Square Appointments vs Calendly: Which Should You Choose in 2026?
Choosing between Square Appointments and Calendly comes down to understanding what each tool does best. This comparison breaks down the key differences so you can make an informed decision based on your specific needs, not marketing claims.
By Toolradar Team · Last updated February 28, 2026 · Methodology
Short on time? Here's the quick answer
We've tested both tools. Here's who should pick what:
Square Appointments
Manage appointments, staff, and services with free online booking and scheduling software.
Best for you if:
- • You need resource planning features specifically
- • Provides free online booking and scheduling for appointments and classes.
- • Integrates payment processing, automated reminders, and no-show protection.
Calendly
Scheduling automation platform
Best for you if:
- • You want the higher-rated option (8.8/10 vs 8.4/10)
- • You need automation features specifically
- • Meeting scheduling automation
- • Calendar integrations
| At a Glance |  Square Appointments |  Calendly |
|---|---|---|
Price | Free + Paid | Free + Paid |
Best For | Resource Planning | Automation |
Rating | 84/100 | 88/100 |
| Feature | Square Appointments | Calendly |
|---|---|---|
| Pricing Model | Freemium | Freemium |
| Editorial Score | 84 | 88 |
| Community Rating | No ratings yet | No ratings yet |
| Total Reviews | 0 | 0 |
| Community Upvotes | 0 | 0 |
| Categories | Resource PlanningMeeting Scheduling | AutomationMeeting Scheduling |
How Square Appointments and Calendly Compare
Square Appointments
Manage appointments, staff, and services with free online booking and scheduling software.
Free tier available · 84/100 score
Calendly
Scheduling automation platform
Free tier available · 88/100 score
Square Appointments is a resource planning tool. Calendly is in automation.
Who Should Use What?
On a budget?
Both are freemium. Compare plans on their websites.
Go with: Square Appointments
Want the highest-rated option?
Square Appointments: 84/100. Calendly: 88/100.
Go with: Calendly
Value user reviews?
Neither has user reviews yet.
Go with: Calendly
3 Questions to Help You Decide
What's your budget?
Both are freemium. Pricing won't help you decide here.
What's your use case?
Square Appointments is a resource planning tool. Calendly is in automation. Pick the category that matches your needs.
How important are ratings?
Calendly scores higher: 88/100 vs 84/100.
Key Takeaways
Calendly
- Higher score: 88/100 vs 84
- Free tier available
- Our pick for this comparison
Square Appointments
- Better fit for resource planning
The Bottom Line
Calendly (88/100) is our pick.
Frequently Asked Questions
Is Square Appointments or Calendly better?
Calendly scores 88/100 in our evaluation. Both are freemium.
What are Square Appointments and Calendly used for?
Square Appointments: Manage appointments, staff, and services with free online booking and scheduling software.. Calendly: Scheduling automation platform.
What does Square Appointments cost vs Calendly?
Square Appointments is freemium (free tier + paid plans). Calendly is freemium (free tier + paid plans). Visit their websites for detailed pricing.