Bookkeeping for STRs: What to Track to Maximize Deductions

(A 5-Minute Read for STR Owners Who’d Rather Be Earning Than Guessing)

You didn’t get into short-term rentals to become a bookkeeper… but you did probably get into it to make money — and that means keeping your books tight.

If you want to maximize your deductions, avoid IRS headaches, and make tax season feel more like a refund party than a paperwork panic, then it’s time to level up your STR bookkeeping.

Let’s walk through what to track, how to track it, and why it matters — in plain English.

🧾 Why STR Bookkeeping Matters (Even for “Small” Hosts)

Whether you’ve got one beachside bungalow or 20 high-performing properties, bookkeeping can make or break your ROI. Here’s why:

• ✂️ Tax deductions: Every dollar you forget to track is a dollar you can’t deduct.

• 📊 Profit clarity: You’ll actually know what you’re making (not just gross bookings).

• 💸 Investor readiness: If you ever want to refi or sell, clean books make you look sharp.

• 👮 Audit protection: If the IRS knocks, you’ll have the receipts (literally).

In short? Good bookkeeping = more money in your pocket.

🛠️ Tools of the Trade: STR-Friendly Bookkeeping Systems

Here are your top 3 options depending on how hands-on (or hands-off) you want to be:

1. QuickBooks Online

✅ Pros: Industry standard, integrates with bank accounts
⚠️ Cons: Steep learning curve if you’re not financially savvy
💡 Tip: Use a QuickBooks ProAdvisor familiar with real estate

2. Stessa (Free!)

✅ Pros: Built for real estate investors, auto-categorizes STR income/expenses
⚠️ Cons: Less control/customization
💡 Tip: Great for DIYers who want 90% of the benefits for free

3. Heirbnb or REI Hub

✅ Pros: STR-specific accounting tools; often integrates with Hostaway, Airbnb, etc.
⚠️ Cons: Monthly cost
💡 Tip: These are ideal if you manage multiple STRs and want automation

Pro tip: Open a separate bank account and credit card for each property. This makes it 10x easier to track transactions and spot red flags.

🧾 What to Track — The Master Checklist

Here’s your go-to list of deductible expenses and income categories. Track every one of these to reduce your taxable income:

INCOME

• Airbnb/VRBO payouts

• Direct booking income

• Cleaning or pet fees paid by guests

• Security deposits (record, even if refunded)

OPERATING EXPENSES

• Cleaning fees (paid to vendors or staff)

• Lawn care and pool maintenance

• Property management fees

• Booking platform fees (Airbnb takes their cut — deduct it!)

• Internet, cable, and utilities

REPAIRS & MAINTENANCE

• Handyman work

• HVAC or appliance fixes

• Plumbing and electrical issues

SUPPLIES

• Guest amenities (shampoo, coffee, etc.)

• Paper goods and cleaning supplies

• Linens and towels

MARKETING & SOFTWARE

• Airbnb photography

• Listing copywriting

• PMS software (like Hostfully or Guesty)

• Dynamic pricing tools (like PriceLabs or Beyond)

PROFESSIONAL SERVICES

• Bookkeeping and accounting fees

• Legal or consulting fees

• Cost segregation studies

TRAVEL & MILEAGE

• Property visits (log those miles!)

• Lodging while traveling to your STRs

• Meals when meeting vendors

INSURANCE & TAXES

• STR-specific insurance

• Property taxes

• Local occupancy/lodging taxes

💡 Capital Expenses vs. Operating Expenses

Not everything you buy is immediately deductible.

Capital expenses must be depreciated over several years. But thanks to bonus depreciation, you can often deduct a huge portion upfront (especially with a cost seg study).

👉 Read: How STR Investors Save $10K+ a Year with Bonus Depreciation

🧮 Automate Where You Can

Let’s be real — no one wants to manually track 243 Amazon orders and 13 trips to Home Depot.

Here’s how to automate without losing control:

• Use receipt scanning apps like Expensify or Dext

• Connect your STR business accounts to QuickBooks or Stessa

• Categorize transactions once, then set rules to auto-label recurring charges

• Create a monthly review habit to check profit & loss (P&L) at a glance

📅 Monthly Bookkeeping Schedule (The Easy Version)

🗓️ WEEKLY

• Reconcile recent transactions

• Upload receipts or forward them to your expense app

• Check for any guest reimbursements or deposits

🗓️ MONTHLY

• Review your P&L

• Track occupancy and ADR changes

• Pay your local lodging taxes

🗓️ QUARTERLY

• Reconcile any vendor 1099s

• Review write-offs with your CPA

• Adjust your strategy if needed

🧑‍💼 Should You Hire a Bookkeeper?

If you’ve got more than one STR or STR + another business, a dedicated bookkeeper is worth it — especially one who knows STR-specific rules.

Ask your bookkeeper or CPA:

• Do you understand short-term rental tax treatment?

• Will you help with capital vs. operating classification?

• Can you prep documents for my cost seg?

We see too many investors leave money on the table just because their accountant doesn’t get STRs.

💡 Bonus tip: A good STR CPA can save you more than they charge.

🧠 Bookkeeping Red Flags for STR Hosts

Avoid these common traps:

❌ Mixing personal and STR funds
❌ Not logging mileage for trips to/from your property
❌ Forgetting to deduct platform fees (Airbnb takes 3% or more)
❌ Throwing all furniture costs into one big “expenses” pile
❌ Ignoring state/local lodging tax rules

Clean books = clean audit trail = cleaner profit.

📦 Want a Shortcut?

Deal Room members get access to:

• STR-optimized bookkeeping templates

• Monthly checklists

• CPA-vetted deduction cheat sheets

• Referrals to STR-friendly bookkeeping pros

👉 Sign up here and get your first year’s tax prep dialed in from Day 1.

✅ Final Thoughts

Bookkeeping for short-term rentals isn’t glamorous. But it’s the foundation of profitable, tax-smart investing.

Track the right things, set up solid systems, and don’t be afraid to call in the pros. Your tax bill (and future self) will thank you.

Next Up: Tax Strategy for Couples — Passive Income, Active Losses & Combining W-2 Income with STR Gains
📘 Let’s get those dual-income deductions working double-time.