A leave management system (LMS) automates the leave requesting, granting, and scheduling process—taking a lot of the busywork off your HR or manager’s hands. The best software allows you to set time-off policies and holidays and automatically notifies managers of requests and employees of approvals or denials. It also includes a calendar that lets you see who is off and when. We looked at many types of leave management software and narrowed our list down to five.
- Calamari: Best overall leave management system
- LeaveBoard: Best free leave management system
- Timetastic: Best for multinational companies
- PlanMyLeave: Best for businesses wanting some basic HR tools as well
- Built for Teams: Best for integrating with other software
If you need general time tracking software with just basic leave management features vs a stand-alone system, consider Homebase. It allows you to track employee work time and set up PTO and paid sick leave policies, tracking any accruals or carryovers accordingly. Employees can request time off via mobile or web, and you can always see their balances. It’s free for a single location and affordable for multiple locations.
Best Leave Management Systems Compared
Built for Teams
$2 per user
$1.35 per user;
Free plan for 1–9 users
$1.30–$2.50 per user
$1 per user
$3 per user
Minimum monthly charges
$13.50 for paid plans
Number of countries
250+ (for holidays), English only
Customize language for anywhere
Custom, English only
Automatic calculations, accruals
Syncs with Outlook, Google Calendar, etc.
In-app, email, Slack
In-app, email, Slack, HipChat
Email, Slack, Microsoft Teams
Chat, email, guides, some video
Contact form, account manager w/ Enterprise plan, guides
Contact form, guides
Contact form, in-app help, in-app chat
Email primarily, can schedule a phone call
Calamari: Best Overall Leave Management Software
Calamari works in over 70 countries and is available in English, German, Polish, French, and Spanish. You can use it for teams in multiple countries and for remote workers as well. It has competitive pricing (PlanMyLeave being the best) and the most features. In fact, it offered some tools that most of the others lacked. It’s especially good for remote teams and multinational companies as it works with many languages and holiday schedules; however, Timetastic is best for businesses with international employees because it’s preloaded with holidays from 250+ countries whereas Calamari has none.
In Fall 2021, Calamari changed its pricing structure to $2 per user, per month, for leave management ($1.70 per user, per month, if you pay annually). It offers custom pricing if you have over 100 employees and requires a minimum of 10 employees, which means $20 a month. While this is one of the best minimums available, the pricing is the most expensive, next to Built for Teams. For the best deal if you have fewer than 10 employees, consider LeaveBoard’s free plan.
Calamari earned a 4.3 out of 5 on our evaluation. It was hardest hit because it lacked a free version (only LeaveBoard has one) and its reports are not fully customizable. Calamari has a terrific set of features for tracking leave, great customer service, and an intuitive interface.
- Document attachment: Calamari alone offered document attachment capabilities. This is handy for special-case leave requests like that allowed by the Family Medical Leave Act or for internal use.
- Manager/employee communication: Other leave management software on our list allow your employees to make comments. A few integrate with Slack or Microsoft Teams for communication. Calamari, however, has built-in communications features so that managers can discuss leave requests with the employee or other supervisors. It also works via Slack.
- Widespread workforce: Calamari’s leave management program lets you track remote workers and communicate with them in-app. It also has holiday tools for over 70 countries and comes in five languages: English, French, German, Spanish, and Polish. LeaveBoard and PlanMyLeave are also good choices for international teams.
- Mobile app: Calamari has apps on Android and iPhone, with 3.1 stars each on user reviews. They are not widely reviewed, with 114 reviews on Google Play and only 8 reviews on App Store at the time of this writing. Both Built for Teams and Timetastic rated higher.
What Calamari Is Missing
- Customizable reports: Calamari’s leave module provides six basic reports, from entitlement to payroll. While they are good enough for analysis and compliances, if you want custom reports or deep dives, you’ll need to download the data. LeaveBoard is best for reports.
- Free plan: Like most of the software on our list, Calamari only offers a limited free trial. LeaveBoard has a free plan.
All of the LMSes on our list have APIs to connect with HR payroll programs. However, if you want a tool that includes leave management, consider Gusto.
LeaveBoard: Best Free Leave Management Plan
LeaveBoard is available for businesses in 44 countries and works for teams that span multiple countries. It’s the only LMS on our list that provides an indefinite free plan for up to nine employees. It has excellent automation features and makes it easy for managers to see and approve leaves. It’s also got the strongest reporting feature of those on our list.
Its free plan is good for up to nine employees and has all the features except priority support and advanced leave policies. The Pro plan costs $1.35 per employee, per month, with managers and admins counting as employees. The Enterprise plan is for over 80 employees and comes with an account manager. The prices compare well against other services on our list, although PlanMyLeave is the cheapest.
LeaveBoard earned 4.13 out of 5 on our evaluation. Like Calamari, it topped the chart for functionality and earned a perfect score for reporting. The lack of a mobile app is a mixed blessing, as it is designed to be accessed on mobile through the web, so you don’t really need one. Support is through a contact form and the integrations or sparse.
