What’s in Store for 2026? Industry Leaders Give Their Predictions for Vacation Rentals

Abode Worldwide
1/5/2026

Another year is here. After tightening regulations, shifting guest behavior, and rapid technological developments, property managers are quite rightly wondering whether the second half of the decade will follow the unpredictable pattern of the first.

To offset some of that uncertainty, we asked industry leaders what their predictions are for the short-term rental sector in 2026. Some insights hint at a return to what’s always mattered most—trust, familiarity, and real hospitality—while others suggest a more disruptive leap, with AI reshaping everything from discovery to day-to-day operations. What’s clear is that property managers who pay close attention and adapt to changing trends will be the ones to succeed.

1. Revenue Resilience in a Last-Minute World

With booking windows compressing and stays getting shorter, revenue is at risk. 2026 performance can only be successful with smarter revenue strategies and flexibility.

Quinn Monescalchi, senior data insights analyst at Key Data, a global short-term rentals analytics platform, said:

“For short-term rentals, 2026 won’t be a volume story. Demand is steady, but travelers are booking later and staying shorter, which puts the burden, and the opportunity, squarely on pricing discipline. With flat occupancy, shorter stays, and compressed booking windows, rate strategy becomes the industry’s true performance lever.

“When we look at forward adjusted paid occupancy for the next 180 days, demand is essentially holding steady, which means revenue teams shouldn’t bank on volume. The upside lives in rates and smarter revenue strategy.

“Forward average daily rates (ADR) is running ahead of last year every single month for the next 180 days, with the gap widening into Easter and Spring Break. If current strategies hold, 2026 should set up for a healthy rate premium over 2025.

“The same story goes for revenue per available rental (RevPAR); it’s coming in flat to better each month, with the biggest lift in April and May. The outlook looks solid, but it’s powered almost entirely by rate strategy. Operators that hold pricing discipline and implement a data-driven revenue strategy will see gains follow.”

Michele Fitzpatrick, CEO of eviivo, a property management system used by 28,000+ vacation rentals and hotels in North America and Europe, said:

“In terms of booking behavior, we’re already seeing guests booking later and staying slightly shorter this year, and we believe this will continue into 2026. That unpredictability is putting pressure on operators to optimize pricing, inventory, and staff workflows in real-time. As we approach 2026, margins are tightening, and competition is intensifying. Operators will need smarter, more connected technology to protect profitability, streamline operations, and stay ahead of changing guest expectations.”

Monescalchi added: “In terms of traveler behavior, trips are getting shorter. The combination of flat occupancy and shorter stays means operators will need more bookings to hit the same room night totals. Shorter stays also put pressure on shoulder nights—fewer Thursday to Monday trips, more isolated weekends. This makes revenue strategy even more critical. It reflects the broader trend of a more cautious, wait-and-see consumer, where economic uncertainty and flexible travel habits continue to push buying decisions closer to arrival.

“We’re also seeing booking windows compress by another two days, giving revenue teams less early visibility and reinforcing the shift toward late, flexible travel decisions. The compression trend isn’t slowing. Operators need to be ready for faster pickup cycles and shorter forecasting horizons; this will be the new normal for 2026.”

David Angotti, chief digital officer at Casago, a top-rated vacation rental management company, said:

“In 2026, I believe flexible cancellation becomes one of the biggest quiet revenue levers in vacation rentals. Operators who lean into flexible policies early will see a meaningful jump in bookings, in the range of 25%-30%, while only giving back a small margin to cancellations, roughly around 10%. That nets out to higher occupancy, stronger revenue, and a clear competitive edge. But the real unlock is on the homeowner’s side. The brands that win will be the ones that come to owners with data in hand, explain the trade-offs clearly, and lead with transparency instead of fear. We saw the same pattern with pet-friendly homes: The early adopters took what felt like a risk and ended up owning the most loyal, highest-performing segment. Flexible cancellation will follow that same arc, and the operators who move first will set the standard everyone else scrambles to match.”

