Is holiday management weighing you down?
Let an online staff holiday planner handle the heavy lifting for you.
Manually managing requests, balancing schedules, and avoiding conflicts can feel like you’re running a marathon. But the right holiday management software will have you breezing through it all without breaking a sweat! A staff holiday booking system keeps requests and schedules together.
Say goodbye to manual spreadsheets and hello to a simpler, more organized way to track your team’s time off. Ready to explore the best options?
Quick answer: the best holiday management software in 2027
We’d choose Vacation Tracker for teams working in Microsoft Teams or Slack, especially across several offices, states or countries, and Timetastic for small teams wanting a simple standalone planner. BrightHR, Breathe HR, and CharlieHR suit buyers looking for a full HR suite. If you want leave alongside other HR modules from one vendor, consider Calamari.
| Tool | Best for | Microsoft Teams | Slack | Google Workspace | Monthly price (per user) | Free trial |
|---|---|---|---|---|---|---|
| Vacation Tracker | Multi-location teams using Microsoft Teams or Slack | Yes | Yes | Yes | Core: $2 per user per month. Complete: $4 per user per month. Both plans have a minimum of 25 users. | 14 days; no credit card |
| LeaveBoard | Employee self-service and HR records | Not listed | Yes | Not listed | PRO: $1.35 per employee per month; Enterprise: on quote. | 14 days |
| BrightHR | A full HR suite | Not listed | Yes | Not listed | Core HR software: £16.67; Enhanced HR support: £21.20; Full HR, health and safety support & EAP: £31.30 per employee per month on fixed-term contracts (GBP only). | Not stated; demo |
| Breathe HR | Recruitment, performance and leave | Via third-party app | Via third-party app | Not listed | £24 to £579 per business per month by headcount (GBP only). | 14 days |
| Timetastic | Small teams wanting a simple planner | Pro plan only | Yes | Yes | Business: $1.50; Pro: $2.50; Rota & Time Clock: $5.50 per user per month. | 1 month |
| LeavePlanner | Absence trends and staffing limits | Not listed | Not listed | Not listed | No monthly price published. £13.80 to £20.70 per person per year, billed annually (GBP only). | 30 days |
| CharlieHR | HR from onboarding to benefits | Not listed | Yes | Not listed | £21 to £754 per company per month by headcount (GBP only). | 7 days |
| BambooHR | Centralized HR tasks | Not listed | Yes | Not listed | Core: $10; Pro: $17; Elite: $25 per employee per month. For 25 staff or fewer, flat monthly prices are Core: $250; Pro: $425; Elite: $650. | Length not stated |
| FactorialHR | HR, payroll and expenses | Not listed | Yes | Yes | Per-plan pricing not published; request a quote. | Length not stated |
| Calamari | Leave plus other HR modules | Yes | Yes | Yes | Time Off module: $2.50 per employee per month, 10-seat minimum. | 14 days |
Prices checked on the vendors' sites on October 22, 2026.
Managing a team in the UK? See our guide to the best leave management systems for UK companies, with prices in pounds and UK bank holidays.
Watch: I Tried Every Holiday Tracking Software, These Are The Best
Why you need a staff holiday booking system
Juggling time-off requests on paper or spreadsheets is time-consuming and chaotic. For growing teams, manual processes can quickly spiral out of control, leading to mistakes that cost your business both time and money.
Did you know it takes up to 47 minutes just to calculate and update one employee’s PTO balance manually? According to EY, that can cost your business between $23.37 and $46.43 per edit!
Meanwhile, a leave tracking solution costs as little as $2/employee per month.
The numbers don’t lie: annual leave software saves time and helps you avoid costly errors.
Staff holiday tracking also gives managers a shared view of who’s off before they approve another request.
Ready to make the switch? We’ll help you make the best choice!
The 10 best holiday management software tools (2027)
Vacation Tracker
Vacation Tracker is the #1 solution for effortless and effective holiday management.
Manual errors and lack of visibility are a thing of the past. Vacation Tracker’s intuitive interface and one-click PTO approvals make managing time off feel painless. The best part? Complex calculations like accruals and rollovers are done for you, like magic!
Key Holiday Management Features:
Integrations: Easy integration with Microsoft Teams, Slack, Google Workspace, or email lets users manage leave through their preferred platform. Employees request holiday and approvers approve it inside Microsoft Teams or Slack through the bot; Google Workspace users use the dashboard and email.
