At Streamline, we believe the most valuable insights come from listening to what’s happening on the front lines and pairing that perspective with the technology shaping what’s next.
Our recent webinar brought together experts in STR marketing, insurance, payments, and technology to recap 2025 trends and break down what property managers can expect to see in the year ahead. Whether the panelists were outlining evolving booking trends or previewing new AI-powered features, everything boiled down to one core question: how can PMCs remain competitive, profitable, and confident in an ever-evolving landscape?
Watch the full replay:
Revenue Strategy: What Will Separate Top Performers in 2026
We already know that the most successful revenue strategies are proactive, not reactive. Haphazardly lowering rates to fill a gap may get a property booked today, but it probably won’t change the long-term trajectory of your revenue. Understanding the unique demand of your market and acting strategically is key.
But getting a property booked is only one part of the strategy. With trends like shrinking booking windows anticipated to persist in 2026, maximizing value through the entire guest lifecycle will be crucial.
Many guests won’t hesitate to increase their spend when add-ons clearly enhance their stay—whether it’s early check-in, late checkout, experiences, or trip protection, add-ons can be simple ways to improve guest satisfaction and drive major revenue. Simply put, giving more to your guests equates to getting more from your guests.
Differentiation won’t come from racing to the bottom on price—it will come from understanding what guests want and seamlessly integrating it into their experience.
AI, Operations, and the PMS of the Future
Artificial intelligence is already shaping how the short-term rental industry operates, and adoption is speeding up. Although new AI-powered features will continue to roll out, 2026 will be less about the novelty of the tools and more about meaningful, responsible integration of them.
In practice, that looks like:
- Taking full advantage of AI tools that help teams work faster and smarter
- Optimizing your booking website for AI-first searches
- Simplifying your tech stack with unified ecosystems
The goal isn’t more tech—it’s better outcomes. Though it may seem counterintuitive, more AI won’t equate to less human connection; instead, it will improve operating efficiency and free up time to focus on the hospitality and guest experiences that define the industry.
Did you know: Streamline uses AI, too! By working closely with real PMCs to understand their needs and using AI-supported development processes, we’re able to create new features faster, and make sure they are compliant, tested, and strong when they reach users.
Payments, fraud, and guest experience expectations
Guests, especially Millennials and Gen Z travelers, are increasingly opting to pay for bookings with mobile wallets (think: ApplyPay, PayPal, and Buy Now, Pay Later options) over traditional credit or debit cards.
The benefits of a frictionless booking experience also extend to both PMCs and guests:
- Wallet-based checkout reduces barriers to booking and improves search-to-book conversion
- Familiar payment methods give guests confidence to bypass OTAs, enjoy a seamless user experience, and book directly on your site
- Buy Now, Pay Later options enable travelers commit to higher-value stays
Thanks to safeguards like two-factor authentication, mobile wallets carry an exceptionally low risk of fraud. At the same time, advancements in technology have lowered the barrier to committing fraud with other payment methods—making protection and verification more important than ever.
Tools that integrate verification into the booking flow help close that gap. Automated solutions like Lynnbrook’s Guest ID use public phone records to assess a guest’s fraud risk within minutes, adding an extra layer of confidence for PMCs without sacrificing the guest booking experience.
Risk protection and owner confidence
Although insurance may not change as drastically as tech or travel trends do year-over-year, protection and peace of mind are becoming fundamental expectations for owners, PMCs, and guests alike.
Owners increasingly want assurance that their assets—and their income—are protected. PMCs are looking for ways to reduce risk without adding operational complexity. Guests want peace of mind knowing their investment isn’t lost if circumstances change.
AI is also beginning to play a role here, from faster claims processing to more dynamic risk assessment in the future. Automated communication ensures guests are educated about protection options at multiple points in the booking journey, helping dramatically increase adoption rates.
The result is a win-win-win: stronger owner confidence, additional revenue opportunities for PMCs, and more peace of mind for guests.
OTA tightening, privacy shifts, and new direct booking reality
OTAs aren’t going away in 2026, but the power balance is shifting.
Rising fees, tightening margins, and changing privacy rules are pushing PMCs to rethink how they approach distribution. At the same time, AI-driven search and evolving user behavior are reshaping how travelers discover and evaluate rental properties, often before they ever even visit a booking website.
Direct booking strategies anchored in strong UX, first-party data, and clear value propositions will be more important than ever in the year ahead. PMCs who invest in their own sites, understand guest behavior through on-site analytics, and highlight the advantages of booking direct will be better positioned as guest booking journeys continue to change.
The bottom line
In 2026, the market will belong to PMCs who embrace innovation, invest in the guest experience, and identify untapped revenue opportunities in their workflows. Think holistically and strategize thoughtfully—and you’ll be equipped to tackle whatever the new year may hold.
Make 2026 Your Best Year Yet with the Industry’s Leading PMS!