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Calendars · head to head

Outlook Calendar vs SimplyBook.me

Outlook Calendar logo

Outlook Calendar

Calendars

Professional calendar management for Microsoft 365

From
Free
Rated
-
Full reviewWebsite
SimplyBook.me logo

SimplyBook.me

Scheduling

Online booking system for service businesses

From
Free
Rated
-
Full reviewWebsite

The short version

  • Each has a real cost: Outlook Calendar offline support limited to only past 30 days of events, older events unavailable; SimplyBook.me pricing model includes many features locked behind custom add-ons
  • They diverge on capability: Outlook Calendar covers Meeting scheduling, SimplyBook.me covers Booking website.
  • Prices and features above were last checked on 30 August 2026.

Where they differ

Only the attributes on which Outlook Calendar and SimplyBook.me actually diverge.

Attributes where Outlook Calendar and SimplyBook.me differ
AttributeOutlook CalendarSimplyBook.me
Pricing modelUnknownfreemium
PlatformsWeb, Windows, macOS, iOS, AndroidWeb, iOS, Android
CategoryCalendarsScheduling
Founded19752009

Identical on both: starting price (Free), free tier (Yes), user rating (Not yet rated).

What each one covers

Drawn from each product's published feature list. An absence here means we hold no record of it - not that the product lacks it.

Only in Outlook Calendar

  • Meeting scheduling
  • Shared calendars
  • Room booking
  • Availability sharing
  • Recurring events
  • Microsoft Teams
  • OneDrive
  • SharePoint

Only in SimplyBook.me

  • Booking website
  • Client management
  • Payment processing
  • Marketing tools
  • Custom branding
  • Google Calendar
  • Outlook
  • Stripe

Both cover

  • Zoom
  • Web support
  • Ios support
  • Android support

What people use each for

The jobs each tool is most often brought in to do.

Outlook Calendar

  • Scheduling
  • Appointment booking
  • Time tracking
  • Resource management
  • Team coordination

SimplyBook.me

  • Scheduling
  • Appointment booking
  • Time tracking
  • Resource management
  • Team coordination

Both are used for scheduling, appointment booking, time tracking, resource management, team coordination, on those jobs the choice comes down to price and fit rather than capability.

Where each one falls short

Documented limitations, not opinions. Every one is a constraint you would hit in normal use.

Outlook Calendar

  • Offline support limited to only past 30 days of events, older events unavailable
  • Shared calendars and group calendars not available offline
  • Cached Exchange Mode issues can limit available offline data
  • Occasional sync conflicts when coming back online

SimplyBook.me

  • Pricing model includes many features locked behind custom add-ons
  • No built-in video conferencing, requiring third-party integration
  • Limited CRM capabilities compared to dedicated sales platforms
  • Free plan capped at 5 bookings per month, limiting small business use

Pricing, plan by plan

Outlook Calendar

Free
  • FreeFree
    • Outlook.com email and calendar
    • 50MB attachment limit
    • 1GB cloud storage
  • Microsoft 365 Basic$19.99/year
    • Outlook with limited features
    • Cloud storage
  • Microsoft 365 Personal$99.99/year
    • Premium Outlook
    • Ad-free email
    • 100GB mailbox storage
  • Microsoft 365 Business Basic$6/month
    • Business-class email
    • 1TB cloud storage
    • Microsoft Teams

SimplyBook.me

Free
  • FreeFree
    • 50 bookings/month
    • Booking website
    • Basic features
  • Basic$8.25/month
    • 100 bookings
    • Custom features
    • Payments
  • Standard$24.9/month
    • 500 bookings
    • All features
    • Multiple locations

Which should you pick?

Choose Outlook Calendar if

  • You need meeting scheduling.
  • You want to start without paying.
  • You work on Web, Windows, macOS, iOS, Android.
  • You also want shared calendars.
Outlook Calendar review

Choose SimplyBook.me if

  • You need booking website.
  • You want to start without paying.
  • You work on Web, iOS, Android.
  • You also want client management.
SimplyBook.me review

Questions people ask

Is Outlook Calendar or SimplyBook.me better?
Neither clearly leads. Outlook Calendar starts at Free and SimplyBook.me at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Outlook Calendar or SimplyBook.me?
Outlook Calendar starts at Free and SimplyBook.me at Free.
Does Outlook Calendar or SimplyBook.me run on more platforms?
Outlook Calendar runs on Web, Windows, macOS, iOS, Android. SimplyBook.me runs on Web, iOS, Android.
Can I use Outlook Calendar for free?
Both have a free tier, so you can try either at no cost before committing.
What is Outlook Calendar best used for?
Outlook Calendar is most often used for scheduling, appointment booking, time tracking, resource management.
What can Outlook Calendar do that SimplyBook.me cannot?
Outlook Calendar covers Meeting scheduling, Shared calendars, Room booking, Availability sharing. SimplyBook.me covers Booking website, Client management, Payment processing, Marketing tools. Both handle Zoom, Web support, Ios support, Android support.

Answered from the vendors’ own pages

Outlook Calendar: Is Outlook Calendar free?

Outlook.com with calendar is free via a Microsoft account. Outlook Calendar also comes with Microsoft 365 Personal ($99.99/year), Family ($129.99/year), or Business plans starting at $6/user/month.

Source
SimplyBook.me: Does SimplyBook.me offer a free plan?

Yes, SimplyBook.me offers a free plan for small businesses, though advanced features and custom add-ons require paid plans.

Source
Outlook Calendar: Does Outlook Calendar work offline?

Outlook Calendar has limited offline support. New Outlook caches only the past 30 days of calendar items. Shared calendars and group calendars are not supported offline. Changes sync when you reconnect.

Source
Outlook Calendar: What platforms does Outlook Calendar support?

Outlook Calendar is available on Windows (desktop and web), macOS (desktop and web), iOS, and Android. Real-time synchronization works across all devices.

Source
Outlook Calendar: Does Outlook Calendar integrate with Slack?

Yes. Outlook Calendar integrates with Slack to sync your status and receive meeting notifications. You can RSVP to invites directly in Slack and join Microsoft Teams meetings from Slack reminders.

Source
Outlook Calendar: Can you share calendars and set delegate permissions?

Yes. Outlook Calendar supports calendar sharing with delegate permissions, color categories for organization, and the Scheduling Assistant to view attendee availability for meeting times.

Source
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