Free Staff Holiday Booking System: Best Tools & Software

Okay so I just spent the last three weeks testing every free staff holiday booking system I could get my hands on because one of my coaching clients was completely losing it trying to track everyone’s time off in a shared Excel sheet and honestly it was a disaster waiting to happen.

The Actual Free Options That Don’t Suck

Right so Teamup Calendar is the first one I’m gonna tell you about because it’s technically not marketed as a holiday system but here’s the thing – it works perfectly for small teams. You get up to 8 sub-calendars on the free plan which means you can color-code each person or department. I set this up for a team of 6 last month and they’re still using it. The interface is super clean, you can make certain calendars read-only so staff can’t accidentally delete someone else’s holiday, and you can embed it on your website or intranet if you want.

The annoying bit is that it doesn’t have built-in approval workflows on the free version. So like, Emma requests holiday and it just… goes on the calendar. You’d need to set up some kind of process where people email their manager first or something. Not ideal but for really small teams where everyone just talks to each other anyway it’s fine.

Timetastic Free Tier

Oh wait I forgot to mention Timetastic first because honestly this is probably the one most people should actually use. They have a genuinely good free plan for up to 10 users which includes the approval system. Your staff submit a request, it pings the manager, they approve or deny it, done. It also shows you a wallchart view so you can see at a glance who’s off when and whether you’re gonna be understaffed.

I tested this with my own tiny team (me plus two VAs) and the setup took literally 15 minutes. You put in everyone’s holiday allowance, they can see how many days they have left, and it automatically calculates it when they book time off. The email notifications are decent too – not too spammy but enough that you don’t forget to approve things.

The catch with the free version is you don’t get the Slack integration or the advanced reporting stuff. But like, if you just need people to book holidays and not lose track of who’s off when, this does the job.

When Oncall Actually Works Better

This is gonna sound weird but if you’re in a business where you need to track who’s covering what shifts or on-call periods as well as holidays, Oncall has a free tier that’s pretty solid. I discovered this one by accident when I was looking for something else entirely – my dog knocked over my coffee and while I was cleaning it up I had their website open and just… kept reading.

The free version handles unlimited users but only 2 teams. The holiday booking part is basic but functional. What makes it worth considering is if you ALSO need rotation schedules or need to see who’s available for urgent stuff. It’s more aimed at IT teams and healthcare but honestly anyone with on-call requirements could use it.

Leave Dates For Tiny Teams

Leave Dates has a free plan for up to 5 users and it’s properly designed as a holiday booking system not something you’re repurposing. The interface is really straightforward – almost too simple? But that’s not necessarily bad. You get the calendar view, approval system, email reminders, and it tracks allowances.

I set this up for a client who runs a small marketing agency and she said it was the first system her team actually used without complaining. The bar was on the floor but still. The mobile view works properly which is more than I can say for some of the paid systems I’ve tested.

One annoying thing is the free version has their branding on it and you can’t customize much. If that bothers you you’d need to upgrade but honestly for internal use who cares.

The Google Calendar Method Nobody Talks About

Okay so funny story – I had a client absolutely refuse to use any new software because his team was already using Google Workspace for everything. So we built a holiday system using shared Google Calendars and it actually works surprisingly well if you set it up right.

Here’s what you do: create a shared calendar called Staff Holidays or whatever. Give everyone write access. Set up a simple rule that people have to title their entries in a specific format like “Emma – Annual Leave” so it’s searchable. You can set up different calendars for different types of leave if you want – annual leave, sick days, whatever.

The approval part is clunky – you’d need people to send a calendar invite to their manager first before adding it to the main calendar, or just have a policy that they ask first then add it themselves. It’s not elegant but it’s free if you’re already paying for Google Workspace anyway, and everyone knows how to use Google Calendar.

I use this method myself actually because my team is so small it felt ridiculous to add another system. We have a policy that you ask in our Slack channel first, someone approves it there, then you add it to the calendar. Takes about 30 seconds total.

Calamari’s Free Tier Limitations

Calamari offers a free plan for up to 10 people but I’m gonna be real with you – it’s pretty limited. You get basic leave management and a calendar but no approval workflows on the free version. Everyone just… books their own time off and it shows up. Which might be fine if you have a very autonomous team who you trust completely.

