Setting Honest Expectations with Vacation Rental Homeowners with Kimberly Layton of SkyRun
June 17, 2026
Kimberly Layton spent years in corporate America helping Fortune 500 companies cut through complexity and align their strategy with real results. As the owner of SkyRun Naples, she's now applying those same disciplines to vacation rental property management, where honest homeowner communication and proactive owner relationships are the foundation of everything she does. This episode is sponsored by iTrip Vacations.
In this episode, Lynell sits down with Kimberly to explore what separates good property managers from great ones. The conversation covers how Kimberly brings her enterprise background to every part of her short-term rental business, from setting realistic revenue expectations with new homeowners to navigating the growing tension between property managers and Online Travel Agencies (OTAs) over guest data ownership. Kimberly also shares how she's using artificial intelligence (AI) tools to work more efficiently, why she chose the franchise model when entering the industry, and the leadership principles that carry over from the boardroom to property management. If you're looking to build a vacation rental business on a foundation of trust and transparency, this episode is for you.
This episode is sponsored by iTrip
Kimberly Layton spent decades in corporate America working with Fortune 500 organizations in healthcare, finance, and retail, helping executive teams cut through noise and align their strategy with results. After leaving Dell Technologies, she applied that same discipline to a new challenge: vacation rental property management. As the owner of SkyRun Naples, Kimberly is building a short-term rental business grounded in honest homeowner communication, genuine accountability, and a willingness to have the hard conversations that many property managers avoid.
What you'll learn:
- Why setting false revenue expectations during onboarding is one of the most costly mistakes in vacation rental management
- How Kimberly's corporate background shapes her approach to every owner relationship and team-building decision
- The growing battle between property managers and Online Travel Agencies (OTAs) over guest data and who really owns the guest relationship
- How to build and maintain lasting owner trust, especially when something goes wrong
- Why the franchise model gave Kimberly the operational support to focus on what matters most: acquiring owners and serving guests
- How artificial intelligence (AI) tools and a structured monthly review practice are helping her scale more efficiently
About Kimberly Layton:
Kimberly Layton is the owner of SkyRun Naples, a franchise location of SkyRun Vacation Rentals. Before entering the vacation rental industry, she spent decades in enterprise technology and strategic business development, most recently at Dell Technologies. She brings the same communication discipline, value-driven sales approach, and results-focused mindset from her corporate career into her day-to-day work as a property manager, business owner, and franchise operator.
If you enjoyed this episode, make sure to:
- Subscribe, rate, and review
- Share this episode
👉 Apple - https://apple.co/3lYc2gU
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 RSS - https://feeds.fame.so/the-vacation-rental-show
👉 Spotify - https://spoti.fi/3InYanV
👉 Fame Host - https://bit.ly/hwg-podcast
👉 iheartradio - https://ihr.fm/3Z8qqlg
👉 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
Tune in to hear your answer featured on The Vacation Rental Show.
Are you a vacation rental industry leader looking to share your expertise? We're seeking innovative voices to join our conversation about growing and scaling vacation rental businesses.
The Vacation Rental Show reaches thousands of property managers worldwide. We're particularly interested in perspectives on:
- Scaling your vacation rental portfolio
- Optimizing guest experiences
- Revenue management strategies
- Industry trends and market insights