Calendly or Microsoft Bookings: calendars, reminders, payment and the booker's details

Calendly sells its own plans. Microsoft Bookings is not sold on its own: Microsoft lists it in Microsoft 365 Business Basic, Business Standard and Business Premium, among other plans, and Outlook on the web has to be switched on to use it. The prices below are as each vendor's page showed them in October 2026.

Calendly connects to Google Calendar, Office 365 or Outlook.com, and Exchange: one calendar on the free plan, and up to six per user on the paid plans. It checks the connected calendars for busy times and adds each new booking to the one you choose as the main calendar.

Bookings works from Outlook and Exchange. Personal Bookings, for your own appointments, uses your Outlook calendar and handles one-to-one meetings only. Shared Bookings, for a team, reads each staff member's busy times once they share their calendar and the Events on calendar affect availability setting is on. Staff without a Microsoft 365 account can be added with any email address and still get the confirmation and the calendar invite. Microsoft notes that Bookings appointments can be edited only in Bookings itself, not in Outlook.

Calendly's reminders start on the paid plans. Every paid plan can send basic email and text reminders, and Standard and the plans above it add Automations, which send reminders and follow-ups at set points before and after a meeting. Texts go through Twilio from random US numbers, the person booking has to opt in to them, replies are not delivered, and none can be sent during the trial.

Calendly's list of supported countries for text messages includes Ireland (+353), with Calendly's own warning that some phone carriers outside the US may block the messages.

Bookings sends email confirmations and reminders, set per service on a shared booking page and per meeting type in Personal Bookings. It can send texts as well, but Microsoft says the person booking needs a valid United States, Canada or United Kingdom phone number to receive them, which leaves out an Irish (+353) number, and that text notifications for virtual appointments are now part of Teams Premium.

Calendly takes payment through Stripe or PayPal on Standard and the plans above it. The person booking pays during the booking, and the meeting is confirmed once the payment goes through. The money goes straight to your Stripe or PayPal account, refunds are made there, and Stripe payments can be taken in euro. Calendly does not calculate or collect VAT; it says to include any tax in the event's price or set out the tax details in the payment terms.

Microsoft's Bookings FAQ answers the question in one line: there is no payment support in Bookings. Payment for a Bookings appointment has to be taken separately.

Both tools hold the name, email address and answers of everyone who books. The business decides why those details are collected, which makes it the controller, and the tool handles them on its behalf as a processor. Both vendors put that in writing in their terms. Controller or processor explains the two roles, and what a data processing agreement must contain is the list to check their terms against.

Calendly's Data Processing Addendum is part of its customer terms, with Calendly LLC, a US company, as processor. It says the processing takes place in the United States and in other countries outside those where the people booking live, and that transfers from the EU rely on the EU-US Data Privacy Framework, with the EU's standard contractual clauses if the Framework stops being available. When we read the Framework's list in October 2026, Calendly LLC's entry was active for non-HR data under the EU-US Framework, its UK Extension and the Swiss-US Framework. The addendum also lists purposes for which Calendly uses some personal data as a controller in its own right, under its own privacy notice, such as detecting fraud and improving its products.

Calendly's customer terms also say the data you put into it must not include special categories of data, which rules out booking questions about health. What counts as special category data lists the rest.

Bookings stores what a booker enters in Exchange Online, in a mailbox Microsoft 365 creates for each Bookings calendar. Microsoft's Products and Services Data Protection Addendum makes the business the controller and Microsoft the processor. Transfers out of the EU run on the 2021 standard contractual clauses, and Microsoft says it is also certified under the Data Privacy Framework; Microsoft Corporation's entry on the list was active for HR and non-HR data when we read it. The booking page has three settings worth knowing: a consent box the booker must tick to complete the booking, with the date and time recorded; one that limits booking to people in your organisation; and one that stops search engines indexing the page.

With either tool, Article 13 of the GDPR requires the booker to be told, at the time they book, who you are, why you want their details and who receives them, and Article 13(1)(f) adds any transfer outside the EEA. Sending personal data to the US from Ireland covers what to check before relying on the Framework, and what the notice has to say.

From what each vendor documents: