Calendly vs Square Appointments vs SimplyBook.me Comparison
Calendly
Starting at $8 /User/Month
- Free Trial
- Individuals
- Freelancers / Consultants
Calendly is free meeting scheduling software that dramatically increases your booking rates with Web-based meetings, while making it easy to book face-to-face time with busy clients. With Calendly, you can book an appoin…
Square Appointments
Starting at Contact for pricing
- Individuals
- Medium Business
Square Appointments is an appointment scheduling and reminder software that helps you book appointments with less time on the phone. Square Appointments is a browser-based application that you install on your computer an…
SimplyBook.me
Starting at $8.25 /Month
- Free Trial
- Freelancers / Consultants
- Large Enterprises
SimplyBook.me is a simple and easy to use online appointment scheduling software. The site allows you to set up your appointments in seconds, provides a platform for visitors to contact you and view any available appoint…
Calendly leads on user satisfaction with a 4.5-star rating across 1,680 reviews.
Calendly vs Square Appointments vs SimplyBook.me — at a glance
| Feature | Calendly | Square Appointments | SimplyBook.me |
|---|---|---|---|
| Rating | 4.5 / 5 | 4.4 / 5 | 4.6 / 5 |
| Reviews | 1,680 | 218 | 480 |
| Starting price | $8 /User/Month | Contact for pricing | $8.25 /Month |
| Free trial | Yes | No | Yes |
| Free version | No | No | No |
| Best for | Individuals, Freelancers / Consultants, Large Enterprises | Individuals, Medium Business, Small Business | Freelancers / Consultants, Large Enterprises, Medium Business |
| Category | Appointment Scheduling Software | Appointment Scheduling Software | Appointment Scheduling Software |
| Platforms | SaaS/Web/Cloud, Mobile - Android, Mobile - iOS | SaaS/Web/Cloud, Mobile - iOS | SaaS/Web/Cloud, Mobile - Android |
| API | Available | Available | Available |
| Support modes | Business Hours, Online | Business Hours | 24/7 (Live rep), Online |
| Certifications | SOC 2, GDPR | GDPR | GDPR |
| Data residency | US | US | Global |
Key differences between Calendly and Square Appointments
- Pricing: Calendly starts at $8 /User/Month. Square Appointments pricing is not publicly listed.
- Free trial: Calendly offers a free trial; Square Appointments does not.
- User satisfaction: Calendly scores higher with a 4.5-star average.
- Deployment: Calendly supports SaaS/Web/Cloud, Mobile - Android, Mobile - iOS; Square Appointments supports SaaS/Web/Cloud, Mobile - iOS.
Compare Calendly vs Square Appointments vs SimplyBook.me — and walk away knowing which one fits.
Which tool fits your team best
Which is actually cheaper for your team size
Where each product wins, per real buyers
Most Appointment Scheduling Software tools look identical on paper. This comparison cuts to the differences that matter — pricing structure, team fit, and what real buyers found after signing up.
Biggest differences
Features
Pricing
Buying details
Security
Buyer feedback
Integrations
Product tour
Other options
Talk to an expert Talk to an expert | Talk to an expert Talk to an expert |
Biggest differences
Start here before you go deeper into features.
Best for simple, efficient scheduling with strong calendar integrations.
- You need to streamline meeting bookings and reduce scheduling back-and-forth.
- Your team uses multiple calendar platforms and requires seamless integration.
- You want an easy-to-use tool suitable for freelancers, small businesses, and mid-sized teams.
- You require extensive onboarding support and detailed user training.
- Your organization depends on a large marketplace of third-party app integrations.
Best for small businesses needing simple, easy online appointment scheduling.
- You run a small service-based business or salon with up to 200 employees.
- You want quick setup with minimal technical complexity and straightforward pricing.
- You need automated reminders and client self-scheduling integrated into your website.
- Your business requires extensive customization for industry-specific workflows.
- You need robust calendar syncing with external platforms like Google Calendar.
Best for small to medium businesses needing simple, customizable appointment scheduling.
- You are a freelancer or small business seeking an easy-to-use booking platform.
- You want customizable booking forms and personalized client notifications.
- You value responsive and knowledgeable customer support for setup and usage.
- Your business requires extensive third-party integrations or marketplace apps.
- You need to manage highly complex or industry-specific scheduling workflows.
