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The question isn’t whether Kissimmee vacation rental property management costs are high or low. The real question is whether you make more money with it or without it. Most owners start here because they’re staring at a management fee and thinking, “I could keep that money and do this myself.” Fair enough. But after managing … Continued

Pricing is the single fastest way to either make or lose money on an Orlando vacation rental. Get it right, and a 5-bedroom in a resort community clears $55,000 to $70,000 a year. Get it wrong, and you’re stuck at $28,000 wondering what happened. I review owner portfolios every week. The properties, the locations, and … Continued

Your Orlando vacation rental income should be climbing right now. The market had 76.7 million visitors last year, Epic Universe is drawing record crowds, and family travel demand is the highest it’s been in five years. So why does your calendar still have gaps in it? I talk to owners every week who bought into … Continued

Storey Lake Resort sits 4.2 miles from Disney World in Kissimmee. It’s one of the few Orlando vacation rental resort communities that was built specifically for short-term rentals, not converted into one after the fact. That matters more than most people realize. We manage over 100 Storey Lake Airbnb properties at FunStay Florida. Some owners … Continued

You’re comparing vacation rental management companies in Orlando and every website says the same thing. “Full-service management.” “Competitive fees.” “We treat your home like our own.” Then you sign a contract, and the 25% commission somehow becomes 38% after booking fees, cleaning fee retention, and vendor markups you never agreed to. The local vs national … Continued

A Kissimmee host called us last year after getting a letter from the Osceola County Tax Collector. She’d been on Airbnb for two years. Assumed the platform handled all her Florida vacation rental taxes. Turns out, Airbnb never collected a dime of her county’s tourist tax. She owed $7,200 in back taxes, plus penalties. She’s … Continued

Your cleaner texts you at 7am: the AC is blowing warm air. Guest checks in at 3pm. It’s August in Florida. You have eight hours to find an HVAC tech, get them to the property, diagnose the problem, and fix it before a family of six walks into a 92-degree house. That’s vacation rental emergency … Continued

AirCover promises $3 million in free protection. It won’t cover hurricanes, pool accidents, or your VRBO bookings. AirCover is free, automatic, and the numbers look great: $3 million in damage protection, $1 million in liability. Then a guest trashes your pool deck. A storm rips off the lanai. Someone slips on a wet tile, and … Continued

Let’s skip the legal jargon and talk numbers. Setting up an LLC for a vacation rental in Florida costs about $375. A single slip-and-fall lawsuit in Florida settles for $75,000 to $175,000 on average. Severe cases? A Broward County jury returned a $7.5 million verdict in 2024 for a spinal injury on a commercial property. … Continued