Work · alternatives · 2026
24 alternatives to Stretch Your Annual Leave
Tool to help workers get the longest possible vacations
Below are 24 products that do a similar job, ranked by how close each is in meaning and then by launch-day votes. Prices are shown for the 1 we have checked on their own sites, 1 of them free or with a free tier. Stretch Your Annual Leave launched in 2018; newer entries below may have overtaken it.
- 1SM
Hey HN! I built StretchMyTimeOff as a quick experiment using Cursor (Anysphere's AI code editor) and GPT-4o to see how far AI could go in building a simple, functional site. What it does: The site helps you get the most out of your vacation by suggesting optimal days to take off around national holidays, maximizing long breaks with minimal vacation days, anywhere in the world and for any calendar year. It's an idea I've had for a while, and building the algorithm with GPT was a fun challenge. Any feedback or ideas I'm all ears :)
2024 · stretchmytimeoff.com · its alternatives →
- 2
Optimize your vacation days with AI-powered planning
2024 · stretchmytimeoff.com · its alternatives →
- 3
- 4TT
2018 · stretchyourannualleave.com · its alternatives →
- 5
- 6
Vacation Tracker▲137The easiest way to track your team’s vacations and days off.
2019 · its alternatives →
- 7
- 8
Annually▲2Turn your annual leave into smart mini-vacations
Feb 2026 · annually.app · its alternatives →
- 9
- 10
- 11
Your AI assistant for your first day back
2024 · its alternatives →
- 12A1
2023 · stretch15.com · its alternatives →
- 13
- 14
- 15
- 16
- 17
Take your job on a month-long work & travel experience 💻
2020 · its alternatives →
- 18
StretchMinder▲111Work break timer with guided movement & breathing exercises
2020 · its alternatives →
- 19VM
Hey! In my last job I was constantly wondering when it would be best to take days off so I could enjoy the most days off in a row, so I made this tool! It tries to schedule PTO around holidays so that you get the most consecutive time off while spending as few days as possible. You can set some constraints, customize the holidays and define mandatory vacation days (in case your company mandates them). If you try for 2025, you should see results for the rest of the year. If there are unscheduled days, it's because there isn't a particularly good period to take them off. (I should make this…
2025 · vacation-maximizer.com · its alternatives →
- 20
- 21
Smart Family Leave Planner and Optimizer
Sep 2025 · leaveproplanner.com · its alternatives →
- 22
Remote-friendly leave tracking solution for Microsoft Teams.
2021 · its alternatives →
- 23
- 24
Stretch and break reminder to prevent RSI and office pain
2022 · its alternatives →
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Ranked by how close each launch is in meaning, then by votes. Prices were read from each product’s own site when checked and can change. Refine with your own description →