Microsoft Bookings vs. Calendly: Which Calendar Tool is Best?

Choosing between Microsoft Bookings and Calendly isn’t just about scheduling, it’s about finding the tool that best aligns with your workflow and business needs.

Both platforms offer online booking, automation, and integrations, but they are built for different types of users and businesses.

This in-depth guide breaks down everything you need to know, comparing features, pricing, integrations, and customization to help you make the best choice. 

What is Microsoft Bookings, and Who is it For?

Microsoft Bookings is part of the Microsoft 365 ecosystem, making it a great option for businesses already using Outlook, Teams, and other Microsoft apps. 

If you’re running a service-based business, managing a team, or handling client appointments daily, Microsoft Bookings can help you stay organized without the hassle of manual scheduling.

Key Features

Microsoft 365 Integration: Because Microsoft Bookings is part of Microsoft’s ecosystem, it syncs with Outlook calendars. This means fewer scheduling conflicts and an easier way to manage appointments without switching between apps.

Team Scheduling and Calendar Syncing: If you have a team, Microsoft Bookings makes it easy to assign appointments based on availability. Everyone’s schedule updates in real-time, so there’s no risk of double bookings or miscommunication.

Custom Booking Pages: You can create a professional-looking booking page where clients choose a time that works for them. It saves time and reduces back-and-forth emails.

Payment Integration (Limited): While Microsoft Bookings doesn’t have built-in payment processing, you can connect it with external tools to accept payments when clients book an appointment.

Microsoft Bookings Cons

Microsoft Bookings works well for businesses integrated into Microsoft 365, but it’s not for everyone. Here are some drawbacks:

Requires a Microsoft 365 Subscription: You can’t use Microsoft Bookings on its own. It’s only available with Microsoft 365, which can be expensive if you don’t need the full suite of Microsoft apps.

Few Third-Party Integrations: Since Microsoft Bookings is built for Microsoft 365, it mostly integrates with Outlook, Teams, and Excel. If you rely on tools like Zoom, PayPal, or Salesforce, you won’t get the same level of compatibility that other scheduling apps provide.

Limited Customization: While you can create a branded booking page, the design options are basic. You can only change colors and add a logo. If you want full control over the look of your scheduling page, like embedding it into your website with advanced styling, Microsoft Bookings doesn’t give you that flexibility.

What is Calendly, and Who is it For?

If you’ve ever gone back and forth over email trying to find a meeting time that works, you know how frustrating scheduling can be. That’s exactly the problem Calendly was built to solve.

Calendly works for individual professionals, small teams, and large organizations by letting others book time based on your availability.

Unlike Microsoft Bookings, which is designed primarily for businesses already using Microsoft 365, Calendly is a flexible solution that works across different platforms.

Key Features

Simple and Easy to Use: One of Calendly’s biggest advantages is its clean, intuitive interface. Setting up your availability is quick, and sharing your booking link makes scheduling easier. Instead of endless emails figuring out a time, invitees just pick a slot from your calendar.

Works with Multiple Calendar Platforms: Unlike Microsoft Bookings, which mainly integrates with Microsoft 365, Calendly syncs with Google Calendar, Outlook, Office 365, and iCloud. 

Automated Reminders and Notifications: It helps reduce no-shows by sending email or text reminders before and after meetings. You also get notifications if someone cancels or reschedules.

Built-In Payment Processing: Unlike Microsoft Bookings, which requires third-party integrations for payments, Calendly directly connects with Stripe and PayPal. This makes it a good choice for consultants, coaches, and service providers who charge for their time.

Reporting and Analytics: You can get insights from a dashboard that tracks popular meeting types and team performance. This helps businesses understand scheduling trends and optimize workflows.

Advanced Team Scheduling: Calendly offers advanced team scheduling features like round-robin booking, which automatically distributes meeting requests among team members. This is suitable for sales and support teams that want to manage their workload without manual coordination.

Calendly Cons

Calendly is a popular scheduling tool, but it’s not perfect. Here are a few drawbacks to keep in mind:

Limited Features on the Free Plan: Calendly’s free plan is great for individuals who just need basic scheduling, but if you need advanced features like multiple calendar connections, automated workflows, or team scheduling, you’ll have to upgrade to a paid plan.

