Your point-of-sale system sits at the heart of daily retail operations, and picking the wrong one costs more than you'd think. A stalled checkout line or an item that rings up at the wrong price chips away at margin. A store running on the wrong contract terms or hardware can rack up avoidable fees nobody notices. Toast and Square continue to dominate conversations among retail owners in 2026. This analysis breaks down pricing, inventory tools, and real-world performance for both platforms, so you can pick the one that fits how you actually run your retail business.
TLDR:
Toast's hardware is proprietary and built for durability: the Toast Flex, Toast Go 2, and Toast Tap use spill-resistant, Android-based designs suited to high-traffic retail. Terminal pricing is quoted by Toast instead of published, plus monthly software fees, though a pay-as-you-go option trades the upfront cost for higher processing fees.
Square lets retailers use existing iPads or Android devices (BYOD) to cut costs, or choose dedicated hardware like the Square Terminal ($299), Square Handheld ($399), or Square Register ($899), purchased outright or financed. That BYOD flexibility makes Square appealing for smaller or newer retailers, though it trades some of Toast's purpose-built durability for a lower initial investment.
Toast's payment processing fees page lists no flat rate: Toast builds a custom rate for each business, what is in your quote is what you pay, and card-not-present sales like online and phone orders cost more than card-present ones. Get your retail card-present, card-not-present, and Amex rates in writing before you sign.
Square's payment processing fees run 2.6% plus 15 cents per in-person transaction on the Free plan, tiered down to 2.4% plus 15 cents on Premium, 3.5% plus 15 cents for keyed-in sales, with no Amex surcharge. Deposits land next-day for free or same-day for a small fee.
Toast's retail pricing page lists inventory and item management, SmartScan, and barcode printing, with PAR levels, low-stock alerts, COGS, cycle counting, inventory variance reporting, and purchasing and supplier management on its Pro tier. Toast's pages do not list FIFO/LIFO costing, so confirm any advanced costing need with a rep.
Square was built with retail in mind: low-stock alerts, product bundles, inventory history, vendor and purchase order management, bulk intake, and barcode label printing, plus COGS and inventory reporting and purchase orders on Plus ($49/month), with transfer orders on Premium. You can import your existing catalog in bulk.
Phone orders are a gap a POS alone doesn't close. If your retail business also runs a deli, bakery, or food counter that takes orders by phone, that gap applies to you. Loman is a 24/7 voice AI phone agent for restaurants, and it handles phone orders at a food counter the same way it does at a restaurant. This AI for restaurants technology integrates directly with POS systems like Square, Toast, and Clover, so it supplements the POS you already run instead of replacing it. If your business is retail only, with no food service and no phone orders, you can skip this section.
Toast's loyalty suite covers points-based rewards, automated campaigns, and digital gift cards, but most of it sits behind premium add-ons.
Square builds more in from the start: a free customer directory, paid loyalty that plugs into checkout, email marketing with ROI tracking, and gift cards tied to Square Online. For small and mid-size retailers, that means fewer stacked add-on fees.
Both platforms offer solid reporting, real-time sales data, and trend analysis, but access differs. Toast gates deeper analytics, like comparative period analysis and product mix evaluations, behind higher-tier plans. Square keeps dashboards and item and category-level reports on all tiers, including Free, with forecasting and cohort analysis added at the paid level. For retailers who want full visibility without a premium tier, Square's approach is more accessible.
Toast integrates with accounting and e-commerce tools, though the catalog leans restaurant-first.
Square's App Marketplace spans accounting, e-commerce, and marketing apps, most with minimal setup, plus an open developer API. For retailers with an existing tech stack, that self-service ecosystem is the stronger fit.
Toast's retail Point of Sale plan starts at $90/month with hardware chosen separately, and the $69/month plan and $0 Starter Kit are restaurant listings. Contract length, retail processing rates, hardware, and add-ons like digital ordering and loyalty come by quote, so confirm them with a Toast rep.
Square's free plan charges 2.6% + $0.15 per transaction. Square for Retail pricing adds inventory and reporting tools on Plus at $49/month (2.5% + $0.15) and Premium at $149/month (2.4% + $0.15), both month-to-month with no cancellation fees. Hardware is optional. Loyalty runs $45/month and email marketing starts at $15/month, both billed separately with no long-term lock-in.
| Toast | Square | |
|---|---|---|
| Base Plan | From $90/month (retail Point of Sale); custom quote for Build Your Own | Free, $49/month (Plus), or $149/month (Premium), per location |
| In-Person Processing Rate | Custom rate by quote; Toast's fees page lists no flat retail rate | 2.6% + $0.15 (Free) / 2.5% + $0.15 (Plus) / 2.4% + $0.15 (Premium) |
| Amex Rate | Set in your quote | Same flat rate as all cards |
| Contract | Typically multi-year; confirm terms in your quote | Month-to-month, no cancellation fees |
| Deposits | Confirm timing in your Toast agreement | Next-day free; same-day for a small fee |
Toast deepened its retail push with new integrations through DIGI America and Upshop 360, adding connected weighing and labeling for grocery and specialty retail. Square shipped August 2026 updates covering group ordering on Point of Sale for Plus plans and above, built-in camera barcode scanning on Android devices, and sales report updates such as seeing all refunds and comparing matching timeframes.
