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Stay Sidekick is a full-stack, multi-tenant web platform built for vacation rental operations teams. It works as a satellite layer alongside your existing Property Management System (PMS) — not as a replacement, but as the operational layer that covers all the tasks your PMS leaves unresolved. Born from 2.5 years of direct front-desk experience managing a vacation apartment portfolio, Stay Sidekick was designed after observing that the start and end of every shift was consumed by repetitive tasks spread across PMS dashboards, Google, and spreadsheets — friction shared by every team member on rotation. What began as a JavaFX prototype and evolved through a MERN version still in real use today, Stay Sidekick is the mature evolution of that journey: a focused, purposeful layer that adapts to the concrete operations of each company.

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Core Features

Apartment Catalog

Centralised inventory management with PMS sync (Smoobu), bulk XLSX import, and logical soft-delete. The catalog underpins every other module.

Operational Heat Map

Visualise daily check-in and check-out volume across a date range to anticipate operational peaks. Works with PMS API or XLSX upload — no data is persisted.

Late Check-in Notifications

Automatically detect same-day check-ins, apply per-company cut-off rules, and send standardised notifications using fully editable message templates.

Google Contacts Sync

Connect via OAuth 2.0 to Google People API and sync guests from your PMS into your team’s Google Contacts, with CSV export as a GDPR-safe fallback.

Communications Vault

A categorised, multi-language template library with an optional AI assistant for rewriting and translating messages. Bring your own API key or use the shared free tier.

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Who Is It For?

Stay Sidekick is built for the people who actually work the front desk and manage daily operations — not just for property owners or managers reviewing dashboards from a distance.
  • Receptionists and operations staff who handle check-ins, guest communication, and daily coordination.
  • Property managers overseeing multiple units across one or more companies who need a single place to track operational load.
  • Operations team leads who want standardised communication templates and consistent guest contact management across rotating shifts.
Stay Sidekick is designed to be picked up quickly. Each module includes a built-in “how this tool works” modal to reduce the learning curve for new team members.
If your team currently handles any of the above tasks manually — across tabs, spreadsheets, or by copying and pasting messages — Stay Sidekick is for you.

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What Stay Sidekick Is NOT

Stay Sidekick does not replace your PMS. It sits alongside Smoobu, Beds24, KrossBooking, and similar systems, complementing them rather than duplicating their core functions.
  • It does not manage bookings or reservations.
  • It does not process payments.
  • It does not act as a channel manager or OTA integration hub.
  • It does not replace guest-facing booking portals.
Think of Stay Sidekick as the operational control layer your team actually uses every day, while your PMS remains the source of truth for reservations and revenue.
It reads reservation data from your PMS (or from XLSX exports when no API is available) and transforms that data into operational actions — notifications, contact syncs, heat maps — without ever duplicating your PMS data into persistent storage unnecessarily. Guest-facing data is processed in memory and never stored in the database, keeping the platform aligned with GDPR principles by default.

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Multi-Tenant Architecture

Stay Sidekick is built as a genuine multi-tenant platform. Every company that onboards gets fully isolated data at the query level — no company can see or interact with another company’s apartments, users, templates, or configuration.
  • A superadmin role manages company onboarding and global platform supervision.
  • Each company has its own admin who manages users, roles, integrations, and module configuration from the panel — no code changes required.
  • Sensitive credentials (PMS API keys, AI provider keys) are stored encrypted in the database using Fernet symmetric encryption.
  • All modules respect the per-company configuration: thresholds, templates, sync preferences, and AI settings are isolated per tenant.
Multiple companies can share the same Stay Sidekick instance. Each operates in its own isolated environment without any visibility into other tenants’ data.
This architecture means Stay Sidekick can be run as a self-hosted platform for a single company, or as a shared service for multiple independent vacation rental operations teams on the same deployment.

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