January 24th, 2026

Good morning STR Report Community, and welcome to The STR Report’s Weekend Digest!

In today’s issue, you will find:

📱Weekend Digest: The Rental Resource Rundown

📬 See our collection of newsletters here: Prior Newsletters

☕ Good morning, STR Report Community!

Welcome back to The STR Report’s Weekend Digest — today we’re sharing an insightful podcast in our Rental Resource Rundown:

2026 STR Predictions: What Smart Hosts Need to Prepare for Now

In this episode of the Boostly Podcast, Mark Simpson, Founder, is joined by voices from across the industry to break down what’s coming next and what hosts and property managers need to prepare for now.

Drawing on insights from operators, tech leaders, consultants, and founders, they cover the biggest shifts already happening beneath the surface, including:

• AI moving from hype to table stakes

• Direct bookings becoming a survival strategy, not a nice-to-have

• Automation reshaping guest communication, marketing, and operations

• Rising guest expectations and the return of high-touch experiences

• Consolidation across software and management companies

• Regulation, tourist taxes, and what they could mean for supply

• Longer stays, digital nomads, and stronger shoulder seasons

• Why revenue management and marketing are finally merging

Simpson also shares his own prediction for 2026 and why he believes this is the year the industry fully crosses into a new operating model.

This episode features insights from industry leaders who kindly lent their names and expertise:

• Lucy Hiden of Breezeway

• Jessica Singer of Bookings Cloud

• Jan from Guestaway Rose from Your Family’s Place

• Alex, Co-Founder of Event Concierge

• Jack Zappa of Haven Vacation Rentals

• Ben, Independent Advisor in the Short Term Rental Industry

• Alex Dawson, Co-Founder of Company Offsites

• Tihana Sarkic from Bloqq

If you’re a host or property manager who wants to stay profitable, future-proof your business, and reduce reliance on OTAs like Airbnb and Booking.com, this episode will help you see what’s coming before it hits.

Listen now and decide which side of the change you want to be on.

🎙️YouTube link: 2026 Predictions: The Future of Short-Term Rentals, AI, Direct Bookings and Regulation

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