What Smily, formerly BookingSync does

Smily (formerly BookingSync) is a French-headquartered SaaS company that provides an all-in-one vacation rental management platform for professional property managers, agencies, conciergeries, and individual property owners. Founded in 2012 and rebranded from BookingSync to Smily in 2022, the platform synchronizes listings and calendars across more than 6,000 booking channels including Airbnb, Booking.com, Expedia, Vrbo, Abritel, and Google Vacation Rentals, while centralizing payments (SmilyPay, Split Payment), guest communications (Unified Inbox, Smart Replies), revenue management, task automation, and direct-booking website capabilities. The company reports over 1,000 property manager customers managing 23,000+ properties and processing approximately €1.5 billion in annual bookings through its platform.

The platform is built on Ruby on Rails with Apache Kafka for distributed messaging and AWS RDS for database infrastructure, with an open-source engineering footprint (e.g., Dionysus-rb). Smily's AI layer (Smily AI) covers NLP, computer vision, generative video, anomaly detection, listing optimization, and autonomous audit agents, and the FinTech layer adds PCI-DSS-compliant payment processing, automated owner payouts, cancellation protection, and damage protection. The legal entity is SAS BookingSync, registered in Gap, France, with five co-founders including Sébastien Grosjean (CEO), Karol Galanciak (CTO), Florian Stenström (COO), Philippe Grosjean (CFO), and Ella Fraase Storm (CCO).

Smily monetizes via a hybrid model: a 1.2% commission on gross booking value OR tiered minimum monthly fees (whichever is higher), with pricing of €1,777/month for a single-property manager down to roughly €124/property at 20 properties, plus one-time setup and training fees from €690 and a full suite of optional add-ons. GTM is hybrid sales-led (enterprise field sales with dedicated account managers for 50–2,000+ property portfolios) combined with product-led growth via a free Airbnb Listing Audit tool. The company holds Preferred Partner status simultaneously with Airbnb, Booking.com, and Expedia, was named "World's Best Connectivity Partner" in 2021, and operates a fully distributed team across 17 countries.

Name

Smily, formerly BookingSync

Legal name

SAS BookingSync

Website

https://smily.com

Company type

Private

Founded year

2012

Operating status

Operating

Headcount range

11–50 employees

Short description

Smily (formerly BookingSync) is a French SaaS company providing an all-in-one vacation rental management platform, combining channel management across 6,000+ booking sites, AI-driven listing optimization, FinTech payments, and direct-booking tools for 1,000+ property managers managing 23,000+ properties.

Ownership category

akta.pro rank

Product category

Vacation rental management software

SIC

Services-Prepackaged Software (7372)

akta.pro primary industry

Professional/Managed Inventory Vacation Rental Marketplaces (THAMALAB)

akta.pro secondary industries

Direct Booking Platforms & Booking Engines for Hosts/Managers (THAMALAE), Full-Service Vacation Rental Property Management (BPAJAIAA)

Keywords

• Vacation rental software
• Property management system
• Channel manager
• Payment processing
• AI automation

Headquarters

HQ city

Névache

HQ country

France

HQ region

Europe

Offices1 record

Markets served

GTM type

B2B

Offering type

Software

Cost components

Personnel, Technology or R&D, Operations, Marketing or Sales, Infrastructure, Others

Revenue model

1. Transaction-based Commission: Smily charges a commission of 1.2% of the gross booking value (calculated on TTC amount of bookings with departure date in the previous month), with a minimum monthly fee based on property count. This aligns incentives with customers since fees are tied to bookings. Commission excludes cleaning fees and tourist tax.
2. Monthly Subscription: Tiered pricing model based on property count: 1 property at €1,777/month, 20 properties at €2,475/month (29% savings). Customers pay the higher of fixed fees or commission. Subscription includes user license, hosting, security, maintenance, updates, support, booking system, and App Center access.
3. Setup and Training Fees: One-time setup/training fees starting at €690 for onboarding services including property and reservation imports, pricing rule configuration, emails, website setup, and account customization. Refundable if onboarding completed within 14 days.
4. Optional Add-ons: Various optional add-ons available for customization, allowing customers to pay only for features they need beyond the base subscription.

Pricing tiers

Go-to-market motion2 records

Distribution channels3 records

Marketing channels8 records

Core offering

Smily offers an all-in-one, AI-reimagined vacation rental management software platform for property managers and agencies. It synchronizes listings and calendars across 1,000+ booking platforms (Airbnb, Booking.com, Expedia, Vrbo), processes payments with automated owner split payouts, centralizes guest messaging with AI Smart Replies, and applies AI (computer vision, NLP, generative AI) to optimize listings, improve photos, generate videos, detect emergencies, and dynamically price rentals. The platform is sold on a tiered subscription plus 1.2% transaction commission model with one-time setup fees.

