Calendly vs. Microsoft Bookings: 2026 Comparison

Online booking is a hallmark feature of appointment scheduling software. It allows users to reserve appointments, meetings, and other events online, avoiding the hassle of in-person or phone conversations during regular business hours. Both Calendly and Microsoft Bookings offer online booking features that offer convenience and automation-driven efficiency. The booking pages offered by each platform have a similar look, featuring a calendar with available dates and meeting times, with the option to display a company logo, as well as meeting type, duration, service provider, and pricing.

Calendly allows users to extensively customize their daily availability, with time zone selection, daily meeting limits, and optional buffer periods between meetings. This tool also integrates with video conferencing platforms like Zoom, Microsoft Teams, Google Meet, and Webex, so users can generate a video conferencing link automatically at the time of booking. 

Calendly users like that they can allow clients to book instantly via a shared link through a booking portal that integrates with Google Calendar and other platforms to ensure up-to-date scheduling based on user availability. They like that they can customize booking options, including meeting formats, meeting duration, and time zones. They say Calendly’s automatic reminders help reduce no-shows, which is a significant time saver.  

Similarly, Microsoft Bookings users like the 24/7 availability and efficiency of the online booking feature, which allows clients to schedule appointments based on availability without staff intervention. They especially appreciate the integration with Microsoft Outlook, which enables calendar synchronization and notifications such as booking confirmations. That said, some Bookings users mention a lack of flexibility in customizing booking links and presenting information to customers. Additionally, some complain about an inability to adjust booking time durations.

Calendly’s online booking feature is rated 4.8 out of 5 by reviewers, giving it an edge over Microsoft Booking’s, which has an average rating of 4.58. A key differentiator is that Calendly integrates with a wider variety of tools for video conferencing and calendar management, while Bookings is limited to integrations with other Microsoft tools within the 365 ecosystem, including Outlook and Teams. Also, Calendly allows for payment collection at the time of booking through integrations with Stripe or PayPal, while Microsoft Bookings does not offer payment support.

Online booking for Calendly: Our analysis of the 439 Calendly user reviews mentioning online booking, 98% rated this feature as important or highly important to their business. Calendly is a better option for businesses that need to collect payment at the time of booking.  

Online booking for Microsoft Bookings: Of the 13 Microsoft Bookings user reviews that mention online booking, 100% rate this feature as important or highly important. This tool is best suited for teams that already use Microsoft 365, as Bookings is included at no additional cost.

Calendly and Microsoft Bookings also offer highly rated calendar sync features, which use data from multiple online calendars to display mutual availability and schedules. This allows internal users to only display available times during the day, and external users to easily view and select an appointment time slot that works with their own availability. 

Calendly users like that this tool integrates with various online calendar platforms, including Google Calendar, Outlook, and iCal, which is essential for avoiding conflicts and maintaining a cohesive schedule. They say the feature prevents double bookings and ensures real-time updates, making it easier to manage personal and professional commitments. Users also appreciate the automatic updates and the ability to maintain organization within their scheduling workflow. 

Unlike Calendly, Microsoft Bookings offers calendar integration only with Microsoft Outlook. This is a big limitation for businesses that do not primarily use Microsoft Outlook for employee calendars. Users can work around this problem by using a third-party integration platform like Zapier, but that comes with additional subscription costs and setup time. 

That said, the calendar sync feature is highly rated among reviewers for Bookings, who say it helps them avoid overbooking and scheduling conflicts. They appreciate the effectiveness of the Outlook and Teams integrations, as well as the fact that alerts and reminders are synced across all calendars, and that calendar synchronization helps them manage resource availability. While complaints about the feature are scarce, some users note that initial setup can be challenging. 

Calendar sync for Calendly: Of the 354 reviewers who gave detailed accounts of their use of Calendar Sync, 97% rated this feature as important or highly important. Calendly is suited to businesses that need their scheduling tool to synchronize data from multiple online calendar platforms, such as Google Calendar or iCal. 

Calendar sync for Microsoft Bookings: Of the 10 reviewers who gave detailed accounts of their use of Calendar Sync, 100% rated this feature as important or highly important. Bookings is best suited to companies that already use Outlook, or that are willing to pay for an integration service like Zapier to synchronize Bookings with calendar platforms outside the Microsoft 365 suite.

The confirmations/reminders feature for both Calendly and Microsoft Bookings allows users to automatically send and receive notifications about booked appointments. This keeps clients and providers up to date on scheduling and helps prevent no-shows and last-minute cancellations. 

Calendly offers two delivery systems for notifications: calendar push notifications and email notifications, which contain an event file (.ics file) users can easily add to their calendar. While both calendar and email notifications are customizable, calendar notifications are responsive to real-time updates to bookings and are compatible with various online calendar platforms such as Outlook, Exchange, or Google calendars. Calendly also offers Workflow notifications, which are customizable SMS notifications users can send before or after appointments as appointment reminders or thank-you notes. 

Calendly users find the confirmation and reminder feature crucial for improving attendance rates and reducing no-shows. Automated notifications via email and SMS help users stay organized and on top of their commitments. They highly appreciate the ability to customize reminder messages and include necessary details like Zoom links. Users also value the flexibility to set multiple reminders and the convenience of automated confirmations.

Bookings also offers customizable email and SMS notifications. Reviewers value the integration with Outlook/Office for managing bookings effectively, with confirmation and reminder notifications being essential for keeping appointments on track. The ability to receive reminders across devices is especially beneficial for scheduling numerous conferences and meetings in a busy work environment. 

Our analysis of Microsoft Community queries shows that many users have encountered issues trying to send Microsoft Bookings notifications to non-Outlook email addresses, including Gmail and Yahoo addresses. 

However, some users feel the reminder customization options are limited and that the reminder process could be improved. The average rating for the confirmations/reminders feature is 4.33.

Confirmations/reminders for Calendly: Of the 329 reviewers who gave detailed accounts of their use of confirmations/reminders, 94% rated this feature as important or highly important. Calendly is best suited to businesses that want to send calendar notifications to clients who use non-Outlook calendar tools, such as Google Calendar or iCal. 

Confirmations/reminders for Microsoft Bookings: Of the 9 reviewers who gave detailed accounts of their use of confirmations/reminders, 89% rated this feature as important or highly important. Bookings is best suited to businesses that primarily serve Outlook users.