Both can put time on a calendar. The difference appears after the click: what gets reserved, whether money moves, what staff need, and how the client returns.

• A meeting tool stretched into chairs, rooms, classes, or service inventory.
• A service platform bought for simple introductory calls.
• Two tools both writing availability.
• Reminders, payment, cancellation, and follow-up handled in separate manual steps.

• Write the most complicated real appointment.
• Name calendars, staff, resources, deposit, checkout, and reminders.
• Build and cancel that appointment in each trial.
• Compare the plan and payment terms needed for the complete flow.

Calendly builds around event types, which are reusable meeting templates. It has four: one-on-one, group, collective (several hosts meet one invitee), and round robin (meetings rotate across a team). Group and collective start on Calendly’s Standard plan; round robin needs Teams or Enterprise.

That fits time with a person: a consult, a call, a walkthrough. In Square Appointments, an appointment is booked with a client and stands for a service to be performed. Its payment rules sit in the same system. If clients book a cut, a treatment, or a lesson, start there. If they book a conversation, a meeting tool is usually enough.

• Calendly connects to Stripe or PayPal, and its help center lists payments on paid plans, not the free plan. On a paid event type, the client pays during booking, and the meeting is confirmed once the payment goes through. The money goes straight to your Stripe or PayPal account, and refunds happen there, not in Calendly.
• Square Appointments sets booking payment rules in Square Dashboard under Appointments > Settings > Payments & cancellations. You pick one of three: no requirement, full prepayment for fixed-price services, or hold a card in case of a no-show.
• Square says enforcement and refunds on prepaid appointments are up to you. Whether clients can cancel a prepaid booking online depends on your settings: if you let clients cancel or reschedule online, they can; if you also accept or decline requests, they have to contact you once you accept. You can charge a cancellation fee up to 14 days after the appointment. Refunds for cancellations more than 60 days after booking have to be issued outside Square. A card held for no-show protection covers that one appointment, unless the client chooses to save it.
• Square’s help article lists these settings for Square Appointments Plus and Premium subscribers. Check the current plans before you count on them.

• Calendly checks connected calendars for busy times and adds each new meeting to one main calendar you choose. The free plan connects one calendar; paid plans connect up to six per user. Connected calendars apply to every event type, so you can’t send different kinds of meetings to different calendars.
• Square Appointments can import from Google Calendar, export to it, or both. Busy Google events block time on the appointments calendar. Only appointments go to Google, and only personal events come back to Square. Square warns against adding events to the synced appointments calendar from Google, because a re-sync can wipe them. Square lists Google sync for its Plus and Premium subscribers too.

Pick one tool to own availability. Book a test from each side, cancel it, and check both calendars. For the full routine, see how to stop double bookings. Running a salon? Compare Square Appointments vs. GlossGenius.

We connect the chosen booking door to the website and follow-up. We do not replace a working calendar because a comparison page needs a winner.

Get a plain-English second opinion

Product features and rules can change. Use the linked source as the current word.

• Calendly features — Official calendar, meeting, process, and connections between tools source.
• Square Appointments plans and features — Official scheduling, staff, deposit, and communication features.
• Calendly Help: Event types overview — The four Calendly event types and which plans include them. Checked October 19, 2026.
• Calendly Help: Payments FAQs — When invitees pay, where the money goes, and how refunds work. Checked October 19, 2026.
• Calendly Help: Connect your calendar to Calendly — How Calendly checks calendars for conflicts and where bookings land. Checked October 19, 2026.
• Square Support: Manage booking cancellations and prepayment policies — Square Appointments prepayment, no-show, and cancellation fee settings. Checked October 19, 2026.
• Square Support: Sync your Google Calendar with appointments — How Square Appointments imports and exports Google Calendar events. Checked October 19, 2026.
• Calendly Help: Calendly + Stripe — Collecting payment at booking. Checked October 19, 2026.