Winner of The Shortyz 2026 Best Travel Influencers of the Year

Videos

June 11, 2026

Call Center Solutions | VTrips

Call Center Solutions | VTrips

⭐ We’re excited to welcome Call Center Solutions as one of our sponsors! Call Center Solutions helps businesses improve customer engagement, streamline operations, and provide reliable support through customizable contact center services. Their team supports customer care, administrative services, and sales operations, helping companies create better customer experiences while giving…

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June 11, 2026

Introducing Monarch Collective

Introducing Monarch Collective

⭐ We’re excited to welcome Monarch Collective as one of our sponsors! Monarch Collective is a national vacation rental management platform built for local brands that want to grow without losing what made them successful in the first place. They acquire and operate established vacation rental companies across the U.S.,…

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June 11, 2026

Barefoot | Padre Getaways

Barefoot | Padre Getaways

⭐ We’re excited to welcome Barefoot as one of our sponsors! Barefoot is a property management software platform built for vacation rental companies that need strong operational tools, reliable trust accounting, and the flexibility to manage growth with confidence. From reservations and owner management to accounting, reporting, and guest services,…

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June 11, 2026

Introducing BookingPal

Introducing BookingPal

⭐ We’re excited to welcome BookingPal as one of our sponsors! BookingPal is a channel management platform that helps vacation rental property managers distribute listings across top channels like Airbnb, Booking.com, Vrbo, and more. Through one connection, operators can expand visibility, manage listings, rates, and reservations more efficiently, and access…

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June 11, 2026

Introducing Lasoh

Introducing Lasoh

⭐ We’re excited to welcome Lasoh as one of our sponsors! Lasoh is the industry’s only AI-native guest marketing platform, built to help vacation rental operators increase revenue per stay, stays per guest, and booking conversion rates. Through its SMART Marketing and Guest Portal products, Lasoh helps operators turn guest…

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June 11, 2026

Direct Booking Tools | Casago NSB & Casago Daytona

Direct Booking Tools | Casago NSB & Casago Daytona

⭐ We’re excited to welcome Direct Booking Tools as one of our sponsors! Direct Booking Tools is a premium conversion and intelligence platform designed specifically for professional vacation rental operators. Their platform helps improve the guest journey, increase direct revenue, and give management teams clearer booking insights to make more…

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June 11, 2026

Hospitable | Lahaina Studios

Hospitable | Lahaina Studios

⭐ We’re excited to welcome Hospitable as one of our sponsors! Hospitable helps short-term rental operators automate guest communication, streamline workflows, and stay on top of daily operations with less manual work. Built to help operators run their rentals on autopilot, Hospitable supports everything from messaging and task management to…

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June 11, 2026

Hospitable | Ashley Kehr

Hospitable | Ashley Kehr

⭐ We’re excited to welcome Hospitable as one of our sponsors! Hospitable helps short-term rental operators automate guest communication, streamline workflows, and stay on top of daily operations with less manual work. Built to help operators run their rentals on autopilot, Hospitable supports everything from messaging and task management to…

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June 11, 2026

BookingPal | Hosteeva

BookingPal | Hosteeva

⭐ We’re excited to welcome BookingPal as one of our sponsors! BookingPal is a channel management platform that helps vacation rental property managers distribute listings across top channels like Airbnb, Booking.com, Vrbo, and more. Through one connection, operators can expand visibility, manage listings, rates, and reservations more efficiently, and access…

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June 10, 2026

Trust Accounting Isn’t Back Office: It’s the Foundation, with Ed Ulmer of Barefoot

Trust Accounting Isn’t Back Office: It’s the Foundation, with Ed Ulmer of Barefoot

Trust accounting may not be the flashiest part of vacation rental management, but it is one of the most important. In this episode, we’re joined by Ed Ulmer, CEO of Barefoot, for a conversation about why trust accounting should not be treated as a back-office function. Ed shares how his…

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June 9, 2026

Trust Accounting Isn’t Back Office: It’s the Foundation, with Ed Ulmer of Barefoot

Trust Accounting Isn’t Back Office: It’s the Foundation, with Ed Ulmer of Barefoot

In this episode, we are joined by Ed Ulmer, CEO of Barefoot, for a conversation about trust accounting, vacation rental technology, and what operators need from their systems as their businesses become more complex. Ed shares how his background in tourism, destination marketing, real estate, and software all shaped the…

