1099 work from home contractor - Can I write off a hotel stay while visiting family?

You need to be careful with this deduction. The IRS looks at the primary purpose of travel when determining deductibility. Since your main reason for going to Florida is to visit family (personal), the travel costs themselves (airfare, etc.) would not be deductible regardless of your parent company's location. However, there might be a partial deduction possibility for the hotel room. If you can clearly document that you need this space specifically for business purposes, you might be able to deduct a portion of the hotel costs based on business use. For example, if you're using the room 3-4 hours in an 8-hour workday, that's roughly 50% business use during working days. Keep detailed records of your work activities while there, take photos of your work setup, save email correspondence about work completed during this time, and track hours spent working versus personal time. The better your documentation, the stronger your position if questioned.

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In my experience as a long-time 1099 contractor, the hotel deduction in this case is risky. Since you're primarily going to visit family, the IRS would likely consider this a personal trip. The fact that your parent company is there doesn't help unless you're actually conducting business with them in person. A better approach might be to look at coworking spaces in the area instead of the hotel. You could deduct the daily fee for the coworking space as a clear business expense since it's only being used for work, while staying with family. This creates a cleaner separation between personal and business expenses.

As someone who's been a 1099 contractor for 5+ years, I would strongly recommend against trying to deduct the hotel in this case. I tried something similar in 2021 and it triggered an audit. The IRS agent specifically cited the primary purpose test and disallowed my deduction since the primary purpose of my travel was personal. One thing no one has mentioned - have you considered checking if your company might have a corporate rate at any hotels in the area? My client company had a business rate at several hotels that was cheaper than regular rates, even though they didn't pay for my stay.