- Intuitive interface: While we found all the programs easy to use (and users agreed with us), LeaveBoard especially impressed with its bright, easy-to-use interface. The card-style dashboard keeps your most important information right where you need it.
- Free version: LeaveBoard’s free version works for nine employees or fewer. It’s a great option for small businesses or those that don’t expect to increase their employee base soon. PlanMyLeave has a free version, but that expires in 2022. None of the others on our list offered a free plan.
- Reports: We found Leaveboard had the best options for reports because you can build your own custom reports and manipulate the leave reports it already supplies. For further analysis, such as chart creation, you need to download to Excel.
- Additional leave options: You can set the system to do extra functions, such as automatically approve leaves or have employees automatically ask for a replacement, a great help for service industries like restaurants. There are options to retroactively request leave and set up leave intervals, so expiring leave is used first. Only Calamari comes close in terms of options.
- Overlap warning: LeaveBoard not only supplies employees with a calendar that shows who has already applied for days off but can send a warning if an employee asks for a day off and a colleague has already taken that day. This can save managers from dealing with staffing issues. Calamari and Built for Teams, for example, let you manually check, while others provide a list or a calendar to show who is off when.
What LeaveBoard Is Missing
- Mobile app: LeaveBoard has made its application fully mobile-optimized. Therefore, it does not offer an app for your smartphone. Rather, you access the program through a browser. For the best app, look at Built for Teams.
- Several integrations: LeaveBoard only integrates with Microsoft 365, Google Calendar, Slack, and Apple Calendar. For the best range integrations, check Built for Teams.
Timetastic: Best for Multinational Companies
Timetastic is headquartered in Great Britain and can work in multiple countries- and includes pre-loaded holidays for over 250 countries. Over 7,000 businesses use it, many switching from spreadsheets to old-fashioned wall calendars. Like the other LMS software on our list, the automations and PTO customization policies are top-notch.
At $1.30 per user, per month, Timetastic is right in with the other best leave management software. In addition, it has no minimum employee requirements, so for businesses with 23 and fewer employees, only LeaveBoard is cheaper. It offers discounts for some types of British companies.
Timetastic earned 4 out of 5 on our evaluation. It earned perfect marks for functionality and high scores for features and took hits for not having a report builder and for support being available only by contact form and during working hours in England.
- Customizable approvals: Most of the software on our list automatically alerts all the managers or makes a request to an administrator if the manager is not around. Timetastic, however, allows you to create a customized workflow for approvals.
- Pre-loaded holidays: Most of the programs on our list have holidays for the locations they work in. Timetastic, however, boasts the most with over 250 countries, 3,000 regions. You set the country and staff member and the software selects the holidays for you.
- User favorite: All the leave management software earned over 4.6 out of 5 stars, but most only have a few reviews. Timetastic has over 570 reviews, second only to Built for Teams. Further, it had the highest score with 4.7 out of 5 stars. Users say it’s easy to use and efficient.
What Timetastic Is Missing
- Implementation assistance: The rest of the software on our list comes with free implementation setup. Timetastic offers help if you have questions.
- Phone and chat support: You need to contact Timetastic by contact form. Its team usually responds within two hours during the working day, 9:30 a.m.–16:30 p.m. Greenwich Mean time, Monday–Friday. Calamari and PlanMyLeave both offer live support via phone or chat.
PlanMyLeave: Best for Basic HR
If your company needs some basic employee management tools, like onboarding support along with leave management, but you don’t want to purchase a more expensive or complex HR program, then consider PlanMyLeave. It has the cheapest system on our list and comes with free HR modules to help you manage your teams. It also lets you manage comp time automatically.
PlanMyLeave is the cheapest leave management system by per-user rate. However, it has a $30 per month minimum, so depending on how many employees you have, LeaveBoard, Timetastic, or Calamari may provide better deals. It offers discounts for nonprofits, educational institutions, and businesses with over 300 employees.
PlanMyLeave is providing free use of its software through the end of 2021. No other software has made such an offer.
Plan My Leave earned a 3.84 out of 5 on our rubric. It did very well in price, features, and functionality, although the lack of custom reports brought its score down some. It’s not as popularly rated and does not have a mobile app. However, it offers more extras than the other leave management software on our list.
- Comp Time: PlanMyLeave is the only leave management system we found that can automatically calculate comp time, including extra time, like time-and-a-half for working a holiday. Other software will let you add extra days manually instead.
- Bonus Modules: In addition to leave management, PlanMyLeave offers modules for tracking skills and employment history, managing documents, onboarding and offboarding workflows, travel requests, employee appreciation, and more. None of the other LMSes on our list offer extras like these. If you are a small business that doesn’t need full HRIS software, PlanMyLeave could provide you a complete solution.
