The Boostly Podcast – Episode Summary
2026 STR Predictions: What Smart Hosts Need to Prepare for Now
Host: Mark Simpson
Date: December 22, 2025
Special Guests: Liam Carolan, Jan from GuestAway, Alex (MyEvent Concierge), Jack Zappa (Haven Vacation Rentals), Alex Dawson (Company Offsites), Ben (Independent STR Consultant), Rose (Your Family’s Place), Lucy (Breezeway), Jessica Singer (BookingsCloud), Tihana (Various)
Overview
This annual predictions episode of The Boostly Podcast is dedicated to exploring what 2026 holds for the short-term rental (STR) and hospitality industry. Host Mark Simpson, founder of Boostly, is joined by industry voices from the Boostly Slack community to share insights, forecasts, and actionable advice for property managers and hosts. While technology—especially AI and automation—is a standout theme, the episode dives deep into trends around guest expectations, direct bookings, regulatory challenges, and the continual need to differentiate by enhancing guest experience.
Key Discussion Points & Insights
1. The Rise of Robots and Automation in Hospitality
Host: Mark Simpson
- Prediction: "2026 will be the year of the robots." (00:16)
- Automation is expected to revolutionize STR operations, especially in repetitive tasks like laundry and cleaning.
- Mark cautions the first wave of these robots and automation tools will likely be “shocking” and prone to failures, but adoption will skyrocket after early hurdles.
- "The beauty of robots is they never get tired, never complain, never get ill." (01:18)
2. AI Becomes Ubiquitous and Standard
Jan, GuestAway (02:29)
- AI as Standard: "AI won't be a discussion anymore in 2026. It will be standard." (03:00)
- Property managers will be expected to not just have AI, but excel at leveraging it.
- AI will help boost margins through automating guest communications, upsells, and internal workflows.
- Emerging tech will be orchestration engines, coordinating real-world tasks end-to-end, rather than just automating single processes.
- Quote: “Property management starts running like a more tech-enabled, software type of business, with higher margins.” (04:26)
3. Human Touch & Guest Experiences Remain Crucial
Alex, MyEvent Concierge (05:04)
- Despite the AI wave, “humans buy from humans”—focus should stay on creating memorable, people-centered guest experiences.
Jack Zappa, Haven Vacation Rentals (05:40)
- The best operators will use AI to free up time, but truly win by excelling in direct customer service for both guests and property owners.
- Quote: “It really is returning back to a true service-based business.” (06:18)
4. Corporate Bookings & Venue Adaptation
Alex Dawson, Company Offsites (06:40)
- Predicts a significant shift where companies will seek creative venues over traditional hotels for meetings/offsites.
- Venue owners must upgrade websites, add corporate-targeted info (transport, single occupancy rooms, catering, team building), and develop targeted marketing strategies.
5. Legislation, Tax, and Economic Trends
Ben, Independent STR Consultant (08:08)
- Three Predictions:
- Renters Rights Bill: Could force traditional landlords into STR, increasing supply.
- Tourist Tax & Regulation: New taxes, like the UK’s London 90-day rule, will tighten enforcement and could shock the market.
- Rising Guest Numbers: With real wages up and inflation easing, increased disposable income should lead to higher bookings and occupancy.
6. Standardization and Guest Expectations
Rose, Your Family’s Place (10:34)
- Quote: “2026 is going to be about standardization and elevating guest experiences. Our guests are becoming more savvy and have higher expectations.” (10:40)
- More consistent, high-standard guest experiences will be critical.
7. Tool Consolidation & Regulatory Pressure
Lucy, Breezeway (10:59)
- Operators will reduce tech stack complexity—“less tools that do more.”
- Predictions of growing regulation across Europe, with hosts needing to be adaptable.
- Increase in remote work will boost occupancy in shoulder/low seasons, especially for properties catering to digital nomads with appropriate amenities.
- Quote: “Guests are choosing the properties with the amenities needed for working remotely.” (11:55)
8. Direct Bookings Become Essential—No Longer 'Nice to Have'
Jessica Singer, BookingsCloud (12:21)
- Direct Bookings: "Direct bookings really kind of become a survival strategy." (12:30)
- Not a 'nice to have' anymore but crucial for profitability and independence.
- Owners are savvier, demanding property managers have clear direct booking strategies.
- Shift from passive to “always-on, automated demand generation systems.”
- Revenue Management + Marketing Merge: Real-time demand data and automation will guide marketing spend dynamically, property by property.
- Automation's Impact: “The managers that are winning next year are going to be the ones who embrace systems that build creatives automatically, no longer manually.” (16:48)
- Performance Gap: "We're already seeing an 8-18x return on ad spend for teams that are leaning into Bookings Cloud's ad automation." (16:42)
9. Direct Booking, Customization, and Longer Stays
Tihana (18:28)
- Professional hosts will double down on direct bookings due to constant OTA changes.
- Smaller platforms may emerge to fill new market gaps.
- Customization like extended check-in/out and bonus add-ons will differentiate hosts.
- Longer stays and digital nomad-friendly properties will grow, encouraging more predictable income.
- Check-in instructions will become more visual and engaging: “More visual content like instruction videos and interactive guidebooks.” (19:38)
Notable Quotes & Memorable Moments
- Mark Simpson (01:18): "The beauty of robots is that they never get tired, they never complain, they never get ill, they never have to finish early."
- Jan, GuestAway (03:00): "AI won't be a discussion anymore in 2026. It will be standard."
- Jack Zappa, Haven Vacation Rentals (06:18): "It really is returning back to a true service-based business."
- Lucy, Breezeway (11:55): "Guests are choosing the properties with the amenities needed for working remotely."
- Jessica Singer, BookingsCloud (12:30): "Direct bookings really kind of become a survival strategy."
- Jessica Singer (16:42): "We're already seeing an 8-18x return on ad spend for teams that are leaning into Bookings Cloud's ad automation."
- Tihana (19:38): "Expect to see more visual content like instruction videos and interactive guidebooks."
Timestamps for Key Segments
- 00:00-02:29: Mark Simpson lays out his “year of the robots” prediction.
- 02:29-05:04: Jan from GuestAway on AI as standard and tech orchestration.
- 05:04-05:40: Alex (MyEvent Concierge) on creating memorable, guest-centered experiences.
- 05:40-06:40: Jack Zappa on the importance of the 'human touch' and homeowner service.
- 06:40-08:08: Alex Dawson explains the rise of corporate/midweek bookings and necessary venue adaptations.
- 08:08-10:34: Ben breaks down legislation, tourist tax, and economic tailwinds for STRs.
- 10:34-10:59: Rose highlights the need for industry-wide standardization.
- 10:59-12:21: Lucy predicts tool consolidation, increased regulation, and higher demand from remote work.
- 12:21-18:28: Jessica Singer gives an in-depth analysis on automation, merging of marketing and revenue management, and the critical nature of direct bookings.
- 18:28-19:52: Tihana discusses differentiation via customization, longer stays, and engaging guest comms.
Final Thoughts
The 2026 STR landscape, according to Boostly’s community of experts, is headed for significant transformation driven by automation, data-driven decision making, and rising guest expectations. While the efficiency of AI and robotics will power back-office operations, staying competitive will also depend on delivering personalized, memorable guest experiences and embracing direct booking strategies as a business imperative. Hosts should be ready to adapt their service, marketing, and technology to keep pace—or risk being left behind.
For more trends and direct booking tips, catch Boostly’s video content at boostly.co.uk/youtube.