If you're running a service-based business—whether you're a coach, consultant, freelancer, or wellness professional—your scheduling tool should do more than just book appointments. It should also help you get paid. The best tools combine calendar syncing and payment processing in one clean workflow, saving you hours of admin and reducing friction for your clients.
In this article, we’ll look at scheduling tools that integrate directly with Stripe, PayPal, and other processors, so your clients can book and pay in one smooth step. Whether you’re selling one-off consults or structured packages, the right tool can make your business feel more professional from day one.
Why Payments Built Into Scheduling Matter
The average small business owner spends a surprising amount of time chasing invoices, sending payment reminders, or switching between tools. When payments are built into the scheduling flow, it shifts that experience from reactive to automated:
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Clients confirm and pay at the time of booking.
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You only show availability to people who’ve already committed.
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Refunds, reschedules, and cancellations are easier to track.
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You build trust with a seamless, polished client experience.
This is especially valuable for solo professionals who don’t have a back-office team or billing department to handle follow-up.
3 Scheduling Tools That Handle Payments Beautifully
Let’s look at a few platforms that do this well—not just offering payment as a side feature, but integrating it directly into the booking experience.
Acuity Scheduling – For Deep Customization and Structured Services
Acuity has long been a favorite for coaches, nutritionists, and other service providers who need more than just simple appointment booking. One of its standout features is how deeply it integrates with Stripe, Square, and PayPal—letting you charge per session, offer packages, or set up recurring payments.
Want to require a deposit up front? Done. Need to include intake forms, waivers, or onboarding questions? Also done—before the client even sees your calendar.
Best for: Service-based businesses with a structured process—think discovery calls, onboarding, and multi-session offers.
Pricing: Plans with payment features start at $16/month.
Book Like a Boss – For Solopreneurs Selling Services and Products
Book Like a Boss isn’t just a scheduling tool—it’s more like a mini website builder built around booking. The payment features here go beyond the basics: You can set up pricing tiers, sell add-ons, offer coupons, and even bundle digital downloads or coaching sessions together.
It integrates with Stripe and PayPal, and you can control whether payment is required, optional, or collected at a later stage.
Best for: Entrepreneurs who offer a mix of services, consultations, and digital products, and want one branded landing page for all of it.
Pricing: Starts at just under $9/month. Most service-selling features are in the Solo or higher-tier plans.
SimplyBook.me – For Brick-and-Mortar and Hybrid Service Providers
SimplyBook.me offers robust payment support with Stripe, PayPal, and Square, and even accepts local payment gateways in select countries. Unlike some tools that feel overly focused on digital-only businesses, this one is great for massage therapists, clinics, or wellness practitioners with physical locations—or hybrid models.
You can charge at the time of booking or accept payment later. What makes SimplyBook.me stand out is its client-facing features: mobile-friendly booking pages, loyalty program options, and multi-location support.
Best for: Professionals with a mix of in-person and online offerings—especially in health, wellness, or beauty.
Pricing: Free plan available; payment integrations come with paid plans starting around $9.90/month.
What About Payment Security?
Each of the platforms above relies on major third-party processors like Stripe and PayPal for payment security. That means:
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You never store client payment data directly.
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All transactions are encrypted and PCI-compliant.
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Refunds and chargebacks are handled through trusted providers.
If you’re concerned about compliance (especially in the EU or UK), look for platforms like SimplyBook.me or Acuity that clearly outline their GDPR policies.
Common Questions
Do I need a business account to accept payments?
Yes, most payment processors (like Stripe and PayPal) will require you to set up a business profile. It’s free and usually takes just a few minutes.
Can I set different prices for different services?
All three tools mentioned allow you to assign prices to individual services or packages. Book Like a Boss also lets you upsell.
What if I want to offer free calls and paid sessions?
You can mix and match. Just set up different appointment types—one with pricing, one without.
Final Thoughts: Choose the Right Tool for How You Work
There’s no one-size-fits-all option—but there is likely a perfect match for your workflow.
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If you want complete control over intake, payments, and scheduling in one place, Acuity is a safe bet.
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For those selling services like products—and wanting it all branded—Book Like a Boss delivers.
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If you’re managing bookings for a hybrid or local practice, SimplyBook.me offers the flexibility and integrations you need.
Ultimately, the goal is simple: Let clients pay and book in a single step, and stop spending your energy on busywork that software can automate.
Want help deciding which tool is best for you?
Browse our full [Scheduling Tools Directory on CalCompanion] for side-by-side comparisons, reviews, and setup walkthroughs.
Acuity Scheduling
SimplyBook.me
Book Like a Boss