In 2016, Open Road Stays was founded by Ron Kimura and Nick Jacobson—two friends who saw first-hand what the industry was missing. Property managers lacked an owner’s mindset, guests lacked confidence in what they’d booked, and the systems behind it all were disjointed and inefficient. Inspired by Walt Whitman’s poem Song of the Open Road, they set out to do things differently. When Ron decided to exit the business in 2022, Nick’s wife, Amy, joined the team, and together they’ve continued to build on that founding vision.
We’re a boutique vacation rental management company focused on delivering more joy to guests and more profit to owners. Our deep experience in real estate, travel, and hospitality drives every decision we make—from maximizing booking performance to ensuring each home is clean, well-equipped, and exactly what was promised. We’re not just managing homes—we’re building the infrastructure for modern travel. Open Road Stays is more than vacation rentals. It’s a better way to stay, and a smarter way to own.
We bring hands-on expertise, owner-first management, and proven marketing strategies to your vacation home—all for a competitive fee backed by our Risk-Free Guarantee. With no long-term commitment, Open Road Stays helps you start, manage, and grow a more profitable short-term rental.
When you book with Open Road Stays, you get homes that are thoughtfully prepared, professionally managed, and always guest-ready. Our support team is just a message away to make sure your stay is smooth, comfortable, and exactly what you expected—day or night.
We work with top-tier professional cleaners, photographers, and service pros who help deliver five-star stays. Our partnerships create real growth opportunities for quality-focused professionals who care about consistent results and long-term collaboration.
Reliable, responsive, and consistently top-rated—because great hospitality should be measurable.
Guest Review Score
Never left hanging
Past 12 months
Proven reliability
CEO
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.
Guest Services
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—and takes pride in making sure every guest feels supported, heard, and at home from check-in to check-out.
Field Tech
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, detail, and a can-do attitude. Off the clock, he’s often tinkering with his beloved vintage Volvos.
Mascot
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 a little personality—Luka brings his daily.
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,
Nick Jacobson
Founder, Open Road Stays
Whether you’re an owner, guest, partner, or team member, working with Open Road Stays means being part of something thoughtfully built.
We care deeply about delivering great experiences—for the travelers who stay with us, the owners who trust us, and the partners who support it all. From the way we manage homes to the way we serve people, care is the foundation of everything we do. This is hospitality with purpose—and a business you can believe in.