Product overview

Smily (formerly BookingSync) is a unified, all-in-one vacation rental management platform designed for property managers, agencies, and owners. The platform is built around a core architecture consisting of Channel Manager for multi-platform listing synchronization, Payment Solutions including SmilyPay and Split Payment for financial management, and Smily AI for intelligent automation. Additional integrated modules include Direct Booking Website, Unified Inbox, Revenue Management, Task Management, Performance Dashboard, Email Marketing, Reviews Management, CRM, Mobile App, Remarketing, Owners Portal, and Account Management. The platform also offers the 'Your Own Portal' white-label solution for branded booking sites, along with a free Airbnb Listing Audit tool and expert training through Smily Courses. The system is priced on a transaction-based commission model (1.2% of gross booking value) with tiered pricing based on property count, and is trusted by over 1,000 property managers managing 23,000+ properties across Airbnb, Booking.com, Expedia, Vrbo, and 1000+ other platforms.

Differentiator

Problem solved

Functional benefit

Products and services

• Channel Manager Synchronizes property listings, availability calendars, rates, and content across Airbnb, Booking.com, Expedia, Vrbo and 1,000+ booking platforms to prevent double bookings, maximize visibility, and centralize multi-channel distribution for vacation rental property managers and agencies.
• Payment Solutions (SmilyPay) Integrated payment processing for Smily-managed properties that centralizes credit card acceptance, reconciliation, and revenue distribution across Airbnb, Booking.com, Expedia, and direct bookings; backed by PCI-DSS Level 3 compliance.
• Split Payment Automated payment splitting between property owners and managers with a lawyers-reviewed setup, PCI-DSS and GDPR compliance, real-time monitoring, and transparent dashboards for vacation rental agencies and conciergeries.
• Unified Inbox Centralizes guest communications from all booking channels (Airbnb, Booking.com, Expedia, Vrbo, direct booking websites) into one secure inbox with AI-powered Smart Replies for automated guest responses.
• Smily AI AI suite of capabilities for vacation rental managers including Emergency Detection (anomaly detection in messages), Smart Replies (NLP-driven auto-responses), Listing Audit (multimodal AI agents that analyze listings), Photo Improvement (computer vision), Listing Optimization, Seasonal Listings, Personalized Listings, and AI-generated Listing Videos.
• Direct Booking Website Customizable, branded booking website solution enabling vacation rental property managers to capture direct bookings with built-in optimization, world-class listing quality, and instant book functionality.
• Revenue Management Dynamic pricing and yield management module with integrations to PriceLabs, Beyond, and Wheelhouse, plus API support for custom pricing engines with LOS settings and seasonal markups for Smily's property manager and agency customers.
• Airbnb Listing Audit Free AI-powered audit tool that analyzes an Airbnb listing and delivers actionable recommendations within 24 hours, including a Performance Summary, Listing Health Snapshot, and detailed feedback on property name, description, and photo order.
• Mobile App iOS and Android mobile application that lets vacation rental managers operate properties, manage tasks, and respond to guests from anywhere with real-time updates.
• Owners Portal Secure role-based portal for property owners to view real-time property performance, financials, and bookings managed by their vacation rental agency.
• Cancellation Protection AI-powered cancellation protection that balances traveler flexibility with property manager revenue security, reconciling the expectations of travelers, owners, and property managers.
• App Center Marketplace of third-party integrations and partner solutions that extend Smily's vacation rental platform functionality, covering dynamic pricing, cleaning management, upselling, and more.
• Smily Courses Expert hospitality training platform offering online courses for vacation rental professionals to improve operational, marketing, and guest experience skills.

Quantifiable outcome

• 40% revenue increase on average for customers
• +2 more outcomes

Named customers13 records

Segments3 records

Ideal customer profiles3 records

Technology focussed Yes

API detail

Has API

Yes

API docs

API detail

Core technology

AI maturity

App detail

Integration5 records

AI capability11 records

Feature8 records

Partnerships

Ten partnerships are on record, tiered core and minor.

