Square Point of Sale vs Windward System Five

PayPal

Venmo

Fishbowl

Clover

STORIS

EBMS

Compare Square Point of Sale and Windward System Five based on features, pricing, verified reviews, integrations & more on GetApp. Find out which software is best for your business in 2026.

PayPal provides an end-to-end suite of tools that can integrate with a business's existing systems and service providers. Its network of shoppers and businesses provides AI-driven data insights to help businesses reach new customers and drive results.

Stripe

Stripe is a financial infrastructure platform that enables businesses to accept payments online and in person. It offers a suite of APIs for payment processing, subscription management, fraud prevention, and financial services integration Stripe provides both developer-focused tools with extensive documentation and no-code solutions for businesses without technical staff.

Epos Now

Epos Now is a leading global cloud-based point-of-sale and payment system that specializes in helping US retail and hospitality businesses trade efficiently.

Thanks to a selection of tools, and an extensive app store, users can create bespoke systems that make running a business simple.

Square Point of Sale is the customizable point-of-sale system built for businesses of all shapes and sizes.

Access Controls/Permissions

Accounting

Accounting Integration

Activity Dashboard

Alerts/Notifications

Barcode/Ticket Scanning

Billing & Invoicing

Cash Management

Clock In/Out

Commission Management

Contact Database

Contact Management

Credit Card Processing

Custom Cake Orders

Customer Accounts

Customer Database

Customer History

Customer Management

Customizable Branding

Customizable Invoices

Customizable Reports

Customizable Templates

Data Import/Export

Data Security

Data Synchronization

Delivery Management

Device Enrollment

Discount Management

Document Storage

eCommerce Management

Electronic Payments

Electronic Signature

Email Marketing

Employee Management

For Bakeries

For Bars/Clubs

For iPad Devices

For Liquor Stores

For Restaurants

For Retail

Fraud Detection

Gift Card Management

Inventory Control

Inventory Management

Inventory Tracking

Invoice Creation

Invoice History

Invoice Management

Invoice Processing

Item Management

Labor Cost Calculator

Layaway Management

Loyalty Program

Menu Builder

Mobile Access

Mobile App

Mobile Payments

Multi-Location

Offline Access

Online Invoicing

Online Ordering

Online Payments

Order Entry

Ordering Automation

Order Management

Partial Payments

Payment Processing

PCI Compliance

Point of Sale (POS)

Point of Sale (POS) Integration

Price/Margin Management

Pricing Management

Projections

Promotions Management

QR Codes

Quotes/Estimates

Real-Time Data

Real-Time Reporting

Real-Time Updates

Receipt Management

Recurring Invoicing

Recurring/Subscription Billing

Reminders

Remote Access/Control

Reporting/Analytics

Restaurant POS

Retail Inventory Management

Retail POS

Returns Management

Sales History

Sales Reports

Sales Tax Management

Sales Trend Analysis

Search/Filter

Security Management

Separate Checks

SMS Marketing

Split Checks

Reviews for Square Point of Sale come from a wide variety of industries, including retail (12% of reviewers), health, wellness and fitness (8%), and food & beverages (6%). The most frequent use case for Square Point of Sale cited by reviewers is payment processing (67% of reviewers).

Users and use cases

Most users consider Square Point of Sale to offer strong value for money, with affordable, transparent pricing and low-cost hardware options. However, some reviewers say costs increase with transaction fees, hardware upgrades, and add-ons as businesses grow.

Value for money

The Square Point of Sale integrations most frequently cited by reviewers are: QuickBooks Online (an accounting product rated 4.6 out of 5 for its integration with Square Point of Sale) and Wix (a website builder product, 4.6).

Integrations

Square Point of Sale is a payment processing program offering key features such as payment processing, data security, electronic and mobile payments, point of sale functionality, and online payments, among others.

Square Point of Sale

iPad

Web-based

Android

iPhone

Square Free

Square Plus

Square Premium

Operations

It offers a debit card tied to the account, that allows me to have instant access to funds, and if I use the transfer option, it takes one day to reach my bank account, or instant for another fee.

Tier III Technician

The setup process was confusing as it required an another app epically if you were using the lighting reader and a verification process, as well as linking your bank accounts and test transactions.

Secretary

This has allowed our PTO to quickly collect online and POS payments at events and after a slight learning curve, it is relatively easy to maintain.

President

I liked the simplicity of using it, although Square charges the same fee for debit cards as for credit cards and is a point higher if you have to manually process the charge.

Digital coordinator

I didn't like the integration and confusion of tipping in regards to multi-card payments and other technical formalities of the service.

Managing Director

We've used this for around 6 years and found it to work for our business as we've grown and new features / ways to take payment have developed.

