Alex and Annie: The Real Women of Vacation Rentals

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Many vacation rental operators are working to grow direct bookings, but the real opportunity is not just driving more traffic to their website. It is understanding what happens once guests get there.
In this episode, we are joined by Chris Walker, Owner of Luxury Homes of Hilton Head and CEO of Direct Booking Tools.
Chris shares what he has learned from nearly two decades in property management and how his experience as an operator led to the creation of Direct Booking Tools.
Through his own property management experience, Chris saw how important it is for guests to clearly understand the value of booking direct at the moment they are making a decision. Operators may know that value, but it has to be visible, trustworthy, and easy for guests to act on.
We discuss:
00:06:13 - Why trust is central to direct booking conversion
00:09:43 - How price transparency can influence guest decisions
00:15:16 - What website traffic can reveal about booking behavior
00:28:12 - How operators can use data to improve pricing decisions
00:49:26 - Why direct booking strategy needs more than awareness
00:28:12 - How to strengthen conversations with owners using real data
00:42:31 - Why Chris believes quality and intentional growth still matter 
Whether you are trying to increase direct bookings, improve website conversion, or better understand how guests are making booking decisions, this episode offers a practical look at what operators can do to turn more interest into revenue.
Connect with Chris:
LinkedIn: https://www.linkedin.com/in/chriswalkerhhi/ 
Website: https://directbookingtools.com/

✨ Exclusive Offer to Alex & Annie Listeners: 
Strengthen your direct booking strategy with Direct Booking Tools.
Alex & Annie listeners get 50% off for the first 3 months.
👉 Get started: https://directbookingtools.com/alex-annie-landing-page/ 

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 #directbookings

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In this episode, we welcome back Mike Flaskey, President and Chief Operating Officer of Marriott Vacations Worldwide.
Mike shares what brought him back to the industry, what his new role looks like, and how Marriott Vacations Worldwide is approaching loyalty, customer experience, owner engagement, and long-term value.
The conversation looks at the timeshare and vacation club model through a hospitality lens, including how major brands build trust, keep owners engaged, and create value beyond the initial sale or stay.
Alex, Annie, and Mike also explore what short-term rental operators can learn from Marriott Vacations Worldwide, especially when it comes to consistency, brand standards, guest experience, and creating reasons for people to stay connected over time.
Episode Chapters:
02:32 - Why Mike returned to the industry and joined Marriott Vacations Worldwide
10:06 - How Marriott Vacations Worldwide thinks about loyalty
11:02 - The role of Marriott Bonvoy in brand affinity and direct bookings
18:53 - What vacation rental operators can learn from timeshare
19:30 - How brand standards help build guest trust
28:20 - Why lifetime value matters in the customer journey
29:00 - Viewing vacation ownership as a subscription business
31:09 - Using experiences to strengthen loyalty and engagement
40:11 - How Marriott Vacations Worldwide is using AI in sales training
41:41 - How AI is changing digital search and hospitality marketing
47:52 - Why prepaid vacations create resilience
51:43 - What is ahead for Marriott Vacations Worldwide
Connect with Mike:
LinkedIn: https://www.linkedin.com/in/mike-flaskey-13496094 
Instagram: https://www.instagram.com/thevacationdr/reels/ 
Connect with Marriott Vacations Worldwide:
Marriott Vacation Club: https://www.instagram.com/marriottvacationclub/ 
Westin Vacation Club: https://www.instagram.com/westinvacationclub/ 
Sheraton Vacation Club: https://www.instagram.com/sheratonvacationclub/ 
✨ 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 #timeshare

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Revenue strategy does not happen on autopilot.
Markets shift, booking windows move, owners ask harder questions, and guests become more price sensitive. For vacation rental managers, the strategy that worked last month may need a second look today.
That is the focus of Revenue Reality Check, a 6-part bimonthly series brought to you by Beyond. Each episode takes a closer look at the pricing decisions, demand trends, owner conversations, and revenue moves property managers should be paying attention to right now.
For the first episode, Alex & Annie are joined by Julie Brinkman, CEO of Beyond, to talk about one of the biggest topics in revenue management today: AI.
Julie shares how AI is already helping operators make sense of large amounts of data, reduce repetitive work, and give revenue managers more time to focus on strategy. She also explains why human oversight still matters, especially when it comes to pricing decisions, owner communication, and the revenue line of the business. For Julie, the opportunity is in using AI to support stronger decisions while keeping operators involved in the strategy.
We discuss:
00:37 - Why revenue strategy needs regular review
03:01 - How AI is being used in vacation rental revenue management
08:39 - Where automation can help reduce repetitive work
11:12 - Why owner communication needs market context
19:21 - How AI may affect OTAs, direct bookings, and listing visibility
28:22 - Julie’s Stop, Start, and Scale advice for using AI thoughtfully
31:43 - What operators should watch as World Cup demand develops
Tune in for the first episode of Revenue Reality Check, brought to you by Beyond, and follow along as we look at the trends, data, and revenue decisions vacation rental managers should be paying attention to now.
Connect with Julie:
LinkedIn: https://www.linkedin.com/in/jrbrinkman/ 
Connect with Beyond:
Website: https://beyondpricing.com/
LinkedIn: https://www.linkedin.com/company/beyond-pricing/ 
Instagram: https://www.instagram.com/beyondpricing/ 
Facebook: https://www.linkedin.com/company/beyond-pricing/ 
#vacationrentals #shorttermrentals #strindustry

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In this episode, Alex & Annie sit down with Pierre-Camille Hamana, founder and CEO of Hospitable, to talk about the evolution of vacation rental software and why adoption across the industry still has so much room to grow.
Pierre-Camille shares how his own experience as an Airbnb host in Brussels led to the creation of Smartbnb, which later became Hospitable. What started as a solution for repetitive guest messaging has grown into a broader property management platform supporting communication, operations, channel management, direct bookings, payments, and more.
The conversation also explores why many hosts and operators still hesitate to adopt property management software, how Hospitable is working to make software more accessible, and what AI could mean for guest communication, support, direct bookings, and the future of vacation rental distribution.
In this episode, we discuss:
02:27 - How Pierre-Camille’s experience as an Airbnb host led to the creation of Hospitable
04:22 - Why guest messaging became the starting point for a larger software platform
09:45 - How Hospitable evolved from Smartbnb into a broader property management system
20:16 -  Why software adoption remains low across parts of the short-term rental industry
21:55 - The challenges that keep smaller hosts and operators from adopting software
23:44 - Hospitable’s approach to making property management software more accessible
17:47 - How self-managers can grow into co-hosts or professional property managers
41:47 - The role of AI in guest messaging, customer support, and software usability
44:07 - Why AI should make tools easier to use, not simply add more complexity
53:07 - What AI agents could mean for OTAs, direct bookings, and property discovery
53:07 - Why strong owner service, guest experience, and operational consistency still matter as technology evolves
Connect with Pierre-Camille:
LinkedIn: https://www.linkedin.com/in/pchamana/ 
Connect with Hospitable:
Website: https://hospitable.com/partners/alex-annie 
LinkedIn: https://www.linkedin.com/company/hospitable/ 
Instagram: https://www.instagram.com/hospitable_com/ 
Facebook: https://www.facebook.com/hospitable/ 
✨ 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 #pms

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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