Thank You, Midterm Rental Summit 2026: The People Make the Industry

We just got back from the 2026 Midterm Rental Summit in San Diego, and we are still buzzing. Three days surrounded by some of the sharpest operators, investors, and entrepreneurs in the short and midterm rental world is the kind of thing that recharges your belief in what this industry can be. We came to learn. We left with a notebook full of ideas and a phone full of new friends.

A Huge Thank You to Jesse Vasquez and His Community

None of it would have happened without Jesse Vasquez. Jesse has built something rare: a community that is genuinely generous with its knowledge, its time, and its connections. From the moment we walked in, his team made us feel like family. The hospitality was second to none, and the energy he creates in a room is the reason people travel across the country to be there.

If you have spent any time in the midterm rental space, you know Jesse does not gatekeep. He opens doors. We are grateful to have been welcomed in, and even more grateful for the relationships that came out of it.

The Connections We Made

The real magic of an event like this is not on the stage. It is in the hallway conversations, the dinners that run long, and the side chats over coffee. We met operators running portfolios from a single market to dozens of doors across the country. We met first-year hosts taking notes on everything, and seasoned investors who have weathered every cycle the industry has thrown at them.

What struck us most was how willing everyone was to share. Pricing strategies, screening systems, lessons learned the hard way — nobody held back. That spirit of open collaboration is exactly what makes this community special, and it is the same spirit we try to bring to everything we build.

Why It Matters for Direct Booking

Every conversation kept circling back to the same theme: owning your guest relationship. The hosts thriving in this market are the ones building direct relationships, controlling their own pricing, and refusing to hand a quarter of their revenue to a platform that treats them like a number.

That is the whole reason TripSkip exists. Midterm and short-term operators are realizing that the smartest long-term play is to drive guests to their own booking channels and keep 100% of what they earn. The Summit only confirmed what we hear from hosts every day — the future of this industry is direct, and the community is ready for it.

Carrying the Momentum Forward

We left San Diego with a renewed sense of purpose and a long list of people we cannot wait to keep building with. To everyone we met, thank you for the conversations, the introductions, and the generosity. And to Jesse and his entire community — thank you for the hospitality and for setting the standard for what a host community should feel like.

If you are a host who believes you should own your guest relationships and your revenue, we would love to have you with us. List your property on TripSkip or explore the marketplace to see the direct-booking movement in action. The best is still ahead.