Repeat bookings accepted for beautiful home, pets and location. Especially in a warm climate and sea views 
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I always choose sits that have animals, locations, and homes that I will enjoy.
So the main variable is how I am treated by the humans.
I do repeat sits when I also enjoy the humans, or at least, am appreciated and trusted by them.
I adore visiting the animals again, and I love how they remember me as an old friend.
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I have a few sits that I would call regulars. They all have appreciative homeowners. Mostly they are in areas where I get to visit friends who have moved away. They also have clean houses, nice kitchens and easy pets. I always send pictures at least once a day along with anything they should know about. Daily pictures are a must. I’m currently on my 7th sit for the same family. My regulars are family.
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We have only had one pet sitter so far and we had such a super experience with her that we have already invited her back for two more trips that we’ll be taking. As someone else said - there was a “connection” there, plus she sent pictures almost daily and even gave us a little photo album of her and our dog’s “adventures” together when we returned. The clincher was when she said that her friends were worried that she would be going through withdrawal after leaving our dog! She was just wonderful!
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We’re hoping to find one or two great sits in Perth Australia where we can stay when visiting family every year- it’d be perfect to find repeat HOs and build up a relationship over the years.
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From a sitters perspective, location is definitely at the top of the list as is a combination of the home, the pets and the owners. I’ve gone to some lengths to help out owners who have been kind and generous to me even if it doesn’t 100% suit me as those have been relationships I have valued. I wouldn’t do the same for owners that haven’t made me feel welcome or made things harder than they needed to be or not valued my time generally eg expecting a cross town track for a meet.
As a homeowner, someone who has demonstrated similar values in terms of communication and consideration and taken good care of my property and pets. Unfortunately my home is an area with significant transience and HS tend to have moved on by the time the next trip rolls around.
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As a sitter, I’d return to 3 of my sits due to perfect location, straightforward pets, comfortable house, and lovely owners.
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For me, it almost always boils down to my relationship with the home owners. I have several that I’ve really clicked with and two that are like family now, so I’m happy to return to help them anytime I can. I even get a bit jealous when I’m not available and they have to find other sitters!
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