The booking problem no travel site has solved for parents

Going on holiday with kids, especially young ones, is hard enough. What I didn't expect was that finding somewhere to actually stay would be part of the challenge, and I say that from experience.

A trip that taught me the hard way

We've been travelling with our two year old for the last year, and a few things have become non negotiable for us. The type of cot matters. A secure garden and pool perimeter matters. Steps up to the front door matter. And yes, whether the front door locks from the inside matters too. That last one isn't hypothetical. It happened to us.

None of these things are unusual asks. They're just basic questions any parent would want answered before booking. The problem is finding the answers.

Why the search itself is the hard part

Try searching Airbnb, Booking.com or any major travel site for a place with a proper cot, a secure outdoor space, or step free access, and you'll come up short. The filters simply aren't built for it.

What actually happens is this: you send a message to the host, wait for a reply, and eventually find out the apartment is on the eighth floor with no lift. By the time you know that, you've already spent twenty minutes you didn't have.

There are actually two different problems here

The more I thought about this, the more it split into two separate issues that need different fixes.

The first is information that's buried. The platform almost certainly knows whether a listing has a lift, it's just sitting three menus deep under an accessibility tab nobody thinks to open. This one's the easy fix. An agent can simply translate "no stairs please" into whatever filter already exists, instantly, without you needing to know what it's called or where it lives.

The second is information that's genuinely missing. This is the door lock story. There was never a field for "does the front door lock from the inside," because nobody designing the booking form thought to ask. No amount of clever conversation invents a fact that was never captured anywhere.

The second problem is the interesting one, and it's where I think agentic approaches can actually do something new:

Reading between the lines. Host descriptions, photos and old guest reviews often already contain the answer, it's just never been tagged as data. A review that mentions "warning, no lift, we're on the fourth floor" is useful information sitting in plain text that no filter was ever built to catch.

Looking at the photos properly. Stairgates, pool fencing, a cot in the corner of a room, the number of steps up to a front door. All of it is visible in listing photos an agent could actually look at, rather than everyone relying on a checkbox that may or may not have been filled in honestly.

Asking on your behalf, once, for everyone. This is the one that would have solved our actual problem. Instead of you messaging the host and waiting for a reply, the agent spots the gap and asks the host the moment it matters, then stores the answer as real data for the next parent who searches the same thing. The twenty minute wait becomes a one off cost the platform absorbs, rather than something every single guest pays individually.

Giving hosts a conversation instead of a form. Hosts don't fill in long forms well, especially for the odd specific details no dropdown ever anticipated. A host describing their place out loud, with an agent quietly structuring that into proper data behind the scenes, captures far more of the genuinely useful, slightly odd detail than any checklist ever will.

Conversation is naturally schema-less, which is exactly why it's good at catching the long tail of things a form never thought to ask about. But that's only half the job. The other half is turning those conversations into either a match against data that already exists, or a trigger to go and get the data that doesn't.

So I built a quick prototype

I wanted to see what it would look like if the search itself understood what you needed, rather than making you dig for it. Instead of picking a destination, dates and guest count, then manually filtering through a list, I put a simple conversational layer on top of the search.

You tell it about your trip in your own words. It asks you one relevant question at a time, builds a list of your requirements as you go, and only shows you results once you've confirmed it's got everything right.

It's a small idea, built in about twenty minutes to see what was possible, not a finished product. But it points at something real.

This isn't just a parent problem

Cot types and secure gardens are one version of this. Step free access, wheelchair friendly bathrooms, and ground floor rooms are another. Anyone with a specific, non negotiable requirement runs into the same wall when booking accommodation: the information exists somewhere, it's just never where you need it, when you need it.

A conversation is a much more natural way to surface that than a wall of checkboxes ever will be.

Where this goes next

This started as a quick experiment, but it's opened up a lot of questions worth exploring further: what a proper requirements based search could look like, how hosts would supply this information reliably, and where else a conversational layer like this could replace a form.