Among the clients I work with, including ultra-high-net-worth individuals and professional athletes, villas have become the preferred way to travel. 

The reasons are clear: privacy, space, security, and the ability to create a genuine home environment for family and close teams.

For many, it is the only way to properly switch off.

But there is a growing disconnect between how these clients travel and how the villa market continues to operate. 

This becomes especially visible at this time of year.

As the football season draws to a close, I am currently handling multiple villa requests for players planning short breaks between the end of the season and the start of pre-season. It is a narrow window, often just a few days or a week, and it is rarely fixed far in advance. These trips also need to work around media commitments, sponsorship obligations, and personal schedules that can change quickly.

Flexibility in these cases is essential.

The same applies to UHNW clients more broadly. Time is their most limited resource. Travel is built around demanding professional lives, family logistics, and often last-minute decisions. They are not planning their movements around traditional booking cycles.

And yet, much of the villa market still operates on rigid structures, most notably the long-standing Saturday-to-Saturday model.

While historically practical, this approach increasingly creates frustration.

Requests that run Thursday to Monday, or Wednesday to Tuesday, are now commonplace. Shorter, more fluid stays are the reality. But instead of accommodating this, we often find ourselves trying to force these plans into fixed weekly blocks. 

Clients are asked to extend stays unnecessarily or adjust travel in ways that do not suit their schedules. At the same time, property owners risk leaving gaps between bookings or missing out on high-value clients altogether. 

It is worth emphasising that the issue is not the product itself. The quality of villas available today is exceptional, often surpassing the hotel experience in terms of privacy and personalisation.

The challenge lies in the model underpinning them. 

At the top end of the market, flexibility is an expectation. The ability to offer adaptable check-in days, shorter minimum stays, and a more fluid approach to bookings is becoming increasingly important.

The good news is some suppliers are already evolving in this direction. Working with them, the difference is immediate: smoother booking processes, stronger client satisfaction, and a quicker turnaround from enquiry to booking.

Ultimately, this is about aligning the structure of the villa market with the reality of modern luxury travel.

Demand from UHNW clients and professional athletes is only increasing. But their time constraints, and the way they move, require a system that can respond accordingly.

Those who adapt to this shift will not only improve the client experience, but they will also place themselves firmly at the centre of one of the most valuable segments of the market.

Words by Jack Stean, Personal Travel Manager at Winged Boots 

Winged Boots offers bespoke villa recommendations and end-to-end travel planning tailored to UHNW clients and elite athletes. Discover more at www.wingedboots.co.uk or explore their latest insights via the Winged Boots magazine.