Free Staff Holiday Planner: Best HR Scheduling Tools

Okay so I just spent the last two weeks testing like eight different free holiday planners because three of my coaching clients asked about this exact thing and honestly I was getting tired of giving vague answers.

The Actual Free Ones That Work

Let me start with Timetastic because that’s the one I ended up recommending to two out of three clients. Their free plan covers up to 10 people which sounds limiting but honestly if you’re a small team that’s literally all you need. The interface is ridiculously simple and I mean that as a compliment because I’ve seen HR managers cry over complicated software.

You can see everyone’s holidays on one screen, color-coded by department if you set it up that way. The approval workflow is just… it works. Employee requests time off, manager gets an email, clicks approve or deny, done. No logging into seventeen different portals or whatever. My cat knocked over my coffee while I was testing this one and I didn’t even lose my progress because it autosaves everything.

Oh and another thing about Timetastic – the calendar syncs with Google Calendar and Outlook which seems obvious but you’d be surprised how many tools don’t do this properly. I tried syncing one of the other planners last week and it created duplicate entries and I wanted to throw my laptop out the window.

When Timetastic Gets Annoying

The 10-person limit is firm. Like they will not budge on this. Once you hit person number 11, you gotta pay. It’s £1 per person per month which isn’t terrible but it’s not free anymore obviously. Also their reporting features on the free plan are pretty basic – you can see who’s off when but if you need detailed analytics about holiday patterns or whatever, that’s a paid feature.

Calamari Is Weird But Useful

This is gonna sound weird but Calamari has this slack integration that actually made me like it more than I expected. Free for up to 10 employees again – seems to be the magic number for free plans. The whole vibe is more casual than Timetastic, like it feels less corporate which some teams love and some teams hate.

I was watching that new show on Netflix (the one about the restaurant) while testing this and I kept getting distracted but honestly the setup was so straightforward I finished it during one episode. You can track different leave types – sick days, vacation days, parental leave, whatever you need. The free version gives you absence calendar, leave requests, and approval workflows.

Wait I forgot to mention – Calamari also does clock in/clock out tracking on the free plan which is random but if you need that it’s a nice bonus. Most holiday planners don’t include time tracking at all so that’s something.

The Calamari Problems

Their mobile app is kinda clunky. I tested it on my phone and it’s functional but not pretty. Also the notifications can get overwhelming if you don’t configure them right – I was getting pinged every time someone on the test team breathed basically. You can turn most of them off but it takes some clicking around in settings.

Toggl Plan Used To Be Teamweek

Okay so funny story, I recommended Teamweek to a client six months ago and then they got acquired by Toggl and rebranded and my client emailed me all confused. It’s the same tool just different name. Free for up to 5 people which is less generous than the others but the visual timeline is chef’s kiss.

It’s more of a project management tool that happens to be really good at holiday planning. You can color-code people, drag and drop their time off blocks, and see at a glance if you’re gonna be understaffed during certain weeks. I use this one myself actually because I like seeing my clients’ availability alongside my own schedule.

The thing with Toggl Plan is it’s almost too visual? Like if you just want a simple list view you have to click around to find it. Everything is timelines and boards and cards. Some people love this, some people (especially older HR managers I work with) find it confusing at first.

What You’re Missing On Free

The free plan doesn’t include the resource scheduling features which are honestly the best part of the paid version. Also you can’t set up automated reminders for people to book their holidays or whatever. And only one workspace which means if you’re managing multiple teams or locations you’re stuck.

When A To B Works Better Than You’d Think

This one’s actually called When I Work but everyone calls it When A To B because the URL is wheniwork.com and I don’t know it’s a whole thing. Free for one location and up to 75 people which is wild actually. That’s way more generous than the others.

It’s designed more for shift scheduling than holiday planning but hear me out – if you’re in retail or hospitality or anywhere with shift workers, this is the one. You can block out people’s holidays and then the shift scheduler automatically knows not to roster them. My client who runs a cafe uses this and she says it cut her scheduling time in half.

The time-off requests work basically the same as the others – request, approve, calendar updates. But the integration with actual shift patterns is where it shines. Also employees can swap shifts with each other through the app which reduces the amount of texting and Facebook messaging and general chaos.

The Limitations Are Real Though

One location only on free. If you have multiple sites you need the paid version. Also they’re pretty aggressive about upselling – you’ll see a lot of “upgrade to unlock this feature” messages which gets annoying. And the holiday/PTO tracking isn’t as detailed as dedicated holiday planners. It’s more basic like “person is unavailable these days” rather than “person has used 12 of 25 annual leave days.”