Scheduled Alerts: Receive daily or weekly notifications of upcoming time off.
Real-Time Dashboard: Gain total visibility of time-off requests, approvals, and balances.
Powerful Reporting: Access up-to-date, exportable reports to maintain accurate data and make well-informed decisions.
Global Reach: Available in 9 languages with custom leave policies to keep you compliant across regions.
Public Holidays by Location: Import each country’s and region’s public holidays in one click. These holidays aren’t deducted from leave balances.
Pricing: Core: $2 per user per month. Complete: $4 per user per month. Both plans have a minimum of 25 users. 14-day free trial, no credit card.
What Others Are Saying:
“I found it very easy to set up Vacation Tracker for our remote team! Since we work from three different locations, this tool has been of great help. It allowed us to completely eliminate spreadsheets and automate our time off management. Highly recommend” - Capterra Review, 2022
Capterra Rating: 4.8
LeaveBoard
This comprehensive HR software simplifies holiday management while providing a wide range of HR functionalities, with a focus on employee management.
Key Holiday Management Features:
Employee Self-Service: Employees view their time-off balance, submit time-off requests, and manage their personal HR data from a comprehensive HR dashboard.
Automated Leave Management: Automate everything from tracking leave requests and approvals, to calculating leave balances, accruals, and rollovers.
Who’s Off Calendar: Enjoy real-time visibility into employee availability.
Pricing: PRO: $1.35 per employee per month; Enterprise: on quote. 14-day trial.
Capterra Rating: 4.5
BrightHR
BrightHR is a human resources platform that automates all HR processes, including employee management, holiday tracking, scheduling, and more.
Key Holiday Management Features:
Vacation Clash Alerts: Users are notified if there is any overlap between vacation requests to prevent scheduling conflicts.
Vacation Balance Tool: Managers get an overview of their team's PTO balances to ensure compliance and reduce burnout.
Mobile App: Make and approve requests on the go, right from your phone.
Pricing: Core HR software: £16.67; Enhanced HR support: £21.20; Full HR, health and safety support & EAP: £31.30 per employee per month on fixed-term contracts (GBP only). Trial not stated; demo available.
Capterra Rating: 4.7
Breathe HR
Breathe is a comprehensive HR software that includes everything from recruitment to performance tracking and holiday planning.
Key Holiday Management Features:
Simplified Holiday Booking: Employees can book and approve holiday requests effortlessly online or through their mobile application.
Detailed Records: All requests are saved to the cloud to keep a detailed account of your company’s leave history.
Holiday Usage Reports: Gain insight into your team’s PTO trends with leave balance reports.
Pricing: £24 to £579 per business per month by headcount (GBP only). 14-day trial.
Capterra Rating: 4.4
Timetastic
For small businesses with basic PTO needs, Timetastic is a super simple staff solution solely focused on holiday management. For a plan-by-plan look, see Timetastic pricing compared with Vacation Tracker.
Key Holiday Management Features:
Individual Calendars: Each employee receives a personal calendar and summary to track their time off, upcoming holidays, and remaining allowance for the year.
Digital Leave Requests: Users can submit and approve time-off requests digitally, eliminating paperwork.
Customizable Work Schedules: Tailor schedules and break times to each employee for a clear view of team calendars.
Pricing: Business: $1.50; Pro: $2.50; Rota & Time Clock: $5.50 per user per month. 1-month trial.
Capterra Rating: 4.7
LeavePlanner
LeavePlanner is an absence management software for SMEs that helps understand and manage absenteeism while doubling as a basic staff holiday planner software.
Key Holiday Management Features:
Bradford Factor Reports: Built-in Bradford Factor calculators help HRs understand their team's absence trends.
Customization Features: Admins enjoy total control over their organization with the ability to customize employee working hours, working patterns, and establish blackout periods.
Minimum Attendance Levels: Ensure you’re always adequately staffed by setting a minimum number of employees who need to be available or a maximum number of employees who can be absent at the same time.
Pricing: No monthly price published. £13.80 to £20.70 per person per year, billed annually (GBP only). 30-day trial.
Capterra Rating: N/A
CharlieHR
CharlieHR is an all-in-one HR solution to automate everything from onboarding to performance, benefits, and holiday planning.
Key Holiday Management Features:
Assign Approvers: Delegate responsibility by assigning managers to approve time off for their teams.
Smart Notifications: Approvers get notified if someone is due to take time off.
