Winner of The Shortyz 2026 Best Travel Influencers of the Year

Videos

Oct. 21, 2026

Why Your AI Is Only as Good as Your Data

A polished AI report is only as reliable as the data behind it. 📊 For vacation rental operators, that presents a real challenge. Your PMS, revenue management platform, and accounting software can all report different numbers, making it difficult to get a clear picture of your business. As more operators…

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Oct. 21, 2026

CraftedStays Signature Story | Chris Petzy

⭐ Get to know CraftedStays, featured on the Alex & Annie Podcast! CraftedStays helps vacation rental operators build conversion-focused direct booking websites designed to improve search visibility, attract travelers, and generate more reservations. In this Signature Story, Chris Petzy of Seacoast 2 Summit Vacation Rentals shares his experience working with…

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Oct. 21, 2026

CiiRUS | Alex & Annie Brand Spotlight

⭐ Discover CiiRUS, featured on the Alex & Annie Podcast! CiiRUS is an all-in-one vacation rental property management platform designed to help professional managers streamline operations and grow their businesses. From reservations and channel management to trust accounting, guest communication, and owner management, CiiRUS brings essential tools into one connected…

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Oct. 21, 2026

dormakaba | Alex & Annie Brand Spotlight

⭐ Discover dormakaba, featured on the Alex & Annie Podcast! dormakaba provides secure access solutions for vacation rentals, helping property managers simplify how guests, staff, and vendors access their properties. With keyless entry, remote access management, and flexible access credentials, dormakaba helps operators streamline check-ins, improve property security, and manage…

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Oct. 21, 2026

Breezeway | Alex & Annie Brand Spotlight

⭐ Discover Breezeway, featured on the Alex & Annie Podcast! Breezeway is a property operations and guest experience platform that helps vacation rental managers streamline daily workflows, coordinate teams, and maintain high property standards. From housekeeping and maintenance to inspections, task scheduling, and guest messaging, Breezeway helps operators manage their…

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Oct. 21, 2026

ICND | Alex & Annie Brand Spotlight

⭐ Discover InterCoastal Net Designs (ICND), featured on the Alex & Annie Podcast! ICND specializes in vacation rental website development and digital marketing, helping property management companies strengthen their online presence and increase direct bookings. With expertise in website development, SEO, paid advertising, and conversion optimization, ICND provides digital solutions…

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Oct. 21, 2026

CraftedStays | Alex & Annie Brand Spotlight

⭐ Discover CraftedStays, featured on the Alex & Annie Podcast! CraftedStays helps vacation rental operators build professional, conversion-focused direct booking websites designed to attract more guests and generate bookings. With PMS integrations, AI-powered website tools, and a focus on search visibility, CraftedStays helps property managers strengthen their online presence and…

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Oct. 21, 2026

Savvy Signature Story | Mike Norde

⭐ Get to know Savvy, featured on the Alex & Annie Podcast! Savvy is a direct-booking marketplace that connects travelers with professionally managed vacation rentals, helping operators expand their reach while maintaining control over their bookings and guest relationships. In this Signature Story, Mike Norde highlights Savvy's approach to supporting…

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Oct. 21, 2026

Savvy | Alex & Annie Brand Spotlight

⭐ Discover Savvy, featured on the Alex & Annie Podcast! Savvy is a direct-booking marketplace built for professional vacation rental property managers. It connects travelers with professionally managed properties while giving operators control over their pricing, bookings, and guest relationships. Learn how Savvy is helping make professionally managed vacation rentals…

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Oct. 21, 2026

Vacation Finder Signature Story | Josh Throneburg

⭐ We’re excited to welcome Vacation Finder as one of our sponsors! Vacation Finder is a vacation rental listing platform built by vacation rental managers, for vacation rental managers. It exclusively features professionally managed properties, helping operators reach more travelers while maintaining control over their pricing, policies, and guest relationships.…

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Oct. 21, 2026

Bad Data, Bad Decisions: Why Your AI Is Only as Good as Your Data with John An of TechTape

Your property management system says one thing. Your revenue management platform says another. Your accounting reports tell a different story. So which numbers can you actually trust? As AI becomes more integrated into vacation rental operations, inconsistent data across systems can lead to misleading reports, unreliable AI insights, and costly…

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Oct. 20, 2026

Are You Really Protecting Your Vacation Rental Property?