Breathe HR Has A Weird Free Trial Thing

Okay so Breathe isn’t technically free forever but they have a 14-day trial and then if you’re a small charity or nonprofit they sometimes extend it? I have mixed feelings about including this but one of my clients got it free because they’re a community organization so it’s worth mentioning.

It’s proper HR software not just a holiday planner. Like you get absence management, performance tracking, employee records, all of it. The holiday planning bit is probably the most polished I’ve tested – you can set up different allowances for different people, track TOIL (time off in lieu), handle Bradford Factor scoring if you’re into that.

I was testing this at like 11pm last Tuesday because my client needed an answer by morning and honestly I was impressed. The reporting is detailed, you can export everything to Excel, and the mobile app actually works properly unlike some others.

Why You Probably Won’t Get It Free

Because it’s not really free unless you qualify for their charity program. The trial is genuinely useful for figuring out if you wanna pay for it but that’s not the same as a free tier. Pricing starts at £5 per person per month after trial which adds up fast. But if you need full HR software anyway and not just holiday planning, it’s good value.

Google Sheets Is Still Valid Actually

Look I know this sounds lazy but three of my smallest clients just use a shared Google Sheet and it works fine for them. You can set up a simple template with columns for employee name, start date, end date, type of leave, status. Add some conditional formatting so approved requests are green and pending ones are yellow.

The advantage is everyone already knows how to use Google Sheets. There’s no learning curve, no new logins to remember, no subscription that might get cancelled if someone forgets to pay. I made a template last month that has formulas to calculate remaining holiday allowance and it took maybe an hour.

Obviously this doesn’t scale. Once you’re over like 15 people it gets messy. And there’s no automated approval workflow so managers have to remember to check the sheet and update it manually. But for micro businesses or teams just starting out? Honestly it’s fine.

What Actually Matters When You’re Choosing

Okay so after testing all these here’s what I tell clients to think about. First – how many people. If you’re under 10 you have way more options than if you’re at 25 or 50 people. Second – do you need just holiday planning or full HR stuff. Some of these tools try to do everything and if you only need one thing that’s overkill.

Third thing is mobile access. If your team actually works in an office at computers all day maybe you don’t care. But if people are remote or on the road or whatever, the mobile app quality matters a lot. I tested all the apps and honestly some of them felt like they were designed in 2012.

Integration is another thing – what do you already use? If you’re all in on Google Workspace you want something that syncs with Google Calendar. If you use Slack every day get something with Slack integration. Don’t make people check another separate system if you can avoid it.

The Approval Workflow Thing

This is gonna sound obvious but check who can approve what in the free version. Some tools let you set up multiple approval levels (like team lead approves first, then HR, then manager or whatever). Others just have one approver per person. Depending on your company structure this might matter or might not.

Also check if employees can see each other’s holidays. Some companies want full transparency so everyone can see when everyone else is off. Other companies think that’s weird and only want managers to see the full picture. Most of these tools let you configure it but not all of them on the free tier.

What I Actually Use And Recommend Most

For most small teams I end up suggesting Timetastic because it just works and people don’t get confused. The interface makes sense, the emails are clear, and I’ve never had a client complain about it being broken. It’s not the fanciest option but it’s reliable.

If you need more than 10 people free, When I Work is the move. The 75-person limit is generous and even though it’s really designed for shift work, the holiday planning part works fine for regular teams too.

For teams that are already using project management tools and like visual planning, Toggl Plan fits better. It feels more modern and the timeline view is genuinely useful for seeing coverage gaps.

And honestly if you’re tiny and scrappy just use Google Sheets. There’s no shame in it. I’d rather see a team using a simple spreadsheet effectively than struggling with complicated software they don’t understand.

Random Tips That Helped My Clients

Set up the tool before you announce it to the team. I had one client who gave everyone access immediately and then tried to configure settings while people were already requesting holidays and it was chaos. Spend an hour getting everything set up first.

Import existing holiday data if people have already booked time off. Most of these tools let you manually add past and future absences so the calendar is accurate from day one. Otherwise you end up with people saying “but I already told you I’m off that week” and it’s not in the system.

Actually train people on how to use it. Even simple tools need like a 10-minute explanation. Record a quick Loom video showing how to request time off and where to see the calendar. You’ll get way fewer confused Slack messages.

Turn off notifications you don’t need immediately. Most of these tools have notifications turned on for everything by default and it’s overwhelming. Go into settings and be selective about what actually needs a notification versus what can just sit in the app.

Check the calendar view on mobile before you commit. I’ve seen tools that look great on desktop and then on mobile the calendar is impossible to read. If your team actually uses their phones for this stuff, test it properly first.