← Embedded Finance Index 2026

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.

Last 12 months

2024

Rebranded from BookingSync to Smily and launched FinTech suite (SmilyPay, Split Payment, Cancellation Protection, Damage Protection)

2025

Launched experimental MCP Server enabling AI agents (Claude, OpenAI Codex) to query Smily accounts via Model Context Protocol

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

Stripe IngenicoSmilyPay (self-operated)

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.

BookingSync — frequently asked

Who is BookingSync's payment processor?

BookingSync processes payments through Stripe, Ingenico and SmilyPay (self-operated).

Who handles BookingSync's FX and cross-border payouts?

BookingSync uses SmilyPay (self-operated) for FX and cross-border payouts.

Which accounting software does BookingSync integrate with?

BookingSync integrates with QuickBooks and Zapier.

What is BookingSync's embedded finance stack?

The Embedded Finance Index 2026 maps 3 layers in BookingSync's stack: Payments / PSP (Stripe, Ingenico and SmilyPay (self-operated)); FX & payouts (SmilyPay (self-operated)); Accounting (QuickBooks and Zapier).

Who founded BookingSync?

BookingSync was founded by Sébastien Grosjean and is founded in 2010, headquartered in Névache, France.

How much funding has BookingSync raised?

BookingSync has raised $1M in total (latest round: Angel).

Benchmark your own stack

Request an embedded finance strategy assessment

Get a read on where your own stack stands against BookingSync and the rest of its category — what they built versus bought, which providers they use, and where the gaps in your own strategy and competitive set actually are.

Your category, mappedHow your stack compares to BookingSync and the other companies in its category.
Build vs. buyWhere a provider relationship would close a gap faster than building it.
A named analyst, not a form replyA short call to scope what's actually worth assessing for you.