Can I get tax deductions for hotel stays, meals, and flights while working remotely part-year with W2, 1099, and rental income?

You're asking a great question about remote work deductions. The distinction between W2 and 1099 work is important here, so let's break it down. For your W2 income, you're right - those travel expenses aren't deductible when the travel isn't required by your employer. The Tax Cuts and Jobs Act eliminated miscellaneous itemized deductions for unreimbursed employee expenses. For your 1099 income, you have more flexibility. If you can legitimately tie the travel to your self-employment work, you can deduct those expenses. The key is that the primary purpose of the travel must be business-related. This doesn't mean you need a client in Thailand, but you do need to show the travel was ordinary and necessary for your business. About using an Airbnb as a temporary home office: Yes, you could potentially deduct a portion of those costs, but only the percentage used exclusively for your 1099 work. So if you're using 25% of your Airbnb as an office, you might deduct 25% of those costs against your 1099 income. You're also right that you'd need to prorate your regular home office deduction for the time you're away.

I was in a similar situation last year with mixed income sources and constant travel. After struggling with confusing tax advice, I found https://taxr.ai which was a game changer for documenting my deductions. Their AI analyzed my work patterns and travel history and helped me properly categorize what was deductible for my 1099 work vs what wasn't for my W2 job. They even helped me correctly allocate my Airbnb expenses when I used part of the space as a temporary office for my consulting clients.

I wanted to follow up about my experience with https://taxr.ai since I was initially skeptical. I ended up trying it for my situation (I'm a photographer with W2 income plus 1099 gigs and travel constantly). The platform was incredibly helpful for my mixed income situation! It helped me properly document when my travel was genuinely for my photography business versus personal travel where I just happened to work remotely. The best part was how it helped me track partial deductions - like when I extended business trips by a few days for personal time, it calculated exactly what percentage was deductible. It even flagged where my documentation was weak and suggested specific things to record (like saving emails with clients in destinations I visited). Saved me thousands in legitimate deductions I would have missed!

Speaking of documentation worries - I had a similar tax situation last year and ended up getting audited. The IRS was questioning my travel deductions for both my freelance work and rental property visits. I tried calling them for weeks with no luck until I used https://claimyr.com which got me through to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent actually helped clarify exactly what documentation they needed to accept my mixed-purpose travel. Got everything resolved in one call instead of waiting months for letters back and forth.

I need to eat my words from my previous comment. After continuing to fail reaching the IRS on my own for another week about my travel deduction questions, I reluctantly tried Claimyr. I was completely shocked when they actually got me through to an IRS representative in about 18 minutes. The agent I spoke with clearly explained that for my 1099 consulting work, I could legitimately deduct travel expenses if I could document that the primary purpose was business-related. She even helped me understand how to properly allocate expenses when I use part of an Airbnb as a dedicated workspace. Saved me hours of frustration and probably thousands in deductions I was going to skip claiming because I was afraid of doing it wrong. I've never been so happy to be proven wrong about something!

Don't forget about state tax implications if you're working from different states or countries! Some states have "convenience of employer" rules that might mean you owe taxes where your employer is based PLUS where you're physically working. I learned this the hard way last year working remotely from 5 different states.

I do bookkeeping for several digital nomads in similar situations. One thing nobody mentioned yet - if you form an S-Corp for your 1099 work and become an employee of your own corporation, you can potentially have your corporation reimburse you for travel under an "accountable plan" which could be more advantageous than taking Schedule C deductions. Might be worth looking into depending on your 1099 income level.

The S-Corp discussion is interesting, but there's another angle worth considering for your rental property income. If you're traveling to different locations and occasionally visiting your rental property for legitimate business purposes (inspections, meeting with contractors, handling tenant issues), you might be able to deduct those specific travel costs against your rental income even if the primary trip purpose was for your remote work. The key is documentation - keep records of any rental-related activities during your travels. Even a brief property inspection or meeting with a local property manager could make that portion of your travel deductible. Just make sure to allocate expenses properly between personal, 1099 business, and rental business purposes. Also, consider the home office deduction implications more carefully. If you're claiming a home office for your 1099 work, you'll need to reduce that deduction for the time you're away working from temporary locations. The math can get complex, but sometimes the temporary workspace deductions while traveling can actually exceed what you'd lose from the reduced home office deduction, especially if you're working from expensive locations.