The Real Cost of a Vacation Home What if instead of buying that vacation home, you invested the money? Share | Have A Question About This Topic? Name Email Address Message Thank you! Oops! Related Content Insuring Your Second Home There are unique risks of owning a second home and obtaining the proper coverage may protect you from financial risk. Home Mortgage Deduction Use this calculator to assess the potential benefits of a home mortgage deduction. You May Need to Make Estimated Tax Payments If… Have income that isn’t subject to tax withholding? Or insufficient withholdings? You may have to pay estimated taxes.