Why Early Tax Preparation Matters for Vacation & Investment Properties Near Disney

For many vacation home owners, tax season is something that only gets attention when deadlines approach. But as the 2026 tax filing season brings new IRS rules and reporting changes, early preparation is especially important for owners of short-term rentals and investment properties near Disney.

Filing early isn’t just about avoiding stress, it’s about maximising deductions, ensuring accurate reporting, and protecting your investment income.

Why the IRS Is Encouraging Early Preparation in 2026

The IRS has launched its “Get Ready” initiative, urging taxpayers to prepare well ahead of filing season due to:

• Changes to refund delivery methods

• New and updated tax rules

• Increased scrutiny of digital income and reporting

• Expanded use of IRS online accounts

For vacation home owners with rental income, expenses, and multiple income streams, waiting until the last minute increases the risk of errors and missed deductions.

Key Tax Considerations for Vacation Home & STR Owners

🏡 Rental Income Must Be Reported - Even if It’s Seasonal

Income earned from short-term rentals, Airbnb, Vrbo, or property managers is taxable and must be reported,  even if the property is only rented part-time.

You may receive:

• Form 1099-K

• Form 1099-NEC

• Statements from property management companies

Even if no form is issued, the income is still reportable.

💰 Common Tax Write-Offs Vacation Home Owners Often Overlook

While every situation is different, vacation and investment property owners may be able to deduct:

• Mortgage interest (rental portion)

• Property taxes

• HOA fees

• Property management fees

• Cleaning & turnover costs

• Repairs and maintenance

• Utilities (electric, water, internet, cable)

• Insurance premiums

• Pest control & pool service

• Supplies & furnishings

• Marketing & listing fees

• Depreciation (a major benefit for investors)

• Accounting and tax preparation fees

📌 Important: Personal use vs. rental use must be tracked carefully to ensure deductions are calculated correctly.

Filing Early Helps Avoid Common STR Tax Issues

Filing early allows time to:

• Clarify mixed-use deductions (personal vs rental)

• Resolve missing or incorrect 1099s

• Account for depreciation accurately

• Review changes in federal and state reporting rules

• Avoid delayed refunds or IRS notices

Owners who wait often find themselves rushing,  which is when mistakes happen.

Direct Deposit Is Now Essential

The IRS is phasing out paper refund checks. If you’ve relied on mailed refunds in the past, now is the time to ensure:

• Your bank account is active

• Direct deposit details are correct

• Your IRS profile is updated

This helps prevent refund delays and lost payments.

Digital Income & Reporting Requirements

If you:

• Accept payments through booking platforms

• Use payment apps

• Receive funds digitally

• Own cryptocurrency or digital assets

These transactions may now trigger additional reporting requirements. Understanding what needs to be disclosed early helps avoid penalties later.

Use Your IRS Online Account

The IRS strongly recommends setting up or reviewing your IRS Individual Online Account, which allows you to:

• View tax records

• Track payments and balances

• Manage communication preferences

• Monitor notices or discrepancies

Having this ready before tax season reduces surprises and last-minute stress.

Final Thought for Vacation Home Owners

You don’t need to be planning changes to benefit from early tax preparation. For vacation home owners near Disney, being organised and informed is one of the simplest ways to protect long-term returns.

A little preparation now can make tax season smoother,  and help ensure you’re keeping more of what your investment earns.

📞 Need Guidance?

While tax professionals should always provide specific advice, I regularly help vacation home owners understand how ownership decisions, income, and timing intersect with long-term value.

If you’d like to talk through how ownership trends or market changes affect your property, I’m always happy to help.

Vacay & Co Real Estate

Michelle Baydemir
Broker-Owner | Vacation Home & Investment Specialist
📧 [email protected]
📞 321-333-1338
🌐 https://www.vacayreflorida.com