MidTown Stays and Hostaway: Seamless Onboarding, Scalable Property Management

Six years ago, armed with a deep-seated passion for travel and an entrepreneurial spirit, Tim Hubbard founded MidTown Stays to capitalize on a burgeoning opportunity in the vacation rental market. 

"I launched MidTown Stays in 2019, driven by a vision to manage and expand a portfolio of properties that could cater to travelers globally while operating remotely," he recalls the inception of his company, born from his experiences as a digital nomad and a savvy real estate investor.

Expanding MidTown Stays across several states and even internationally presented numerous challenges, including logistical complexities and the need for streamlined operations. However, Tim's strategic decision to integrate Hostaway's software became a transformative step for the business, facilitating remarkable growth.

Reflecting on the impact, Tim notes, "Adopting Hostaway's comprehensive property management solutions was crucial for MidTown Stays, propelling us into new markets efficiently." This strategic implementation has reinforced MidTown Stays' prominent position in the competitive rental market, with Tim attributing much of the company's operational success and scalability to Hostaway's robust software.

MidTown Stays Vacations Bio

• Founded: 2019

• Headquarters: Fully Remote

• Locations: Tennessee, Oklahoma, California, Pennsylvania, Vermont, Wisconsin, Utah, Ontario

• Listings: 82+ (30 added in the past year, 10 subleased)

• Employees: 14 full-time, 5 part-time, plus cleaners, handymen, and contractors

• Hostaway Partnership Start: June 2021

The Genesis of MidTown Stays

The nomadic inspiration

The inception of MidTown Stays traces back to Tim Hubbard’s early exposure to the travel bug in 2002, which inspired his ambition to integrate travel with work. His journey into property management began with his first real estate investment in 2010—a fourplex that served as a gateway to the industry.

"Starting with a simple fourplex opened my eyes to the potential of real estate as a tool for achieving my dreams of traveling the world while building a sustainable business," Tim reflects.

The shift to short-term rentals

By 2015, Tim had expanded his holdings and started transitioning his properties to short-term rentals, realizing their potential. The success of these endeavors led to the formal establishment of MidTown Stays in 2019, which was organized to manage his growing portfolio effectively. By 2022, Tim had managed over 70 units, hosted over 25,000 guests, and amassed extensive international experience by staying in Airbnb across over 80 countries.

"Each property was a step towards refining our approach, which really took shape when we transitioned to short-term rentals," Tim remarks on the evolution of his business strategy.

The Distinctiveness of MidTown Stays

MidTown Stays differentiates itself through its fully remote operations and focus on scaling operations for property owners. The company offers comprehensive services including property onboarding, marketing, pricing analysis, and guest communication, all managed remotely. 

This approach allows property owners to handle direct expenses, while MidTown Stays focuses on maximizing revenue with a competitive 20% commission structure.

"Our model is all about empowering property owners to succeed without the overhead of traditional property management," Tim explains the company’s philosophy.

Challenges Before Hostaway

Before adopting Hostaway, MidTown Stays used another PMS that did not fully meet their needs for efficient scalability and integration. Tim's prior experience in selling all-in-one business management software underscored his understanding of the significant impact that such tools can have on operational effectiveness.

Choosing Hostaway

The decision process

The decision to switch to Hostaway was driven by Tim’s software industry background and positive feedback from industry peers. After comparing various competitors, Tim chose Hostaway due to its comprehensive features and scalability potential.

"The software's capabilities aligned perfectly with our vision of streamlined, scalable property management," Tim notes on selecting Hostaway.

Onboarding experience

The switch to Hostaway featured a supportive onboarding process, enabling MidTown Stays to integrate the new system smoothly, thanks to ongoing support and training from the Hostaway team.

"The onboarding process with Hostaway was seamless, which helped us transition without disrupting our operations," Tim comments on the initial experience.

Taking advantage of Hostaway’s key features 

The MidTown Stays team utilizes Hostaway to manage their channels, direct booking plugins, multi-calendar management, owner portals, and review management. These features have significantly reduced administrative burdens, allowing the team to focus on expanding and improving guest experiences.

"Hostaway has been a game-changer for us, enabling a level of automation and integration essential for managing multiple properties remotely," Tim enthusiastically states.

Actualized benefits

The comprehensive PMS capabilities of Hostaway have enabled MidTown Stays to manage operations remotely—an essential aspect of their business model. The automation and integration have been key in enhancing service delivery and operational efficiency.

The Way Forward for Midtown Stays 

Advice for industry peers

Tim advises other property management companies to adopt a measured scaling approach and prioritize guest and owner satisfaction over rapid expansion. He recommends a hybrid management approach to minimize overhead and maximize control while leveraging PMS solutions to handle complex operations effectively.

Future growth plans

Looking ahead, MidTown Stays plans to continue expanding domestically and internationally, leveraging its deep market knowledge and data-driven strategies to optimize property performance and owner satisfaction.

Innovation and Growth are the Pillars of Midtown's Success

MidTown Stays' success clearly shows how innovative management practices can be combined with advanced technological tools like Hostaway to achieve significant industry success. 

By concentrating on strategic growth and efficiency, Tim Hubbard and his team have set new standards for property management. They demonstrate that long-term success in the competitive short-term rental industry can be achieved through strategic management and technological leverage.