AI is everywhere now. These are the questions you need to ask to help you choose.

Every software vendor in the vacation rental space is currently racing to add “AI” to their product suite. For property managers, the noise is deafening. At this point, asking if a tool has AI is like asking if a car has wheels: it’s becoming a redundant question.

The challenge now is figuring out which AI will actually help you run your business better, rather than overcomplicating your tech stack and increasing costs.

When evaluating AI solutions, you need to look past the marketing. Focus less on the shiny claims and more on what it can really do for you. Before you sign another contract, ask these eight questions to determine if the “intelligence” you’re buying is truly built for the complexities of vacation rental management.

1. What problem are you actually solving?

The most common mistake is implementing AI without a strategy. Do you have a real business need, or is this just a shiny new toy? The best tools go beyond performing basic operational tasks, and actively improve workflows, acting as a real partner to grow your business. If the AI doesn’t kill off repetitive admin work or help your team scale without you having to hire three more people, it’s probably not worth it. If you can’t explain the problem it solves or the number it’s trying to move in one sentence, consider looking elsewhere.

2. Does this AI understand vacation rentals, or is it just a general-purpose tool?

Generic AI models are great at surfacing information and writing simple messages, but they have no idea what to do when a guest locks themselves out at 2 AM.

Vacation rental operations are complex and require a careful balance of business acumen and guest service. A useful tool understands the guest journey, channel policies, and what to do when the power goes out or the World Cup suddenly triples your occupancy.

Similarly, not all AI providers have real dirt under their fingernails. Check their background. Do they have a track record in the short-term rental space? Do they maintain strong relationships with major channels like Airbnb and Vrbo? Do they offer local, human support in your region for when things go sideways? Does it connect with other STR-specific tools that you use? The quality of the AI is tied directly to the depth of industry knowledge behind it.

3. Does the AI adapt to and understand our business?

With any external tool, there’s work to be done to adapt, but a good AI tool should help towards this. Does it allow you to codify your standard operating processes (SOPs) so that AI can help accelerate running the business in the way you want, not the way the AI thinks it should be run?

This makes AI an accelerator for you to scale up your business, while retaining your unique value as the business manager, the best judge of what processes help you run your business in the most streamlined and efficient way.

4. Does it save time or create more work?

Sophisticated tools often require a massive amount of babysitting, even after the long set-up time. Will your team need to log in and out of another system? Does this reduce manual work or shift it elsewhere?

Good tools integrate into your existing workflow to make the team productive without requiring a PhD to manage. If a tool needs extra set-up or ongoing management time, make sure it’s really worth it.

5. Is the intelligence embedded into your platform?

Many generative AI tools are very helpful, but require another tab or another app to be used. If it is inside your system, how deep are its connections? Does it have access to the data it needs? Can it act within your system, or does it need human intervention?

Avoid tools that require you to copy and paste information between windows, leaving room for human error and creating manual work. Does it provide context-aware intelligence and sit alongside your day-to-day work to support you, rather than separately, outside your workflows?

AI without context can give tone-deaf or irrelevant recommendations. AI provides the most value when it performs actions directly within your systems with full context of your business. Gaps in data lead to gaps in service.

6. Can it help us respond faster while still protecting the guest experience?

Speed matters, but guests hate feeling like they’re speaking to robots. Your AI needs to sound like a human. Can the AI maintain your brand voice, and access the info it needs to answer questions?

It also needs to know when to shut up and escalate the conversation to a real person. Your goal is to help your team deliver better service at scale, while keeping people in the process for oversight. If an AI tool threatens those relationships, it might actually make your guest experience worse rather than improve it.

7. Can it help the whole business, not just guest messaging?

Guest communication is often where AI starts, but it shouldn’t be where it ends. Useful tools support many more capabilities, including dynamic pricing, reporting and analytics, owner communications and proactive issue identification.

The best AI isn’t just performing tasks when requested, it’s supporting business decisions, proactively making recommendations, and helping you run your business in a smarter way. The greatest value often comes when intelligence is applied holistically across multiple parts of the business rather than a single workflow.

8. Who maintains the AI?

Market conditions shift daily and OTA policies change every other week. If your AI doesn’t have the latest info, it’s a liability that can misinform guests and cause costly headaches. Ask who maintains the AI. How does it stay current with platform updates? An AI solution functions well only when expertise keeps it relevant. And if there’s ever an outage, who’s responsible for fixing the tool?

How to build AI into your systems

The winners over the next few years won’t necessarily be the property managers with the flashiest tech. They’ll be the ones who actually know their business and use AI as a superpower, not a crutch.

That means tools that are deeply connected to their operations, built on real vacation rental expertise, and embedded into the workflows their teams use every day. AI that really learns from experience, taking the data and work that your team generates day to day and transforming it into insights and recommendations to help you run and scale a smarter business.

It’s too late to be asking “does this have AI?” The question now is how that AI helps you deliver a better guest experience, operate more efficiently, and grow your business with confidence.

By Rick van der Plas, Chief Technology Officer of Hostaway