If your retail store also runs a food counter, deli, or bakery in Florida, there's a 2026 development that touches how your POS handles charges. As of July 1, 2026, the state's new "operations charge" law requires public food service establishments to clearly disclose the amount and purpose of any mandatory fee, including service charges, automatic gratuities, credit card surcharges, and delivery fees, on menus, websites, apps, contracts, and receipts.
That makes how each system labels and prints fees a practical checklist item, not merely a back-office detail. If you add a card surcharge or a service charge, confirm your POS can show the amount and purpose on the receipt and the menu, and keep displayed and system prices in sync. Ask each rep whether the POS supports service charges and card surcharges, and get specifics on exactly how those print on receipts and display on menus.
As of October 2026, Toast publishes a standard rate of 2.49% + 15¢, while Square publishes 2.6% + 15¢ on Free, 2.5% + 15¢ on Plus, and 2.4% + 15¢ on Premium. Toast builds a custom rate per business, so the real gap between the two cannot be pinned down until you have a Toast quote in hand. Square lists online selling tools on every plan, including Free, while Toast prices online ordering through its Digital Storefront add-on, which carries additional fees, a gap that shows up fast in the monthly total.
Toast's hardware and add-on cost is quoted, not published. Square lists every device price, from the $59 Reader up to the $1,999 Kiosk (with the Register at $899), so you can price a full setup before you talk to anyone.
Neither Toast nor Square picks up the phone when the counter is three deep, and the call goes to voicemail or to a competitor down the street.
Loman closes that gap without asking a restaurant to pick a side. It integrates natively with Square POS and Toast POS, along with Clover, so calls get answered around the clock and tickets land directly in the connected POS, no re-keying required. Operators comparing options can also weigh the best AI phone agent for Square against Toast-specific picks.
Crust Pizza owner Nick Haselidis says Loman paid for itself in 10 days: "Phones are calm, tickets are bigger, and my team refuses to go back." Pricing starts at $199 a month for unlimited calls, and most restaurants go live in under 24 hours, regardless of which POS sits at the counter.
Start by checking whether the system integrates natively with your POS or just claims compatibility, because a native integration is what lets an order flow into Toast or Square without a staffer re-keying it. General VoIP tools like Talkroute or OpenPhone are built to route and forward calls and do not publicly position around taking orders into the POS, and reservation-first tools like Slang.ai do not publicly position around phone ordering or POS order injection. A restaurant voice AI agent that answers every call, closes the full order, and syncs it into Toast or Square fits better when the goal is recapturing phone revenue, which is where a dedicated AI phone agent for Toast earns its keep. Loman integrates natively with Toast, Square, and Clover and goes live in under 24 hours; ask any vendor to demo the live POS sync before you commit.
Pizza shops usually need two things covered: full delivery and pickup orders over the phone, and reservations if you run a dine-in room. Some tools do one well and the other not at all, so confirm scope before you buy. Reservation-first tools like Slang.ai focus on bookings through OpenTable and SevenRooms but do not publicly position around phone ordering or POS order injection. Loman handles both, taking complete phone orders into Toast, Square, or Clover and booking reservations through OpenTable, Resy, or SevenRooms on the same call line. Ask each vendor to show the order-to-POS flow and the reservation sync live, so you can confirm the one tool covers both jobs before you commit.
Look for native, two-way integration with your specific POS, since that is what lets the system read your live menu and write orders back without a staffer re-typing them. From there, check that it closes the full order and takes payment on the call instead of just taking a message, how many concurrent calls it answers during a rush, whether it handles reservations if you need them, and how long setup takes. Loman integrates natively with Toast, Square, and Clover, answers unlimited concurrent calls, and goes live in under 24 hours. Whatever you shortlist, demo the live POS sync first; that is the detail you can verify before you sign.
Toast and Square both handle in-person transactions well. The real differences show up in contract terms, hardware cost, and how deep the inventory tools go once a catalog grows past the basics. Square's flat rates, month-to-month terms, and wider integration set make it the safer default for most independent retailers, while Toast's durability and dedicated support still suit high-volume operations willing to commit to a longer contract. Whichever system sits at the counter, the phone is a separate problem: Loman answers every call and pushes the order straight into Toast, Square, or Clover.
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