When You Fall in Love With a House Sit and Don't Want to Leave

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Somewhere around three months into our current sit in Portugal, it stopped feeling like a house we were looking after and started feeling like home. We've joked with the homeowners about not giving it back. We know we will. This is what that feeling actually is, why extending almost never happens the way you'd hope, and what genuinely does work instead.

We found this sit through TrustedHouseSitters, and if you're hoping to find something that grabs you the same way, a 25% discount on membership is available here.

What follows isn't really about this one property. It's about what happens when a sit stops being a place you're staying and starts being a place you don't want to leave.

What This Actually Feels Like

It's hard to describe without sounding like we're exaggerating, but it genuinely feels like home. Every window looks out onto something worth looking at. Stepping onto the terrace is enough to reset a bad mood. It's given us time, space, and quiet in a way that's changed how we actually work, we're more focused on our businesses now than we've been in years, genuinely productive in a way that surprised us.

It's only three months in that I've properly understood why writers disappear somewhere beautiful to finish a book. There's something about a genuinely inspiring environment that gets the cogs moving. It's hard to feel frustrated or stuck when everything around you is that good. The productivity isn't willpower, it's the setting doing half the work.

We've Asked, Sort of

We message the homeowners jokingly now and then, telling them if they ever change their minds, they're welcome to just stay in Switzerland a bit longer. We know they won't. They love this place as much as we do, more, really, since they bought it. From what we understand, it's the home they're building toward for retirement. We get to dream inside someone else's dream for a while. That's a genuinely strange and wonderful thing that house sitting makes possible, homes in Switzerland, Italy, Greece, places we'd otherwise only ever see in photos.

They return to Switzerland for work over summer, then come back here. There's a real, fixed date, and we understand exactly why it has to end. If anything, the timing works out well. Portugal is brutally hot right now, and the cooler months ahead, when they're actually planning to be back, will suit the house better than we currently do. You don't know what you've got until it's raining somewhere else and you're still waiting for your first proper drop in months.

Why This Hasn't Really Happened to Us Before

Across 20 sits, this specific feeling has only shown up once before, mildly, in Athens, looking after a French Bulldog who properly stole our hearts. But even then, it wasn't quite this. We'd done a full month-long sit in France before this one, and it didn't hit the same way, because we still had somewhere to go back to. A home. Jobs. Things waiting for us.

That's gone now. Everything we own fits in the van, and the road ahead is genuinely open. I think that's a real part of why Portugal feels different, there's no home pulling us back into contrast against it. This sit isn't competing with anything. It's just, currently, all we have, and it happens to be extraordinary. When we show people back home what our life actually looks like, family, friends, they're openly jealous, and honestly, we understand why.

What Actually Happens Next, Realistically

In most cases, the dates simply don't move. Homeowners set them for real reasons, a job, their own travel plans, a life waiting on the other side of the trip, and no amount of us wanting to stay changes that. Trying to talk a homeowner out of their own return is not a realistic strategy, and we wouldn't recommend attempting it as though it were.

What we do think matters, and what's realistic, is the relationship itself. We're in regular contact with the Portugal homeowners, a good sign, the same pattern we've seen with a few other homeowners who've reached back out to us directly for future opportunities once their plans changed again. Good communication throughout a sit, being genuinely easy to deal with, keeping the pets comfortable and the homeowner informed, is what actually gets you invited back, not asking to extend in the moment.

We don't know if we'll return to this exact house next year, we're already looking ahead to Scandinavia for next summer, and separately at listings in France. But a couple of years from now, genuinely, who knows. The relationship is there, it's warm, and that's worth more long-term than trying to squeeze a few extra weeks out of this particular stay.

If You're in This Situation Yourself

Don't push for an extension that isn't realistic, it puts real pressure on a homeowner who has their own genuine reasons to come home, and it rarely goes anywhere good. Instead, focus on what actually compounds over time: communicate consistently, look after the pets properly, keep the homeowner in the loop without them needing to ask.

A return sit, when it happens, is genuinely one of the best things this lifestyle offers. You already know the house, the routine, the pets are comfortable with you, there's none of the usual first-sit uncertainty. Over enough time, the people you sit for stop being homeowners and start being something closer to long-distance friends.

Conclusion

Falling for a sit is a good sign, not a problem to solve. It means you're genuinely present somewhere, not just passing through it. The honest answer, almost always, is that you can't extend, the homeowner has their own real life waiting on the other side of their trip, same as you do on the other side of yours. What you can do is leave the relationship strong enough that the invitation might come again, on its own terms, whenever that ends up being.

Caro and I have completed 20 house sits across 12 countries, driven 19,000km across Europe in our 1998 VW T4, and saved over $26,500 in accommodation costs over three years of house sitting. If you've ever fallen for a sit and had to hand it back, tell us about it in the comments, we'd genuinely like to know. DM us @housesittersguide, we answer everyone.

Frequently Asked Questions

• Can I ask a homeowner to extend a house sit if I love it?

  You can ask, but in most cases the answer will be no, and it's worth going in with that expectation. Homeowners usually have a fixed, genuine reason to return, work, their own travel plans, a life waiting for them at home, and that rarely bends just because a sitter would like more time.

• Is it normal to not want to leave a house sit?

  Yes, and it's a good sign rather than something to worry about. It usually means the sit genuinely suited you, the pace, the environment, the pets, rather than indicating anything is wrong with how you're approaching the lifestyle.

• How do I increase my chances of being invited back to a sit I loved?

  Consistent, genuine communication throughout the sit matters most, keeping the homeowner informed, looking after the pets properly, and being easy to deal with. Homeowners who've had a good experience often reach back out directly for future sits, well before they'd ever repost a public listing.

• Should I bring up wanting to return during the current sit?

  A light, genuine mention is fine and often appreciated, but it shouldn't come across as angling for special treatment or an extension. Let the relationship develop naturally rather than treating it as a negotiation.

• What if I don't have anything to go back to after a sit ends?

  That's genuinely part of what can make a sit feel more emotionally significant, without a fixed home pulling you elsewhere, a great sit can feel like the only anchor you have. It's worth recognising that dynamic honestly rather than assuming the sit itself is unusually perfect, sometimes it's really about what you don't currently have waiting for you elsewhere.

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