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2025 was not a year of easy growth for the vacation rental industry. Instead, it was a year of pressure: on margins, teams, guest experience, and operational execution. Performance didn’t move in a single direction; it split. Some operators grew stronger, while others struggled to keep pace in an increasingly competitive and complex environment.
Booking windows shortened. Stay lengths became harder to predict. Guest expectations rose, even as labor costs, distribution fees, climate volatility, and regulatory pressure intensified across many regions. At the same time, artificial intelligence moved from buzzword to baseline, reshaping how travelers discover destinations, how bookings happen, how data is interpreted, and how teams operate day-to-day.
As leaders from across data, OTAs, pricing, and property management organizations shared in Hostaway’s vacation rental predictions webinar, one theme became unmistakably clear: the operators who succeed in 2026 will not be the loudest marketers or have the biggest portfolios. They will be the ones who are most operationally disciplined, most intentional about quality and differentiation, and most prepared to let technology amplify, not replace, strong foundations.
Below are the most important 2026 vacation rental predictions, grounded in real-world insights from industry leaders, and what they mean for professional vacation rental operators preparing for the year ahead.
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The webinar made it clear that 2025 was not a down year; it was a divergent year, and that divergence accelerates into 2026.
Simon Lehmann, CEO & Founder at AJL Atelier, described 2025 as a year of “widening gaps,” noting that performance varied dramatically by market, asset quality, and operator sophistication rather than following a single global trend. That same pattern continues as AI, pricing tools, and operational systems disproportionately benefit operators who already have strong foundations.
Jason Sprenkle, CEO at Key Data, reinforced this by pointing to a growing “K-shaped” market, where the strongest operators pull further ahead while others fall behind. Technology, data access, and AI are no longer leveling the playing field; they are amplifying execution quality.
In 2026, being average will be riskier than ever, not because demand disappears, but because competition becomes more precise.
What this means for vacation rental operators in 2026:
While 2025 saw relatively flat supply growth, panelists agreed this was more of a pause than a permanent shift.
Jason Sprenkle shared that early indicators point toward renewed supply growth in 2026 as interest rates ease and investor confidence improves, especially after a stagnant year. That return of supply will test pricing strategies that benefited from scarcity over the past 12–18 months.
At the same time, Steve Schwab, CEO at Casago/Vacasa, cautioned that while supply growth can be healthy for property managers, it isn’t always good for individual homeowners, as more competition puts pressure on unit-level economics.
In 2026, operators will need to balance growth with competitiveness, recognizing that simply adding inventory will no longer guarantee stronger performance.
What this means for vacation rental operators in 2026:
Shorter booking windows and shorter stays are no longer temporary disruptions, they are structural shifts heading into 2026.
Jason Sprenkle noted that guests continue to book closer to arrival, while staying less nights, making it harder to rely on traditional pacing and forecasting models. These shifts are influenced by economic uncertainty, return-to-office policies, and more flexible travel decision-making.
Marcus Rader, Co-Founder & CEO at Hostaway, added that last-minute travel is increasingly common because travelers are no longer planning extended stays far in advance, the way they did during the pandemic years. This puts pressure on operations teams to execute faster without sacrificing quality, especially when turnovers become more frequent and less predictable.
What this means for vacation rental operators in 2026:
One of the most consistent themes in the webinar was that guests are shifting from “searching” to “asking.”
Marcus Rader shared how conversational AI is already changing the way travelers discover restaurants and destinations, enabling them to consider locations they would never have found on their own. In 2026, that same behavior increasingly applies to vacation rentals, where guests describe experiences rather than filtering listings.
This shift has major implications for destinations and operators alike. Instead of competing solely within crowded, well-known markets, AI-driven discovery allows lesser-known destinations and well-positioned properties to surface based on intent, like family needs, accessibility, lifestyle, or trip purpose, rather than name recognition alone.
What this means for vacation rental operators in 2026:
As discovery becomes intent-driven, the ability for AI to understand your inventory depends entirely on data quality. Jason Sprenkle summed this up succinctly by saying that “data quality is the new marketing,” emphasizing that AI cannot recommend what it cannot interpret. Listings that lack structure, detail, or consistency simply won’t surface when guests ask nuanced questions.
This goes beyond basic amenities. AI evaluates semantic meaning, whether a home works for toddlers, remote workers, multigenerational families, or pet owners. In 2026, operators who treat data as a living asset rather than a static setup will gain a significant visibility advantage.
What this means for vacation rental operators in 2026:
As AI-driven discovery grows, traditional SEO signals lose influence while trust signals gain importance.
Steve Schwab explained that AI is effectively returning to early search principles, where credibility, reputation, and authority matter more than keyword tactics. In his words, brand becomes the mechanism AI uses to decide what it can confidently recommend.
Koryn Okey, VP Community & Engagement at Breezeway, added that brand is ultimately shaped by operational execution. Reviews, guest sentiment, and consistency across touchpoints tell a story that AI can interpret far more effectively than polished marketing language alone.
In 2026, brand strength is inseparable from operational discipline.
What this means for vacation rental operators in 2026:
The conversation around AI shifted noticeably from hype to realism during the webinar. Steve Schwab described agentic AI as the next phase, where systems can move across platforms, pull reports, compare data, and act autonomously. However, Marcus Rader cautioned that the pace of change will be uneven, and that many tools built today will be obsolete within a year.
The takeaway for 2026 is not to chase every AI solution, but to build understanding and foundations. Operators who invest time in learning how AI works, and structuring their data and workflows accordingly, will be best positioned to adopt agentic capabilities as they mature.
What this means for vacation rental operators in 2026:
Despite rapid automation, panelists consistently emphasized that hospitality remains deeply human. Koryn Okey noted that while AI can handle repetitive issues, guests still expect empathy and judgment during high-stakes or emotional moments. Poor escalation paths can quickly undermine trust, even if automation performs well elsewhere.
Rather than replacing teams, operators are redeploying them toward higher-value interactions. Simon Lehmann observed that the industry is shifting human capital toward guest and owner value creation, especially as AI absorbs repetitive tasks.
What this means for vacation rental operators in 2026:
Regulation remains one of the most significant external forces shaping 2026, particularly in Europe. Simon Lehmann emphasized that regulation is now a top concern for investors and operators alike, driven largely by housing affordability narratives rather than tourism performance. While pressure continues to increase, it does not affect all operators equally.
Jason Sprenkle and Koryn Okey both stressed that professional operators who comply, document impact, and engage early are better positioned to adapt. Regulation acts as a filter, pushing out informal operators while rewarding those who can demonstrate standards, accountability, and community alignment.
What this means for vacation rental operators in 2026:
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Ready to raise the standard across your portfolio? |
The future of vacation rentals isn’t about chasing every trend, it’s about operational maturity.
The predictions for 2026 point to a clear shift in how vacation rental operators will succeed. Performance gaps are widening as AI, data, and operational discipline reward those with strong foundations, while changing booking behavior, returning supply, and regulatory pressure raise the bar for everyone else. Discovery is becoming intent-driven, brand is replacing traditional SEO, and consistency is now inseparable from growth.
In this next phase of the industry, success won’t come from chasing every trend or tool. It will come from disciplined execution, clear differentiation, and using technology to amplify strong operations without losing the human side of hospitality.
The operators who win in 2026 will:
As the industry continues to evolve, one truth remains unchanged:
exceptional operations create exceptional experiences, and those experiences power everything else.
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