours.
6. We intentionally keep a limited number of homes in our portfolio because we understand and value the time, care, and attention to detail required to maintain each property at the highest standard. We believe the best way to ensure our standards of care are met, is to keep a smaller number of homes. Bigger is NOT better in our opinion. Each team member uniquely knows each home, its owner, and their return guests!
7. We are proud to have earned Premier Partner status with VRBO, Superhost status with Airbnb, Partnered with Marriott HVMI (Invite Only) and Host of the Month recognition on FlaRBO.com. These achievements directly enhance the visibility, credibility, and marketability of our homes, driving stronger performance and increased bookings for our owners.
8. We know how to prepare, showcase, and market each home to its fullest potential — from crafting detailed, compelling listings and ensuring the home is fully stocked and guest-ready, to capturing stunning, high-quality photos and fostering positive guest experiences that lead to exceptional reviews.
9. We are proud of our strong reputation for honesty and integrity on the island and the trusted partnerships and relationships we’ve built over the years. These connections allow us to enhance the experience for both our guests and our owners, ensuring every stay and every interaction reflects the high standards we uphold.
10. We manage all of our personalized marketing in-house! From building our website from the ground up to maintaining a strong, engaging social media presence, we oversee every detail of our daily marketing efforts. We also leverage expanded distribution platforms, Google Ads, Yelp, and more to maximize visibility and ensure our homes receive the broadest and most effective exposure possible.
11. We are fortunate to have an incredible team working alongside us — from our talented design partners and meticulous cleaners to our reliable pool service, maintenance crew, and more. With an expansive network of trusted contacts, we’re always ready to handle any task quickly and efficiently, ensuring every home is maintained to the highest standards.
12. In addition to providing pristine, well-maintained homes, we create a memorable experience for our guests — from thoughtful welcome baskets to special gifts that celebrate their milestones and occasions. We also offer detailed rental binders and an interactive website filled with insider tips and local recommendations to help guests explore and enjoy the island like a true local.
Discover More About Working With Us
✨ Need help stocking or reviving your vacation rental? Explore our Rental Revitalization Services to see how we can refresh, enhance, and bring your property to life for guests and owners alike.
✨ Curious about who we are and why we love what we do? Visit our About Us page to learn more about our story, our passion for Anna Maria Island, and the values that set our boutique company apart.
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