BookingSync
“Can a European vacation rental PMS graduate into the financial and AI operating system for short-term rental managers?”
Founded2010
HQNévache, France
FoundersSébastien Grosjean
Total raised$1M
Latest roundAngel
IndustryVertical SaaS / Vacation Rental
The story
Founded 2010 as BookingSync, a French cloud-based vacation rental PMS and channel manager. Rebranded to Smily and pivoted from a pure SaaS PMS into an AI + FinTech platform, layering SmilyPay (embedded card acceptance), Split Payments (automated owner payouts), Cancellation Protection, and Damage Protection on top of the core property management product to capture payment economics rather than just subscription revenue.
Product timeline
2010
BookingSync founded in France as a cloud-based vacation rental management platform· launch
2014
Public re-launch with rebranding, full property management, rates engine, and Roomorama distribution partnership· product
2015
Became first vacation rental software available on Zapier· product
2024
Rebranded to Smily; introduced SmilyPay payments, AI features, Cancellation Protection, and Damage Protection· pivot
The stack
3 layers disclosed in BookingSync’s embedded-finance stack
Payments / PSP
FX & payouts
in the full report
Accounting
in the full report
Accounting gap: significant
3 more providers across 2 layers, with confidence-scored evidence and source URLs, are in the Embedded Finance Index report.