Alex and Annie: The Real Women of Vacation Rentals

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In this special episode, Alex and 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:
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/ 
✨ Exclusive Offer to Alex & Annie Listeners:
Automate your short-term rental operations with Hospitable. Start a 14-day free trial and get 25% off your bill for the first 6 months.
👉 Get started: https://hospitable.com/partners/alex-annie
Reach more guests across top travel sites with BookingPal. Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Get started: https://alex-and-annie-offer.bookingpal.com/ 
Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie. Valid through May 31, 2026.
👉 Access the offer here: https://explore.lasoh.io/alex-annie 
#vacationrentals #shorttermrentals #vrbovacationrentalsoftheyear

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Not every guest stay ends with a five-star review.
Some leave behind a mess. Some turn into a serious operational headache. And some become the kind of story you end up telling for years.
That is the idea behind Pour Decisions: When Stays Go Sideways, a special series presented by Safely. 
In this series, Alex & Annie sit down with the Safely team and industry guests to unpack the kinds of guest incidents that rarely make it into the marketing copy but often leave the biggest operational impact. Through real stories, practical insight, and a little cocktail-fueled commiseration, the series explores what went wrong, how it was handled, and what operators can do to better protect their homes, teams, and owners.
About Episode 1:
In this kickoff episode, Alex & Annie are joined by Amanda Martins, Vice President of Business Development at Safely, to introduce the series and set the stage for the conversations ahead. Amanda shares what Safely sees behind the scenes when guest-related damage claims come in and why these stories can be some of the most useful lessons in the business.
The episode also dives into one recent case involving a large home that became the site of a 50-person party, complete with police involvement, extensive damage, smoke remediation, and a long list of cleanup issues. Amanda walks through what happened, the documentation that helped support the claim, and what operators should be thinking about when it comes to guest screening, damage protection, liability, and owner communication.
It is a practical conversation that sets the tone for the series ahead, showing how real guest incidents can reveal where systems hold up, where they fall short, and what operators can do to better protect their business before the next stay goes sideways.
In this episode:
01:41 - Meet Amanda Martins of Safely
03:34 - Why Alex & Annie launched this special series with Safely
08:34 - A real story involving a party that caused major property damage
15:01 - How Safely’s claims process works
16:31 - What happens if an operator does not have damage protection
19:01 - When operators should involve police or pursue legal action
24:06 - Why guest screening can help deter the wrong bookings
28:28 - Protecting homeowners and reducing business risk
30:20 - How Safely works alongside homeowner insurance
36:55 - Why this matters for operators of every size
Have a story to share?
We want to hear your worst guest stories. If you have a stay that went completely sideways and a lesson to go with it, submit it for a chance to be featured on a future episode.
Submit your story here: https://form.jotform.com/261032817700044
Connect with Amanda:
LinkedIn: https://www.linkedin.com/in/amandakatmartins/ 
Learn more about Safely:
Website: https://safely.com/alex-and-annie 
LinkedIn: https://www.linkedin.com/company/safely-stay/ 
This episode’s cocktail: Checkout 75
A little classy, a little dangerous, and apparently best enjoyed seated.
Ingredients:
1 oz tequila
0.5 oz GranGala
0.5 oz fresh squeezed lime juice
0.5 oz fresh squeezed orange juice
Sparkling wine, such as prosecco or a dry brut, to top
How to make it:
Shake the tequila, GranGala, lime juice, and orange juice with ice. Strain into your favorite wine glass, then top with bubbly.
Amanda’s final tip:
Don’t stand up too fast when finished.
#vacationrentals #shorttermrentals #guesthorrorstories

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What does it take to grow a vacation rental company without losing the local identity that made it successful in the first place?
In this episode, we are joined by Jakob Dwyer, CEO of Awayday, to talk about how the company is scaling through a model built on local leadership, shared support, and strong operational foundations.
Instead of forcing every market into the same mold, Awayday supports growth through shared resources across accounting, HR, revenue management, business development, and technology, while local teams continue to lead the day-to-day business. Jakob also shares how that approach influences the way Awayday evaluates partners, supports local operators, and balances growth with owner and guest experience.
This conversation offers a clear look at how Awayday is building scale through stronger operations and support without losing the local identity at the core of each business.
Episode Chapters:
00:00 - Intro to Awayday CEO Jakob Dwyer
01:14 - Jakob Dwyer’s background in vacation rentals and RealJoy’s growth
05:52 - How Awayday scales local vacation rental companies
10:50 - Why local market knowledge matters in vacation rental growth
13:07 - What Awayday looks for in a vacation rental partner
18:17 - Founder transitions, succession planning, and exit options
23:15 - Why strong vacation rental operations matter more than growth at all costs
27:01 - Awayday’s onboarding process and value creation strategy
31:41 - Shared services, local leadership, and centralized support
37:05 - How Awayday is thinking about AI in vacation rental operations
46:11 - SOPs, company culture, and empowering vacation rental teams
50:57 - Awayday’s growth strategy for 2026 and beyond
58:43 - Why every team member plays a role in company growth
This episode is brought to you by Awayday. If you are interested in being part of a company that values local leadership, strong operations, and long-term growth, connect with Jakob at [email protected].
Connect with Jakob:
LinkedIn: https://www.linkedin.com/in/jakob-dwyer-19516033/ 
Connect with Awayday:
Website: https://www.awayday.com/
LinkedIn: https://www.linkedin.com/company/awayday-vacation-rentals/ 
✨ Exclusive Offer to Alex & Annie Listeners:
Streamline your short-term rental operations with Hostfully.
Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).
👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ 
Reach more guests across top travel sites with BookingPal.
Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/ 
#vacationrentals #shorttermrentals #localidentity

