Microsoft Bookings vs SimplyBook.me (2026) compared

Choose SimplyBook.me if you need to take payments or deposits at booking, want SMS reminders without a Teams Premium licence, need your own domain on the booking page, or want intake forms, classes, memberships and packages built around appointments, and a flat price per plan suits you better than per-user pricing. Keep Microsoft Bookings if your staff work in Outlook and Teams, you want appointments to be ordinary Exchange calendar items with the data in your own Microsoft 365 tenant, and your services don't need payment at booking.

SimplyBook.me is a standalone booking system aimed at service businesses such as salons, clinics, gyms, tutors and consultancies. It charges by bookings per month and by how many "custom features" you switch on, not per user. Bookings is part of Microsoft 365. SimplyBook.me can sync with Outlook calendars and create Teams meetings, but each appointment lives in SimplyBook.me first and is copied to the calendar.

Side-by-side comparison#

Prices are in USD as listed on the SimplyBook.me pricing page in October 2026. They change, so check before you buy.

Scheduling and routing#

Both tools let the customer choose a service and a person. On a shared Bookings page, choosing "Anyone" means staff are "assigned randomly", and the FAQ adds that "there's no way to ensure equal distribution… or to cap the number of assigned appointments to each staff member". Round robin in Microsoft Bookings covers the workarounds.

SimplyBook.me's Any Employee Selector custom feature adds an "Any provider" choice that shows the free times of every provider. It can also hide the provider step and "auto allocate any available provider for selected service randomly". That is close to what Bookings does. A round-robin or weighted rule is not stated on their site.

SimplyBook.me goes further on appointment types. Its pricing page lists recurring appointments, event bookings and a per-provider limit on clients at once on all plans, plus classes, group bookings, waiting lists, packages and memberships as custom features. Bookings has no recurring appointments as of October 2026 (recurring appointments). For classes, it offers a group service with a maximum number of attendees (group bookings).

Forms differ too. SimplyBook.me's Intake Forms custom feature offers number, single-line, multi-line, checkbox, dropdown, date and file-upload fields (file uploads go to Google Drive), and each form can be attached to specific services. When we captured the public Bookings page in September 2026, custom questions came in only two types, free text and single choice (custom fields).

Embedding and branding#

SimplyBook.me gives you an iframe widget, a booking button and a WordPress widget. Its help centre has guides for Shopify, Squarespace, Joomla, Weebly, GoDaddy and SITE123. A widget can open on a set service, provider, category or location, and can carry a known client's details. The Custom CSS custom feature has separate tabs for the booking pages and the widget. SimplyBook.me's help page marks it as free, but warns that big or complex CSS requests may be treated as paid setup help.

A custom domain is a one-time charge of $119, including three years of SSL. The help article says the "/v2/" part of the booking URL can't be changed, Cloudflare proxying isn't supported, and setup usually takes 24 to 48 hours. White label for the page footer starts at Premium. Full white label and a branded favicon are Enterprise only.

Bookings has one documented embed, an iframe from the Booking page tab, plus colour and logo settings. The "Powered by Microsoft Bookings" footer can't be removed (footer), and there's no custom CSS (custom CSS). The custom-domain setting Microsoft documents only changes the mailbox domain used in new booking page addresses (changing the page URL).

Tracking and analytics#

SimplyBook.me has three custom features for tracking: Google AdWords and Analytics, Google Tag Manager and Facebook Pixel. The Analytics tutorial still describes the old "UA-" ID format, which Google has retired. If you use GA4, ask SimplyBook.me how it is handled, or load GA4 through the Tag Manager feature instead. The Facebook Pixel feature is "not compatible with Facebook and Instagram Bookings". These features are set up for SimplyBook.me's booking site. Whether events reach your own page when the widget is embedded in an iframe is not stated on their site.

Bookings records a RefID campaign value in its activity export and documents no GA4, Google Ads or Meta integration. There's also no redirect to a thank-you page after booking. The options are in tracking Bookings conversions in GA4.

Integrations and webhooks#

Outlook. SimplyBook.me's Calendar Sync custom feature syncs both ways with Google and Outlook calendars. It sends bookings to the calendar and blocks time taken by calendar events. Two caveats from its help page: "this feature works with web calendars only - it may not work with Microsoft Exchange calendars", and changes can take up to 10 minutes. Outlook events must not be marked "free" if they are to block time. Microsoft 365 mailboxes run on Exchange Online, so test with a real staff account before you commit. Bookings needs no sync, because every appointment is already an Exchange event on the staff member's calendar.

