Being travel planner for a group holiday is a pain. It just got easier

When I floated the idea of a group trip to Mexico with friends last year, I all but sealed my fate as designated holiday architect. Cue months of rental research, group polls, messy text threads, payment chasing, bill splitting, fielding questions – then answering the same questions repeatedly because some people only check their WhatsApp once a fortnight. Yay.

Group travel has always had its challenges – albeit, with great rewards.

Our group trip to tropical Tulum fell to me … but it was easier than expected.Credit: Getty Images/iStockphoto

Only this time was different. I found myself courting six-bedroom Airbnbs in May, just as the booking giant introduced a raft of new trip planning tools aimed squarely at groups.

The most game-changing addition, and certainly the one I’ve had the most use of, is a new shareable wish list feature. Think curated wish lists (I grouped my favourite Airbnbs by city: Guadalajara, Mexico City and Sayulita), which you can then invite friends to weigh in on via a simple thumbs-up or thumbs-down icon.

Want to raise issues with a particular listing? No worries. Anyone invited to vote on a wish list can add questions or notes underneath properties to help whittle down the creme de la creme. Anything from a gently nudging “Lovely, but do we think it’s too far from the ocean?” to a decisive “No A/C! Abort!”

Another useful update is the ability to send trip invitations as digital postcards to potential guests, enabling access to reservation details and group message threads with the host. Why is this such a game-changer? Need I remind you of a time when group holidays necessitated a single organiser to act as host liaison and communicate all details, from alarm codes and housekeeping to where to find the house key lockbox?

The days of relaying check-in times and Wi-Fi passwords over a chaotic text thread are nearly over. Huzzah!

Group travel is now more streamlined, thanks to a raft of new tech across booking platforms.Credit: Getty Images

Airbnb in-app host updates, I noted over the course of our Mexico travels, frequently featured the disclaimer: “This is an automated message reminder” – something users should expect to see more of as hosts and property managers increasingly take advantage of the platform’s new AI-powered quick reply technology. The automated responses can get surprisingly granular – instant answers to common questions around check-in processes and the like can prove extremely useful in a pinch (particularly when your husband, say, forgets to add you to a booking and waits until we’re on our way in an Uber from the Mexico City airport to request check-in procedures from the property manager).

It’s no coincidence Airbnb launched the features when it did – group travel is booming. Companies, including Expedia Group, and US and Europe-based apps Mindtrip, WeTravel and Joyned, have implemented new tools to cater to a growing contingent of group travellers.

You may have already noticed the new crop of premium host and property categories, which by design all but guarantee a smooth, stress-free trip with all the mod-cons you could dream of.

Our Tulum rental, Villa Lagu, is a guest favourite.Credit: Airbnb

Our first rental of the trip Villa Lagu, a beautiful jungle-flanked luxury Airbnb on the outskirts of Tulum, is stamped a “guest favourite” – a relatively new category reserved only for the platform’s most-loved homes. This category goes beyond luxury amenities like pools, jacuzzis, gourmet kitchens and laundry facilities, determined by an internal scoring system factoring ratings, reviews and reliability data.

Additionally, Villa Lagu is managed by a “Superhost”, a status doled to those who meet Airbnb’s strict criteria and who, according to a description on the platform, generally go “above and beyond to provide excellent hospitality”. This ratings system has done for holiday rental guests what ride-hailing apps have done for taxi users. Property managers and owners work extra hard to hold on to elite host status, there’s no resting on laurels.

Superhost status … Villa Lagu’s master bedroom twilight bathtub and shower.Credit: Airbnb

Our decision to book with a Superhost was a great comfort back in June when Tropical Storm Alberto, the first major storm of the season in the Gulf of Mexico, whipped through our beautiful property, toppling a giant tree into a security fence and its deep roots ripping up plumbing and sending a bubbling stream into the grassy courtyard.

No one was hurt, thankfully, and our extremely responsive Superhost was able to organise after-hours plumbing within the hour, meaning we were only minimally inconvenienced by the ordeal, which under different circumstances could have ruined a holiday.

A 2024 survey from travel booking giant Expedia Group, which owns Stayz, Wotif and Trivago, revealed nearly one-third of travellers plan to take more group trips this year than in 2023. More than one-quarter of respondents also said they would choose a holiday rental with outdoor amenities so they’d never have to leave the property.

Given the sharp uptick in group bookings – an area that shows no sign of slowing – it’s hardly surprising that Airbnb, along with a slew of other major booking apps, has introduced new features to cater to multi-person trips.

Airbnb’s shareable wish lists are just the beginning.

Holiday rental platform Stayz, Expedia Group’s Australian holiday rental arm, also has a version of this: a collaborative Trip Board feature tool that allows groups of travellers to find, share and choose a holiday home together.

Like Airbnb, Stayz has also introduced a “Premier Host” category, that highlights homes with a 4.4-star rating or higher for at least three reviews, and an owner cancellation rate of 1 per cent or lower.

Airbnb isn’t the only one jumping on the AI bandwagon. In May, Expedia Group launched its first AI-powered trip planning tool, Romie, which is pitched as a digital travel agent, concierge and personal assistant in one.

It’s designed to get “progressively intelligent” by observing your travel preferences over several trips, and even eavesdropping on vacation talk in your SMS group chat. It can even collate travel information from emails you’ve sent. Once a user has invited Romie to join a group conversation, you can @Romie for advice at any time and import a trip-talk summary of the takeaways straight into the Expedia app to begin building a personalised itinerary.

The alpha version of the Romie experience is currently available on EG Labs in the US, though there is no timeline yet for when it will become available in Australia.

The writer travelled at her own expense.

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