Midterm rentals promise steady income—but the reality is far more complex

The buzz around midterm rentals is hard to ignore. For many hosts, it sounds like the perfect solution to slow seasons or unpredictable booking windows—longer stays, fewer turnovers, and less work. But as Sarah and Annette share in this week’s episode, the truth is a little more complicated.

After three years of running hybrid models that include both short- and midterm stays, they’ve learned that midterm rentals come with a unique set of operational, legal, and financial challenges that most hosts don’t anticipate.

For starters, the income isn’t guaranteed. Guests on temporary work assignments or medical stays can cancel early or request unpredictable extensions. Then there’s the juggling act of keeping your listings visible across multiple platforms—Airbnb, Furnished Finder, and your own direct booking site—while trying to maintain a steady stream of reviews.

Even the “fewer turnovers” myth doesn’t hold up under scrutiny. When guests live in your property for months, the cleanings become deeper, more time-consuming, and more expensive. Add in the legal requirements for leases longer than 28 days, maintenance access challenges, and changing insurance implications, and you start to see why midterm rentals require just as much effort—if not more—than short-term stays.

The takeaway? Midterm rentals can absolutely work, but only if you understand what you’re getting into. They aren’t easier—they’re just different. Go in prepared, systemize your operations, and you’ll be ready to make the most of every opportunity that comes your way.

Download a transcript of this episode.

Resources:

• Breezeway — Operations management software to streamline turnovers, maintenance, and property care.
• Furnished Finder — A platform connecting property owners with traveling professionals and midterm guests.
  Minoan – Outfit your short-term rental with guest-loved brands at insider pricing.
•  Avalara – Book a demo to save $100
• #STRShareSunday: @whimsicalmousemanor
• Submit your property for our next #STRShareSunday at strshare.com

#STRShareSunday

@whimsicalmousemanor

Whimsical Mouse Manor is pure Disney magic from the moment you walk in. Every room has its own theme—from Frozen and Moana to Beauty & the Beast and even a Villains suite—so you’re truly stepping into a storybook world. This really is the most magical place on earth!

Beyond the bedrooms, there’s a Dumbo-themed game room with arcade games and a giant screen, plus a private heated pool that’s perfect for unwinding after the parks. Since it’s in Windsor Hills Resort, you also get access to water slides, a splash pad, and all the family-friendly amenities that make it feel like a vacation village.

What we love most are the thoughtful family touches—cribs, toys, books, and even dress-up clothes—all sprinkled in to make the stay extra magical and stress-free. It’s the kind of place that makes your trip feel like part of the Disney adventure itself.