Teams. The Online Video Meetings custom feature creates Zoom or Teams links. For Teams, SimplyBook.me says "it is not possible to connect personal/private Microsoft Teams account". The setup has you add Microsoft Teams under Azure Active Directory (now Microsoft Entra ID), Enterprise applications, and assign the user there. By default one Teams account hosts the meetings, and providers can connect their own accounts. Bookings creates a unique Teams link for each online appointment with no extra setup.

Automation. SimplyBook.me is a Zapier trigger app, which its help page calls a "1-way integration". The connector doesn't work when two-step login is on, and that includes the HIPAA feature. The API custom feature issues API keys for a JSON-RPC API and a public REST API, and its settings include a Callback URL option. Bookings has no webhooks. Its Power Automate connector is in preview with three triggers (created, cancelled, updated), only Bookings admins can build flows, and each Bookings mailbox allows five. Graph covers shared pages only and needs tenant admin consent for application permissions (webhooks).

Payments#

The Accept Payments custom feature asks clients to pay to confirm a booking or purchase, through the payment gateway you pick (gateways vary by country). Payments, deposits and tips start at Basic. Premium adds "Payments PRO": refunds, payment links and saved cards. SimplyBook.me says it charges no transaction fees of its own, though your payment processor does. Memberships, packages, add-ons, products and gift cards all need Accept Payments switched on.

The Bookings FAQ: "No, there's no payment support in Bookings." Can Bookings take payments covers the workarounds, such as a payment link in the confirmation email.

Data and compliance#

SimplyBook.me's GDPR statement says it has a Data Protection Officer and a Data Processing Agreement, with a list of sub-processors, in its terms. The HIPAA custom feature is on Standard and above. It forces two-step login, logs users out after a set time, blocks access for SimplyBook.me support staff and removes client and service names from email and SMS notifications. The pricing FAQ says a Business Associate Agreement is "available on request". HIPAA can't be used together with the API or the Zapier connector. Choosing a data location (UK, US, AU and others) is an Enterprise feature. Where data sits on the other plans is not stated on the pages we read.

Bookings keeps its data in Exchange Online shared mailboxes in your tenant, under your shared-mailbox compliance policies, and each booking calendar also creates an unlicensed user in Microsoft Entra ID. Where Bookings stores data has the detail.

Pricing#

SimplyBook.me, as listed on the SimplyBook.me pricing page in October 2026 (USD per month):

Add-ons are priced separately: SMS credits ($8 per 100), WhatsApp credits ($8 per 100), extra bookings ($4 per 100), a custom domain ($119 one-time with three years of SSL) and your own SMS gateway ($149). The custom-feature limit applies to "premium" features; the FAQ names point of sale, intake forms, memberships, gift cards, custom email, HIPAA and SOAP notes as examples. The Free plan "needs to be renewed monthly", and there's a 14-day trial with no card.

Bookings has no price of its own. If your staff already hold a Microsoft 365 plan that includes it (licence requirements), SimplyBook.me is an added cost. Because it doesn't charge per user, a 15-person team on Standard pays the same as a 5-person team, as long as bookings stay under 500 a month.

When to keep Microsoft Bookings#

• Staff already work in Outlook and Teams, and you want bookings to be ordinary Exchange appointments with no sync step.
• You don't want another vendor or data processor to review.
• Choosing a staff member, or random assignment, is fine for your volume.
• You don't charge at booking, and email reminders are enough.

When to switch#

• You take payments, deposits or tips when someone books.
• You need SMS reminders outside the US, Canada and the UK, or without Teams Premium (Bookings SMS).
• A custom domain, custom CSS or white label is a requirement.
• You run classes, memberships, packages or recurring sessions, or need a HIPAA feature with a BAA from the scheduling vendor.

Keeping Bookings and filling the gaps with BookingsXP#

If what's pushing you towards SimplyBook.me is how booking looks on your website, or that you can't measure it, BookingsXP keeps Microsoft Bookings and replaces only the part on your site. You paste your public booking page link (no Microsoft sign-in or admin consent), choose from the templates (four on Free, all eight on Pro) and set your brand colour, fonts and corner radius. The widget pushes every step to the dataLayer and GA4 on every plan, fires Google Ads, Meta and LinkedIn conversions on Pro, and writes UTM parameters and click IDs into the booking notes (analytics). Bookings still creates the appointment, so the confirmation email, Outlook event and Teams link work as they do today.

It doesn't add payments, SMS, recurring appointments or a custom domain (its hosted page lives at bookingsxp.com/book/<your-name>). If those matter, SimplyBook.me is the better fit. There's a free plan with no card (pricing), and you can try a widget without signing up at /try.

BookingsXP is independent and not affiliated with or endorsed by Microsoft. Microsoft, Microsoft 365, Microsoft Bookings, Outlook and Teams are trademarks of the Microsoft group of companies. Other product names are trademarks of their respective owners.