Calendly: Best for simple, efficient scheduling with strong calendar integrations. Square Appointments: Best for small businesses needing simple, easy online appointment scheduling.
Description | Calendly is free meeting scheduling software that dramatically increases your booking rates with Web-based meetings, while making it easy to book face-to-face time with busy clients. With ... Read More about Calendly | Square Appointments is an appointment scheduling and reminder software that helps you book appointments with less time on the phone. Square Appointments is a browser-based application that ... Read More about Square Appointments | SimplyBook.me is a simple and easy to use online appointment scheduling software. The site allows you to set up your appointments in seconds, provides a platform for visitors to contact you ... Read More about SimplyBook.me |
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Entry Level Pricing |
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Free Trial Availability |
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Spotsaas ScoreWhat's this? ↗ | 9.8/10 | 9.2/10 | 9.1/10 |
User RatingsBased on verified Spotsaas reviews | |||
Best Company Size | 1-50 employees51-500 employees | 1-50 employees51-200 employees | 1-50 employees51-500 employees |
Get pricing help | Get pricing help | Get pricing help |
Software Demo
Demo |  Calendly has not given any software demo yet If you're the owner of this profile, add your demo.Contact us |
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How do Calendly, Square Appointments and SimplyBook.me Compare on Features?
Total Features | 10 Features | 12 Features | 12 Features |
|---|---|---|---|
Unique Features | No unique features | No unique features | No unique features |
Get Quote | Get Quote | Get Quote |
Compare Calendly, Square Appointments and SimplyBook.me on pricing
Review starting price, plan structure, and free-trial access side by side so you can see which option fits your budget and buying process.
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Other Details
Organization Types supported |
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Platforms Supported |
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API Support |
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Get help choosing | Get help choosing | Get help choosing |
Security & Compliance
Certifications, data handling, and security controls for IT and compliance evaluators.
SOC 2 | ✓ Yes | — | — |
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HIPAA | ✗ No | ✗ No | ✗ No |
GDPR | ✓ Yes | ✓ Yes | ✓ Yes |
ISO 27001 | ✗ No | — | — |
Single Sign-On (SSO) | ✓ Yes | — | — |
Multi-Factor Auth (MFA) | ✓ Yes | ✓ Yes | — |
Data Encryption | ✓ Yes | ✓ Yes | ✓ Yes |
Data Residency | 🇺🇸 US | 🇺🇸 US | 🌐 Global |
Calendly vs Square Appointments User Reviews & Rating Comparison
User Ratings | |||
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Rating Distribution | |||
Spotsaas Editor’s POV generated by AI | Buyer sentiment Users generally praise Calendly for its ease of use, efficient scheduling, and strong calendar integrations, though some find onboarding and advanced features limited. What buyers like
Common complaints
| Buyer sentiment Users generally appreciate the ease of use and streamlined appointment scheduling but express frustration over limited customization and calendar integration issues. What buyers like
Common complaints
| Buyer sentiment Overall, users express high satisfaction with SimplyBook.me’s ease of use, customization options, and customer support, despite some setup challenges. What buyers like
Common complaints
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Pros and Cons |
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Positive Reviews | No reviews available for the product | No reviews available for the product | No reviews available for the product |
Media and Screenshots
Screenshots |  1 Screenshots | No screenshots available. | No screenshots available. |
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Videos | No videos available. |  2 Videos |  2 Videos |
Alternatives
Alternatives |
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Disclaimer: This research has been collated from a variety of authoritative sources. We welcome your feedback at [email protected].
Frequently asked questions
- Which is better, Calendly or Square Appointments?
- Calendly edges out the other on user ratings (4.5 vs 4.4). That said, the best pick depends on your use case — use the comparison tables above to evaluate each dimension.
- Do Calendly and Square Appointments offer a free trial?
- Calendly offers a free trial. Square Appointments does not.
- What is the starting price of Calendly vs Square Appointments?
- Calendly starts at $8 /User/Month. Square Appointments starts at Contact for pricing.
- What are the top alternatives to Calendly?
- Top alternatives to Calendly include Appointy, Acuity Scheduling, Setmore, Microsoft Bookings, Cogsworth.
- What are the top alternatives to Square Appointments?
- Top alternatives to Square Appointments include Appointy, Acuity Scheduling, Setmore, Calendly, SimplyBook.me.