Turning first stays into loyal guests: How group payments transform holiday rentals

In travel and hospitality, growth is often framed as an acquisition problem. Brands spend heavily to attract new guests, optimise discovery and drive first bookings. Yet the real commercial opportunity sits beyond the first stay, in how effectively a brand turns an initial booking into repeat behaviour and long-term guest lifetime value.

Group booking and paying, supported by split payments, is emerging as a powerful lever in that journey. While often discussed as a checkout feature, its real impact is felt over time. It improves first-booking conversion, removes friction from group coordination and increases the likelihood that guests return together.

Other premium sectors have already learned this lesson. Wine merchants and wineries, in particular, have used group buying models to move buyers from first purchase to repeat engagement and long-term loyalty. For rental brands, there is a clear opportunity to apply the same principles to travel.

Why group buying works in wine commerce
Wine merchants and wineries operate in an environment where trust is fundamental. Buyers must trust provenance, quality and fulfilment before they are willing to commit, often alongside others and often at scale. Group buying works because it builds on established relationships rather than replacing them.

Wine clubs, allocation lists and private client networks show how collective purchasing supports repeat behaviour. Guests are comfortable committing together when they understand the value of what they are buying and feel confident in the experience. Over time, these shared purchases become habits rather than one-off transactions.

Crucially, group buying in wine is rarely about price. It is about access to limited releases, curated cases and early access to new vintages. The shared purchase elevates the experience and reinforces loyalty.

Urgency also plays a role, but not through discounts. In wine, urgency is social. Allocations are finite. Others are committing. Conversations happen between friends and collectors. Momentum comes from participation rather than pressure.

The cost of acquisition versus the value of returning guests
Travel and hospitality companies spend significant sums acquiring new guests. Paid search, metasearch platforms, OTAs and social advertising consume a large share of revenue, often to secure bookings that may only happen once.

Most rental websites are heavily optimised for discovery, but far less for self-service booking journeys that reflect how guests actually plan, commit and pay together. Even less attention is paid to what happens after a successful stay, when the opportunity to drive repeat behaviour is highest.

At the same time, guest expectations have changed. Many younger travellers and families are digitally savvy by default. They are accustomed to splitting payments, managing shared expenses through apps and completing transactions instantly online. Coordinating money is no longer a barrier.

Against this backdrop, it is striking that some travel and tour operators still rely on offline booking processes, manual payment handling or enquiry-led journeys that require follow-up calls and invoices. When guests cannot book and pay online, particularly as a group, momentum is lost. What begins as strong intent often never converts. These are not just lost bookings, but missed opportunities to build long-term guest value.

Increasingly, group booking and paying is being built directly into checkout journeys, rather than handled informally outside the booking flow. This shift aligns booking experiences with how modern groups already behave and removes friction at the moment when intent is highest.

Wine merchants have taken a different approach. While acquisition still matters, their commercial focus is on repeat purchasing. Wine clubs and shared buying experiences are designed to bring guests back regularly, often with minimal incremental marketing spend.

Rental brands face the same opportunity. Once a group has successfully booked and stayed together, the likelihood of repeat travel as a group is high. Friends travel again. Families return annually. New guests are invited into the same booking circle.

Group booking and paying, supported by split payments, makes this repeat behaviour easier to activate by removing coordination and payment friction.

Rather than spending more to acquire the next guest, brands can reduce customer acquisition costs and increase guest lifetime value by enabling existing guests to return through group booking and paying, supported by split payments.

What rental brands can learn from wine merchants
The parallels between wine commerce and rental accommodation are clear. Both are experiential. Both rely on trust. Both involve meaningful financial commitments. And in both cases, decisions are often made by groups rather than individuals.

Wine merchants understand that when costs are shared, confidence increases. Guests are more willing to commit to higher-quality options or larger purchases when financial responsibility is distributed. The overall value of the transaction rises without discounting.

For rentals, the same dynamic applies. When the cost of a stay is split across a group, larger properties, longer stays and premium options become more accessible. Group booking and paying does not reduce value. It expands what feels possible and strengthens repeat behaviour.

Looking ahead
Wine merchants and wineries have shown that group buying can be a premium growth strategy when it is built on trust, experience and social momentum rather than discounts.

For rental brands facing rising acquisition costs and increasingly digitally savvy guests, the path to growth is not simply more traffic or more promotions. It is about designing booking journeys that convert once and repeat naturally.

By enabling guests to book and pay together through split payments, brands can turn first bookings into repeat stays and build guest lifetime value over time. That is where sustainable growth now lies.