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June 9, 2026

What Lasoh’s Founding Member Program Is All About

What Lasoh’s Founding Member Program Is All About

In our latest First of the Month Wrangle, Orlie Benjamin talks about why Lasoh is opening its Founding Member Program to a small group of vacation rental operators. The idea is to build Lasoh with the people who are actually going to use it. Orlie shares how founding members can…

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June 8, 2026

Why PMS Updates Feel So Risky

Why PMS Updates Feel So Risky

Launching new tech features can feel a little like pressing a mystery button and hoping the whole house does not start blinking. Every system touches another system, and when they do not talk to each other, even a small update can turn into a much bigger operational headache. In this…

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June 4, 2026

How To Make Vacation Rental Marketing More Personal With AI

How To Make Vacation Rental Marketing More Personal With AI

Guest data is only valuable when it helps teams take action. For many vacation rental operators, the challenge is turning the data they already have into the right message for the right guest at the right time. In this clip, Orlie Benjamin shares how that workflow can become more streamlined…

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June 4, 2026

Live at Short Stay Summit 2026 | Hospitality Elevated: Where Tech and Human Connection Work together

Live at Short Stay Summit 2026 | Hospitality Elevated: Where Tech and Human Connection Work together
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June 3, 2026

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

The vacation rental industry has gone through major waves of change over the last two decades, and AI is quickly becoming one of the biggest shifts yet. In this episode, we welcome back John Suzuki, Chief Technology Evangelist at Staylist, for a conversation about the evolution of vacation rental technology,…

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June 3, 2026

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

From Fax Machines to AI: Lessons from 20 Years of Industry Transformation, with John Suzuki

The vacation rental industry has gone through major waves of change over the last two decades, and AI is quickly becoming one of the biggest shifts yet. In this episode, we are joined by John Suzuki, Chief Technology Evangelist at Staylist, for a conversation about the evolution of vacation rental…

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June 1, 2026

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Can we stop marketing properties and start marketing to people? That is the question at the center of Episode 2 of First of the Month Wrangle, brought to you by Lasoh. In this conversation, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to talk…

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June 1, 2026

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Turn every guest interaction into more revenue with Lasoh. Apply to become a Founding Member and/or get 20% off Lasoh products with code AlexandAnnie. Valid through July 31, 2026. 👉 Learn more: https://explore.lasoh.io/alex-annie In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are…

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June 1, 2026

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

Can We Stop Marketing Properties and Start Marketing to People? with Lasoh CEO Orlie Benjamin

In this second episode of First of the Month Wrangle, presented by Lasoh, Alex & Annie are joined again by Orlie Benjamin, Founder and CEO of Lasoh, to continue the conversation around vacation rental marketing and what it takes to make it more effective, more personal, and more guest-centered. This…

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May 29, 2026

Are You Building a Business or Buying Market Share?

Are You Building a Business or Buying Market Share?

It is easy to look at a lower management fee as a way to stay competitive. But for vacation rental operators, the real question is not just whether the fee helps win the property. It is whether that fee can support the level of service the owner and guest expect…

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May 27, 2026

Why Invited Home Bet on Ski Markets Instead of Bigger Scale with CEO, James Smith

Why Invited Home Bet on Ski Markets Instead of Bigger Scale with CEO, James Smith

Growth is exciting, but in luxury vacation rentals, more does not always mean stronger. The real test is whether the business can keep delivering the level of service promised to owners and guests. In this episode, James Smith, CEO of Invited Home, joins Alex & Annie to talk about why…

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May 27, 2026

Why InvitedHome Bet on Ski Markets Instead of Bigger Scale with CEO James Smith

Why InvitedHome Bet on Ski Markets Instead of Bigger Scale with CEO James Smith

In this episode, we are joined by James Smith, CEO of InvitedHome, for a conversation about focused growth, luxury vacation rental operations, and what it takes to build a more sustainable business in high-end destinations. James shares how InvitedHome evolved from a broader multi-market vacation rental company into a luxury…

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May 26, 2026

Outsourcing Guest Support the Right Way

Outsourcing Guest Support the Right Way

Scaling guest support takes more than adding more people to the phone. The team representing your business needs to understand your standards, your properties, your guests, and the situations they may need to solve in real time. In this clip, Amanda Szubert shares how Call Center Solutions approaches that process,…

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