LevelUp Stays Aims to Remake Vacation Rentals with 1,000-Home Goal

KISSIMMEE, Fla. – March 20, 2026 – In the bustling and highly competitive short-term rental markets of Florida and Texas, one company is making a bold claim: it can double, triple, or even quadruple the revenue of underperforming vacation homes. LevelUp Stays, a property management firm co-founded by Derek and Lauren Gisriel, has announced ambitious plans to scale its portfolio from just over 70 properties to 1,000 homes in the next five years, betting on a strategy that merges data-driven finance with five-star hospitality.

The company has already made significant inroads, hosting over 10,000 guests in the last year and achieving a near-perfect 99.6% five-star review rate. This performance, they argue, is not a matter of luck but the result of a disciplined system designed to transform languishing properties into high-yield assets for their owners.

The New Science of Vacation Rentals

At the heart of LevelUp Stays' strategy is a departure from the traditional "set it and forget it" approach to rental pricing. The company employs a sophisticated, data-centric model to maximize owner revenue, a practice that is becoming a key differentiator in a crowded field. This includes advanced revenue management and dynamic pricing, which adjust rental rates in real-time based on a multitude of factors like seasonality, local events, day of the week, and competitor pricing.

"Most vacation rental homes are dramatically underperforming," said Derek Gisriel, founder of LevelUp Stays. "When you combine the right pricing strategy, marketing exposure, and guest experience systems, these properties can often generate two to four times the revenue of comparable homes in the same market."

This claim, while ambitious, is grounded in the realities of the market. In a destination like Kissimmee, which boasts over 8,800 active Airbnb listings and an average occupancy rate of 57%, simply being present isn't enough. LevelUp's approach involves professional listing optimization—using high-quality photography and expertly crafted descriptions—and distributing those listings across a wide array of platforms, including Airbnb, VRBO, Booking.com, and its own direct-booking site. By doing so, they aim to capture not just more bookings, but higher-value bookings that significantly lift a property's average daily rate (ADR) above the area's typical $192. For a property owner who previously relied on static pricing or subpar marketing, the transition to such a managed, data-informed strategy can indeed yield dramatic financial results.

A Blueprint for Scaling

The audacious goal of expanding to 1,000 properties might seem daunting, but it is rooted in co-founder Derek Gisriel's extensive experience with rapid, large-scale growth. His entrepreneurial journey began long before LevelUp Stays, starting with a door-to-door sales business at age 12 and evolving into profitable eBay stores by 15. After college, his career trajectory accelerated.

His most notable success came as a key shareholder at Sunpro Solar. There, he was instrumental in scaling the company into a national powerhouse with over 10,000 employees. That explosive growth culminated in Sunpro's acquisition by ADT Security in late 2021 for an enterprise value of approximately $825 million. At the time, Sunpro was one of the largest residential solar installers in the United States. This background in building systems, managing logistics, and driving growth in a distributed, service-based industry provides a proven blueprint that the Gisriels are now applying to the hospitality sector. The transition from solar panels to poolside patios is one of industry, but the core principles of operational excellence and aggressive scaling remain the same.

The Five-Star Snowball Effect

While financial optimization and scaling experience form two pillars of the company's strategy, the founders insist the entire structure rests on a third: the guest experience. The company’s 99.6% five-star review rate is not just a vanity metric; it is presented as the central engine of their business model.

Gisriel refers to this phenomenon as a "snowball effect." As he explained, "Better reviews lead to higher rankings on booking platforms, which increases visibility, occupancy, and ultimately revenue for property owners." In the algorithm-driven world of online travel agencies, a property with consistently high ratings is shown to more potential guests, creating a virtuous cycle of increased bookings and revenue. This philosophy directly counters a major challenge in the industry: maintaining quality while scaling.

The short-term rental industry is grappling with significant operational hurdles, including persistent staffing shortages for cleaning and maintenance, which nearly 40% of managers find difficult to solve. For LevelUp Stays, achieving its 1,000-home goal will mean successfully replicating its high standards for service and cleanliness across a vastly larger and more complex portfolio. Their success will depend on whether their "hospitality-focused operational systems" can withstand the immense pressures of rapid growth.

Navigating a Crowded Coastline

LevelUp Stays is entering markets that are anything but empty. In the Orlando/Kissimmee area, it competes with national giants like Vacasa and Evolve, as well as established local boutiques such as FunStay Florida and Home Vacation Group. Similarly, on the Texas coast, it faces entrenched players like BeachBox in Crystal Beach, which itself manages over 200 properties.

To stand out, LevelUp Stays is targeting a specific niche: owners of three-bedroom or larger vacation homes equipped with family-friendly amenities like pools, hot tubs, and game rooms. These are often the properties with the highest revenue potential but also the most demanding operational needs. By positioning itself as an expert in optimizing these specific types of high-value assets, the company aims to attract owners who are seeking a premium, hands-off management solution.

The company's guiding philosophy of integrity and accountability—"do what you say you are going to do"—serves as both a mission statement and a marketing tool. In an industry where owner-manager relationships can be fraught with mistrust, a reputation for reliability, backed by a track record of scaling a major enterprise, may be its most compelling competitive advantage. As it pushes toward its 1,000-property milestone, the broader hospitality industry will be watching to see if this combination of data, discipline, and high-touch service can truly level up the vacation rental landscape.