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We’re kicking off a new special series, First of the Month Wrangle, in partnership with Lasoh, where we’ll dig into the strategies, systems, and blind spots shaping one of the most important and often misunderstood areas of vacation rentals: marketing.
Throughout the series, Alex & Annie will be joined by Orlie Benjamin, Founder and CEO of Lasoh, a vacation rental marketing platform built to help operators drive more direct bookings and increase profit through deeper relationships with every guest.
Together, they explore what it really takes to build stronger guest relationships, improve direct booking performance, and think more strategically about marketing in vacation rentals.
In this first episode, Orlie shares the thinking behind Lasoh and the problem she believes the industry still has not solved. While many of the core systems in vacation rentals are designed to manage properties, pricing, and distribution, far fewer are built to help operators understand guests, strengthen relationships, and market in a way that creates long-term value.
The conversation looks at what happens when hospitality gets overshadowed by operations, why guest data matters far beyond the initial booking, and why marketing deserves a bigger role in growth strategy.
Episode Chapters:
01:56 - Why Orlie Benjamin built Lasoh for vacation rental marketing
04:19 - What’s missing from most vacation rental PMS platforms
07:58 - Vacation rental tech vs. hotel tech: where the gaps still exist
09:47 - Asset management vs. guest experience in hospitality
11:01 - Why hospitality gets harder to scale in vacation rentals
13:42 - Why revenue management and marketing should work together
16:33 - The real levers of growth: customers, spend, and repeat stays
21:03 - How Lasoh helps operators capture guest data and personalize marketing
25:46 - Guest-first marketing vs. inventory-first marketing
This episode sets the tone for the series ahead and offers a valuable perspective for anyone looking to build a more thoughtful, guest-centered marketing strategy.
✨ Exclusive offer for Alex & Annie listeners ✨
Enjoy 20% off a monthly or annual subscription to Lasoh’s Guest Portal or House Manual when you use code: AlexandAnnie.
Access the offer here: https://explore.lasoh.io/alex-annie 
Valid through May 31, 2026.
Learn more about Lasoh:
Website: https://tinyurl.com/52nvyw8t
LinkedIn: https://www.linkedin.com/company/lasoh/
Facebook: https://www.facebook.com/people/Lasohio/61575721958679/
Instagram: https://www.instagram.com/lasoh.io
Connect with Orlie:
LinkedIn: https://www.linkedin.com/in/orliebenjamin/
Facebook: https://www.facebook.com/profile.php?id=61585160391720
Instagram: https://www.instagram.com/lasoh.io/
#vacationrentals #vacationrentalmarketing #directbookings

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In this episode, Tom Stewart, COO of Resort Realty, joins Alex & Annie to talk about the realities of running a vacation rental business in the Outer Banks, one of the most established and distinctive markets in the industry. They get into what makes the market different, from its geography and seasonality to its mix of inventory and long-standing operating norms.
Tom also shares what it takes to keep a legacy operation strong as market conditions change. The conversation explores weather and erosion challenges, guest and owner communication, selective growth, direct bookings, linen and laundry logistics, dynamic pricing, onboarding complexity, and the reset in owner expectations after the COVID boom. 
If you work in vacation rentals, especially in a mature or highly seasonal market, this episode offers a practical look at what long-term success requires behind the scenes. 
Episode Chapters:
04:20 - Tom Stewart’s path into vacation rentals
08:18 - What makes the Outer Banks such a unique vacation rental market
11:37 - Weather, erosion, road access, and operating through disruption
20:56 - Why legacy markets function differently from newer STR markets
25:05 - Professionally managed inventory and Resort Realty’s direct booking mix
27:18 - Growth vs. scale and why selective inventory matters
30:41 - Laundry, linens, and simplifying operations at scale
36:13 - How Resort Realty approaches dynamic pricing
44:16 - Expanding into long-term rentals and building steadier cash flow
49:01 - Why onboarding large homes is more complex than it looks
54:15 - How owner expectations changed after the COVID boom
58:43 - Why pricing and demand look different now
1:00:38 - Tom’s advice for people getting into vacation rental operations
Connect with Tom:
LinkedIn: https://www.linkedin.com/in/tom-s-8b607938/ 
Website: https://www.resortrealty.com/ 
✨ Exclusive Offer to Alex & Annie Listeners:
Streamline your short-term rental operations with Hostfully.
Mention the Alex & Annie Podcast when you sign up and get free onboarding ($1000 value).
👉 Click here to get started: https://www.hostfully.com/influencers/alex-annie/ 
Reach more guests across top travel sites with BookingPal.
Alex & Annie listeners get onboarding fees waived + 20% off the first two months.
👉 Click here to get started: https://alex-and-annie-offer.bookingpal.com/
#vacationrentals #shorttermrentals #outerbanks