The AI Guest Whisperer Taking Over Vacation Rentals

Short-term rental operators spent years pricing by hand, answering guest messages at midnight and chasing cleaners between checkouts. A growing number have stopped: artificial intelligence (AI) now handles pricing, guest communication, staff scheduling and maintenance coordination. Some operators are spending $30,000 to $50,000 a month on it. That’s enough that at least one company is creating a dedicated finance role just to manage AI spend.

More than 70% of vacation rental managers now use AI tools in some form, according to Hostaway, nearly double the share from six months ago. That puts short-term rentals ahead of most other real estate segments in AI deployment. Operators say the tools have moved well past basic automation.

How Operators Are Deploying AI

The most common entry point is pricing. AI platforms like PriceLabs and Wheelhouse pull from historical booking data, seasonal demand, local events and competitor rates to adjust nightly prices automatically, removing the need for daily manual updates. Hostaway reported that operators using these tools see stronger occupancy rates and cash flow compared to static pricing models.

Guest communication follows close behind. Vinayak Mahtani, CEO and co-founder of bnbme Holiday Homes, told Forbes that his company’s in-house AI assistant, built on a commercial large language model and customized for their systems, independently handles about 70% of guest needs. Human agents take over only when the system’s confidence falls below 90%. “The assistant is a literal guest whisperer,” Mahtani said, noting it manages inquiries across multiple time zones and languages without adding headcount.

Beyond messaging, AI handles task assignment after checkouts, flags maintenance issues before they become repairs, syncs availability across booking channels to prevent double bookings and screens guest reservations for fraud indicators. Mahtani reported that internal efficiency, lead qualification speed and marketing output all improved after deployment, with no team size increase.

Where Costs and Model Capability Matter

The efficiency gains come with a growing price tag. Graham Donoghue, group CEO of Forge Holiday Group, said that his company is spending between $30,000 and $50,000 per month with Anthropic on AI tokens and is considering creating a dedicated finance role to manage token optimization.

Steve Schwab, founder and CEO of Casago, said token costs represent only 20% to 30% of the total compute expense today.

“We’re going to be in a situation where investors say, ‘we have to make money,’ and the compute cost of running these cycles is going to be really expensive,” Schwab said. He added that arbitrage strategies and architectural changes in AI infrastructure may be needed to keep the economics viable for operators of all sizes.

Donoghue said Forge started using AI more than a year ago, beginning with repetitive tasks like image retouching and call transcriptions before moving to what he described as complicated algorithmic processes. Tasks that previously took weeks now take days. The company also built an AI tool called Vivid Stay that converts static property images into video and drone-like footage in 25 minutes, at a fraction of the $2,000 to $3,000 it previously cost per property.

That said, not every initiative has delivered. Donoghue cited failed experiments with conversational search and the difficulty of getting employees to adopt AI tools without making them mandatory.

How Compliance and Distribution Are Entering the Picture

AI adoption to manage short-term rentals is also moving into regulatory infrastructure. Holmes Beach, Florida, saw a measurable rise in short-term rental compliance after the city implemented an AI monitoring platform, according to WFLA. The system tracks unlicensed activity and code violations at a scale that manual enforcement can’t match.

On the distribution side, both Donoghue and Schwab raised the prospect of AI eventually challenging the position of the large online travel agencies. Donoghue said groups of consumers will become comfortable enough with AI that it disintermediates some large online travel agencies. Schwab put it more directly: he thinks someone is currently writing code that will change how rental search works in ways the industry can’t yet anticipate.

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