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Short-Term Rentals

220 articles

The 14-Day Rule for Short-Term Rentals: How the IRS Classifies Your Vacation Home and What It Changes for Your Taxes
Regulations

The 14-Day Rule for Short-Term Rentals: How the IRS Classifies Your Vacation Home and What It Changes for Your Taxes

Under IRC Section 280A, using your vacation rental for more than 14 days eliminates your ability to take a rental…

June 8, 2026 18 min read
How to Calculate Airbnb Cash Flow Before You Buy: A Step-by-Step Guide for STR Investors in 2026
Data

How to Calculate Airbnb Cash Flow Before You Buy: A Step-by-Step Guide for STR Investors in 2026

A first-time STR buyer complete guide to modeling cash flow step by step: gross revenue, vacancy, operating expenses, NOI, cash-on-cash…

June 8, 2026 17 min read
The Financial Case for Your Second STR: What the Numbers Actually Look Like When You Scale from One Property to Two
Airbnb Stories

The Financial Case for Your Second STR: What the Numbers Actually Look Like When You Scale from One Property to Two

Three STR hosts share what buying their second Airbnb property actually looked like in 2026: the numbers, the surprises, and…

June 7, 2026 16 min read
These STR Markets Have Frozen New Permit Applications in 2026. What Buyers Need to Know Before They Bid.
Hot Topics

These STR Markets Have Frozen New Permit Applications in 2026. What Buyers Need to Know Before They Bid.

Richardson TX just enacted a 90-day freeze. Birmingham MI and Nashville have blocked new permits for months. At least 8…

June 6, 2026 16 min read
Hudson Valley NY Short-Term Rental Market 2026: What StaySTRA Data Shows for the Wine Country and Agri-Tourism Corridor
Data

Hudson Valley NY Short-Term Rental Market 2026: What StaySTRA Data Shows for the Wine Country and Agri-Tourism Corridor

Hudson Valley STR properties average $40,500 in annual revenue, with peak August at 62% occupancy and $288 ADR. StaySTRA data…

June 6, 2026 11 min read
Airbnb AI and Automation Features for Hosts in 2026 Which Ones Actually Improve Your Revenue (And Which to Skip)
Short-Term Rentals

Airbnb AI and Automation Features for Hosts in 2026 Which Ones Actually Improve Your Revenue (And Which to Skip)

Airbnb has shipped Smart Pricing, AI listing descriptions, photo ranking, and messaging automation in 2026. Here is what professional hosts…

June 5, 2026 13 min read
How STR Investors Are Structuring Their Deals to Survive City Crackdowns in 2026
Legal

How STR Investors Are Structuring Their Deals to Survive City Crackdowns in 2026

Moratoriums, commercial reclassification, and retroactive permit bans are the three biggest regulatory threats to STR investors in 2026. Here is…

June 5, 2026 13 min read
STR Due Diligence: What Your Buyers Agent Doesnt Know About Vacation Rentals
Editorial

STR Due Diligence: What Your Buyers Agent Doesnt Know About Vacation Rentals

Your buyer's agent was trained to help you buy a home. Not an STR business. Here is what gets missed,…

June 5, 2026 18 min read
These STR Hosts Run Profitable Properties Without Paying for a Single Piece of Software. Here’s How They Do It.
Airbnb Stories

These STR Hosts Run Profitable Properties Without Paying for a Single Piece of Software. Here’s How They Do It.

Roughly 1 in 4 STR hosts manages without any paid property management software. We spoke with hosts who built profitable…

June 5, 2026 12 min read
The Best Short-Term Rental Software for New Hosts in 2026 (Before You Get Overwhelmed)
Short-Term Rentals

The Best Short-Term Rental Software for New Hosts in 2026 (Before You Get Overwhelmed)

A first-time host guide to the STR software tools worth buying in year one, what to skip until you have…

June 4, 2026 16 min read
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