Overview
Tripadvisor’s Vacation Rentals business transitioned to operate as a full meta provider, making Holiday Lettings the default booking experience for Tripadvisor’s owned inventory. This shift heightened the importance of trust and clarity at the point of booking — the existing flow had a 29% exit rate, a 50% increase in dropped sessions, and ~20% of customers unable to complete bookings due to errors or incorrect details. Improving it was critical, while staying true to its existing brand and design language.
My Role
I led design and research in close partnership with the Product Manager, collaborating with a User Researcher, Copywriter, and Design Manager.
How we tested
Using data insights, competitor analysis, and design critiques, we formed hypotheses and validated them through user testing.
- 8 remote moderated sessions via Usertesting.com
- 4 desktop · 4 mobile web
- Participants from the USA and UK, all having booked a vacation rental in the past two years
- Tested across: existing experience, Concept 1 (single page), Concept 2 (staged flow)
The existing flow — cluttered, lengthy, and losing users
The original booking page was visually inconsistent within the Holiday Lettings experience. Limited clarity around pricing and payment increased the risk of user error, frustration, and drop-off.
Direction 1: Everything visible, upfront
A clean, concise single-page form focused on transparency and upfront visibility of key booking details.
Direction 2: One step at a time
A three-step flow designed to guide users through the process with a more conversational tone and clearer progression.
Additional Concepts
Express Checkout
Explored a faster booking path by allowing signed-in users to move through checkout more quickly.
Refund Protection Add-On
Tested traveler understanding, perceived value, and price sensitivity around a refund protection product.
What users told us
User testing consistently showed a preference for the revised designs over the existing experience, driven by a few core factors:
- Fixing the basics: Refining the UI to feel more on-brand for Holiday Lettings and visually consistent improved clarity, credibility, and trust.
- Greater transparency: Clearer expectations at each step reduced uncertainty and increased booking confidence.
- Platform-specific optimisation: The booking flow needed to adapt by device to deliver a smooth, low-friction experience across desktop and mobile.
The critical insight — platform changes everything
The same design principles needed to be expressed differently depending on the device — desktop and mobile users had fundamentally different preferences for how the booking flow should work.
For desktop, users preferred a clean, one-page format that surfaced all relevant information upfront.
Mobile users preferred a staged, step-by-step format that allowed them to focus on one action at a time without feeling overwhelmed.
Together, these learnings reinforced the importance of adapting booking flows to user context and platform constraints—while maintaining clarity, trust, and brand consistency.
The platform insight from this research was one of several factors that later informed my confidence in launching the accordion checkout on desktop first for Tripadvisor Experiences, while retaining the multi-step flow on mobile.
