StayFinder AI

01 — The Problem

More filters don't mean a better decision

There's a well-documented effect in decision psychology called choice overload — past a certain point, adding more options doesn't make people more satisfied with their decision, it makes them less confident in it and more likely to second-guess or abandon it entirely. Booking sites are built almost in defiance of that finding: location, price, dates, guests, amenities, cancellation policy, host rating, and on and on, each filter narrowing the list while widening the mental load of the person using it.

Nobody plans a trip by thinking in checkboxes. You think in a sentence — "somewhere walkable to the beach, pet-friendly, under $200 a night, room for the dog" — and then you spend twenty minutes translating that sentence into a form. StayFinder skips the translation step.

02 — Design Approach

Conversation as the interface

The core interaction is a chat with Claude that asks the right follow-up questions — destination, dates, guests, budget, vibe — and searches real listings once it has enough to work with. The design challenge wasn't the chat itself; it was making an AI-driven flow feel trustworthy and legible rather than like a black box.

A live preference sidebar solves that. As the conversation progresses, a running summary fills in — destination, dates, budget, amenities — so the user always sees exactly what the AI understood, with a progress bar toward "ready to search." Results land on an interactive map with clickable pins, and any two or three listings can be pulled into a side-by-side comparison table with best-price and top-rated call-outs.

03 — What Shipping Taught Me

The chat UI was the easy part

The interesting growth on this project happened underneath the interface, rewriting decisions I'd made too quickly the first time through. My first version called the Anthropic API directly from the browser with the key sitting in localStorage — fine for a demo, unshippable for real people. I rebuilt the whole request flow behind a Vercel Edge Function so the key never leaves the server, and moved off regex-parsed <TAGS> in plain text onto structured Claude tool calls, so the model returns typed, reliable data instead of me hoping its output matches a pattern.

Before the link went public, I added per-IP rate limiting at the edge and a hard monthly spend cap — the cap exists specifically as a backstop in case the rate limiter itself ever fails. And when it does fail, it fails open: a Redis hiccup degrades to an unthrottled request rather than taking the whole app down. That's a deliberate tradeoff between cost protection and availability, not an oversight.

I also learned that owning a mistake is part of the job. An early commit accidentally hardcoded a live Mapbox token directly in client-side code. Instead of quietly fixing it, I documented the token as burned in the deployment notes, rotated it, and wrote down why — so the next credential doesn't end up in a commit either.

The most deliberate decision in the whole app might be the smallest one: there's no "Book Now" button. Real booking requires affiliate-level API access I don't have yet, so rather than fake a booking flow that can't actually confirm a reservation, every listing links out to a real search on Airbnb or Booking.com. It's a permanent product decision, not a launch-week shortcut — an AI product should never let a confident-sounding interface promise something it can't back up.

04 — Outcome & Reflection

A live product, not a portfolio piece

StayFinder is deployed and usable today, not a mockup sitting in a design file. That distinction mattered to me — it's one thing to design a flow, another to see it survive contact with a real API, real network conditions, and real edge cases. Getting it from "looks right in Figma" to "works when someone else opens the link" was the actual project.

The goal was to make vacation planning feel less like a second job — for someone booking their first trip or their fiftieth. It's still evolving, and the repo is public if you want to see exactly how it's built.