Prorated PTO: Automate holiday allowance calculations for part-time workers.
Pricing: £21 to £754 per company per month by headcount (GBP only). 7-day trial.
Capterra Rating: 4.7
BambooHR
BambooHR centralizes all your HR tasks in one software to completely overhaul your HR workflow.
Key Holiday Management Features:
Leave Balance Calculator: Employees can access their current PTO balances, view their upcoming time off, and visualize how much holiday leave they’ll have accrued by a future date.
Unlimited PTO Policies: Create as many leave policies as needed, and customize them based on department, team, location, or even employee.
Who’s Out Calendar: Gain visibility over who’s on holiday and who’s working to make workforce planning easier than ever.
Pricing: Core: $10; Pro: $17; Elite: $25 per employee per month. For 25 staff or fewer, flat monthly prices are Core: $250; Pro: $425; Elite: $650. Free trial; length not stated.
Capterra Rating: 4.6
FactorialHR
FactorialHR is an all-in-one HRIS that offers a complete suite of tools, including talent management, payroll, and expense management.
Key Holiday Management Features:
Endless Integrations: With over 80 integrations, connect FactorialHR with all of your favorite software from Slack to Quickbooks.
Customizable Policies: Customize leave policies as needed, based on anything from location to employment type.
Employee Leave Insights: With centralized data and instant reporting, managers can easily track employee leave patterns, providing actionable insights to optimize workforce planning and enhance performance.
Pricing: Per-plan pricing not published; request a quote. Free trial; length not stated.
Capterra Rating: 4.4
Calamari
Calamari is built for global teams, with features designed to simplify holiday management no matter where your employees are based. We compare it feature by feature in Calamari vs Vacation Tracker.
Key Holiday Management Features:
Software Integrations: Manage your team’s PTO through your software of choice thanks to easy integration with Microsoft 365, Slack, and Google Workspace.
Automate Calculations: Everything from accruals to rollovers is automatically calculated for you.
Support for Global Workforces: Multiple languages, calendars, and time zones make it easy to manage teams spread throughout the globe.
Pricing: Time Off module: $2.50 per employee per month, 10-seat minimum. 14-day trial.
Capterra Rating: 4.7
Key Features to Look for in an Annual Leave Solution
Local compliance with labor laws
With growing companies spread across the globe, compliance can become a challenge. Your annual leave software should support global teams with features to help you adhere to leave laws across several regions. This includes ensuring calendars account for different regional holidays and accrual calculations.
Employee self-service options and automation
Let your team manage their own PTO with a user-friendly, self-service solution. When teams can access their own balances, manage their PTO requests, and track approvals, it minimizes errors and the amount of time spent on admin work.
Customizable reporting and analytics
Effective workforce planning requires data-driven insights. Holiday management software helps HRs understand leave trends, monitor usage, and ensure their team is properly staffed. For a benchmark, our Leave Trends report shows the median vacation request is booked 14 days ahead.
Integration with Other Tools
Automation works best when all your tools can talk to one another. Integration with Microsoft Teams or Slack, email, and calendar of choice makes it easy to make and manage requests without switching platforms. Choose a solution with an Open API for connecting to other systems, like HRIS or payroll, or one that offers pre-built integrations.
Public holidays for every location
A good holiday booking system lets you load public holidays for each country or state. It keeps those days out of leave balances and shows them on the team calendar, so managers can plan around each location’s days off.
Choosing the Right Holiday Management Tool for Your Business
Why let holiday management be an uphill battle when, with the right software, it can be a smooth stroll?
With powerful automation and easy-to-use features, you can turn the chaos of tracking time-off requests into an organized process. No more juggling schedules or scrambling to avoid conflicts. These tools do the heavy lifting for you, ensuring everything runs smoothly.
Vacation Tracker offers a solution to managing PTO while applying each location’s own leave rules and holidays, making it a top choice for HR professionals.
“Our company is delighted with Vacation Tracker. The app's seamless implementation and user-friendly interface made it a breeze to set up. From request to approval, the process is intuitive and efficient. With automated notifications and insightful analytics, Vacation Tracker has significantly improved our vacation management process. Highly recommended for its ease of use and effectiveness.” - Capterra Review, 2023
Ready to take the stress out of holiday management? Try every feature free for 14 days, no credit card needed.
Manage leave across all your locations Leave policies and public holidays for every office, state or country, in Microsoft Teams, Slack or Google Workspace.
