3. May 2026

Hostaway launches Cohost AI

Hostaway has been at the forefront of AI integration into its property management system (PMS). I remember sessions at their first user conference in Miami in 2024 that showed off some early AI integrations, but hold on to your hats - their integrated AI, called Cohost, is not your father's AI.

Cohost is in Beta right now and quietly sits next to your notifications in the top menu bar, patiently waiting for you to ask for some help. You know that my wife and I run a data-driven short-term vacation rental business, at Miami Vacation Stays, down here in Miami. And if you've talked with me about data, you've heard me say that the best data is worthless unless you put it into action.

Well, here's a new thought: the best data is powerless if you don't know it. For months now, I've been hounding my friend, E., the head of design at Hostaway, to let me download my guest conversations so that I can build a relevant FAQ page based on the questions our guests ask all the time.

Well, yesterday I noticed Cohost sitting in my PMS. So I asked it to read through 2.5 years of guest conversations and rank the top 20 frequently asked questions so I can build an FAQ page for our new website. Hostaway's AI thought for a few minutes, read through all message threads, ranked the questions in order of how often they are asked, built an FAQ section, and then told me what it thought those questions meant operationally for our business and which steps to take to avoid the questions in the first place!

Now, unfortunately, it can't make guests actually read our messages or help them remember that much of that info is already in their inbox (that's precisely why we send out a TL;DR check-in message 2 hours before check-in), but I didn't ask for operational advice, but love that it gave it to me.

In the past, I've downloaded our reservation data, dug through spreadsheets, created custom formulas to calculate date ranges, exported CSV files to AI, and prompted Grok. Gemini or ChatGPT to cull the data and create graphs for the average length of stay, booking windows, etc.

Now I can do all that right inside Hostaway. With access to much more data specific to our listings and guests. And get answers in a few seconds. I guess I no longer have an excuse to make decisions based on generic, partial, outdated, or incomplete datasets.

How do you use AI in your STR business?