A fleet of nine vans does not usually go shopping for software because the paperwork is disorganized. It goes shopping because something ran out — an insurance certificate, an inspection, a service that was due four thousand miles ago — and somebody had to find that out the embarrassing way.
The market that answers this is priced per vehicle, per month, which means the question worth asking first is not which product is best. It is what does this meter cost me at the size I am, and at the size I will be.
Here is what four vendors published on 22 August 2026, quoted from their own pricing pages.
The four figures
| Vendor | Published price | Basis |
|---|---|---|
| Simply Fleet | Essential $2 per vehicle per month, and the page prices five vehicles at $10 /mo itself | Per vehicle |
| Fleetio | Essential $4 per vehicle, per month, billed annually ($5 billed monthly); Professional $7, Premium $10, annual only | Per vehicle |
| Whip Around | Standard $5 USD /asset/mo; Pro $9 USD /asset/mo. A free Basic tier was listed (pricing page withdrawn by 26 September 2026) | Per asset |
| Samsara | No published price. The pricing page asks "How many vehicles or assets do you have?" — a fleet-size menu running from 1–5 to 5,000+ — and routes you to a quote; the /resources/plans page it points at shows only "Get pricing" (both read 5 September 2026) | Quote only |
(All four read 22 August 2026 — the single day this article's title refers to.)
Three of the four were re-read on 5 September 2026 and every figure above held. The fourth, Whip Around, would not render its plan cards to us on that date at either /pricing or /pricing/, so its $5 and $9 keep their 22 August reading rather than borrowing a date they did not earn.
By 26 September 2026 Whip Around had withdrawn its pricing page. /pricing and /pricing/ now redirect to the homepage, which shows no price at all — only "Free Trial" and "Book a Demo". Its $5 and $9 are the last figures it published, kept here with their 22 August date; its rows in the tables below are that history, not a price anyone can buy at today.
Two things the August reading had missed, both on Simply Fleet's page. The first is a floor: the plans carry a minimum of five vehicles (read 5 September 2026). A three-van operation therefore pays the five-van price — $10 a month, an effective $3.33 per vehicle rather than $2 — the same shape as every minimum in this catalog, quietly doubling the rate for the smallest customer. The second is a free plan, which this guide had not recorded at all. For a very small fleet that is the honest first stop.
Simply Fleet also prices the year differently from the month. Essential is $2 per vehicle per month or $20 per vehicle per year, and Advanced $4 or $40 (read 5 September 2026). Twelve months at $2 is $24, so paying annually saves $4 a vehicle a year — at twenty-five vehicles, $500 instead of $600. Two optional add-ons sit beside them: $0.50 per vehicle per month for the WEX fuel card and $0.50 per item per month for small-equipment tracking.
*And Fleetio's Essential tier has a ceiling as well as a band: "Up to 100 vehicles"*** (read 5 September 2026). Below five you are priced as five; above a hundred you are somewhere this page does not go.
The meter, multiplied out
This is arithmetic on the figures above, not a quote from anyone.
At five vehicles:
| Per month | Per year | Three years | |
|---|---|---|---|
| Simply Fleet Essential | $10 | $120 | $360 |
| Fleetio Essential | $20 | $240 | $720 |
| Whip Around Standard | $25 | $300 | $900 |
At twenty-five vehicles, the same published rates:
| Per month | Per year | Three years | |
|---|---|---|---|
| Simply Fleet Essential | $50 | $600 | $1,800 |
| Fleetio Essential | $100 | $1,200 | $3,600 |
| Whip Around Standard | $125 | $1,500 | $4,500 |
Nothing here is a trick. Per-vehicle pricing is a fair way to charge — a bigger fleet genuinely costs a vendor more to serve. The point is only that the line has no end on it. Grow the fleet, and the bill grows with it, in perpetuity, for a register that is mostly holding dates.
The footnote worth reading
Fleetio's own page carries a qualifier under the prices, and it deserves quoting because it is more honest than most:
Fleetio subscriptions are priced based on plan, fleet size range, contract term, and payment term.
And immediately after, the assumption behind the numbers on display:
Prices shown above assume a fleet with 5 assets subscribing to an Essential 5, Professional 5, or Premium 5 annual plan band.
So $4 per vehicle is a five-vehicle band price. The $100/month figure above is that same rate multiplied out, which is the right way to think about the cost, but it is not a quote Fleetio has given anybody. At twenty-five vehicles you are in a different band and you find out what it is by asking. Treat the table as a floor.
Whip Around's free tier, read carefully
Whip Around published a genuine free plan (read 22 August 2026, before the pricing page was withdrawn), and free plans deserve to be taken seriously rather than waved past. This one said:
Up to 1 asset (vehicle & equipment) Up to 1 user
One vehicle, one login. That is a sole trader with a van, and for that person the free tier was the correct answer. From the second vehicle the meter started, and it did not stop.
Where the honest answer is "keep paying"
Two of these are not beaten by owning software, and pretending otherwise would be the kind of comparison-page lie that this catalog exists in opposition to.
Simply Fleet at five vehicles costs $10 a month. That is $360 over three years, which is not a burden any small operator needs rescuing from. If price is the whole of your argument at that size, the subscription wins and you should take it. The case for owning the register instead is about where the data lives and whether anyone can change the terms on you — not about the money.
Samsara is not the same product at all. It sells devices fitted into vehicles: live GPS, routing, AI dash cams, hours-of-service compliance. Its own page summarizes the platform as "Real-time GPS, routing, fuel, compliance". If you need to see where a vehicle is right now, nothing in this article replaces that. A register cannot tell you a location it was never told.
What you are actually choosing between
Strip the feature grids away and there are two different products wearing similar names.
A fleet operations platform — Fleetio, Whip Around, Simply Fleet at the Advanced tier — carries work orders, parts inventory, technician apps, telematics feeds. If your maintenance happens in your own workshop with your own mechanics and your own stock, you want that, and you should pay for it.
A register answers one narrower question well: what expires next, across every vehicle and every kind of deadline at once. Documents with dates on them. Services due by mileage or by calendar. Faults a driver reported. Who has the keys. That is the whole job, and for a large number of operators it is the only part that was ever actually failing.
Fleetora is the second kind, bought once, running on your own server — $69, and one of the five products in the Field-Service Suite. It has no telematics, no work orders, no parts inventory and no inspection-form builder — that list is on its product page, because a limitation you have to discover after buying is a defect. It installs to a phone home screen, but its pages are network-only by design, so it is not something a driver uses out of signal. What it does carry is the one screen the whole thing exists for: every expiry and every service due in the fleet, ranked worst first, each row dealt with where it sits.
Try the Fleetora demo ↗Live, on sample data, no sign-up.
It also refuses to guess. A service tracked by distance with no odometer reading behind it is marked unknown rather than given a plausible date, and it stays out of the calendar feed entirely. The reasoning is in the companion guide on due-by-date versus due-by-distance.
How to decide in ten minutes
- Count your vehicles and multiply. Use the tables above. If the three-year figure does not bother you, stop reading and buy the subscription that fits.
- Ask what is actually failing. If it is missed dates, a register fixes it. If it is workshop scheduling and parts, a register will not, and no amount of ownership makes up for the missing feature.
- Ask where the data should live. This is the question the price comparison cannot answer for you, and it is usually the real one. The Fleetora demo is open without a sign-up if you want to see the expiry board before deciding anything; the field-service stack, bought once shows the register beside the job book, the tool crib and the inspection calendar.
Every figure in this article is linked to the page it came from and dated. If a vendor has changed a price since 22 August 2026, the source link is right there to check us with — and we would rather you did.