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Calendly vs Outlook Calendar

Calendly logo

Calendly

All industries

Scheduling automation platform for eliminating back-and-forth

From
Free
Rated
-
Full reviewWebsite
Outlook Calendar logo

Outlook Calendar

All industries

Professional calendar management for Microsoft 365

From
Free
Rated
-
Full reviewWebsite

The short version

  • Each has a real cost: Calendly the free plan allows one event type and one calendar connection, so it cannot handle different meeting formats; Outlook Calendar offline support limited to only past 30 days of events, older events unavailable
  • They diverge on capability: Calendly covers Calendar sync, Outlook Calendar covers Meeting scheduling.

Where they differ

Only the attributes on which Calendly and Outlook Calendar actually diverge.

Attributes where Calendly and Outlook Calendar differ
AttributeCalendlyOutlook Calendar
PlatformsWeb, iOS, AndroidWeb, Windows, macOS, iOS, Android
CategoryAll industriesUnknown
Founded20131975

Identical on both: starting price (Free), pricing model (Unknown), 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 Calendly

  • Calendar sync
  • Automated scheduling
  • Custom availability
  • Time zone detection
  • Reminder emails
  • Buffer time
  • Meeting polls
  • Embed on website

Only in Outlook Calendar

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

Both cover

  • Zoom
  • Slack

What people use each for

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

Calendly

  • Sales meetingsnot Outlook Calendar
  • Interview schedulingnot Outlook Calendar
  • Customer callsnot Outlook Calendar
  • Office hoursnot Outlook Calendar
  • Webinar registrationnot Outlook Calendar

Outlook Calendar

  • Schedulingnot Calendly
  • Appointment bookingnot Calendly
  • Time trackingnot Calendly
  • Resource managementnot Calendly
  • Team coordinationnot Calendly

Where each one falls short

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

Calendly

  • The free plan allows one event type and one calendar connection, so it cannot handle different meeting formats
  • Automated reminders and multiple calendars need Standard at $10 per seat per month
  • Round-robin routing, lead qualification and Salesforce integration require Teams at $16 per seat per month
  • SAML single sign-on, audit logs and domain control are Enterprise only, starting at $15,000 a year
  • Advertised prices are the annual rates

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

Pricing, plan by plan

Calendly

Free
  • FreeFree
    • 1 event type
    • 1 calendar connection
    • Basic confirmation email
  • Standard$10/month
    • Unlimited event types
    • Multiple calendars (up to 6)
    • Integrations with HubSpot, Mailchimp, Stripe, PayPal
  • Teams$16/month
    • All Standard features
    • Salesforce integration
    • Round-robin meetings
  • Enterprise$15000/year
    • All Teams features
    • Salesforce routing lookup
    • Microsoft Dynamics 365

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

Which should you pick?

Choose Calendly if

  • You need calendar sync.
  • You want to start without paying.
  • You work on Web, iOS, Android.
  • You also want automated scheduling.
Calendly review

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

Questions people ask

Is Calendly or Outlook Calendar better?
Neither clearly leads. Calendly starts at Free and Outlook Calendar at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Calendly or Outlook Calendar?
Calendly starts at Free and Outlook Calendar at Free.
Does Calendly or Outlook Calendar run on more platforms?
Calendly runs on Web, iOS, Android. Outlook Calendar runs on Web, Windows, macOS, iOS, Android.
Can I use Calendly for free?
Both have a free tier, so you can try either at no cost before committing.
What is Calendly best used for?
Calendly is most often used for sales meetings, interview scheduling, customer calls, office hours. Of those, sales meetings and interview scheduling are not what Outlook Calendar is typically brought in for.
What can Calendly do that Outlook Calendar cannot?
Calendly covers Calendar sync, Automated scheduling, Custom availability, Time zone detection. Outlook Calendar covers Meeting scheduling, Shared calendars, Room booking, Availability sharing. Both handle Zoom, Slack.

Answered from the vendors’ own pages

Calendly: Does the free tier include automatic reminders?

No. The free plan only includes a basic confirmation email when someone books. Automated reminder workflows, SMS reminders, and follow-up sequences require the Standard plan ($10/month or higher).

Source
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
Calendly: Can I offer multiple meeting types on the free plan?

Only one event type can be active at a time. You can create multiple event types, but only one booking link works simultaneously. Switching between different meeting lengths requires manually activating another event type.

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
Calendly: Does Calendly work with Apple Calendar and iCloud?

No longer for new users. As of August 20, 2024, new users cannot connect iCloud or Apple Calendar. Existing connections continue to work, but Calendly ended support for new Apple Calendar integrations citing Apple's security changes.

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
Calendly: What platforms can I use Calendly on?

Calendly is available on Web, iOS, and Android. Browser extensions are available for Safari. There are no dedicated Windows or Mac desktop applications.

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
Calendly: What does the Standard plan ($10/month) add over free?

Unlimited event types, multiple calendar connections (up to 6), integrations with HubSpot, Mailchimp, Salesforce, Stripe, PayPal, Zapier, and webhooks, plus automated reminders and email sequences.

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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Related pages

More on Calendly

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