- Free language customization: PlanMyLeave claims it can be set to any language. The FAQs list English, French, German, Chinese, and Turkish. It also says it can add any language you need at no extra charge.
- Integrations: PlanMyLeave integrates with Xero, QuickBooks, ADP, and other payroll software. It lets you store documents on Google Drive and Dropbox, works with multiple third-party calendars, and integrates with Slack and HipCat. Only Build My Teams offers more integrations.
What PlanMyLeave Is Missing
- Mobile app: Like LeaveBoard, PlanMyLeave does not have a mobile app, but depends on the mobile optimization of its software.
- Ability to attach documents to requests: Like most of the software on the list, PlanMyLeave does not allow you to attach documents to requests. It does have document storage, however.
Built for Teams: Best for Integrations
Built for Teams only comes in English but can be used in any country, as you set the holidays and leave policies. It tops our list for the most integratable, with connectivity to over a dozen apps in payroll and HR, as well as calendars and chat tools like Slack. It’s the most expensive on our list but a strong choice for HR teams that need a full-featured leave management that works with their HR or payroll software.
Built for Teams Pricing
Built for Teams does not list its pricing online, but we were quoted $3 per person, per month, for the PTO management package, with a minimum of $30 per month. It offers discounts once you get over 25 employees. This is more expensive than the other systems on our list.
Built for Teams Features
Built for Teams earned 3.84 out of 5 on our rubric. It took hits for not having a free plan and only occasional phone support and is one of the most expensive on our list. It also lacked some standout features like attaching documents to requests, which took it from a higher slot. However, it excels in integration capability and is loved by users.
- Integrations: While most of the leave management systems on our list only integrate with calendars and Slack, Built for Teams also integrates with popular HRIS systems like ADP and Oracle and payroll software like Paylocity and Paychex. In addition, it integrates with QuickBooks, Okta, and Google. It has a CSV data importer to sync data to other programs as well. Most of the software only offer APIs.
- Leave emails: Every leave management system can send leave-request notifications by email. However, Built for Teams also sends managers the summary, a list of other employees scheduled, and the link to approve or deny. It can also alert other employees and managers when a leave request has been approved.
- Blackout dates: Like Timetastic and PlanMyLeave, you can set specific days when employees cannot request leave or cannot get the day off except for emergencies. We did not find this feature in Calamari or LeaveBoard.
- Mobile app: While Built for Teams does offer a mobile app, it has very few reviews. The ratings are high, however: 4 out of 5 on Android and 4.4 on iOS.
What Built for Teams Is Missing
- More types of customer support: Built for Teams offers email support. It says if there is a need, it can arrange an online conference with screen sharing. In contrast, Timetastic only works through contact forms, while Calamari has live chat or phone support.
- Customizable reports: Built for Teams does not offer much in terms or customizations, although it makes it easy to export data to other programs that can do that. For the best report builder, check LeaveBoard.
How We Chose the Best Leave Management Systems
For this lineup, we weeded out any leave management systems that only came as part of a time and attendance software package or HR software. Those that were left all offered an excellent set of basic features; the distinctions came in the extra details.
Overall, Calamari is the best. While it has a complete human resources system, it offers its leave management as a separate tool you can purchase separately. It offers nearly everything we looked for and has a clean, modern interface that users liked.
Click through the tabs below for our full evaluation criteria:
20% of Overall Score
We looked at affordability and transparency. Only Built for Teams had custom pricing at every level, and most had a monthly minimum of at least $20. LeaveBoard and PlanMyLeave got the highest scores..
20% of Overall Score
These tools make managers’ jobs easier: importing holidays, setting rules, having accruals automatically calculated, and getting automated messages when leave is requested and approved. Everyone scored well here, but Calamari led with 5 out of 5.
20% of Overall Score
This score looked at calendar integrations and customizations. Calamari also got a perfect score in this category.
10% of Overall Score
Here, we looked at feedback from real-world users, especially on customer service. Many of the apps did not have a lot of reviews. Built for Teams and Timetastic earned perfect scores here.
10% of Overall Score
We looked for standard and customizable reports. While all the products had some kind of leave reporting, only LeaveBoard offered much in terms of customization.
20% of Overall Score
We considered interface, customer support, online guides, and dedicated help for integration. Calamari led the way with 4.63 out of 5, with Timetastic last given its 3.25 out of 5 rating.
Tip: To make the best use of LMS software, have your time off policies ready. Be sure to include all types, including time off required by law. Learn more in our article on PTO policy creation.
If you are ready to put aside the spreadsheets and wall calendars but don’t want a full HRIS or time-tracking system, leave management software can provide the automations you need to make leave planning a breeze instead of a chore. They are reasonably priced, and most work in multiple countries.
Calamari tops our list because of its excellent feature set, reasonable price, and high ratings by real-world users. It comes with a free trial with all its features. Try Calamari today.