How LevelUp Stays Outperforms the Market by 53% with Hostaway

At a glance

• Company: LevelUp Stays

• Co-Founders: Derek and Lauren Gisriel

• Founded: 2023

• Headquarters: San Antonio, Texas

• Team: 5 full-time equivalent employees + operations manager

• Portfolio: ~85 properties

• Markets: Crystal Beach, Concan, San Antonio, Texas Coast, Galveston, Boerne, Lake Whitney, Lake LBJ, Johnson City, Houston, and Austin, Texas; Kissimmee, Davenport, Orlando, and Sarasota, Florida; and Myrtle Beach, South Carolina

• Started with Hostaway: 2+ years ago with ~4 properties

• Key results: Average gross revenue 53% above market performance, ~13,000 guests hosted in 2025, 99.5% five-star guest rating, 2-minute guest message response time

• Website: staylevelup.com

From One Vacation Rental to a Business They Never Planned to Build

When Derek and Lauren Gisriel bought their first short-term rental property in Texas Hill Country, starting a property management company wasn't part of the plan.

The couple had built successful careers in the solar industry, and their first venture into vacation rentals was motivated by the tax benefits of investing in real estate. But they soon discovered they had a knack for it.

With thoughtful design, a great guest experience and smart pricing, they turned a property that had previously earned $64,000 in its best year into one generating $190,000 in their first year of management. And guests noticed.

"People are staying at our house and they're saying, 'Derek and Lauren, you've done an incredible job with the guest experience, with the design, and obviously the income. We have a short-term rental. Can you do the same for me?'" The answer was “yes,” and LevelUp Stays was born.

What began by accident soon became a full-time business. Lauren, and then Derek, left their corporate careers behind and set out to bring the same approach, what they call the ‘LevelUp operating system’ to other property owners.

Today, LevelUp Stays manages approximately 85 properties across Texas, Florida, and South Carolina, while the couple's four personally-owned rental properties generate more than $700,000 in annual gross revenue. Their original formula still works, too. On average, LevelUp-managed properties outperform their respective markets by 53% in revenue.

But as more owners came on board, so did more guests, messages, and day-to-day responsibilities. Derek and Lauren needed a way to grow without sacrificing the personal attention that had made LevelUp Stays successful in the first place.

Finding a Property Management System That Could Keep Up

In the early days, Derek and Lauren were never really off the clock. A guest question could interrupt dinner, and a problem at the property could mean a late-night call. Realizing the need for a property management system, they initially used Guesty for Hosts, which worked well enough for a handful of properties. 

But when Derek wanted access to more advanced features, he discovered that upgrading to Guesty for Pros meant meeting a minimum property threshold and having to rebuild their listings. With their first employee joining the business, they didn't want the disruption of a time-consuming migration. More importantly, they wanted a platform they wouldn’t outgrow.

Hostaway gave them one platform with advanced features, integrations, stronger owner reporting, and tiered pricing that supported the company's northstar ambition of managing 1,000 properties.

"We knew that we wanted to grow," Derek explains. "So we should go with someone that is aggressive, that is growing, that offers the features, and that allows competitive tiered billing so that as we grow, we're rewarded as such."

Derek was equally focused on delivering a great experience for owners. "We want five-star reviews from our guests, but we also want a really great owner experience. We want clear statements that are easy for them to follow, and open and transparent communication."

Hostaway gave LevelUp Stays the tools to deliver on both sides of the business.

More Properties, More Guests, More Owners: The Challenge of Scaling Without Losing the Personal Touch

Today, LevelUp Stays provides a fully managed service across three states and continues to onboard  5-10 new vacation rental properties every month. Yet the company operates with a lean team of five full-time equivalent employees and an operations manager, supported by Derek and Lauren.

Keeping things running smoothly means managing hundreds of guest conversations, coordinating staff and cleaners, and making sure owners know exactly how their properties are performing. Hostaway sits at the center of those operations.

How Hostaway Powers LevelUp Stays’ Day-to-Day Operations and Delivers Measurable Results

Managing hundreds of guest messages without missing a beat

Responding to guests quickly is a priority for any vacation rental manager. LevelUp Stays’ target is to answer every guest message within two minutes. Their properties are listed on multiple booking channels, and Hostaway’s Unified Inbox keeps those conversations in one place, shows who is handling each request, and what happens next. 

And with hundreds of incoming guest messages a day, the team relies heavily on automation. Hostaway sends 300-400 automated messages daily, covering check-in instructions, house rules, guest verification, and upsell opportunities.

An integrated AI assistant also answers guest questions accurately, whether it's noon or 2am, and escalation rules send issues like lockouts to a team member when needed. And that attention to the guest experience is paying off. In 2025, LevelUp Stays hosted approximately 13,000 guests and reported 99.5% five-star ratings.

Giving owners visibility and peace of mind

LevelUp Stays promises owners a completely hands-off experience, but that doesn’t mean they don’t want to stay informed. With Hostaway's Owner Portal, owners can check availability, book stays at their own properties, and view financial reports without having to contact the team.

Even cleaning after an owner stay is automatically scheduled through the connected workflow. "You could go macro or micro on financial reporting, graphs and charts, where are we at, and where are we pacing," Derek explains.