Adam Seskis, CEO at RMS, the leading hospitality platform for hotels, serviced apartments, vacation rentals, and outdoor accommodations, said:

“From treehouses and safari tents to boutique motels, short-term rentals, and serviced apartments, the accommodation mix is more varied than ever, and in 2026, that diversity will fuel demand. Travelers are moving away from one-size-fits-all stays. Instead, they’re choosing places that suit their lifestyle, trip type, or even just their mood. The divide between hotels, vacation rentals, and traditional campgrounds is dissolving, and operators who embrace this shift are gaining ground. Offering a mix such as glamping units alongside powered sites, or short-term rentals in a traditionally long-stay model, helps fill occupancy gaps and boosts revenue per square meter. But this variety also brings complexity. In 2026, agile tech will become a core business need. Operators will need systems that flex across inventory types, guest journeys, and operational workflows. The market will reward those who can operate with the ease of a single property, even while managing multiple accommodation models at once.”

2. AI Moves from Guest Messaging to Autonomous, Connected Operations

​​AI is already an everyday part of property management, but in 2026, it will continue to evolve and automate even more operational tasks, allowing teams to really focus on growing their businesses and delivering first-class guest experiences.

Shahar Goldboim, co-founder and CEO of Boom, a pioneering technology firm offering the world’s first AI-powered property management system (AiPMS) for short-term rentals, said:

“In 2026, AI will play a far more integrated role in short-term rental management. Instead of automating isolated tasks, it will begin coordinating entire workflows from start to finish. Guest discovery will change significantly. Rather than navigating filters or scrolling through listings, travelers will be able to describe what they are looking for in their own words, such as a quiet two-bedroom with a desk and access to nature. AI will interpret the request, match it with relevant properties, confirm availability, and complete the booking. This approach will simplify the guest experience and help hosts attract more qualified bookings.

“Operationally, AI will become a core part of the team. Advanced systems will handle most of the day-to-day communication, including guest messages, owner updates, reviews, and scheduling. Cleaning, maintenance, and task coordination will be triggered automatically based on booking data and staff availability. On the financial side, processes like reconciliation and owner reporting will become faster and more reliable through full automation. As these tools continue to evolve, operators will begin replacing disconnected software systems with unified platforms that support the business from end to end. This will allow leaner teams to work more efficiently, with fewer manual tasks and better visibility across operations.”

Marcus Rader, CEO and co-founder of vacation rental software Hostaway, commented:

“It’s been barely three years since ChatGPT was unveiled to the world, but AI has completely revolutionized the way we live and work. AI is completely changing how guests search and travel and, in turn, reframing how property managers operate and market themselves.

“We are very close to guests being able to book entirely using AI, from the first thought that they want to travel all the way through to confirming the booking and getting dinner reservations for when they arrive. For guests, this level of personalization is revolutionary. No more searching through years of reviews—AI will find exactly what you need, and book it for you.

“However, that’s the vision. Today, reality looks quite different. AI isn’t good at picking the right properties and often gets limited visibility. As the market leader in vacation rental technology, it is our duty to ensure vacation rentals are properly included in the recommendations from AI, and we will work closely with the leading companies to achieve the vision together. For vacation rental managers, it means that you’ll have to market your property not only to guests but also make it easy for LLMs to find you, too. That means simple things like FAQs on your website, as well as highlighting what makes your property unique so that AI can bring it to the right guests.

“In the background, AI is also making huge waves in operations. Property managers are automating all the day-to-day tasks that they can, leaving them free to focus on growing their businesses and delivering exceptional service.”

Florian Montag, vice president of business development at Apaleo, the open, API-first property management platform, said:

“In 2026, one of the biggest pressures and opportunities in the hospitality industry will come from agentic AI. It will move from experimentation to deployment, gradually realizing what we call autonomous hospitality. Instead of passively supporting workflows, AI agents will increasingly act, learn, and collaborate across systems.

“The next big leap will be agent-to-agent (A2A) communication. Not long now, we will see operators’ owned agents directly engage and even negotiate with external travel or booking agents, such as those integrated into ChatGPT, to secure the right guests, rates, and experiences in real time. This will reduce reliance on intermediaries and return control of data, pricing agility, and distribution to property managers.

