Guesty, the AI-powered property management platform for short-term rentals, has completed the acquisition of Smily (formerly BookingSync), France's leading PMS and channel manager for vacation rental operators. The deal hands Guesty a 15-year foothold in what is the world's second-largest short-term rental market, one generating more than $9 billion in gross booking value across OTAs in the past year alone, with over 1 million active listings.

Financial terms were not disclosed, though notably all five of Smily's founders and a cohort of its existing shareholders are reinvesting a portion of their proceeds directly into Guesty equity — a signal of conviction in the combined entity's trajectory.

The Platform Stack

Smily's technology suite is a full-featured stack built for the rigors of the European vacation rental segment. It combines a PMS, channel manager, direct booking website builder, integrated payments, and task management — all capabilities that map closely onto Guesty's existing architecture. Smily has held Premier Plus Connectivity Partner status in Booking.com's Connectivity Partner Programme for eight consecutive years, a connectivity credential that carries meaningful weight in the OTA-driven European market.

The platform was originally built in 2005 by Sébastien Grosjean to manage his family's rental portfolio, one of the earliest such operations in the vacation rental industry, before opening commercially in 2010. Since then, Smily has processed more than €3.3 billion in bookings for 13 million travelers, scaling operators from single-digit property counts to portfolios in the hundreds and, in select cases, the thousands.

Post-acquisition, both engineering and customer support teams will consolidate behind a single platform. The near-term product roadmap centers on deploying Guesty's AI capabilities — including its Agent Hub, which automates tasks across revenue management, guest communication, and financial operations — into the French market. Guesty shipped more than 300 product features in 2026, and the company says many were driven directly by customer requests, a development rhythm it intends to extend to Smily's operator base.

Market Context

For Guesty, which is backed by $410 million in funding from investors including KKR and Apax Digital Fund, the Smily deal is a targeted geographic expansion rather than a pivot. The platform already powers more than 500,000 properties across 100-plus countries and integrates with every major OTA — Airbnb, Vrbo, Booking.com, Expedia, Tripadvisor, Hopper, Google Travel, and Homes & Villas by Marriott. France, however, has historically required deep local expertise: regulatory nuance, OTA relationship specifics, and operator preferences that differ materially from Anglo-American markets.

The short-term rental software sector has seen consolidation accelerate as agentic AI reshapes what operators expect from their PMS. Platforms that can automate revenue optimization, dynamic pricing, and guest communications at scale are compressing the competitive field, favoring well-capitalized players with large proprietary training datasets. Guesty's pitch — that its agents act rather than merely suggest — is directly relevant to French property managers managing multi-property portfolios across fragmented OTA channels. For operators evaluating hotel and vacation rental technology platforms, the combination of Smily's local credibility and Guesty's AI depth represents a meaningful upgrade in what's available in the French market.

"France is one of the fastest-growing short-term rental markets in the world, and Smily has earned the trust of operators there for more than fifteen years," said Amiad Soto, Co-Founder and CEO of Guesty. Sébastien Grosjean, Founder and CEO of Smily, framed the decision as a response to the pace of technology change: "With this industry and its technology moving as fast as they are, the better path is to bring Smily's team and everything we know about France and Europe to Guesty, the clear world leader."

For hospitality tech operators tracking short-term rental and PMS consolidation trends, this acquisition signals that the agentic AI era is actively reshaping the competitive map of European vacation rental software.

Written by Michael Politz, Author of Guide to Restaurant Success: The Proven Process for Starting Any Restaurant Business From Scratch to Success (ISBN: 978-1-119-66896-1), Founder of Food & Beverage Magazine, the leading online magazine and resource in the industry. Designer of the Bluetooth logo and recognized in Entrepreneur Magazine's "Top 40 Under 40" for founding American Wholesale Floral, Politz is also the Co-founder of the Proof Awards and the CPG Awards and a partner in numerous consumer brands across the food and beverage sector.