Few sectors in hospitality have risen as dramatically as short-term rentals. What started as a grassroots community movement – with people renting out spare bedrooms and homes through peer-to-peer networks – quickly matured into a sophisticated global industry worth billions. Today’s travellers can book virtually any type of stay they can imagine: remote mountain cabins, slick urban flats, luxury beachside villas – all with a few taps on a screen.
But what’s really changing the game now is what happens after that booking is made. A few years ago, receiving instant replies from an Airbnb host with accurate information or a digital guidebook full of general tips delivered straight to your inbox felt like genuine innovation. But today, that kind of basic automation is the baseline.
Now, guests expect not just responsiveness, but relevance – interactions that feel tailored, not templated. Netflix predicts their next binge-worthy series, Uber remembers their regular routes, and meal-delivery apps anticipate exactly what they’re craving. Naturally, they want the same thoughtful personalisation when they travel. It’s no longer enough to be fast; service has to feel personal.
Yet delivering this level of individualised service consistently and at scale presents an enormous challenge for hosts and property managers. It’s nearly impossible to manually create experiences that make every guest feel individually understood, anticipated, and cared for – particularly for operators managing multiple properties remotely.
How AI makes personalisation possible at scale
This is precisely where AI is stepping in, quietly transforming how hosts interact with their guests by making genuine personalisation achievable at scale, without adding complexity or overhead.
Traditionally, automated messages from hosts were practical but impersonal, often feeling templated and transactional. AI is changing that, moving host–guest communication from merely reactive to genuinely contextual. Instead of standard check-in reminders, guests now receive thoughtful and timely messages crafted with purpose and precision.
Messages no longer simply arrive quickly; they arrive with intention. A guest checking in late might receive a note pointing them to the best nearby spot still serving food. A couple arriving for a weekend escape could be nudged towards a neighbourhood wine bar hosting live jazz that night. A family on holiday might get a heads-up that the weather is perfect for paddleboarding, with equipment waiting at the property.
None of these moments are random or manually curated. They’re powered by sophisticated systems capable of reading between the lines, interpreting subtle signals – the number of guests, the time of day, the length of stay, the season, booking patterns, even local weather and event data. AI connects these dots invisibly, ensuring every interaction feels natural and spontaneous. Yet each one is carefully orchestrated through intelligent technology working in the background.
One of the most interesting aspects of this evolution is that it doesn’t require masses of intrusive data on the guest. Modern AI tools can draw rich insights from public guest reviews or past stays. A simple mention of enjoying quiet neighbourhoods or needing reliable Wi-Fi can become actionable intelligence. Hosts see concise summaries that allow them to tailor the experience – even if they’ve never met or spoken directly with the guest before.
This intuitive use of light data is perhaps AI’s greatest strength in hospitality. It transforms otherwise generic interactions into thoughtful touches that tell guests: you’re seen.
The intelligent infrastructure of hospitality’s future
AI’s role isn’t just limited to communication. It also enables a new level of real-time responsiveness across the entire operation. By integrating with booking platforms, calendars, and smart home devices, AI can adapt dynamically to changing circumstances without requiring host intervention. If a guest’s flight arrives early, the system might check property readiness and offer an early check-in without the host lifting a finger.
It also unlocks smarter revenue opportunities – identifying one-night gaps between bookings, for example, and offering guests a discounted extra night automatically. It’s subtle, but powerful. Guests feel well looked after, while hosts benefit from maximised occupancy and time saved.
Ultimately, AI isn’t a bolt-on to the guest experience; it’s becoming part of the fabric of what makes great hospitality possible at scale. It’s shifting short-term rentals from reactive to proactive, from routine to refined – without increasing the burden on already stretched teams.
And we’re still only scratching the surface. The next phase isn’t just about personalisation, it’s about orchestration. Systems that don’t just respond, but learn and evolve. Tools that support better decisions, spot patterns before problems arise, and offer smarter, more sustainable ways to run a hospitality business. This shift – from one-off automations to intelligent, interconnected systems – will define the next generation of hosting.
Short-term rentals were built on the idea of connection – between people, between places, between experiences that feel more real than a traditional hotel stay. What AI offers is the ability to preserve that connection as the industry scales. Even as portfolios grow and operations become more complex, AI ensures guests still feel like someone is thinking about them on the other side.
It’s not about doing more. It’s about doing better – with less friction, less guesswork, and a lot more intelligence.
