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Dev tools · alternatives · 2026

24 alternatives to Stretch My Time Off

Optimize your vacation days with AI-powered planning

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 My Time Off launched in 2024; newer entries below may have overtaken it.

  1. 1

    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. 2

    Tool to help workers get the longest possible vacations

    2018 · stretchyourannualleave.com · its alternatives →

  3. 3

    Let's stretch your time off from 20 to 54 days or more

    2024 · calamari.io · its alternatives →

  4. 4

    Maximize time off with minimum leave days

    2025 · offday.app · its alternatives →

  5. 5TT

    Get maximum vacation days by taking into account public holidays using the lowest amount of actual vacation days.

    2018 · stretchyourannualleave.com · its alternatives →

  6. 6

    Find the best days for vacation

    2024 · vacaywiser.com · its alternatives →

  7. 7

    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 →

  8. 8

    Stay out of office, more often

    2025 · its alternatives →

  9. 9
    Trameter▲235

    Create a customized vacation plan

    2024 · apps.apple.com · its alternatives →

  10. 10

    The easiest way to track your team’s vacations and days off.

    2019 · vacationtracker.io · its alternatives →

  11. 11A1

    A free 15 min daily stretch routine to help desk workers avoid aches and pains

    2023 · stretch15.com · its alternatives →

  12. 12

    Plan holidays smarter

    Jul 2026 · play.google.com · its alternatives →

  13. 13

    Track your Vacation Days to Take More Time Off to Travel

    2019 · its alternatives →

  14. 14
    Stretch▲162

    Daily stretching that actually sticks

    2025 · apps.apple.com · its alternatives →

  15. 15
    Pause▲396

    A time-off tool that puts the team back in 'team planning'

    2021 · getpause.com · its alternatives →

  16. 16

    Simple stretch breaks when working at the office

    2022 · its alternatives →

  17. 17

    PTO and vacation tracking software

    2021 · day-off.app · its alternatives →

  18. 18

    Hello, I'm Kushagra and I am the indie developer behind LookAway (I've posted about it earlier but it has received quite a lot of updates since the last time so I am posting it again). LookAway is a native break reminder for macOS that doesn't interrupt. I built it because I work from home and I spend a lot of time in front of my screens. It's very easy for me to get lost in the flow and I can end up sitting for hours. Due to this, I started facing issues like eye strain and back pain by the end of the day. The solution to this was simply taking enough breaks throughout the day. But…

    Apr 2026 · lookaway.com · its alternatives →

  19. 19PT
  20. 20

    Work break timer with guided movement & breathing exercises

    2020 · getmoova.app · its alternatives →

  21. 21

    Your AI assistant for your first day back

    2024 · spoke.ai · its alternatives →

  22. 22

    Simple and effective stretch app

    2023 · dailystretch.app · its alternatives →

  23. 23

    Accurate and simple PTO calendar

    2021 · tmetric.com · its alternatives →

  24. 24

    Avoid eye strain, stay focus.

    2019 · apps.apple.com · 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 →