About Us

GuestSmiles was founded by vacation rental owners to provide fellow property owners and managers with the tools and marketing channels to find new guests, book online reservations and spend less time managing their property — all while receiving world-class support. Our goal is to provide strong value and build long-term relationships with our clients.

GuestSmiles has two main components: the GuestSmilesToolbox (GuestSmilesToolbox.com) and the GuestSmiles Marketplace (GuestSmiles.com).

We created the GuestSmiles Toolbox to help individual self-managers get the most out of their vacation rental property, while spending less time and effort. Many self-managers are not sure where to begin or what is available to make life easier. We help them select the appropriate tools in the toolbox and then implement the tools with or for them. If clients have any questions or need support, they simply call or email our US-based support team.

The GuestSmiles Marketplace is a vacation rental marketplace where property owners, managers and guests can communicate, build relationships and book reservations. GuestSmiles.com is not an online travel agency — our mission is to remove the middleman. This means property owners and managers own and control client relationships, and guests are never charged third-party fees. It also means guests and property owners and managers have the option to interact directly OR book online instantly if they please. We provide the vacation rental marketplace with choices. Join us in our fight to give the power back to individuals.

Key team members


Ted Miller

Chief Operating Officer and Partner

A successful Colorado-based expert in the travel industry, Ted has decades worth of experience in vacation rental software creation and development. Ted brings his knowledge of a fast-growing industry and rapidly changing marketplace to the GuestSmiles team.

Ted began his career in the vacation rental industry in 1996 as partner and COO of Country Village Rental and Real Estate, LLC with offices in New England, the Mountain West and the Caribbean.

In 2000 he became partner and CEO of Stay-USA.com, Inc. which was an early provider of online booking technology to the vacation rental management companies. Stay-USA.com disrupted the industry with the first plug-and-play, real-time online booking engine.

In 2003, Stay-USA.com was rolled into Instant Software, Inc. where he was COO. Instant Software, Inc. provided reservation and management systems to vacation rental management companies. Instant Software introduced the industry’s first real-time booking distribution to third party OTA’s. In time, the company’s clients were generating more than $5 Billion in annual reservations, with $2 billion being generated online. 7 years later, Ted and his partners sold the company in 2010.

In 2016, Ted became a partner and CTO of VRM Market Data, LLC, a real-time consolidator and provider of vacation rental industry key performance indicators (KPIs) to the growing rental market. He and his partners sold the company in 2018.

In conjunction with his love for the outdoors, Ted has also been a partner and investor in Adventure Office, LLC since 2011. They provide reservation and management systems, merchant services and online distribution to adventure travel companies in another fast-growing sector of the vacation industry.


Drew King

Director or Business Development

After graduating from the University of Tennessee, Drew spent four years in the logistics industry, where he helped connect customers needing goods shipped with commercial trucking companies across the US. His passion for creating strong working relationships brought him to GuestSmiles, where he’s spent two years building partnerships with property managers and homeowners alike. He enjoys navigating the ever-evolving vacation rental industry and contributing to a team-first culture. When he’s not working, you can find him spending time outdoors with his wife and one-year-old son.


Lisa Watkins

Director of Support and Onboarding

Lisa Watkins has been part of the vacation rental industry since 2009. With an early start in customer service in 1991 in the medical industry, she took her knowledge and passion for helping others and serving her co-workers by launching internal training programs and implementing new software. After a brief time spent in the Property and Casualty industry, she entered the vacation rental industry with Instant Software serving clients in support and quickly adding training and implementation allowing her to assist clients with complex and extended projects for over 10 years.1


Ahsan Ali

Senior Software Developer/Engineer

Ahsan is a Senior Software Developer with more than 5 years of experience in Web and Desktop applications. He is always ready for new challenges and believes in continuous improvement. You can catch him enjoying long bike rides in his spare time.


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