Checkmate Rentals

About Us

Your Trusted Vacation Rental Management Partner

Who We Are

Checkmate Rentals: Personalized, Nationwide Property Management

Founded by Chad Phillis, a visionary with a wealth of experience in the property management industry, Checkmate Rentals emerged from a blend of expertise, resilience, and a commitment to excellence. Before founding our company, Chad Phillis worked with a renowned management firm, expanding its operations across multiple popular short-term rental markets in the United States. His efforts were pivotal in transforming a regionally focused company into a nationally recognized name.

The onset of the Covid-19 pandemic in early 2020 marked a turning point. Faced with unforeseen challenges and personal crossroads – including getting married amidst the global crisis – Chad found himself at a career impasse. It was during this period of uncertainty that the seeds of Checkmate Rentals were sown. Clients, who had come to rely on his expertise, reached out for continued support with their properties. Embracing the opportunity, Chad took a leap of faith and established Checkmate Rentals.

Our ethos is rooted in the lessons learned from industry experiences — understanding deeply what hosts seek and, importantly, what they don't. Checkmate Rentals was born out of a desire to offer a more personalized, flexible, and host-centric approach to property management. We've innovated a unique business model that combines the comprehensive capabilities of a full-service management company with the attentive, personalized service typically associated with local co-hosts.
Today, Checkmate Rentals is proud to be a team of 20 dedicated professionals, providing round-the-clock service to hosts and guests across the country. We manage an array of successful properties nationwide, each a testament to our commitment to delivering the best in the industry.

Our Mission and Values

Fostering Personal Connections and Upholding Integrity in Property Management
At Checkmate Rentals, our mission is to redefine short-term rental management by making our hosts our top priority. We are dedicated to delivering tailored property management solutions, ensuring each host feels not just supported, but valued as an integral part of our community.


Personal Relationships: We place the utmost importance on building and maintaining long-lasting, meaningful relationships with our clients. In an industry often focused on numbers, we choose to see and treat our clients as individuals, each with unique needs and aspirations.

Personalization: Recognizing that each property has its own character, we approach management with a tailored strategy, ensuring that each property is managed in a way that highlights its unique features.

Reliability: Our commitment to being there for our hosts and guests is unwavering. With 24/7 support, we ensure that assistance is always just a call or message away.

Innovation: We continually adapt and evolve our services to meet the ever-changing demands of the short-term rental market, ensuring we stay at the forefront of industry developments.

Integrity and Transparency: Honesty is the cornerstone of our operations. We believe in being upfront about every aspect of the management process, from clear communication to transparent financial dealings, fostering a foundation of trust with our clients.

Community: At Checkmate Rentals, we're more than just a service – we're a community. We strive to build strong connections not just within our team but also with our clients and the wider short-term rental industry.


By staying true to these values, Checkmate Rentals aims to exceed expectations and establish itself as a beacon of quality, trust, and unparalleled service in the property management industry.


Chad Phillis

Chad Phillis

Chad Phillis, the driving force behind Checkmate Rentals, brings over five years of extensive experience in the short-term rental industry to his role as Founder, Owner, and CEO. His journey in the industry is marked by remarkable achievements, including playing a pivotal role in building and scaling five different companies, showcasing his unparalleled expertise and deep understanding of the market dynamics.

As the visionary at the helm of Checkmate Rentals, Chad’s leadership extends across all facets of the business. He is actively involved in managing the operations team, strategizing for growth, and ensuring that both hosts and guests receive exceptional service. His hands-on approach and commitment to excellence have been instrumental in setting the company's high standards of client satisfaction and operational success.

Garrett Bishop

Garrett Bishop

Garrett Bishop, serving as the Co-Owner and Chief Operating Officer at Checkmate Rentals, is a cornerstone of the company's success. He spearheads the crucial department of pricing and revenue optimization, bringing a strategic edge to the properties managed under Checkmate Rentals. As the dedicated pricing manager, Garrett’s expertise lies in meticulously crafting pricing strategies that not only enhance revenue for hosts but also ensure competitiveness in the dynamic market of short-term rentals.

Garrett's role extends beyond just numbers and strategies; he is deeply invested in maintaining and strengthening the relationships with Checkmate Rentals’ hosts. His day-to-day interactions with clients are a testament to the company’s commitment to personal relationships and exceptional service. Through his direct communication and keen attention to host satisfaction, Garrett builds trust with our partners and delivers top-notch results.

Bryan Culler

Bryan Culler

Bryan Culler is a Co-Owner of Checkmate Rentals. In his time with the company, Bryan focused on creating financial management systems and developing long term company strategy. His dedication to client experience bettered Checkmate Rentals but also instilled confidence and trust among clients and partners. Bryan’s commitment to financial excellence is a reflection of the company’s core values and has been instrumental in building lasting relationships based on trust and reliability.

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