The Vacation Rental Show

Building Guest Loyalty Through Cleanliness and Communication with Ann Marie O’Rourke


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In this episode of The Vacation Rental Show, host Lynell Gordon speaks with Ann Marie O'Rourke, owner of Sandpiper Management, about building a boutique property management company through superior cleanliness standards, transparent owner communication, and personal touches that create repeat guests who eventually become property owners themselves.


What You'll Learn:

  • Why cleanliness is the most overlooked aspect of property management and how one unclean discovery makes guests search for every other problem
  • The controversial staffing decision that transformed Ann Marie's business: replacing all cleaning teams and paying staff more to ensure everyone became more profitable
  • How to balance owner loyalty and guest satisfaction without sacrificing either relationship through customized management approaches
  • Small personal touches that cost almost nothing but create lasting memories: handwritten notes, tailored recommendations, and celebration gifts
  • Communication strategies that build trust even when you don't have immediate answers to owner questions
  • Why treating properties as customized investments rather than one-size-fits-all assets creates competitive advantages against corporate competitors


Ann Marie O'Rourke purchased Sandpiper Management without traditional property management experience, bringing instead a background in clinical social work and freelance writing. Drawing on her father's forty years in commercial cleaning, she understood the difference between appearing clean and truly clean. She made the bold decision to replace her entire inherited cleaning staff and pay new teams more than competitors, betting that superior cleanliness would drive profitability for everyone. Six years later, many original team members remain, creating consistency that generates reviews consistently stating "this is the cleanest property I've ever stayed in." Her company now manages properties across Kiawah Island and Seabrook Island near Charleston, South Carolina, competing successfully against larger corporations by focusing on quality over quantity and relationships over scale.


This episode is sponsored by Lynbrook Group.

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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
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  • Revenue management strategies
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