How to Grow Your Vacation Rental Business

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We’re a partner, not just a provider. That’s why we’ve built fast, flexible vacation rental software that covers small homeowners and large PMs alike. OwnerRez is designed from the ground up to help short-term rental operators grow their business and perform at an "elite" level. It’s a powerful, long-term booking foundation for your vacation rental business.

In this guide, you’ll see how three unique vacation rental businesses grew with OwnerRez at the core of their operations. They generously share what worked, what didn’t, and the systems that helped them manage more properties, while still providing an excellent guest experience. We hope you walk away with some helpful insights on how to grow your vacation rental business with OwnerRez.

Stay Hocha Property Management

The first person we spoke with was Vikram Mall, the founder of Stay Hocha Property Management. Vik started just two years ago with two properties he owned and managed. Since then, he’s grown Stay Hocha into a thriving operation managing over 35 properties in the Broken Bow, Oklahoma area. Here’s what Vikram had to say about growing his business with OwnerRez.

Q: What did your business look like when you first started, and what does it look like today?

A: We started 2 years ago with 2 properties we owned and managed. OwnerRez was the perfect tool to manage multiple platforms. We currently manage over 35 properties in the Broken Bow, Oklahoma area, and continue to add more under the Grand Vacations Company Stayhocha platform.

Q: What were the key things you did that helped you grow, and was there a turning point along the way?

A: We used multiple marketing channels. Integrating our Squarespace website with the OwnerRez widget gave our website a nicer look, and gave us the ability to add additional services while maintaining a direct link with the PMS system.

Q: What advice would you give someone looking to grow into a large property management company?

A: OwnerRez makes it a lot easier to manage and communicate with guests, especially with the new AI tool.

Q: If you could go back and give yourself one piece of advice, what would it be?

A: For the first year, keep grinding and don’t look back. Spend money on marketing, as that’s the most valuable part.

Q: How has using OwnerRez helped you grow?

A: Integration is seamless; we take on properties and add them to OwnerRez in 15-20 minutes flat. Connect Pricelabs and sync everything up. At Grand Vacations Stayhocha, we use AI to enhance the listings and use the OwnerRez property share to drive traffic to not just our own properties but hundreds of others.

Visit here to learn more about Stay Hocha.

30A Five Star Properties

Next, we spoke with Chelsea Cutrer, who decided to self-manage her first short-term rental in 2022, and the rest is history. Today, Chelsea owns four rentals and manages 20 more, totaling 24 active listings. Here are the tips, tricks, and insights Chelsea has to share about growing a successful vacation rental business.

Q: What did your business look like when you first started, and what does it look like today?

A: When I first started, I had one short-term rental and made the decision to self-manage, believing I could deliver a better guest experience, maintain the property more effectively, and achieve a higher ROI. That was at the end of 2022, as I was preparing to add a second property. I quickly realized that to stay organized and scale efficiently, I needed a professional system. That’s when I started looking for a platform like OwnerRez. Fast forward to today: I own four short-term rentals and manage 20 others. We now have 24 active listings and were recently ranked one of the top 5 property managers on 30A by AirDNA, based on reviews and overall guest satisfaction. Having the right systems in place early on made that growth not just possible, but sustainable.

Q: What were the key things you did that helped you grow, and was there a turning point along the way?

A: A few key strategies helped us grow. First, we prioritized top-notch customer service for both guests and homeowners. Second, we made design and amenities a major focus, since guests loved the aesthetic, and it helped our properties stand out in a crowded market. That focus on great design and thoughtful amenities led to outstanding guest reviews, which became a key difference for us. Finally, we stayed focused on one area, 30A, which allowed us to really understand the market and build strong local relationships. The real turning point was when we realized that consistently delivering exceptional design and guest experiences was what set us apart and fueled our growth. Once that became our core focus, everything accelerated, and we haven’t looked back since.

Q: What advice would you give someone looking to grow into a large property management company?

A: Don’t wait to set up the right processes and systems, especially if you plan to scale. Get OwnerRez in place early so you can automate the day-to-day and focus on scaling with intention. Also, prioritize delivering exceptional guest experiences and invest time in understanding your local market. Those elements will help you stand out and build lasting relationships with both guests and homeowners.

Q: If you could go back and give yourself one piece of advice, what would it be?

A: I wish I would’ve gone all in on short-term rentals earlier. Once I truly committed, everything started to click and grow quickly. In the beginning, I was still working full-time, so I wasn’t sure how far I could take it. But that’s also what led me to OwnerRez. I needed something that could help automate the business while I was juggling other responsibilities. Looking back, I’d tell myself to think bigger sooner and build like the business I wanted to have, not just the one I had at the time.

Q: How has using OwnerRez helped you grow?

A: OwnerRez made growing and scaling my business so much easier. The automation tools saved me time from the start, and I loved that I could build out more features as my company expanded. The ability to set up digital rental agreements, manage security holds, and streamline guest communications has been a game-changer. It’s not just about saving time; it’s about giving guests a professional, seamless experience while protecting your business behind the scenes.

Visit here to learn more about 30A Five Star Properties.

Beach Stay Getaway

Finally, we spoke with Kim Eicher, the founder of Beach Stay Getaway. Kim started by self-managing her own two short-term rental properties, and in just two years, she has grown her business to 22 listings. Continue reading to see which OwnerRez features and integrations she utilizes to free herself up to focus on building her business.

Q: What did your business look like when you first started, and what does it look like today?

A: I first started as an Owner-Manager for our own 2 STR properties in 2020. I was working a full-time corporate job. I was doing everything manually as far as managing bookings, communications, and direct bookings via our community Facebook groups. No website, no channel integrations. When I decided to add Vrbo to the mix and had my 1st double-booking, I knew I needed a PMS platform. I used another platform for about a year. That platform did not yet have SMS triggered messaging. I was really looking for that feature, as well as a platform that worked well with both direct bookings and channels. Most of my bookings were direct bookings, with channel bookings helping to supplement. I tested one other platform before deciding on OwnerRez.

Once I got my hands on OwnerRez (and with a technology background myself), I dove into setup, and I could not believe the depth of features. Once I had my setup, automations & integrations complete, I was blown away at how stable & seamless everything was. It gave me so much more time back. It made me think... I would actually enjoy doing this for other people. And OwnerRez would really be the support I need to grow this into a business.

In 2024, I got licensed in my state. I started late in the rental season, with 3 homes, plus our own 2 homes. And by the following season, I had grown to 22 STR listings!! Listing all homes on Airbnb, Vrbo, GVR & direct. Leveraging the Property Management module to easily record expenses, generate Owner Statements, and now beta Rezzy AI. Which I could not be more excited about!

Q: What were the key things you did that helped you grow, and was there a turning point along the way?

A:

Q: What advice would you give someone looking to grow into a large property management company?

A: Spend the money on the right software that will support you in scaling up your company size.

Q: If you could go back and give yourself one piece of advice, what would it be?

A: Buy another investment property or two (before prices soared, lol).

Q: How has using OwnerRez helped you grow?

A: Because of everything that OwnerRez can automate, it frees me up for being able to focus more on building my business, marketing, onboarding new listings, working with Owners, finetuning the guest experience, etc.

Visit here to learn more about Beach Stay Getaway.

A big thank you to these three standout businesses that shared their insights into what helped them grow with OwnerRez. If you are not yet using OwnerRez, get started today by signing up for a 14-day free trial or by signing up to join one of our weekly live demo webinars.