In this special episode, Alex & Annie sit down with Tim Rosolio, Vice President of Vacation Rental Partnerships at Vrbo, for a behind-the-scenes look at Vrbo’s Vacation Rentals of the Year program and what it takes to earn that recognition.

Recorded on location at Lakefront Escape on Squam Lake, New Hampshire, one of this year’s winning properties, the episode offers both a platform perspective and a firsthand look at the kind of hospitality Vrbo is celebrating.

Tim shares how Vrbo selects winners from millions of properties across its global network, using a mix of performance data, guest reviews, local market insight, and hospitality storytelling to identify homes that deliver standout guest experiences.

The conversation then shifts to David Rose, owner of Lakefront Escape, who shares how he transformed a dated lake house into an award-winning retreat designed with intention, warmth, and usability in mind.

From intuitive in-home tech and thoughtful labels to tailored recommendations and architectural details, this episode highlights how exceptional hospitality is built through the details.

In this episode, we cover:
00:00 - Welcome to the show
03:50 - Why Vrbo created the Vacation Rentals of the Year program
04:39 - How Vrbo selects its Vacation Rentals of the Year
08:04 - What makes a vacation rental experience feel personal and memorable
13:35 - Meet David Rose and the story behind Lakefront Escape
16:42 - Why intuitive technology matters more than flashy features
23:00 - How David Rose designed Lakefront Escape for connection, comfort, and discovery
25:20 - Why David chose self-management and how Vrbo supports pricing and promotion
26:43 - How personalized recommendations can elevate the guest stay
30:34 - How labels, notes, and in-home guidance reduce guest friction
32:21 - The Japanese design influence behind the home’s guest experience
35:27 - How design, layout, and local insight help create repeat guests

This episode captures both the criteria behind Vrbo’s recognition and the real-world hospitality choices that help a property earn it.

Connect with:

David Rose / Lakefront Escape
https://www.squamlakehouse.com/

Tim Rosolio / Vrbo
https://www.linkedin.com/in/tim-rosolio-434b2a98/

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