Great story!!!
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We love repeat sits near family!
I think about the pets we have taken care of for the last two years and miss them. Although we haven’t wanted to return to the same places, that’s a great idea.
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Also - the sadness of repeat sits.
We looked after Bailey the labrador from 10 months to 14 years. As other sitters have experienced, the owners booked us months in advance to ensure we were there for Bailey.
We were as sad as they were when he was put to sleep and we miss him terribly
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We looked after Barney the border terrier on and off for many years. He passed last year and it was so sad to get the news. We shouldn’t have favourites but he was definitely in the top two. We have some lovely memories and photos of our time with him.
We still keep in touch with the owners who are lovely people.
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Yes I have done the same. And other hosts reach out way in advance and set me up before finalizing their travel plans.
This year I ended up as a house sitter 90% without her dogs. She travels a lot and wanted someone in the house for mail and general oversight of maintenance by others. It’s been a great partnership set up for all of 2025. 2026 may change we’ll see.
It was a win-win as I ended up w an interim remote job that stopped a 6-month trip to Australia and Japan to be the same time zone as the work.
It’s been great having a semi permanent place for me and my stuff. When she’s home I either take a short trip or hotel stay.
You can manifest anything. In my head I had been thinking I’d like to find a house manager gig. She was my last house sit wither her dogs in 2024. Her first house sitter ever.
It works for both of us. 200+ days at the same place mostly without her dogs who are the best companions when they’re here.
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We only sit in the Summer when we return to where we have family and friends. This will be our 4th Summer. We have 1 host family who has invited us back for the 4th consecutive year and another for the 3rd consecutive year. It’s comfortable for both them and us to know their house and pets.
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I have just started to get repeat sits. It is very nice to be confident on the routine, the home etc.
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We had 5 sits this winter. Two were absolutely wonderful, two were quite nice and one was ok at best. It all came down to the attitude of the HOs.
The two wonderful sits were both people that invited us to stay the night before and after. We were a bit uneasy about the first one as we actually overlapped two nights at the beginning (and one at the end) but the people were so incredibly lovely, kind and generous. We are now Facebook friends and keep in touch on WhatsApp. They did ask if we would come back and we said “not in winter”. It’s unlikely we’d go back to the UK for an extended stay very soon but its possible in the future. The second great sit we got on like old friends and we would happily go back. Again, not sure about going to the UK again soon but we could if we combined it with a European holiday. Both homes had lovely dogs, lovely home and surroundings and open, friendly HOs who approached with the attitude of wishing to connect with others. It was the best of what housesitting should be.
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Yes that is sad 
I have to focus on the time we spent with them all
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Yes, bittersweet and we know it’s inevitable.
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That’s a great arrangement!
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We feel exactly the same way about our repeats in summer near family!
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Agreed it’s definitely comfortable!
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I understand the whole winter issue. We absolutely attempt to find mild weather locations year round. It’s probably why we’ve opted for more airbnb stays this year.
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We did only two repeats over 3 years of housesitting - well, one is upcoming, in Guernsey over the next winter and one in Canada. Canadian one is actually one of my favourite sits we’ve ever done - the dog, house, the hosts - I mean everything was just amazing experience. A very peaceful place with spectacular conservatory where you can sit with your morning coffee or glass of wine and watch the wildlife outside, many waterfalls around and trails you can take the dog for walks and the owners, I think the most kind, generous, wise and influential people I’ve met in my life, we spent hours having amazing conversations with them. We did two sits for them (Spring 2023 & 2024) and since then they offered 3 more but unfortunately we couldn’t make it as our schedule but we agreed to come back there next Spring. I’m really looking forward to see all family again! With Guernsey I have similar feelings, we spent over 2 months there last year and happily accepted their offer to come back again. They have such a cosy little house on the cliff and the most spectacular views, two little dogs are joy to care for and the owners are very relaxed and also, so kind.
We received many more offers to do repeat sits, in Canada, Cyprus, Panama…we liked them all and it is always hard to say no, but we are booked for a year ahead now. Still considering one more repeat in Panama next summer though, will see 
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All bar one sit I’ve planned for this year are return sits. Lovely owners and homes, gorgeous pets, both have cleaners that come in once a week so beyond keeping it tidy and sorting the bed at the end, no big end of sit clean-up required. Living the dream 
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what a cutie - he even looks like a bear, I love it! 
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Such a great idea and helpful to post for others! We did the same thing this summer… asked a couple to come sit for us again (they said they would love to 
so we filled in their dates for a few weeks, and it ended up a win-win for everyone! I think the trick is to plan ahead with enough time to rebook the sitters you want, and be flexible too with their availability. In our case, this couple sits locally for the most part, so better chance they might be able to do it, vs. having to make long distance travel arrangements.
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Sounds like some lovely sits with some great pets and owners. It is indeed difficult to say no, or to see a sit pop up in your notifications and realizing you are already booked and unable to return. Reaching out is something we’ve come to do now, and it is definitely a win-win for all parties.
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