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Calendly vs Acuity Scheduling vs Square Appointments: Comparison for Service Businesses, Consultants, Sales Teams and Healthcare Providers By Email Extractor Published October 10, 2026 6 min read
Calendly Acuity Scheduling Square Appointments scheduling tool appointment booking
On this page
Aspect
Calendly
Acuity Scheduling
Square Appointments
Parent company
Calendly (independent)
Squarespace (acquired 2021)
Square (Block, Inc.)
Primary strength
Simple, polished scheduling links; team features; sales workflows
Flexible customisation; intake forms; service business depth
Integrated POS and payments; retail + service hybrid; free tier
Best for
Sales teams; consultants; professional services; SaaS demos
Service businesses (salons, coaches, therapists); complex booking flows
Businesses that also sell products; mobile payments; walk-ins + appointments
Free tier
Yes (1 event type; basic features)
No (14-day trial only)
Yes (free for individuals; generous feature set)
Feature Comparison
Booking and scheduling
Feature
Calendly
Acuity Scheduling
Square Appointments
Booking page / link
Yes (clean, polished design)
Yes (highly customisable)
Yes (integrated with Square Online)
Multiple event / service types
Yes (unlimited on paid plans; 1 on free)
Yes (unlimited on all plans)
Yes (unlimited)
Group scheduling
Yes (group events; round-robin)
Yes (group classes; workshops)
Yes (classes)
Round-robin assignment
Yes (weighted; priority-based)
No (manual or first-available)
No
Collective scheduling (find mutual time)
Yes (team polls)
No
No
Buffer time between appointments
Yes
Yes
Yes
Minimum scheduling notice
Yes
Yes
Yes
Maximum advance booking window
Yes
Yes
Yes
Recurring appointments
Yes (on higher plans)
Yes
Yes
Package / series bookings
No
Yes (packages; series; gift certificates)
No
Waitlist
No
No
Yes
Walk-in management
No
No
Yes (integrated POS)
Multi-location support
Yes
Yes
Yes
Resource / room booking
No
No
No (staff-based only)
Calendar integration
Feature
Calendly
Acuity Scheduling
Square Appointments
Google Calendar
Yes (two-way sync)
Yes (two-way sync)
Yes (two-way sync)
Outlook / Office 365
Yes (two-way sync)
Yes (two-way sync)
No (one-way only)
Apple Calendar (iCal)
Yes (one-way subscription)
Yes (one-way subscription)
Yes (one-way)
Multiple calendar check
Yes (check availability across multiple calendars)
Yes
Limited
Payment collection
Feature
Calendly
Acuity Scheduling
Square Appointments
Online payment at booking
Yes (Stripe, PayPal)
Yes (Stripe, Square, PayPal)
Yes (Square built-in)
Deposit collection
No (full payment or free)
Yes (deposits; partial payment)
Yes (deposits)
Package / prepaid credits
No
Yes (packages; gift certificates; subscriptions)
No
No-show / cancellation fees
No
Yes (configurable)
Yes (configurable)
Invoicing
No
No
Yes (Square Invoices integration)
POS / in-person payment
No
No
Yes (Square POS hardware and software)
Tipping
No
No
Yes
Client communication
Feature
Calendly
Acuity Scheduling
Square Appointments
Confirmation email
Yes (customisable)
Yes (highly customisable; HTML)
Yes (customisable)
Reminder emails
Yes (customisable timing)
Yes (multiple reminders; customisable)
Yes (customisable)
SMS reminders
Yes (on higher plans)
Yes (add-on)
Yes (built-in)
Follow-up emails
Yes (post-meeting)
Yes (customisable timing and content)
Yes
Rescheduling / cancellation links
Yes (in confirmation email)
Yes (in confirmation email)
Yes (in confirmation email)
Custom intake forms
Yes (basic: name, email, questions)
Yes (advanced: custom fields, file uploads, conditional logic)
Yes (basic intake questions)
Client self-service portal
No (link-based only)
Yes (client login to manage appointments)
Yes (client account)
Integrations
Feature
Calendly
Acuity Scheduling
Square Appointments
CRM integration
Salesforce, HubSpot (native); 100+ via Zapier
Zapier (700+ apps); limited native
Limited native; Zapier available
Video conferencing
Zoom, Google Meet, Microsoft Teams (auto-generate link)
