Alex and Annie: The Real Women of Vacation Rentals

Send us a message!
Last week with Moriya Rockman, we explored luxury through the lens of growth, relationships, and what it takes to scale a high-end portfolio without losing the hospitality at the center. This week, Nir Maimon brings the conversation to the definition itself, what “luxury” should mean, how it should be verified, and why the category loses trust when the label gets used too loosely.
“Luxury” has become one of the most overused words in vacation rentals, and that is exactly the problem.
In this episode, Alex and Annie sit down with Nir Maimon, President and Co-Founder of The Maimon Group, to break down how he evaluates luxury with a practical framework that starts with the operator and ends with the asset. Nir shares why luxury cannot be treated as a marketing adjective, what happens when guest expectations fall short, and why platforms and operators need clearer standards if the category wants to keep its credibility.
They also get into what verification can look like in practice, why Nir’s team says “no” far more than they say “yes,” and how their approach to service, personalization, and systems supports the level of trust luxury guests expect.
Episode Chapters:
00:00 – Welcome to Alex & Annie: The Real Women of Vacation Rentals
01:11 – Nir’s background and what The Maimon Group does in ultra-luxury
02:18 – The core issue: “luxury” is being misused in vacation rentals
04:26 – Nir’s framework: luxury starts with the operator, then the asset
06:45 – How Nir scores luxury (location, layout, privacy, finishes, noise, access, amenities)
08:34 – The trust gap: what OTAs get wrong without verification
15:48 – LPMS and the travel advisor workflow (how trust gets protected in bookings)
24:02 – Big-event travel and why groups keep choosing homes
27:45 – Personalization at scale: CRM, surveys, and concierge ownership
31:10 – AI in hospitality: start with clean data, then layer automation with human validation
38:08 – Looking ahead to 2026: “deployment,” standards, and repeatable excellence
Connect with Nir:
LinkedIn: https://www.linkedin.com/in/nir-maimon-59024595/
The Maimon Group: https://www.themaimongroup.com/ 
LPMS: https://thelpms.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/
#vacationrentals #shorttermrentals #luxuryvacationrentals

Send us a message!
In this episode, we sit down with Moriya Rockman, founder of Smiling House Luxury, to explore how a single personal vacation home in the Swiss Alps became the starting point for a global luxury vacation rental portfolio.
Moriya shares her journey from accidental host to global founder, including why she and her husband chose to stay hands-on operators while scaling internationally. She explains how staying close to hospitality standards shaped every stage of growth, from property management to technology.
The conversation also explores Villa Tracker, a B2B-to-C platform she founded that connects luxury homes with travel designers, concierges, and advisors booking on behalf of clients. Moriya breaks down why this channel matters, how it opens untapped demand beyond OTAs, and what it means for hosts and property managers looking to reach a different tier of traveler.
We also dive into global luxury travel trends, emerging destinations, and why private homes continue to outperform hotels for group travel, longer stays, and experience-driven trips.
This episode offers a grounded look at scaling thoughtfully, building through relationships, and creating long-term opportunity in luxury vacation rentals without losing sight of hospitality.
Episode Chapters:
00:00 – Welcome to Alex & Annie: The Real Women of Vacation Rentals
01:18 – Turning a Swiss Chalet Into a Vacation Rental Business
03:25 – How to Scale a Luxury Vacation Rental Portfolio
06:57 – Building a Global Luxury Brand While Staying an Operator
09:49 – B2B Travel Bookings for Vacation Rentals Explained
12:30 – Beyond Airbnb and OTAs for Luxury Rentals
14:33 – How Luxury Travel Advisors Book Private Homes
18:57 – Working With Individual Hosts and Property Managers
22:59 – Technology Partnerships for Luxury Vacation Rentals
25:57 – Is Luxury Travel Recession-Proof?
28:10 – Why Groups and Multi-Generational Travel Choose Private Homes
30:33 – Emerging Luxury Travel Destinations to Watch
33:59 – Experiencing Luxury Properties in the Off-Season
38:19 – Women in Vacation Rental Leadership
Connect with Moriya:
LinkedIn: https://www.linkedin.com/in/moriya-rockman-a3467a13a/ 
Website: https://www.linkedin.com/company/smiling-house/ 
✨ 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://cal.mixmax.com/frankbosi/demo 
#vacationrentals #shorttermrentals #luxuryvacationrentals

