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Why SunnySide Properties
We don't just list your property and hope for the best. We treat your vacation home like it's our own, because your success is our reputation.
Clear updates, fast response times, under 10 minutes for guests and under 4 hours for owners, and proactive outreach that catches small issues before they grow.
Hotel-grade standards across listings, pricing, turnovers, and inspections. A trusted local vendor network, disciplined follow-through, and the systems to keep performance consistent as the portfolio grows.
Property management is more than cleaning and guest communication. We act as a thought partner on the bigger decisions too, from renovations to buying or selling, drawing on what we see across our portfolio and the local market.
Who We Are
SunnySide Properties is led by Nick Conner and John Rupple, a team with deep roots in professional services, operations, and Greater Orlando's vacation rental market. Nick leads revenue strategy and owner relationships. John oversees systems, vendor coordination, and day-to-day execution with the rigor you'd expect from a much larger firm. Together, they manage your property like they own it.
Where We Work
We specialize in STR management across Orlando's most popular resort communities, from Champions Gate to Windsor Island and beyond.
From Signed Agreement to Guest-Ready Launch
SunnySide moves quickly, but the timeline depends on property readiness, owner access, and any work needed before launch. Once the agreement is signed, our team collects the property details, prepares the home, builds the listing, reviews pricing, and gets the property ready for bookings across SunnySide's site and major booking platforms.
Owner portal access is created, property information is collected, and access details, insurance, HOA requirements, Wi-Fi, utilities, and payout setup are confirmed.
SunnySide inspects the home, sets up guest-ready access, installs or configures the smart lock, and calls out any work that should be completed before launch.
Approved work orders are completed if needed. The home is cleaned, staged, and professionally photographed so the listing is ready to present well.
The listing is created and optimized, pricing strategy is reviewed, and the property is synced across SunnySide's direct booking site and 13+ booking platforms.
Owner & Guest Reviews
"Our property manager actually knows our home. Response times went from days to minutes."
"The transparency sold us. We see every dollar in and out, with no surprises."
"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, even during busy weekends. It has been five stars so far."
Full-Service Means Full-Service
From the moment a guest books to the day they check out, and everything in between, we've got it covered.
HDR photography that makes your property stand out on every booking platform.
Real-time rate optimization based on demand, seasonality, and local events.
Listed on Airbnb, VRBO, Booking.com, Expedia, Tripadvisor, and more.
Fast, professional responses to every inquiry, 24/7, 365 days a year.
Top-rated housekeeping teams clean your property after every guest stay.
Every checkout is followed by a thorough inspection to protect your investment.
We coordinate repairs with trusted local vendors, with no calls to you required.
Clear statements showing every booking, payout, and expense. No surprises.
Owner Story
"I was managing two properties in Kissimmee myself. Once I handed them to SunnySide, my revenue went up and my stress went to zero. The whole team is professional and incredibly responsive."
The Properties We Manage
Premium, themed, and consistently booked. These are real properties in the SunnySide Properties portfolio, every one professionally managed with our full-service approach.
From themed retreats to resort-community pool homes across Kissimmee and Davenport. Often the highest-revenue properties given size, amenities, and proximity to the parks.
Vacation rental units in resort communities like Storey Lake and Solara, where HOA rules and shared amenities add a layer of complexity we manage for you.
High-end and specialty-themed homes (think Star Wars suites and private theater rooms) that command premium nightly rates and require premium-level guest service.
Larger homes built to sleep bigger travel groups, common in communities like Reunion Resort, where multi-generational Disney trips are the norm.
Owner FAQs
Education
Practical guidance from our local team: pricing, guest experience, and ownership strategy.
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Read MoreReady to Get Started?
Whether you already own an STR or are just exploring, we'd love to show you what SunnySide can do for your investment. Free, fast, zero-pressure.
We'll be in touch shortly.
No commitment. No pressure. We Respond Promptly.
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