Zoom, Google Meet (auto-generate)
No native video integration
Email marketing
Mailchimp, ActiveCampaign via integrations
Mailchimp, AWeber, ConvertKit, Drip (native)
Square Marketing (built-in)
Website embedding
Yes (inline, popup, widget)
Yes (inline, popup, widget; Squarespace native)
Yes (Square Online; widget)
Zapier / automation
Yes (robust)
Yes (robust)
Yes (available)
API
Yes (developer API)
Yes (developer API)
Yes (Square API: comprehensive)
Team and business features
Feature
Calendly
Acuity Scheduling
Square Appointments
Team member management
Yes (team plans with admin)
Yes (multiple calendars per account)
Yes (staff profiles; permissions)
Admin reporting
Yes (meeting analytics; team activity)
Yes (revenue reports; appointment reports)
Yes (comprehensive business analytics; Square Dashboard)
Branding and customisation
Yes (logo; colours; custom domain on enterprise)
Yes (extensive; CSS customisation)
Yes (Square branding)
HIPAA compliance
No
Yes (BAA available on higher plans)
Yes (BAA available)
Client management / CRM
Basic (contact history)
Yes (client profiles; notes; history)
Yes (client directory; purchase history; loyalty)
Pricing Comparison
Tier
Calendly
Acuity Scheduling
Square Appointments
Free
$0 (1 event type; basic)
No free tier (14-day trial)
$0 (individuals; unlimited appointments)
Basic / starter
$10/user/month (Standard)
$20/month (Emerging: 1 calendar)
$0 (free for individuals)
Professional
$16/user/month (Teams)
$33/month (Growing: 6 calendars)
$29/location/month (Plus: multi-staff)
Business / premium
$16+/user/month (Teams)
$61/month (Powerhouse: 36 calendars)
$69/location/month (Premium)
Enterprise
Custom pricing
N/A
Custom
Payment processing fees
Provider
Calendly
Acuity Scheduling
Square Appointments
Online payment fee
Stripe or PayPal fees (2.9% + $0.30)
Stripe, Square or PayPal fees
Square: 2.6% + $0.10 (in-person); 2.9% + $0.30 (online)
In-person payment fee
N/A (no POS)
N/A (no POS)
2.6% + $0.10 (Square POS)
Use Case Recommendations
If you need...
Best choice
Why
Simplest scheduling link for professionals
Calendly
Cleanest interface; fastest setup; best for "schedule a meeting with me"
Sales team round-robin and CRM integration
Calendly
Round-robin, collective scheduling, Salesforce/HubSpot native
Complex service business booking
Acuity Scheduling
Packages, deposits, intake forms, conditional logic, client portal
HIPAA-compliant scheduling
Acuity Scheduling or Square Appointments
Both offer BAA; Acuity has more health-specific features
Salon / spa with retail products
Square Appointments
Integrated POS for products and services; walk-in + appointment
Free appointment booking
Square Appointments
Most generous free tier; unlimited appointments for individuals
Video meeting auto-creation
Calendly
Best Zoom/Meet/Teams integration; auto-generates meeting link
Package / series / gift certificate sales
Acuity Scheduling
Only option with native packages, series and gift certificates
Walk-in + appointment hybrid business
Square Appointments
Only option with integrated POS for walk-in management
Class / group booking
Acuity Scheduling
Most flexible group class booking with capacity and waitlist
All three platforms collect client email addresses during booking. When consolidating client data from scheduling platform exports (Calendly, Acuity, Square -- CSV), CRM systems (CSV), email marketing platforms (CSV), payment processor records (Stripe, PayPal, Square -- CSV), website contact forms, social media leads and referral partner lists, upload the files to Email Extractor to extract and deduplicate email addresses across all sources. Service business clients interact through booking platforms, payment systems, email marketing, website inquiries and referrals, and the same client who booked online, paid through a separate processor, received marketing emails and was referred by a partner appears in four different systems, so deduplication ensures each client receives one consistent set of communications.
