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Scheduling · head to head

Calendly vs Square Appointments

Calendly logo

Calendly

Scheduling

Scheduling automation platform for eliminating back-and-forth

From
Free
Rated
-
Full reviewWebsite
Square Appointments logo

Square Appointments

Scheduling

Free scheduling for beauty businesses

From
On request
Rated
-
Full reviewWebsite

The short version

  • Only Calendly has a free tier, so it costs nothing to try first.
  • 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.
  • Prices and features above were last checked on 30 August 2026.

Where they differ

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

Attributes where Calendly and Square Appointments differ
AttributeCalendlySquare Appointments
Starting priceFreeOn request
Pricing modelUnknownusage-based
Free tierYesNo
Founded20132009

Identical on both: platforms (Web, iOS, Android), user rating (Not yet rated), category (Scheduling).

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

On request
  • Solo Professional Plan$null/transaction
    • Processing fees apply
    • For solo professionals taking payments and managing schedules
    • Top appointments features
  • Plus Plan$null/transaction
    • Processing fees apply
    • Free trial available
    • For growing teams needing more advanced tools
  • Premium Plan$null/transaction
    • Processing fees apply
    • Free trial available
    • For large salons with complex staff management
  • Square Pro$null/month
    • Custom pricing for businesses processing over $250,000 annually
    • Hardware discounts
    • Onboarding support

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 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 On request, and user ratings are close enough to be indistinguishable. Choose on capability and platform support.
Which is cheaper, Calendly or Square Appointments?
Calendly has a free tier; the other does not. Paid plans start at Free for Calendly and On request for Square Appointments.
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?
Yes. Calendly has a free tier, so you can try it without paying. Square Appointments starts at On request.
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
Square Appointments: How much do Square Appointments plans cost?

Square Appointments pricing is based on processing fees rather than monthly subscription fees. Specific percentages are not listed online. The Solo Professional, Plus, and Premium plans all charge processing fees on transactions. For businesses processing over $250,000 annually, Square Pro offers custom pricing including hardware discounts, onboarding support, and account management.

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
Square Appointments: Is there a free trial for Square Appointments?

Yes, the Plus and Premium plans offer free trials for an unspecified number of days. The Solo Professional plan does not appear to offer a trial period.

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
Square Appointments: What features does the Premium plan add compared to Plus?

The Premium plan includes all Plus features plus Future Bookings Report for tracking upcoming appointments, Service Cost Tracking to monitor service profitability, and Resource Management for scheduling equipment and facilities across multiple staff members.

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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