Owner Retention Is the Conversation Nobody in Vacation Rentals Is Having with Annie Holcombe of Annie and Company Solutions
July 28, 2026
Annie Holcombe has spent more than three decades helping shape the vacation rental industry. As Founder and Chief STRategist at Annie & Co. Solutions, Brand Ambassador for Booking.com, and co-host of Alex & Annie: The Real Women of Vacation Rentals, she helps property managers, suppliers, and technology companies navigate an industry that has become more competitive and more fragmented than ever before. Few people have the relationships, perspective, and industry credibility that Annie has built since entering vacation rentals in 1992.
In this episode, Lynell sits down with Annie to discuss how the vacation rental industry has evolved over the past three decades and what operators need to focus on next. They explore the growing divide between legacy vacation rental companies and newer short-term rental operators, why owner retention deserves more attention than owner acquisition, how Booking.com is working to better serve property managers, and why strong relationships remain the industry's greatest competitive advantage.
Annie Holcombe has been part of the vacation rental industry since 1992, building a career that spans property management, owner relations, OTA strategy, business development, hospitality technology, and industry leadership. Today, as Founder and Chief STRategist at Annie & Co. Solutions, she helps property managers strengthen owner relationships, improve business development, and build long-term growth strategies, while also serving as Brand Ambassador for Booking.com and co-hosting Alex & Annie: The Real Women of Vacation Rentals. Throughout her career, Annie has become one of the industry's most connected voices, known for bringing people together and helping businesses grow through meaningful relationships.
In this episode, Lynell sits down with Annie to reflect on how the vacation rental industry has changed, where it's heading next, and why relationships, not technology alone, will continue to determine who succeeds.
What you'll learn:
- Why the post-COVID boom created a knowledge gap between experienced vacation rental operators and newer short-term rental hosts
- Why owner retention may become a bigger competitive advantage than owner acquisition over the next few years
- How consistent, personal communication helps property managers build stronger, longer-lasting owner relationships
- Why diversification across multiple booking channels remains essential instead of relying too heavily on any single platform
- What smaller property managers should prioritize when choosing technology and building their operational foundation
- Why finding mentors and becoming active within the vacation rental community can accelerate growth far more than trying to figure everything out alone
- How Annie is helping Booking.com better understand the needs of property managers and bridge long-standing gaps between the platform and the vacation rental industry
About Annie Holcombe: Annie Holcombe is the Founder and Chief STRategist at Annie & Co. Solutions, Brand Ambassador for Booking.com, and co-host of Alex & Annie: The Real Women of Vacation Rentals. Since entering the industry in 1992, she has worked across property management, distribution strategy, hospitality technology, and business development, helping operators, suppliers, and technology companies grow through stronger relationships and smarter strategy. Annie also serves on the VRMA Board of Directors and is widely recognized as one of the vacation rental industry's most trusted and well-connected leaders.
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👉 RSS - https://feeds.fame.so/the-vacation-rental-show
The Vacation Rental Show is handcrafted by our friends over at: fame.so
Previous guests include: Jim DeVos of Best Beach Getaways, Stacy Wesson of Cascara Vacation Rentals, Michael Friedman of The Simple Life Hospitality, Steve Caron of Inhabit, John An of TechTape, Jessica Gillingham of Abode Worldwide, Justin Ford of Breezeway, Mahwussh Alam of One Perfect Stay, Sofia Rossato of Inhabit, and many more.
Check out the three most downloaded episodes:
- Vacation Rental Stories: Episode 63 - Driving Innovation and Partnership
- Homeowners Become Family with Michael Godfrey, Owner of Michael’s Vacation Rentals
- Life in Maui as a Property Manager with Scott Jordan, Owner of Maui Life Realty
Got a question for The Vacation Rental Show?
Our host, Lynell Gordon, is answering your vacation rental questions in our new segment: Ask Lynell.
Whether you’re navigating pricing strategy, owner retention, tech stack decisions, franchise growth, or operational scaling — no question is too big or too niche.
Submit your question in writing, audio, or video — whatever works for you. Lynell and her industry expert guests will select real questions from property managers like you and answer them on the show.
👉 Submit your question here: https://lnkd.in/eFy_6ssW
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The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:
- Scaling your vacation rental portfolio
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