AI Transforms Vacation Rentals with Smart Agents

Artificial intelligence is moving from back-office support to center stage in the vacation-rental sector, where a mix of fragmented inventory and high guest expectations makes technology upgrades both urgent and lucrative. Platforms such as RedAwning, Besty AI, Homescreen AI and UnderTheDoormat are investing heavily in flexible architectures that can absorb rapid-fire model releases from providers like OpenAI, Anthropic, Gemini and Llama while delivering tangible improvements in search, communication, upselling and maintenance.

RedAwning, which manages 21,000 properties for 1,000 owners, now relies on large language models to parse detailed guest requests and match travelers to the ideal home—think three bedrooms, a ping-pong table, a grocery store within two miles and hiking trails nearby. The company also automated review responses: five-star feedback triggers an AI-generated, detail-rich thank-you that formerly required a 10-person team but now needs just one employee for a 20-minute daily check. Founder Tim Choate says the results prove the long-promised efficiency gains once training and fine-tuning are complete and the “switch is flipped.”

Besty AI, active across 25,000 units, began as a messaging tool but now positions itself as a “centralized AI brain” for property managers. Its Operator product maps every policy for early check-ins and late checkouts, a question that accounts for roughly a third of all guest queries. If a toilet leaks, Operator detects the report, consults standard operating procedures and dispatches a plumber, eliminating manual coordination. Co-founder Sam Dundas argues that such autonomous workflows will shift managers into a strategic “shot-caller” role as AI handles routine tasks.

Homescreen AI founder Sharad Sundaresan, formerly of Airbnb, sees similar potential but warns that true automation requires deep integration with PMS, CRM, content and team-communication tools. The company’s modular architecture lets it swap foundational models in a day to capitalize on performance or cost advantages. Sundaresan is exploring GPT-4o’s image capabilities to let guests text bills or photos of issues for instant AI clarification, further reducing staff workload.

UnderTheDoormat Group is building a unified dataset spanning guest details, finance, scheduling and pricing so that each new AI release can be layered on quickly. Chief operating officer Richard Bridger believes agentic interfaces will soon communicate directly with traveler-facing robots, demanding interfaces that are readable by both humans and machines. He predicts massive conversion gains once “robot-ready” UX becomes standard.

The sector is also testing AI-driven phone support and multilingual concierge bots to remove language and roaming barriers, critical for rural properties that serve as travelers’ first point of contact with a destination. Yet adoption remains uneven. Some property-management-system vendors refuse to open their APIs, prompting managers to switch providers to access newer AI features. Legal questions about data ownership and copyright loom large as publishers sue model trainers, but operators argue that real-world gains in efficiency, personalization and revenue outweigh the risks.

As the pace of innovation accelerates, the winners will be companies that treat infrastructure and interoperability as strategic assets, allowing them to plug in the best-of-breed models and deliver seamless, personalized guest experiences at scale. In an industry where each home is unique and every booking carries high emotional stakes, AI is quickly becoming the differentiator that turns complexity into competitive advantage.

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AI Transforms Vacation Rentals with Smart Agents

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