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RedAwning's FlexStep drives $5M in extra bookings for property managers

RedAwning's FlexStep drives $5M in extra bookings for property managers
Technology · 2026
Photo · Yuki Saito for Travelmao
By Yuki Saito Travel Technology Sep 18, 2026 3 min read

RedAwning, the California-based hospitality platform, reports that its FlexStep™ program has delivered more than 4,000 incremental reservations for its property management clients, translating into over $5 million in Gross Booking Value (GBV). The company says the results underscore the growing importance of flexible cancellation policies in influencing traveler decisions and improving visibility on online travel agency (OTA) platforms.

According to Tim Choate, CEO of RedAwning, the data confirms a long-held belief: "Flexible cancellation policies have a higher impact on bookings than even price or review score." FlexStep, a proprietary algorithm, dynamically adjusts cancellation terms across major distribution channels to maximize conversion. Properties using FlexStep see a 500% increase in visibility and reservations during the two weeks leading up to check-in, significantly reducing last-minute vacancies.

How FlexStep works

FlexStep is designed to solve a common pain point for vacation rental managers: balancing guest flexibility with revenue protection. By automatically tailoring cancellation policies based on demand, seasonality, and booking window, the tool aims to make listings more attractive to travelers while minimizing revenue loss from cancellations. The algorithm integrates with RedAwning's broader distribution network, which includes major OTAs and direct booking channels.

Choate emphasized that the milestone is a validation of the company's strategy. "We built FlexStep to solve a real problem for both guests and our clients. This milestone is a strong signal that we’re on the right track," he said. The program is part of RedAwning's wider suite of automated solutions designed to help property managers increase revenue and streamline operations.

Industry implications

The success of FlexStep comes at a time when the travel industry is increasingly focused on flexibility as a key driver of bookings. Airlines, hotels, and cruise lines have all introduced more lenient policies in response to changing consumer expectations. For property managers, the ability to adapt cancellation terms dynamically could become a competitive advantage, especially in uncertain economic times.

RedAwning's announcement also highlights the role of technology in optimizing distribution. As travel tech evolves, tools that leverage data to adjust pricing and policies in real time are becoming essential. The company's investment in its distribution network is expected to further enhance booking efficiency and guest satisfaction.

For travel professionals, the FlexStep results offer a data point on the value of flexible policies. While price and reviews remain critical, the ability to offer risk-free booking options may be the differentiator that tips the scale. As the industry continues to recover, expect more platforms to adopt similar dynamic approaches.

RedAwning's platform serves property managers and homeowners worldwide, offering a comprehensive suite of automated solutions. The company's focus on innovation positions it as a leader in the hospitality technology space. With the FlexStep program now proven, the company is likely to expand its capabilities further, potentially influencing how other players in the vacation rental market approach cancellation policies.

For more on how technology is reshaping travel distribution, see our coverage of AI agents and NDC reshaping travel tech. And for a look at how other sectors are driving bookings, check out Trip.com's 9.9 Mega Sale and TAT's LISA campaign.

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