Where We’re Headed Next: Expanding The Joes Beyond Wine Country

We started The Joes in our own backyard, Northern California wine country, and it was the perfect place to begin. It’s where we live, where we’ve spent decades in hospitality, and where we understand what makes a stay feel truly special. Over time, we’ve built a curated portfolio of midterm rentals and monthly rentals across Napa and Sonoma, homes that aren’t just places to stay, but places to live. And that distinction matters. What we’ve seen is that when people book a 30+ night rental or a fully furnished monthly rental, something shifts. They stop traveling like tourists and start living like locals. They find their morning coffee spot, they cook at home, they settle into a rhythm. It becomes less about visiting and more about belonging. That’s the foundation of The Joes and now we’re ready to bring that experience to more destinations.

As we expand, we’re focused on places that naturally lend themselves to midterm rentals and monthly stays, destinations where people don’t just want to visit, but want to experience daily life. We keep coming back to a compelling mix. Along the California coast, places like San Diego, Santa Barbara, Los Angeles, Orange County, and up through Carmel and Monterey offer a balance of lifestyle, climate, and culture that make them ideal for longer stays. On the East Coast, destinations like Charleston, Manhattan, Brooklyn, the Hamptons, and Nantucket each offer their own version of immersive living from historic charm to coastal escape to city energy. Florida continues to stand out with Miami, Palm Beach, and Naples, where demand for fully furnished monthly rentals keeps growing. And then there are the mountain and desert destinations, Scottsdale, Aspen, Vail, Breckenridge, Jackson Hole, Big Sky, places where seasonality naturally encourages people to settle in for longer stretches. These are not just travel destinations - they’re lifestyle destinations. The kind of places where a 30+ night rental starts to feel like home.

One of the biggest insights we’ve had while building The Joes is that the best markets for midterm rentals are often the ones with the most restrictions on short-term rentals. Places like Nantucket, Aspen, Palm Beach, Santa Barbara, and San Francisco have all implemented strict rules limiting permits, requiring longer stays, or restricting non-owner-occupied rentals. For traditional short-term rental platforms, that creates friction. For us, it creates opportunity. When short-term rentals are restricted, the market shifts. High-turnover, investor-driven properties start to fall away, and what’s left are higher-quality homes, true second homes that weren’t designed to operate like hotels. These homes are ideal for a monthly rental platform like The Joes, where guests stay longer, treat the home with care, and engage more deeply with the community.

If we had to prioritize where we go next based on demand, housing quality, and short-term rental restrictions, a few destinations consistently rise to the top. Nantucket stands out for its limited inventory and steady demand for high-end summer monthly rentals. Aspen continues to lead as one of the most desirable mountain destinations, with regulations that naturally support longer stays. Jackson Hole offers a rare combination of natural beauty and limited short-term rental supply, making it an ideal market for 30+ night rentals. Santa Barbara pairs coastal lifestyle with meaningful restrictions, creating strong demand for fully furnished monthly housing. San Francisco remains one of the most regulated short-term rental markets in the country, while still seeing consistent demand for longer stays. Palm Beach and Charleston both stand out for similar reasons, tight rules, strong identity, and a deep base of second homes. And then you have the mountain towns like Vail and Breckenridge, where people naturally want to stay for a season rather than a weekend. These are the kinds of places where midterm rentals don’t just work, they thrive.

What ties all of these destinations together is something simple: they reward staying longer. A few weeks in Charleston feels completely different than a weekend visit. A month in Jackson Hole starts to feel like a lifestyle. Time along the coast in Carmel-by-the-Sea or Monterey allows you to slow down, settle in, and experience a place in a more meaningful way. That’s what monthly rentals unlock. They give you time to build routines, explore more deeply, and connect with a destination in a way that short stays simply can’t match.

As we continue expanding The Joes into new markets, we’re focused on building the best midterm rental platform for travelers who want more than just a place to stay. But we don’t want to do it alone. Which of these destinations would you prioritize? Where are we missing opportunities? Are there places you think we should skip? Where would you want to live for 30 days or more? If you’ve ever searched for a better way to travel through midterm rentals, monthly stays, or fully furnished 30+ night rentals we want to hear from you. Drop your thoughts in the comments, we’re listening.