Calendly vs Square Appointments vs SimplyBook.me: How Plans Differ
Calendly, Square Appointments and SimplyBook.me charge in different ways: per seat, by feature tier or by booking volume. See how each plan is structured.
Calendly, Square Appointments and SimplyBook.me all let customers book online, but they meter and charge in different ways, and that changes which one is cheaper for your business. This article compares how the plans are structured, using each vendor's pricing page as checked on 20 September 2026. It doesn't quote prices, which change and vary by region, and it isn't based on hands-on testing.
This article is part of our guide to choosing appointment scheduling software.
Side by side
| Calendly | Square Appointments | SimplyBook.me | |
|---|---|---|---|
| Plans | Free, Standard, Teams, Enterprise | Free, Plus, Premium, plus Square Pro for high volumes | Free, Basic, Standard, Premium, Enterprise |
| Free plan | One event type, one calendar connection, one-to-one scheduling | For solo professionals; online booking site and integrations | Up to 50 bookings a month, one feature, one provider |
| What sets the price | Seats: people who connect calendars or host meetings need one; invitees don't | Feature tier; the emphasis is on transaction-based processing fees, and the free plan lists unlimited staff calendars | Three things: monthly booking volume, number of premium features and number of providers |
| Payments | Stripe and PayPal integrations on paid plans | Processing fees; deposits and cancellation/no-show fees on higher tiers | Payment integrations on higher tiers |
| Team features | Teams plan adds round-robin scheduling, lead routing and CRM integrations | Plus adds multi-staff booking and waitlist; Premium adds reports and resource management | Provider counts per tier |
How to read the structures
Calendly is priced per person. If one person takes all bookings, the paid plans are simple. If five staff each need a seat, the cost multiplies. Its free plan is generous for a solo user with one type of appointment, but limited.
Square Appointments leans on payments. It suits a business that takes card payments through Square, because the revenue model is processing fees. Deposits and no-show fees sit on the higher tiers, so if reducing no-shows is the goal, check which tier you'd need.
SimplyBook.me prices by volume. Its tiers rise with the number of bookings, features and providers. That can suit a small team with modest volume, but a busy business could hit the limits.
What none of the pricing pages tell you
- How easy it is to set up or for customers to use.
- How well it syncs with your calendar.
- Whether it suits your trade, such as a salon or a mobile service.
Use each vendor's free plan to find out, with your real availability and a test booking on a phone.
How to choose
- Count staff, services, bookings per month and payments.
- Match that against the unit each vendor charges for.
- Try two free plans.
- Compare the twelve-month cost.
See also free appointment scheduling software and Google Calendar appointment schedules.
Frequently asked questions
Which is cheapest?
It depends on how you work. Calendly charges per seat, so cost rises with the number of people hosting. SimplyBook.me's tiers are set by booking volume, features and providers. Square Appointments has a free plan with transaction-based processing fees. Work out your own numbers on each vendor's current page.
Which is best for a salon with several staff?
We haven't tested them, so we can't rank them. Look at how each prices extra providers: SimplyBook.me lists a provider count per tier, while Square's pricing page mentions unlimited staff calendars on its free plan.
Do prices change?
Yes, and they vary by region and billing period. This article describes how each plan is structured, not what it costs.
Sources
- Calendly — Pricing — checked Sep 20, 2026
- Square Appointments — Pricing — checked Sep 20, 2026
- SimplyBook.me — Pricing — checked Sep 20, 2026
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