Limited Microsoft 365 Integration: If your company runs on Outlook, Teams, and other Microsoft apps, Calendly won’t integrate as seamlessly as Microsoft Bookings. While it does support Outlook, it doesn’t have the same built-in experience as Microsoft Bookings, which is directly linked to Microsoft 365.

Microsoft Bookings vs Calendly: Scheduling, Reviews, Pricing and More

Now that we’ve covered the basics of Microsoft Bookings and Calendly, let’s break down their key differences, regarding scheduling features, user reviews, pricing, and more.

Team Scheduling

Both tools help teams manage bookings, but they work differently:

Microsoft Bookings lets you assign appointments to specific team members based on availability. This works well for service businesses like salons, medical clinics, or consulting firms where customers book with a particular person.

Calendly offers round-robin scheduling, which automatically assigns meetings to different team members. This is great for sales and support teams that want to distribute leads or customer calls evenly.

User Reviews

Real user feedback can help you decide which tool is the best fit:

• Microsoft Bookings has a 3.7 out of 5 stars on G2. Users say it works well if you’re already using Microsoft 365, but it can be frustrating if you’re not familiar with Microsoft’s setup.

• Calendly has a 4.7 out of 5 stars on G2. Many people love how easy it is to use, how quick it is to set up, and how well it integrates with other tools.

Integrations

Microsoft Bookings is designed to work best within the Microsoft suite, integrating with Outlook, Teams, and Excel. However, it offers limited connections to tools outside of Microsoft's ecosystem.​

Calendly provides broader integration options. It connects with various calendar services like Google Calendar and Outlook, as well as platforms such as Zoom, Slack, HubSpot, Salesforce, and more.

Customization & Branding

Microsoft Bookings lets you create a branded booking page where you can add your logo, business hours, and staff availability. 

It looks professional, but the customization options are basic. You can’t fully control the page design or how the booking experience feels.

Calendly offers more branding flexibility. You can customize colors, fonts, and even remove Calendly’s branding (if you’re on a paid plan). This makes it a better choice if you want your scheduling page to match your brand’s style.

Pricing

Microsoft Bookings is included with Microsoft 365 Business and Office 365 Business Premium, so if your company already pays for Microsoft 365, you won’t have to pay extra for it. Here are the pricing plans for Microsoft 365:

• Business Basic: $7.20 per user/month

• Business Standard: $15.00 per user/month

• Business Premium: $26.40 per user/month

• Microsoft 365 Apps for Business: $9.90 per user/month

  

Calendly offers a free plan, but it comes with some limits (like only one event type). Paid plans unlock more features, including integrations, team scheduling, and branding customization:

• Free Plan

• Standard Plan: $12 per user/month

• Teams Plan: $20 per user/month

• Enterprise Plan: Starts at $15,000 per year

  

Key Takeaways: Which Tool Should You Choose?

Now that we’ve covered the key differences, which scheduling tool is right for you? It all comes down to how you work, what tools you already use, and the features that matter most.

Choose Microsoft Bookings if:

• You already use Microsoft 365. Since Microsoft Bookings is included in Microsoft 365 Business plans, it’s a convenient choice if you’re already paying for the suite.

• You manage a team with individual bookings. If clients need to book with specific team members, like in a law firm, clinic, or consulting business, Microsoft Bookings is a strong choice.

• You prefer an all-in-one system. If you want everything: email, calendars, meetings, and scheduling, under one platform, Microsoft Bookings keeps it simple within the Microsoft ecosystem.

Choose Calendly if:

• You want an easy-to-use tool. If you don’t want to deal with complex setups, Calendly’s simple interface makes scheduling quick and easy.

• You need more integrations. If you use Google Calendar, Zoom, Slack, Salesforce, or other third-party apps, Calendly offers more compatibility.

• You run a sales or customer service team. With round-robin scheduling, Calendly helps distribute meetings evenly among team members.

• You want more branding control. If a fully customized booking page is important for your brand, Calendly offers more design options.

​​Go Beyond Scheduling with OneCal

Both Microsoft Bookings and Calendly are great scheduling tools, but what if neither one is quite right for you?

At OneCal, we know that managing multiple calendars across different platforms can be a challenge. 

That’s why we built a tool that syncs all your calendars in real-time, so you’re never double-booked. You can test it yourself and try our advanced features for just $6/month.

Sign up for a 14-day free trial, no credit card required.