Greg and I started house sitting in November 2015. There are several websites that bring together homeowners and sitters. Most have a membership fee for potential sitters, but are free for homeowners to join. We do not charge for our services, but exchange them for lodging. House sitting is more popular outside the US than inside, but there is plenty to choose from. Whatever location you choose, you are responsible for travel expenses. Initially we registered with TrustedHousesitters.com. It is the most expensive site to join, but also has the most activity (let me know if you would like to join, I have a discount code for you). Most house sits involve taking care of pets while the homeowners are away. With all of the websites, you create a profile including pictures and lots of details about yourself: why you want to house sit, experience, work history, what makes you trustworthy, etc. You can also include references. I monitored additional websites, but only paid to join them if I saw a listing I wanted to apply to. The other sites are much cheaper to join.
We decided to try this while waiting a year for our new boat to be built. Our house sold Summer 2015 and we just closed on our previous boat. I have two suggestions for getting started. First, begin with a less popular location. Perhaps something you can drive to for a long weekend. This increases your chances of being chosen for the position, thereby earning positive reviews that you can add to your profile. Second, check the websites at least once a day and respond immediately. Time is of the essence in securing these positions. Here’s where we have gone so far:
Loganville, GA – near Atlanta, very large new home in a subdivision, three indoor cats for one week (our son was with us for this one)
McMinnville, TN – near Chattanooga, modest old farmhouse with lots of charm, one indoor cat, one indoor dog, two outdoor cats and one outdoor dog for ten days
Pass Christian, MS – near New Orleans, elegant Acadian cottage two blocks from the beach, one indoor cat for seven weeks (our son and his girlfriend came to visit for a few days during this one)
Eueiki Island, Tonga – caretakers at small eco-resort while closed for the off season, care for two outdoor dogs, transport five workers by boat once a week, for two months
Merrimac, MA – beautiful, three bedroom home near the ocean, one indoor dog, one indoor cat for ten days (our son will be with us for this one)
These are the additional sites that we have joined (much less expensive, ex: $30/year)
Additionally we are house sitting for friends and acquaintances in our former home town for the summer. All of those opportunities were secured through word of mouth, Facebook, etc. Our son will be joining us for all of those.