• AirbnbcoreGTM or Marketing Partner · 1 September 2021Smily is a Preferred Partner with Airbnb, holding the highest level of partnership in the vacation rental industry. This status enables superior integration, priority support, and co-marketing opportunities that benefit all Smily customers listing on Airbnb.
• Booking.comcoreGTM or Marketing Partner · 1 September 2021Smily is a Premier Plus Connectivity Partner with Booking.com, part of the Connectivity Advisory Board since its inception. CEO Sebastien Grosjean is a member of Booking.com's Connectivity Advisory Board.
• ExpediacoreGTM or Marketing Partner · 1 September 2021Smily is a Preferred Partner with Expedia, one of only a handful of companies achieving the highest partnership level across all three major booking platforms.
• Vrbo (Expedia Group)coreGTM or Marketing PartnerVrbo (formerly HomeAway) partnership enables property distribution and synchronization for Smily customers, integrated through the channel manager platform.
• Google Vacation RentalscoreTechnology or IntegrationGoogle Vacation Rentals integration allows Smily-managed properties to appear in Google search results, providing additional distribution channel and visibility for customers.
• Marriott Homes & VillascoreGTM or Marketing PartnerPartnership enables luxury vacation rental properties managed through Smily to be featured in Marriott's luxury rental portfolio.
• HomeToGominorChannel Partner/ Reseller/ DistributorSearch engine for vacation rentals that distributes Smily customer listings to travelers searching for accommodations.
• Enso ConnectcoreTechnology or IntegrationEnso Connect integration enables proactive upselling capabilities for Smily customers, with automated check-in, digital engagement, and upsell offers that can increase margin per reservation by up to 30%. Adopted by 50,000+ properties.
• TurnocoreTechnology or IntegrationTurno integration automates cleaning management, turnover coordination, payments, and quality control for Smily customers. Turno provides access to 55,000+ cleaning professionals globally with photo sharing and reporting capabilities. New Smily customers receive 3 months of Turno premium features.
• Amazon Web Services (AWS)coreOthersAWS provides cloud infrastructure including RDS database services for Smily's platform. Web hosting and core infrastructure powered by AWS.

Scale indicators9 records

Recent moves7 records

Expansion highlights6 records

Direct peers

• Lodgify: Lodgify is a vacation rental software focused on direct booking websites and channel management for individual owners and small-to-mid property managers. It competes with Smily's Direct Booking Website, Channel Manager, and unified inbox capabilities.
• Hostaway: Hostaway provides a vacation rental PMS and channel manager for professional property managers, with integrations to major OTAs. Its feature set (channel management, unified inbox, payment processing, websites) directly overlaps Smily's core modules.
• Tokeet: Tokeet is a vacation rental software combining PMS, channel manager, and unified inbox for individual hosts and small managers. It is a direct, lower-priced competitor to Smily in the channel management layer.
• Smoobu: Smoobu is a channel manager and PMS for vacation rental managers, popular among smaller European operators. It competes directly with Smily on channel management and PMS, particularly in the SMB segment.
• Avantio: Avantio is a European-based vacation rental software provider offering PMS, channel manager, and website builder for property managers and agencies, with strong presence in Spain and Portugal. It is a close regional competitor to Smily in the European market.
• Guesty: Guesty is a leading all-in-one vacation rental management platform offering PMS, channel manager, unified inbox, and payment solutions for professional property managers. It is one of Smily's most direct global competitors with a similar enterprise-focused GTM.

Broad incumbents

• Mews: Mews is an enterprise hospitality PMS expanding into the vacation rental and alternative accommodation space. It competes with Smily for larger operators seeking a unified PMS plus payments stack.
• Cloudbeds: Cloudbeds is a broader hospitality management platform serving hotels, hostels, and vacation rentals with PMS, channel manager, and booking engine capabilities. While not exclusively vacation rentals, it overlaps Smily's offering for hybrid operators.

Emerging players

• Turno: Turno automates cleaning and turnover management for vacation rentals, connecting managers with 55,000+ cleaning professionals. It is both an integration partner and an adjacent competitor operating in property operations software.
• Enso Connect: Enso Connect is a guest experience platform offering smart check-in, upselling, and digital guidebook functionality, and is integrated with Smily. It is a partial competitor and partner operating in the guest-facing layer of the same stack.

Market position

Strengths4 records

Weaknesses4 records

Competitive moat6 records

Key risks5 records

Key highlights6 records

Customer concentration

• YouTubeyoutube.com/@smily-com
• Facebookfacebook.com/wwwsmilyfr

Compliance4 records

Revenue estimate

Valuation estimate

Number of profiles

Profiles9 records

Funding overview

Funding rounds1 record

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Smily, formerly BookingSync