Winner of The Shortyz 2026 Best Travel Influencers of the Year

What's Missing from Vacation Rental Marketing, with Lasoh CEO Orlie Benjamin

We’re so excited to launch First of the Month Wrangle, a new 6-part series 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 improve profitability through deeper relationships with every guest.

In this first episode, Orlie shares a fresh perspective on vacation rental marketing and the opportunity to approach it in a more guest-centered way. From direct bookings and repeat stays to guest data and long-term growth, the conversation highlights how stronger relationships can support stronger results.

We cover:
✅ What’s missing from vacation rental marketing today
✅ Why guest data can support stronger direct booking strategies
✅ The difference between inventory-first and guest-first marketing
✅ The role of repeat stays in long-term growth
✅ How vacation rental operators can build stronger guest relationships
✅ Why marketing and revenue management should work more closely together
✅ How Lasoh is helping operators create more personalized guest experiences

This episode sets the tone for the series ahead and offers a valuable perspective for anyone looking to build a more effective, guest-centered marketing strategy.

#vacationrentals #shorttermrentals #strindustry #vacationrentalmarketing #guestexperience #directbookings #lasoh