Send us a message!
In this episode, Alex & Annie sit down with Frank Bosi, Senior Director of Partnerships at Hostfully, to unpack what it really takes to build a tech company that people trust.
Frank’s journey began in luxury hotels long before short-term rentals became a professionalized industry. That hospitality foundation now shapes how he approaches partnerships, leadership, and growth inside one of the most culture-driven PMS brands in the space.
This conversation explores why culture scales faster than software, how AI can actually bring hospitality back into operations, and what property managers should be focusing on as expectations rise across the industry.
You’ll also hear a behind-the-scenes look at Hostfully’s approach to partnerships, onboarding, and product development, including how real user feedback influences what gets built next.
Episode Chapters:
00:00 – Welcome to Alex & Annie: The Real Women of Vacation Rentals
05:00 – Frank Bosi’s role at Hostfully and his focus on partnerships, education, and industry visibility
09:40 – Frank reflects on his hotel background and why consistency, care, and service still define great guest experience
21:17 – Inside Hostfully’s day-to-day culture, trust, flexibility, and leadership principles
15:14 – Why Hostfully feels different to operators and how people shape the product experience
10:43 – Using AI intentionally to preserve brand voice, personalization, and hospitality
40:28 – The biggest challenges operators are trying to solve right now
16:36 – Collaboration, ecosystem thinking, and why relationships still matter in tech
36:28 – How Hostfully supports operators at every stage of growth
26:00 – Hostfully’s funding story and choosing partners aligned with long-term values
Frank also shares his perspective on industry consolidation, rising professionalism among operators, and why modern property management systems have become the backbone of scalable operations.
This conversation explores what happens when technology is built around people, not the other way around.
Connect with Frank:
LinkedIn: https://www.linkedin.com/in/frank-bosi-375a5817/

Connect with Hostfully:
LinkedIn: https://www.linkedin.com/company/hostfully-inc-/
Website: https://www.hostfully.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/
#vacationrentals #shorttermrentals #PMS

Send us a message!
Welcome to the 1st of the year special episode. Alex & Annie are kicking off 2026 by looking back at the moments that shaped 2025, the lessons they’re carrying forward, and the intentions guiding the year ahead.
They share how the podcast evolved over the past year, including more on site recordings and conference conversations than ever, plus why storytelling is becoming a bigger advantage for vacation rental brands right now. You’ll also hear Alex’s personal announcement, perfectly timed for the Year of the Horse, and the top episodes of 2025 that listeners loved most.
Episode Chapters:
00:00 Welcome to the First Episode of 2026  
01:05 Why This Annual Episode Matters  
02:45 Reflecting on the Moments That Defined 2025  
06:10 Taking the Podcast On Site and Into Conferences  
08:50 Travel Stories, Italy, and Unexpected Highlights  
13:20 What’s Coming in 2026 for the Podcast  
16:45 Words of the Year and Personal Intentions  
27:30 Alex’ Personal Announcement and New Chapter  
35:50 The Top Episodes of 2025  
52:10 Gratitude, Community, and Looking Ahead
What’s your Word of the Year for 2026? Send Alex and Annie a message on LinkedIn. They genuinely want to hear what you’re focusing on this year.
✨ 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://cal.mixmax.com/frankbosi/demo
Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).

👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.
#vacationrentals #shorttermrentals #strindustry

Send us a message!
In this episode, Alex & Annie sit down with Arlen Busenitz to talk about his unconventional path from a Kansas farm to pastoring a small-town church, volunteering as an EMT, working with NASA through a defense contractor, and ultimately becoming CEO of Destin Dreamers. 
Before he was running a luxury vacation rental company on Florida's Emerald Coast, Arlen was hauling 500-pound rocks in a 1976 Jeep pickup to pay for college. It's an unlikely origin story but one that laid the foundation for everything he's built since.
Packed with practical frameworks, hard-won wisdom, and what Annie coins "Arlenisms," this is the story of how grit, perspective, and a relationship-first philosophy built a standout brand in one of the most competitive vacation rental markets in the country.
We cover:
1️⃣ Why people do not buy stays, but experiences, outcomes, and peace of mind
2️⃣ How calm leadership changes the way teams, guests, and owners respond under pressure
3️⃣ Why simplifying operations is the real foundation for scalable growth
4️⃣ How to identify owner fit and why saying no protects your team and your culture
5️⃣ Practical frameworks for preventing issues and responding clearly when they arise
6️⃣ How Destin Dreamers balances systems, structure, and human judgment
7️⃣ Where AI fits in guest communication and where it should not
8️⃣ What it means to lead in a competitive market without panic or burnout
Connect with Arlen:
LinkedIn: https://www.linkedin.com/in/abflorida/
Website:https://www.destindreamers.com/ 
Get 20% off any yearly or bi-yearly Lodgify plan, plus free personalized onboarding (a $3,000 value).
👉 Use code AAA20 at checkout. Offer valid until December 31, 2025.
#vacationrentals #shorttermrentals #propertymanagement