Airbnb vs Guesty

Airbnb CEO: AI agents need their own operating system

Airbnb rolled out AI-powered search as part of its fall update. CEO Brian Chesky discussed the company's AI strategy, expressing skepticism about chatbot-only interfaces for e-commerce. He envisions a new interface type between chatbots and current apps, and plans to explore 'multiplayer' AI for group planning. Chesky argues that AI agents require a dedicated operating system with a software developer kit, rather than being built on top of iOS or Windows. He noted that agents like Instinct and Muse don't work well with Airbnb yet, and that the industry has not 'cracked consumer AI.' Airbnb plans to roll out voice agents this fall for search and customer service. Chesky believes apps will remain central as long as Apple and Google control platforms.

• Airbnb launched AI-powered search as part of its fall update.
• CEO Brian Chesky says chatbots are not suited for e-commerce interfaces.
• Airbnb plans to explore 'multiplayer' AI for group trip planning in the next 3-6 months.

Airbnb 2026 fall update

Airbnb announces its 2026 fall update, along with new partnerships and initiatives including expanding access to OpenAI frontier models, a 'Farm to Stay' grant program, and a housing accelerator.

Airbnb Adds AI Search and Social Features

Airbnb announced a major product update introducing an AI-powered search feature that allows users to find properties via text or voice prompts, with dynamic filters and AI-generated property summaries. The company also expanded its services to include meal delivery, laundry, baby-gear rental, and more. Additionally, Airbnb is enhancing social features, enabling travelers to view their connections' past and upcoming trips on a map, and building neighborhood pages based on guest reviews. CEO Brian Chesky emphasized the challenge of implementing AI search without hurting conversion rates, noting the platform's $100 billion transaction volume. The update reflects Airbnb's dual strategy: competing with hotels through expanded services and leveraging AI and social connections to enhance travel discovery.

• Airbnb introduced AI search features allowing text and voice prompts for property discovery.
• The company expanded services to include meal delivery, laundry, baby-gear rental, and ski/boat rental.
• New social features let users view connections' trips on a map with privacy options.

Guesty completes acquisition of French PMS Smily

Guesty, the AI platform for short-term rentals, has completed its acquisition of Smily (formerly BookingSync), a French property management system and channel manager founded in 2005. This strategic move strengthens Guesty's presence in France, the world's second-largest short-term rental market with over one million active listings and $9 billion in gross booking value over the past year. Smily, which has processed over €3.3 billion in bookings for 13 million travelers, will see its product, engineering, and customer support teams integrated with Guesty's, with a focus on bringing AI capabilities like Agent Hub to the French market. All five Smily founders and some shareholders are reinvesting part of the proceeds into Guesty equity. Terms of the deal were not disclosed, but Guesty is backed by $410 million in funding from investors including KKR, Apax Digital Fund, and Inovia Capital.

• Guesty completed the acquisition of Smily, a French property management system and channel manager.
• Smily was founded in 2005 and has processed over €3.3 billion in bookings for 13 million travelers.
• France has over 1 million active short-term rental listings and $9 billion in gross booking value over the past year.