Protecting homeowners' investments is one of the biggest responsibilities property managers carry. But when guests cause damage, recovering those costs through booking platforms isn't always straightforward. In this clip from Pour Decisions: When Stays Go Sideways, Ali Chaney of 30A Beach Stays & Vacations shares what made her rethink her…

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Oct. 18, 2026

Are Guests Remembering Your Brand?

When a guest books a vacation rental through an OTA, whose brand actually gets remembered? 👀 The spotlight usually goes to the OTA, leaving property managers with limited opportunities to showcase their own brands. In this clip, Michelle Gilliland, VP of Sales at Savvy, explains why giving property managers greater…

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Oct. 15, 2026

Luxury Homes, Nightmare Guests: Who Pays for the Damage?

Even the most carefully managed luxury properties can fall victim to guests who make some very questionable decisions. And when the damage is done, who actually pays for it? In Episode 4 of **Pour Decisions: When Stays Go Sideways**, presented by Safely, we are joined by **Alexandra “Ali” Chaney of…

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Oct. 15, 2026

Pour Decisions: When Guests Wreck the Home, Who Pays?

A high-end vacation rental and a premium nightly rate don't always guarantee well-behaved guests. And when a stay ends with serious property damage, getting the home back in shape can be only part of the headache. In Episode 4 of Pour Decisions: When Stays Go Sideways, presented by Safely, Alex…

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Oct. 14, 2026

Who Gets the Credit for Your Five-Star Stay?

Every five-star stay has a main character. But who gets the spotlight? 👀 When travelers book through OTAs, the platform often becomes the name they remember. So where does that leave the property manager behind the experience? In our latest episode, Michelle Gilliland, VP of Sales at Savvy, joins Alex…

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Oct. 14, 2026

Battle for Brand Recognition: Who Gets the Credit for a Five-Star Stay? Michelle Gilliland of Savvy

A guest books a beautiful vacation rental, has an incredible stay, and leaves with memories worth sharing. But when they tell others about their experience, whose brand do they remember? In this episode, Alex & Annie sit down with Michelle Gilliland, VP of Sales at Savvy, to explore what it…

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Oct. 13, 2026

Why AI Might Not Be Recommending Your Vacation Rentals

How well does AI understand your vacation rental business? 🔎 As AI search becomes part of the travel planning journey, the way property managers present information about their properties, reviews, and local expertise is becoming increasingly important. In this clip, Gil Chan, Founder and CEO of CraftedStays, explains why structured…

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Oct. 12, 2026

Could Airbnb Push More Hosts Toward True Direct Booking?

Could Airbnb’s “direct booking” experiment actually introduce more hosts to true direct booking? That’s the unexpected upside Orlie Benjamin sees in Airbnb’s new program. For hosts who have never built a direct booking strategy, simply being introduced to the concept could open the door to learning how to drive their…

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Oct. 12, 2026

Monarch Collective | Miller Hawkins

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Oct. 11, 2026

What 24,000 AI Searches Revealed About Vacation Rentals?

What actually helps a vacation rental website show up in AI search? 🔎 To find out, Gil Chan and the CraftedStays team ran 24,000 queries across four AI chat engines, examining which property managers appeared in the results and what their websites had in common. Some of the findings challenged…

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Oct. 9, 2026

Are Traditional Keys Holding Your Operations Back?

Lost keys and repeated locksmith calls can quickly turn guest access into a daily operational headache. For properties still relying on traditional keys, these challenges can create unnecessary work for property managers and frustration for guests. In this clip, Matt Seyed of Secure Lodging Systems shares what he continues to…

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Oct. 7, 2026

Is Your Vacation Rental Website Ready for AI Search?

In this episode, we are joined by Gil Chan, Founder and CEO of CraftedStays, for a timely conversation about how AI is reshaping the way travelers discover and book vacation rentals. From direct booking websites to AI-driven search, Gil shares what operators should be paying attention to as the search…

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Oct. 7, 2026

Beyond Google: Winning the New Vacation Rental Search Journey, with Gil Chan of CraftedStays

The way travelers discover vacation rentals is changing. Traditional Google search still matters, but discovery is increasingly expanding into tools like ChatGPT, Gemini, and Claude, where travelers can describe the kind of trip they want and receive recommendations based on that intent. In this episode, Alex & Annie sit down…

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