Microsoft Bookings vs Calendly
A detailed, unbiased comparison to help you choose the right scheduling software for your needs. Updated for 2026.
Key Takeaways
- Microsoft Bookings excels at: Included with M365
- Calendly excels at: Works with any email
- Calendly wins 4 out of 6 categories
- Microsoft Bookings is best for: Microsoft 365 organizations
- Calendly is best for: Anyone wanting premium scheduling
Quick Overview
Microsoft Bookings
Microsoft's Bookings is included with Microsoft 365. Best for organizations already in the Microsoft's ecosystem.
Pros
- Included with M365
- Teams integration
- Outlook calendar sync
- Multi-staff support
- Virtual appointments
Cons
- Requires M365 subscription
- Limited outside Microsoft
- Basic customization
- Clunky interface
Calendly
Calendly is a standalone scheduling platform. Best for users wanting the best scheduling experience regardless of email provider.
Pros
- Works with any email
- Modern, clean interface
- Extensive integrations
- Good free plan
- Easy to use
Cons
- Extra cost on top of M365
- Less deep Microsoft integration
Full Feature Comparison
| Feature | MS Bookings | Calendly | Winner |
|---|---|---|---|
| Cost for M365 Users | Included | Additional | MS Bookings |
| User Experience | Dated | Excellent | Calendly |
| Teams Integration | Native | Via integration | MS Bookings |
| Non-Microsoft Calendars | Limited | Excellent | Calendly |
| Integrations | Microsoft only | Extensive | Calendly |
| Customization | Basic | Good | Calendly |
“Our IT department pushed Microsoft Bookings because it was 'already included' in our 365 license. Six months in, the limitations were painful — clunky UI, poor external sharing, no round-robin across departments. Calendly worked better but adding 200 seats blew the budget. SchedulingKit's team plan saved us about 60% annually.”
Our Verdict
Use Microsoft Bookings if you're fully in the Microsoft ecosystem and want no extra cost. Use Calendly for a better experience and more flexibility. SchedulingKit works with both ecosystems at a better price.
Frequently Asked Questions
How much does SchedulingKit cost for Microsoft Bookings?
SchedulingKit's free plan covers unlimited bookings at $0/month with no credit card required. Paid plans start at $12/user/month for advanced features like SMS reminders and team scheduling.
Can Microsoft Bookings use SchedulingKit's free plan?
Yes. The free plan supports unlimited bookings, calendar sync, automated email reminders, and a hosted booking page. Most Microsoft Bookings solo operators stay on the free plan; teams of 3+ usually upgrade to Standard at $12/user.
How long does setup take?
Under 10 minutes from signup to live booking page. Connect your calendar (Google, Outlook, Apple), define service durations, set availability, and share your booking link.
What integrations does SchedulingKit support for Microsoft Bookings?
27 native integrations: Google Calendar, Outlook, Apple Calendar, Zoom, Microsoft Teams, Stripe, PayPal, Square, Slack, HubSpot, Salesforce, Mailchimp, Zapier, and more. Bidirectional calendar sync prevents double-booking.
Further Reading
Works with Microsoft and everyone else
Try SchedulingKit free and see why thousands of businesses are switching.
Free forever plan available • No credit card required
When this isn't for you
This is not for you if you're committed to your current platform and have deep custom integrations. Microsoft Bookings comparison content helps decision-makers actively evaluating alternatives. Skip if you're not in the market for a switch.