“A2A communication will also make operational autonomy a reality. Imagine a property manager asking, ‘How many guests with children are arriving today?’ The operator’s AI agent instantly queries the PMS, retrieves reservation data, and identifies which bookings include children. It then adds a trace to those reservations, prompting another AI agent to alert housekeeping. A separate housekeeping agent then interprets that trace, checks the room type, and automatically instructs staff, or connected systems, to add a child’s bed, adjust amenities, and note the requirement in the daily report. This seamless agent-to-agent collaboration is the backbone of the next stage of automation in hospitality.”

Alexander Lyakhotskiy, CEO and founder of Pass the Keys, a vacation rental franchise company that manages over 1,700 properties across the UK and Spain, said:

“Using AI for guest messaging and simple marketing tasks is already widespread, so in 2026, it’ll be about not just using AI, but implementing it well across operations, improving productivity, and cutting costs.

“While we can’t control regulations or guest habits, there’s plenty that property managers can do to set themselves up for success in 2026, starting with a clear-eyed assessment of where their business is doing well and where it might need some help. Then, managers can fill those gaps with technology and education to build on their success.”

3. The Return of the Human in Hospitality

With a renewed focus on hospitality, the human element will move to the forefront. That means more direct communication, magical touches, and loyalty built on trust.

Steve Schwab, CEO of top-rated vacation rental management company Casago, said:

“For vacation rentals, 2026 is the year professional, local-first operators separate clearly from the rest of the crowd. Regulation will keep raising the bar and quietly push out low-quality, inconsistent operators. Those who combine professional operations with true local presence will win more homeowners and repeat guests because you cannot outsource local knowledge, and guests feel the difference. AI will keep moving into the background, eliminating most of the friction in booking, check-in, and issue resolution, while frontline teams focus on empathy, problem-solving, and context—making experiences seamless, not soulless. The operators who use tech to amplify human hospitality, not replace it, will be the ones that stand out this year.”

Rebecca Ward, CEO of direct booking site Simply Owners, which offers over 6,000 rentals with no booking fees, said:

“2026 will be the year of reconnection for vacation rentals. Guests and managers are tired of third-party platforms where basic questions go unanswered, and both sides get stuck talking to chatbots. Vacation rentals require hospitality, and that starts with clear and direct communication, enabling skilled managers to fully understand their guests and personalize the whole experience for them.

“We’ll also see property owners and managers taking back control over their business with direct bookings—and as a bonus, they have the opportunity to speak directly to guests and build relationships that turn one-time visitors into lifelong repeat customers.

“Guests are beginning to tire of social media trends and overcrowded ‘hot’ destinations. In 2026, many will think about returning to places they’ve been before and rebooking properties that made them feel at home. Returning to a previous stay means you already know your family loves the place, have an existing connection with the manager to get the best deal possible, and can create family memories that last. Familiarity, trust, and personal connection will become the new luxury.”

4. Professionalization as the Separating Line

Against a backdrop of higher expectations, costs, and regulation, is a “serious operators only” era on its way? In 2026, disciplined, data-driven management and operational maturity might be the deciding factors for success.

Richie Khandelwal, co-founder of revenue management software PriceLabs, said: “The short-term rental industry has long been a tale of two halves, one made up of casual hosts and the other, management companies with varying levels of operational maturity. However, now both of those groups are learning that the key to long-term success isn’t luck or timing, it’s professionalism.

“In such a competitive market, it’s no longer enough to simply have nice photos on your listing and run the property in your spare time. Guest expectations are higher than ever, and the only managers that will succeed are those who invest in operations, technology, and their team. Our recent Global Host Survey found that the biggest concerns for hosts remain visibility on OTAs, financial pressures, and the demands of cleaning and maintenance. While technology may be able to help alleviate some of these concerns, lasting success comes from treating the business with intention—pairing tools with disciplined, strategic management.”

Lyakhotskiy added: “As we head into 2026, short-term rentals are facing uncertainty all around the world, from tightening regulations, rising costs, and changing traveler behavior. But decision paralysis in 2025 will give way to stronger decisions in 2026. If you’re going to stay in short-term rentals, you’ve got to really want it. That means professionalizing and making intentional investments in operations, technology, and teams.

“In hospitality, we often move at a hundred miles an hour, going from booking to booking and fighting fires without pausing to plan strategically. Professionalization means taking a step back, letting your team handle the day-to-day, giving you space to look ahead and build a long-term strategy.”

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