by Jen Mallia
Last updated: 2:25 PM ET, Fri October 2, 2026
Working in group travel can be rewarding and lucrative, but it also can come with its own set of challenges. Competing visions of how the trip will unfold, diverse budgets and conflicting travel styles can all lead to tension when it comes to travel planning for a group.
Renting a villa can be a great way for an extended family or friend group to vacation together, but even then, challenges can rear their ugly heads. VIP Holiday Booker Founder and CEO Darijo Šarić, offers some advice for travellers who are considering a vacation rental for their group holiday while minimizing pain points. Šarić says that while everyone thinks the hard part will be finding the right villa to stay at, the real challenge is usually getting everyone to agree on what they want.
“The biggest mistake is trying to make everybody happy with every decision,” says Šarić. “Instead, figure out your non-negotiables first and then use those to narrow down your options.”
It can lead to headaches if the search begins before the basics have been nailed down. “Perfect” to one may be a great beachside location, while budget may be the most important factor to someone else. If everyone starts throwing their perfect find into the group chat before defining what perfect is, there’s going to be a mess.
Once group size, location and budget have been determined, the search can commence.
“Prioritise the features that matter to the whole group. Everyone will have their own idea of what makes a villa suitable, so it’s worth agreeing on the key, non-negotiable features and qualities before you start your search,” advises Šarić.
“One mistake I see is getting carried away once a villa looks good online and assuming everything will be straightforward. It’s easy to get lost in the excitement of the trip and forget to check the things that could affect your stay once you arrive.”
To mitigate the stress of planning a group holiday, Šarić says it's a good idea to take the discussion out of the group chat and actually talk in person or on the phone. “It can be much easier to settle things in a 10-minute chat than spend days going back and forth over messages,” he says. “If there are a few options on the table, a quick poll can also save a lot of hassle. Everyone can have their say, without the group chat turning into hundreds of messages that nobody wants to read back through.
After the accommodations have been sorted, one of the things that leads to trouble is how to track and divide expenses while on the trip. The New York Times recently shared examples of potentially friendship-ending situations when friends who travelled together had to sort our shared expenses. The article cites a 2026 survey commissioned by PayPal, where 46 percent of respondents said money disagreements created tension or “ruined the vibe” on a trip. Another survey from payment platform Zelle reports about a fifth of millennials saying they ended a relationship because of repayment disputes.
While the reach of a travel advisor can only go so far when it comes to group dynamics, there are a few things they can do to help guide a group to avoid conflict. These include making suggestions that the group have clear budget discussions among themselves and devise a plan to divide supplemental costs, if necessary. Using a cost-splitting app can help track money spent and owed.
Ultimately arranging group travel can be highly rewarding. By setting out with a clear plan and budget, travel advisors can help make it a great experience for everyone involved.
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