Owner, designer, webdeveloper

Online terminal means that I can easily send payment links and if for some reason there is an issue with one way of doing it, Square gives me more options and it’s great.

Owner

It allows our techs to use it in the field via the mobile devices or our office staff can use it through the virtual terminal.

They also offer a line of credit based on amounts processed, which is an added advantage.

Co-Owner

Not everyone knows how to use apple pay, venmo or any of the other apps but do have cards and want to pay that way which can be possible with square point

Master Business And Auto Enhancer  California Electric Sign Contractor

The flexibility it offers for various payment methods, including credit cards, mobile payments, and online transactions, is also a significant benefit.

I can’t say with certainty that I didn’t somehow hit the 3 key a couple times by accident, but I don’t think I did and I know I didn’t intend to. When I saw the amount that was actually charged I IMMEDIATELY REVERSED THE CHARGE  by issuing a refund for a “mistaken charge.”

Rhe pos system workks grear it has a payroll option and i am able to trasfer instantly to my bussiness checking account

We have multiple terminals is the payments are easily identified and reporting is clear.  

Differentiating hidden items vs archived items vs visible and invisible items is ambiguous.

The info at your fingertips on sales trends, item sales, customer average spend, etc can make you realize trends or items you didn't realize were popular.  

Furthermore the lighting reader did not have a chip reader which required us to upgrade.

The correct amount of the charge was $422.57, but the amount that was processed was $42,257.33 ($422.57 plus two 3s).

Clinical Counselor

It has so many options including loans, savings accounts, debit card; and keeps great records for tax related purposes

It's my go to Point of Sale system for my mobile and web.

Photographer

I've used Square over the years to send online invoices to clients, connect it to my website for payment and occasionally in-person transactions when needed.

Farm Market Manager

I love this interface for event transactions because you can easily categorize what you need and you have the ability to have portable POS options.

Additionally, the ability to integrate with other Square services, such as inventory management and customer relationship management, streamlines operations.

You can't use it unless you have an Internet connection, so sometimes at farmers' markets it stops working for credit payments.

Artist

Using Square Point of Sale with my business has been so easy and the portability of the service is a game changer!

Square Point of Sale made managing my daily sales items sold reporting, sales-tax, tips, and credit card sales a very easy task.  

General Manager

I like working with Square, but do think it could do better with taking tab-like payments - we have lost revenue from it not closing out tabs.

Graphic Designer

It's usually between 2 and 3 percent, but large transactions can be eye opening.

Management

store location and description to every item, which makes it much easier when a client is asking for something specific.

It makes collecting payments and tracking inventory going in and out super simple.

Licensed Massage Therapist

However, I will definitely not be utilizing Square for my own business moving forward due to their high transaction fees that take money out of my pocket.

At first I assumed it was just part of the process and it would be refunded to my account. When it didn’t happen I contacted customer service.

We can add items and adjust them with ease to make for smooth in store transactions.

Esthetician

Lack of integration with other systems and concerns about security and account freezes are also on the list of dislikes.

However we we now use the payment via mobile phone so this isn't an issue anymore.

As a small business owner Square is a fabulous tool to be able to take credit card payments, create invoices, and so much more.  

Poor quality equipment and extremely hard to reach for a qualified person to answer queries. When you call you get a person who has to keep putting you on hold to get an answer and then after taking up over 1/2 hour of your time you have gotten v

It was a little difficult to get setup for us in the beginning so that discouraged us for a little while.

I don't like that for some larger reports it emails you to download vs. just taking 30 seconds to run and then downloading automatically.  

I was told that the processing charge was not refundable and there was nothing they could do about it.

Being at the gym parents are able to make payment right then and there and not have to go home or log into an app to pay.

Nail Technician

I love that Square allows small businesses to conduct business almost anywhere from a phone or laptop!

Owner, Manager

Perfect for small business owners to easily deploy and track sales.

Aesthetician

I wish I had more tools available for my business and clear guided support.

Assistant

On the app, we had to manually enter the card number because the "tap" feature wasnt the best while doing transactions.

now it is more normal to see an iPad as a register, but people were blown away when we started and took away the giant clunky Casio cash registers and marveled at how modern and slick it was.

I do appreciate that Square is widely available and well known which provides a level of comfort to clients for using it for transactions.

It was nothing I liked least about square point of sale, but if I had to choose something I would say the fact that it’s dependent on wifi connection

I love that square offers online booking without an extra cost.

It's helped me easily track my inventory and sales.

Square Point of Sale vs Windward System Five Comparison (2026)

Square Point of Sale

Windward System Five

Overview

Video & Screenshots

Pricing

User reviews

Key features

Integrations

Alternatives