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The Future of Vacation Rentals: Annie Holcombe on OTAs, Loyalty Programs, and Industry Challenges

Meet Annie Holcombe, a seasoned hospitality industry expert with a passion for vacation rentals and an impressive track record at major travel tech companies.

Annie’s journey in the vacation rental industry is nothing short of inspiring. Starting from property management, she moved on to pivotal roles at Expedia and Homes and Villas by Marriott, gaining invaluable insights into the world of travel and hospitality.

In this episode, Annie dives into the current state of the industry, emphasizing the importance of standardization and safety in vacation rentals. She shares her thoughts on how new entrants can navigate the complexities of regulations and market demands and offers practical advice on building a brand that stands out in a crowded market.

We’ll explore the challenges and opportunities facing vacation rental managers today, discuss the role of OTAs in the evolving landscape, and consider the potential for loyalty programs within the industry.

This episode is brought to you by our friends at Hostfully.

Hostfully Digital Guidebooks are the easiest way to help your guests get to know your property and discover just how special the community that surrounds it is.

Hostfully Guidebooks give you a dynamic place to store every bit of information you might want your guests to have — from the wifi password to how to work the hot tub to where to take the best selfies at golden hour.

Hostfully empowers you with easy-to-use tools that help you feature a totally curated list of your favorite eateries, pubs, hiking trails, and more — OR Hostfully can automatically create a list of experiences through their Guidebook Wizard if you’ve got dozens of properties and just can’t afford to curate a custom set of recommendations for each one.

Learn more here!

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About the Show

Behind the Stays is brought to you twice a week by Sponstayneous — a free, biweekly newsletter that brings subscribers the best last-minute deals and upcoming steals on Airbnb.

You can subscribe, for free, at

Behind the Stays is hosted by Zach Busekrus, co-founder of Sponstayneous, you can connect with him on Twitter at @zboozee.