American Dream

What Is Tax Deductible: 5 of the Most Unusual, Legitimate Tax Deductions

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Nothing is worse than filing your tax return and then realizing you forgot to include a deduction. The IRS generally allows an expense to be deductible if it’s somehow connected to work, medical treatment, or charity. Under these circumstances, knowing what is tax deductible is a constant guessing game. But as it turns out, there are some pretty unusual deductions that many taxpayers overlook. Here are five that just might apply to you.

1. Swimming Pools

If you have a legitimate medical condition that can be improved with swimming or water aerobics, the cost of installing and maintaining a pool can be tax deductible, according to TurboTax. It won’t be enough if your doctor just tells you to exercise more, but if you have a condition like severe arthritis and a pool could improve the quality of your life, it will most likely qualify as a deduction.

2. Cat Food and Pet Transportation

Many Americans see their pets as children, but the IRS doesn’t agree. There aren’t nearly as many deductions for animals as there are for children, but if you have to move because of your job, you may be able to deduct the cost of transporting your furry friends. The IRS states, “If you meet the requirements… you can deduct expenses for a move to the area of a new main job location within the United States or its possessions… You can deduct the cost of shipping your car and your household pets to your new home.” Also, if you’re running a business and having trouble with mice, you could deduct the cost of food to attract stray cats to help you with your rodent problem.

3. Music Lessons

If you can prove a medical benefit, you’ll be able to deduct the cost of music lessons for yourself or your children. According to, one mother deducted the cost of clarinet lessons for her daughter because playing the instrument was supposed to fix her overbite. The woman had a medical study to support her claim, and the IRS approved the lessons as tax deductible.

4. Babysitting

If you need to hire someone to take care of your kids, this expense can be deductible. If you’re hiring someone so you can go to work, these expenses are covered under the child and dependent care credit, a fairly well-known tax break. What’s less known is that you can also deduct the cost of a babysitter when you go out to volunteer. The IRS sees the money you’re paying the babysitter as a donation to charity because you’re spending money to go help a cause.

5. A Trip to the Caribbean

Have you ever wondered why so many companies hold conventions in the Caribbean? It’s because of a generous tax deduction. The IRS lets companies deduct the cost of holding conventions throughout the Caribbean, in Canada, and in Mexico. More importantly, companies don’t need to show any justification for holding a convention in these areas; they can just go. Keep this in mind next time you’re planning your next company event.

As you can see, the rules for what is tax deductible aren’t always obvious or logical. If you ever run into an expense that you think might be deductible, double check with your accountant. The IRS could surprise you.