The reason I’m even mentioning it is the interface is really nice to use and if you think you might upgrade later their paid plans are reasonably priced and add proper approval chains, Slack integration, all that stuff. So it’s a decent option if you’re treating the free version as a trial period basically.

What About Just Using A Spreadsheet Though

Look I know everyone says spreadsheets are bad for this but lemme be honest – sometimes a shared Google Sheet is actually fine for really tiny teams. I made a template for a client with 4 staff members and they’ve been using it for over a year with no issues.

You need to set it up properly though. I use one tab for the calendar view with everyone’s names down the side and dates across the top, color-coded cells for different leave types. Another tab for tracking everyone’s remaining allowance with formulas that actually work. And a third tab that’s basically a form where people submit requests with the date they’re asking and date requested for.

The problem is there’s no notifications, no automatic approval system, and someone has to manually update everything. But if your team is like 3-5 people and you all sit near each other or talk every day anyway? It works. I wouldn’t recommend it for bigger teams or remote setups where communication is already tricky.

Vacation Tracker In Slack

Oh and another thing – if your team basically lives in Slack anyway, Vacation Tracker has a free tier that integrates directly. Up to 10 users, lets people request time off with a slash command, managers approve it right in Slack, and it posts to a channel so everyone can see who’s off.

I tested this last week and honestly it’s probably the smoothest user experience of anything I tried? Because nobody has to remember to check another system or log into another website. You’re already in Slack 47 times a day anyway, you just type /vacation and it walks you through it.

The free version doesn’t include all the reporting features and you can’t export data or anything fancy. But for just tracking who’s off when and making sure people aren’t booking time off when three other people are already out, it does the job.

Things Nobody Tells You About Free Systems

Okay so here’s what I learned testing all of these – the free versions almost never include automated reminders to use your holiday allowance. Which sounds minor but it’s actually a problem because then you get to December and suddenly everyone wants the last two weeks off and you can’t function.

You gotta manually remind people to spread their holidays out. I literally put a recurring task in my own system to check this quarterly now because I got burned by it.

Also most free systems don’t let you track different types of leave separately with different allowances. Like if you want to track annual leave, sick days, and parental leave all differently with different entitlements, you usually need the paid version. The free tiers typically just have one bucket of “time off” and that’s it.

And integration with payroll systems? Forget it on free plans. You’ll be manually transferring data if you need holiday deductions to show on payslips.

The Actual Setup Process

When you’re setting any of these up, here’s what you need before you start: everyone’s holiday allowance for the year, any holidays they’ve already booked or taken, company closure days like Christmas if you have them, and who needs to approve requests for each person or team.

I learned this the hard way when I set up Timetastic for a client and then realized we hadn’t accounted for the fact that half the team had already taken a week off in January before we implemented the system. Had to go back and manually add historical data which was annoying.

Most systems let you import users from a CSV which saves time if you have more than like 5 people. Otherwise you’re just manually adding everyone with their email and allowance.

The thing that always takes longer than you expect is explaining the system to everyone and getting them to actually use it. I usually recommend doing a quick 10-minute demo call or recording a Loom video showing exactly how to request time off and where to see who else is off. Sounds obvious but you’d be surprised how many people just won’t use a new system if they don’t understand it immediately.

My Actual Recommendation

If you’ve got under 10 people and just need basic holiday booking with approvals, start with Timetastic free tier. It’s the easiest to set up, your team will actually use it, and it covers all the essential features without being complicated.

If you’re already all-in on Slack, go with Vacation Tracker because the friction is so much lower when it’s integrated where people already are.

If you need more than 10 users on the free tier, honestly your options get limited. At that point you’re either looking at the Google Calendar method, paying for software, or using Teamup Calendar and just dealing with the lack of approval workflows.

And if you’re really resistant to adding any new systems and your team is tiny, the spreadsheet method works fine, I don’t care what anyone says. Just make sure someone owns keeping it updated and you have clear rules about how far in advance people need to request time off.

The main thing is just pick something and implement it consistently rather than spending six months researching the perfect system while people continue booking holidays via random email threads that get lost. Trust me I’ve seen teams do this and it never ends well.