My husband and I have been housesitting full time since 2014, and we generally do longer sits–at least a few weeks to a month minimum. Sometimes we will do shorter ones to fill gaps between longer ones. We are also fine doing a series of shorter sits if we are planning on being in one region for awhile and know we can easily fill our schedule.
Because we sit full time and have a lot of flexibility, a lot of opportunities are potentially open to us. Often times, what we plan to do and what we actually end up doing often diverges quite a bit.
For example, we left the Us in mid-January for our first extended trip abroad since Covid. We booked a couple of sits in Greece and Turkey before we left. After that, we wanted to go to Asia or perhaps areas like Morocco or the Middle East.
But then we saw some sits in Europe that really appealed to us, and we really go with our gut when applying. So we ended up doing a sit in Prague and two in London, where we currently are for another 10 days. London in particular was never high on our list, but we absolutely love it, and are so glad we came. The sit in Prague was absolutely fabulous as well.
After London we are headed to Asia for 9 weeks in Vietnam and South Korea. We would like to stay in the region longer but know that plan could change depending on what opportunities arise elsewhere.
So the moral of that story is being open to where you may end up if you are booking as you go along especially. Don’t get too attached to a particular itinerary. Trust your intuition–it may lead you somewhere other than where you think you want to go, but it leads to great experiences.
The less flexibility there is, the more challenging getting sits will be. If someone is looking in a specific country or region, with a very specific start date, length of sit,etc…that will naturally narrow options. It might not be as easy to guarantee you will find the sits where you want them when you want them.
Exceptions would be regions like the UK and the US where any given time frame may have hundreds, or even a thousand or more, available listings.
Landing primarily longer term sits on a full time basis is not really difficult in our experience. The more flexible you can be, the easier it makes it.