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Calendly vs Square Appointments

Calendly logo

Calendly

Software

Scheduling automation platform for eliminating back-and-forth

From
Free
Rated
-
Full reviewWebsite
Square Appointments logo

Square Appointments

Software

Free scheduling for beauty businesses

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; Square Appointments the free plan is aimed at solo professionals; booking across multiple staff requires the paid Plus plan
  • They diverge on capability: Calendly covers Calendar sync, Square Appointments covers Online booking.

Where they differ

Only the attributes on which Calendly and Square Appointments actually diverge.

Attributes where Calendly and Square Appointments differ
AttributeCalendlySquare Appointments
Pricing modelUnknownsubscription
Founded20132009

Identical on both: starting price (Free), free tier (Yes), platforms (Web, iOS, Android), user rating (Not yet rated), category (Unknown).

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 Square Appointments

  • Online booking
  • Client management
  • Point of sale
  • Payment processing
  • Automated reminders
  • Instagram booking
  • Google booking
  • Mobile app

Both cover

  • Google Calendar

What people use each for

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

Calendly

  • Sales meetingsnot Square Appointments
  • Interview schedulingnot Square Appointments
  • Customer callsnot Square Appointments
  • Office hoursnot Square Appointments
  • Webinar registrationnot Square Appointments

Square Appointments

  • Online appointment booking for salons, barbers and personal servicesnot Calendly
  • Taking card payments and deposits at the time of bookingnot Calendly
  • Managing staff calendars, waitlists and no-show policiesnot 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

Square Appointments

  • The free plan is aimed at solo professionals; booking across multiple staff requires the paid Plus plan
  • Cancellation policies, no-show fees and waitlists require the Plus plan
  • Resource management, service cost tracking and the future bookings report require the Premium plan
  • Custom processing rates are reserved for Square Pro, which is aimed at businesses processing over $250,000 a year
  • Card processing fees are charged on top of the plan fee on every tier including the free one

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

Square Appointments

Free
  • FreeFree
    • Unlimited appointments
    • Online booking
    • Client management
  • Plus$29/month
    • Everything in Free
    • Multiple staff calendars
    • No-show protection
  • Premium$69/month
    • Everything in Plus
    • Multi-location
    • Staff management

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 Square Appointments if

  • You need online booking.
  • You want to start without paying.
  • You work on Web, Ios, Android.
  • You also want client management.
Square Appointments review

Questions people ask

Is Calendly or Square Appointments better?
Neither clearly leads. Calendly starts at Free and Square Appointments at Free, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Calendly or Square Appointments?
Calendly starts at Free and Square Appointments at Free.
Does Calendly or Square Appointments run on more platforms?
Calendly runs on Web, iOS, Android. Square Appointments runs on Web, 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 Square Appointments is typically brought in for.
What can Calendly do that Square Appointments cannot?
Calendly covers Calendar sync, Automated scheduling, Custom availability, Time zone detection. Square Appointments covers Online booking, Client management, Point of sale, Payment processing. Both handle Google Calendar.

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
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
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
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
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
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Related pages

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