Our Story
Orlando-Born. Hospitality-Driven.
Owner-First.
SunnySide Properties has been managing short-term rentals (STRs) across Greater Orlando for six years. The people running it are in the homes, with the vendors, and on the phone with you, not just behind a dashboard.
See Us In Action
Meet SunnySide Properties
Who We Are
Meet Nick & John
SunnySide Properties is a boutique STR management company with more than six years operating in Greater Orlando. It's led by Nick Conner and John Rupple, who bring backgrounds in professional services, and that foundation shows up in everything they do.
Nick leads revenue strategy and owner relationships across the Greater Orlando market. His background spans apartment management, facilities operations, and professional services, which means he understands properties from the inside out, and he knows how to build relationships grounded in real accountability, not just promises.
John runs the operations side: systems, vendor coordination, and the day-to-day execution that makes the "hands-off" promise real. His professional services background means every workflow is documented, every vendor is accountable, and the details that protect your investment don't get overlooked.
With 100+ homes under management across Greater Orlando's I-4 corridor, SunnySide is the rare option that combines professional-firm rigor with the on-the-ground accountability you'd expect from people who are personally invested in your results.
Nick Conner
Chief Revenue Officer · Owner Relations & Growth
Background in apartment management, facilities operations, and professional services. Leads revenue strategy, owner relationships, and Greater Orlando market growth.
John Rupple
Chief Operating Officer · Systems & Operations
Professional services background with deep operational depth. Leads systems, vendor coordination, and day-to-day execution that keeps every property running at its best.
What We Believe
Our Values
Owner First, Always
Your property is your investment. Every decision we make is filtered through the question: "What's best for the owner?" Your success is our success.
Hospitality Is Our DNA
We know that details matter, from the first message to the checkout inspection. Five-star guest experiences drive five-star reviews and more bookings for you.
Data Over Guesswork
We use real-time market data, dynamic pricing tools, and platform analytics to make decisions that maximize your revenue, not gut feelings.
Truly Hands-Off
When we say full-service, we mean it. You shouldn't have to field a 2am guest call or chase down a vendor quote. That's our job, not yours.
Community Rooted
We live and work in the Orlando area. We know the communities, the seasons, the platforms, and the quirks of managing property in this specific market. We're not a national chain with a local office.
Radical Transparency
No hidden fees. No buried charges. Clear monthly statements. And if something goes wrong, you hear it from us first, not from a guest review.
Real Homes We Manage
The Homes Behind Our Numbers
Every home in the SunnySide portfolio is held to the same standard: guest-ready, well-maintained, and built to earn.
Properties under SunnySide management · Greater Orlando, FL
What Owners Say
Don't Take Our Word For It
"Our place needed help with vacation rental setup and turnover and these folks NAILED IT from day one. They staged the unit, set up listings, and manage cleanings between guests which went smooth even during busy weekends. I kinda didn't expect it to be this easy but it has been five stars so far."
"We got help setting up our vacation rental and turnovers and it was AMAZING how easy they made it. Kinda took care of everything. Cleaning and guest prep stayed on point and ready each time. Definitely saved us time and effort, LOVE IT."
"My family used them for short term guest support and it was FIVE STARS service. Guests were happy and things stayed organized. They handled questions and small issues pretty quick. Honestly can't complain, they NAILED IT."
"Super thankful for the guest support they give our short term rental. Visitors message at all hours, they respond fast and keep guests happy, which is amazing for us as owners."
"My husband called them during an emergency repair late at night and they coordinated it right away. The issue was fixed fast and we didn't have to stress about it."
"Our experience with them for move in and move out was great. They handled keys, checks, and cleaning all good and made the process feel easy."
Our Property Portfolio
A Few of the Homes We Manage
Ready to Work With Us?
Get a free consultation and revenue estimate for your property.