Hostaway's automated owner statements have also made financial administration more transparent. After previously experiencing issues with tracking and allocating expenses, the team now benefits from statements that pull in expenses and clearly show how owner payouts are calculated.

"I just hover over the amount and it explodes out the formula and tells me exactly how it was calculated." For Derek, that clarity helps build the trusting owner relationships that are so important to LevelUp Stays’ success.

Connecting everything behind the scenes

LevelUp Stays relies on integrations for cleaning coordination, smart locks, thermostats, and dynamic pricing. With the largest marketplace of STR integrations and a reliable two-way API, Hostaway ensures LevelUp Stays enjoys a seamless experience.

Says Derek, "We've never had any issues with it. Everything flows very smoothly and works pretty seamlessly."

Hostaway also keeps calendars synchronized across booking channels, preventing double bookings. Together, these connected tools allow LevelUp Stays to run a growing portfolio without adding unnecessary complexity.

Planning ahead instead of constantly reacting

LevelUp Stays also uses Hostaway for forecasting. Hostaway's dashboard gives the team visibility into upcoming reservations, daily checkouts, and message volumes, helping them anticipate busy periods. Rather than waiting until the team is overwhelmed, Derek can make more informed decisions about when to increase or reduce staffing. It's one of the ways LevelUp Stays continues to operate efficiently despite its fast-growing portfolio.

Outperforming the market

Across its portfolio, the company is achieving significantly higher occupancy and revenue per available rental (RevPAR) than the market average.

These results reflect the strength of LevelUp Stays’ overall approach, combining its property management expertise with the technology and operational efficiency needed to deliver consistently.

Before Hostaway vs. After Hostaway

Vision for the Future: Building for 100 Properties and Beyond

LevelUp Stays is on track to reach 100 properties by the end of 2026, and it plans to lean harder on AI to run operations at that size. 

"Let's say you have 100 houses. You have 100 refrigerators, 100 ACs, 100 locks, and they all fail at some point. Being able to use a system that doesn't allow us to forget, and that guarantees a successful outcome, is the game changer."

For other property managers looking to grow, Derek's advice is simple: "Invest in yourself or the company, and ideally both." He suggests operators examine their tech stack, understand how well their systems work together, and focus on delivering better experiences for both owners and guests. 

"Figure out how you can optimally use tools like Hostaway, its integrations, and AI to deliver a seamless experience. First for your owners, so they give you more properties and more referrals. And second for your guests, so you get the five-star reviews that snowball into more and more reservations."

Company details

• Company: LevelUp Stays

• Co-Founders: Derek and Lauren Gisriel

• Founded: 2023

• Headquarters: San Antonio, Texas

• Primary markets: Texas, Florida, and South Carolina

• Website: staylevelup.com

• Contact: team@staylevelup.com

FAQs

How did Hostaway help LevelUp Stays scale its business?

Hostaway gave LevelUp Stays a property management platform that could continue to support its growth, whether it was 85 properties or 1,000, and competitive tiered pricing. With advanced automation, a Unified Inbox, owner reporting and integrations, LevelUp Stays has grown from approximately four properties to 85 while maintaining a lean team of five full-time equivalent employees and an operations manager.

How does LevelUp Stays answer guest messages within two minutes with a team of five?

Automation handles most of the volume. Hostaway sends 300 to 400 automated messages a day, covering check-in instructions, house rules, guest verification, and upsell offers. An integrated AI assistant answers guest questions at any hour, and escalation rules send issues like lockouts to a team member. Hostaway’s Unified Inbox keeps conversations from every booking channel in one place, shows who is handling each request, and the next steps.

Why did LevelUp Stays move from Guesty to Hostaway?

LevelUp Stays wanted a platform it wouldn’t outgrow. Derek found that moving up to Guesty for Pros from Guesty for Hosts meant meeting a minimum property count and rebuilding their listings. Hostaway offered advanced features, integrations, stronger owner reporting, and tiered pricing that fits LevelUp Stays’ goals for growth.

How does LevelUp Stays keep owners informed without adding work for the team?

Owners get answers from Hostaway’s Owner Portal instead of having to contact the team. In the portal they can check availability, book stays at their own properties, and view financial reports. Cleaning after an owner stay is scheduled automatically. Hostaway’s automated owner statements pull in expenses and show how each payout was calculated, so Derek can hover over an amount and see the formula behind it.

How does LevelUp Stays plan staffing as it adds 5 to 10 properties a month?

Derek uses Hostaway’s dashboard to see what’s coming. It shows upcoming reservations, daily checkouts, and message volumes, which tells him which upcoming periods will bring more guest activity. He adds or reduces staffing ahead of those periods. LevelUp Stays manages about 85 properties with five full-time-equivalent employees and an operations manager, and it’s on track to reach 100 by the end of 2026.

How does LevelUp Stays’ performance compare to the vacation rental market?

LevelUp Stays managed properties generate an average of 53% more gross revenue than their respective market benchmarks. Its adjusted paid occupancy rate of 80.8% is 72% higher than the market average of 47.2%, while its revenue per available rental (RevPAR) of $165 is 47% higher than the market average of $112. These results reflect LevelUp Stays’ property management expertise, pricing strategy, and efficient operations supported by Hostaway.