About Open Road Stays
We manage vacation rentals the way we'd want ours managed — with an owner's mindset, a guest-first standard, and zero excuses.
Our History
In 2016, Ron Kimura and Nick Jacobson kept running into the same problems — as owners and as guests. Managers who disappeared after signing. Listings with beautiful photos and disappointing realities. Maintenance issues that sat for weeks. The bar was low, and nobody seemed bothered by it.
Inspired by Walt Whitman's poem Song of the Open Road, they built a company around a simple idea: manage every property like it's your own. When Ron stepped away in 2022, Nick's wife Amy joined the business, and together they've been sharpening that vision ever since.
What We Do
We're a boutique vacation rental management company, and we're intentionally small. That means we know every property, every owner, and every quirk of every home we manage. Our backgrounds in real estate, travel, and hospitality aren't just resume lines — they show up in how we price, how we prepare, and how we respond when things go sideways.
The result: guests get stays that actually match the listing. Owners get real revenue growth without the 2 a.m. phone calls. And nobody gets the runaround. That's the whole pitch.
"Afoot and light-hearted I take to the open road, Healthy, free, the world before me, The long brown path before me leading wherever I choose."
— Walt Whitman, Song of the Open Road
Who We Serve
You own the property — you should feel like it. We handle the listings, the pricing, the guests, and the headaches, while you keep full visibility and control. No long-term contracts, competitive fees, and a risk-free guarantee that means we earn your trust monthly.
How we manage your propertyWhat you see is what you get — actually. Every home is walk-through ready before you arrive, and if something's off, we pick up the phone. No chatbots, no ticket queues. Just real people who want your trip to be worth the drive.
Browse our homesWe rely on a tight network of cleaners, photographers, and service pros who take the work as seriously as we do. If you do great work and want steady, well-organized clients who pay on time and communicate clearly — we should talk.
Work with usOur Team
Nick founded Open Road Stays in 2016 after seven years as a professional basketball player and another seven in the payroll industry. A private pilot and value-driven investor, he's focused on scaling a hospitality business rooted in strong returns and operational excellence.
A former Division I athlete and General Motors BDA, Amy joined ORS in 2022 to lead guest experience. She's known for her speed, empathy, and reliability — making sure every guest feels supported from check-in to check-out.
Cameron joined ORS with a knack for fixing things and a passion for learning on the fly. Whether handling inspections, tech setups, or tricky field issues, he brings dependability and detail. Off the clock, he's tinkering with his vintage Volvos.
Luka is a rescue dog with a strong background in napping, morale boosting, and field supervision. He brings joy to the office, charm to team photos, and the occasional bark to Zoom calls. Every great stay needs personality.
A Letter from the CEO
To our future guests and owners,
You've made the time. The calendar is cleared. You arrive with high hopes — ready to relax, recharge, and enjoy a change of scenery.
But instead of comfort, you're met with confusion. The home feels off. It's not what you expected. You can't reach anyone when you need help. You're met with rules instead of hospitality. And before long, you're wondering if the whole trip was worth it.
We started Open Road Stays to change that.
We believe vacation rentals can be dependable, professionally managed, and still full of character. We believe guests deserve smooth, enjoyable stays — and that owners deserve partners who think like they do.
At Open Road Stays, we operate with an ownership mindset because that's where we started. We've felt the letdowns. We've seen the waste. And we've built our business to avoid both.
We don't outsource care. We don't cut corners. Every home is fully prepared, every guest supported, and every owner given the tools to grow — not just book.
It's not just about clean sheets or fast WiFi (though you'll have both). It's about delivering confidence at every turn — for the traveler who booked the stay, and the owner who entrusted us to manage it.
We're growing a network of properties that feel personal, perform well, and give everyone involved something to feel good about. For guests, that means clarity and comfort. For owners, it means real results and less stress.
When people stay in homes that are cared for with intention, something changes. The experience sticks. The getaway works. And the business grows stronger.
That's why we're here.
Warmly,
Whether you own a property or you're buying one — let's figure out if we're the right fit.
See if You Qualify