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Calendly vs Square Appointments
Priced at four team sizes, the features checked against both pricing pages.
Take Calendly if you want the one everybody knows, a free plan that works and booking sales calls. Take Square Appointments if you want payment at booking, service bookings with staff and deposits and a free plan that works. Square Appointments is cheaper at every size we price.
What each one actually costs
The real monthly figure at four team sizes with the add-ons each platform forces on you included, from the same engine the shortlist quiz uses. The cheaper of the two is marked on every row.
| Calendly | Square Appointments | Difference | |
|---|---|---|---|
| 1 users | $0 | $0 | level |
| 2 users | $24 | $0 | $24 |
| 5 users | $60 | $0 | $60 |
| 10 users | $120 | $0 | $120 |
What is actually different
- Calendly lists intake questions at booking, round-robin across a team, routing forms, automatic video call links and follow-up workflows where Square Appointments does not, which is their own wording rather than something we verified.
- Square Appointments lists SMS reminders where Calendly does not, which is their own wording rather than something we verified.
No verdict from me yet
I have not used Calendly or Square Appointments on camera, so everything on this page comes from their own pricing pages, re-read weekly, and nothing from my own experience. When I review either, it will be here.
Before you sign up to either
| Calendly | Square Appointments | |
|---|---|---|
| Free trial | 14 days | 30 days |
| Free plan | None | None |
| Contract | Monthly or annual per seat; Enterprise is annual only | Monthly, per location; cancel or switch plans any time |
| Payment fee | None on top | None on top |
Reading further
The full price ladder, every plan and the add-ons charged on top are on each platform's own page. If neither of these two is quite it, each page also has the alternatives ranked against it.
People search for this comparison as: square appointments vs calendly.
Questions people ask about these two
Is Calendly or Square Appointments cheaper?
Square Appointments is cheaper at every size we price.
How much does Calendly cost a month?
Calendly is free at 1 user, $24 a month at 2 users and $120 at 10 users, read off their own pricing page and re-checked every week.
How much does Square Appointments cost a month?
Nothing, at the sizes we price. Square Appointments's Free plan covers 1 to 10 users, so the figure in our table is $0 at all four. Paid plans add features rather than seats.
Does Calendly or Square Appointments have a free trial?
Calendly publishes a 14-day free trial and a Free plan at $0. Square Appointments publishes a 30-day free trial and a Free plan at $0.
Make a third option? If you make scheduling and appointment booking tools and it is missing from this list, ask to be shortlisted. Listings are free and cannot be bought.
Neither, or not sure?
A head to head only helps once you have picked the two. The shortlist asks 6 questions about what people book with you and how many calendars there are, and gives you four picks priced at your own team size, from all 17.
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