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Passionate experience junkie. Lover of the arts and architecture. Want to see and share the world, one village at a time.

Should You Apply to More Than One House Sitting Assignment at a Time?

house sitting travel

Maybe you’ve been house sitting for a while or just venturing into these waters. Either way, knowing how to navigate through the process can help immensely in your overall success.

I do want you to know up front that the process of seeking out and finding the right house sitting assignment can take several months. Give yourself plenty of time to sort through all the details and personalities so you make a solid decision based on reason – and not based on a too-hurried timeframe.

Conrad and I have enjoyed some of the most rewarding and life-changing adventures while house sitting – I get a bit crusade-ey when it comes to this fantastic way to see the world. I want everyone to experience the wonderful world of house sitting!

Front porch

To that end, I want to share with you my philosophy of how to apply to house sitting assignments. And in particular, should you apply to more than one at a time?

The answer is Yes!

Here’s the bare-bones procedure of how the application process works:

  1. Set up email alerts from your chosen house sitting website(s) where you have a membership.
  2. Each day you receive notice of assignments that meet your parameters, such as what countries you want to house sit in, and if you’ll watch after pets.
  3. Respond to the house sits that look good.
  4. Start a communication with homeowners, to see if everyone is a good fit.
  5. Accept the assignment.

House sitting travel

Okay now let’s look at the procedure in more detail, and with a bit of my experience thrown in. When the email alerts start coming in, they can be very exciting with all the romantic and charming photos and descriptions. Apply to all that sound good and meet your criteria.

But here’s the important thing – each and every letter of proposal must be stellar. Just because you’re sending out multiple letters to homeowners doesn’t mean you scrimp on your professionalism or level of attention. Make each one personal to the specific assignment. Always mention something, (or several things), about the homeowner’s description or photos. For instance, one posting I applied to had photos of the home’s interior. A doorway had interesting metal scrollwork in the corners. In my introductory letter, I mentioned how pretty that metalwork was. Other times I have made comments about the homeowner’s pets, like, “Those two guys look like they are sweet and cuddly.” Adding personal responses to their post will put you on the top of the homeowner’s list of possibles for the assignment.

I will also make comments about the post itself, like, “I like that you took a lot of time describing your home and surrounding area. Your descriptions sound like the same way I would describe my own home. It makes me feel like I know you.” Or, “I like that you posted your need for a house sitter so far in advance. I like to get everything all set up ahead of time, too.”

In other words, find a common ground between you and the homeowner. These honest and forthright approaches will make you stand out amongst the other applicants.

Immersion house sitting in tuscany

Applying to more than one house sit at a time allows you choices. By having several possibilities in the works, you have a better chance of getting a desirable assignment.

The truth is that this whole process of applying for house sits can be quite fluid. Some homeowners reject you. You reject some. You may have five potential house sits one day and lose them all the next. I may have 10 – 12 applications out there at one time. I find that the narrowing-down process works fairly organically, resulting in the right fit eventually. There is no right number of house sits to apply to. Just apply to all posts that fit your needs. If it’s 20, fine, work on those. If it’s 3, just as well. Make one of them work.

So let’s say you’re applying to multiple house sits. How do you keep them all straight? I use a wall chart. I write down each assignment I’ve applied to with information about it, such as where it is, for how long, and any other pertinent information on one row of the chart. That way, I see the chart every time I walk through the room. Not only that, but when I Skype with a homeowner, I have the wall chart handy so I can see information about other house sitting possibilities. For instance, if I am in contact with two possible assignments and both have said they want me, I have all the notes and information right there on the wall chart for making an informed decision.

House sitting travel

I enjoy the challenge posed by the application process. By keeping the information organized, my decisions result in the best house sitting assignments for me and Conrad. I take my time, too, so that all the details can be hashed out between us and the homeowner before the two of us commit to any travel plans.

I’d love to hear from you house sitters out there. What does your process look like? Is it the same as mine?

I wish you happy and safe travels always and all ways.


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11 Responses to “Should You Apply to More Than One House Sitting Assignment at a Time?”

  1. Josie, are all the photos in this post of houses that you and Conrad have stayed in? If so, that’s fantastic! They look like some really lovely places.
    Laura Zera recently posted..Travel: The Inevitable Backpacking Cock-Up, Followed by RedemptionMy Profile

    March 27, 2013 at 1:54 am Reply
    • Hi Laura,
      All except the thatched roof house are places we stayed. That one was near our “home” in Denmark where we house sat. I love those thatched roofs and took lots of pictures of them.
      But yes, thanks, we have had the joy and honor of staying in fantastic homes owned by super nice folks!
      So glad you stopped by!

      March 27, 2013 at 6:58 am Reply
  2. As B.H. still works we have a very limited time frame to look for house-sits in. Add in some elderly parents and it shrinks a little more. We hope to be applying for more next year after he retires.

    I think I would find it hard to juggle prospective homeowners – like juggling boyfriends I guess. Having said that, I have applied to more than one at a time, but have not heard back from them.

    We get contacted by lots of Aussie homeowners, but at this stage our sights are set further afield for holidays. I look forward to the day that I can entertain all the Aussie ones as well.

    I think your approach is very organized and when we get into it more I will definitely do something similar.
    budget jan recently posted..Fantastic Friday Sapa ReflectionsMy Profile

    April 6, 2013 at 7:17 pm Reply
    • Hi Jan,
      Haha, it IS a bit like juggling boyfriends! But unlike multiple boyfriends, my homeowners all know I am applying to more than one at a time. But I like the analogy!

      And you’re right — some homeowners never answer back.

      You Aussies seem to love house sitting and are so open to it — more than Americans. I hope you have more opportunities to travel/house sit soon. Thanks for stopping by, Jan.

      April 15, 2013 at 5:46 pm Reply
  3. Wow what some wonderful tips! I’ve never really thought about house sitting before, but I can see now the kids are grown up it would be a great way to see the world 🙂
    Johanna at ZigaZag recently posted..What’s the price of a cup of coffee in your neck of the woods?My Profile

    April 29, 2013 at 5:02 am Reply
    • Hey Johanna,
      Thanks for your kind words. I love making converts to house sitting! I’m so glad you stopped by and please let me know how your travels go.
      Be safe,

      April 29, 2013 at 7:09 am Reply
  4. Hi Josie – What happens if you get more than one positive response – two acceptances in gorgeous places and you have to turn one down because the timing clashes? Do you think that would prejudice your chances of being accepted in the future by the homeowner you have been communicating with, and in the end have to decline? Wow, that all sounds a little convoluted, but I think you know what I mean….
    heather recently posted..Airbus calls for bigger airline seatsMy Profile

    October 29, 2013 at 7:59 pm Reply
    • Hi Heather,

      Yes, it has happened that I have turned down a house sit after they awarded the assignment to me. It’s rare, but does happen. I think it’s important to make decisions in a timely manner so no homeowners are left high and dry. The process is kept “real” by employing a high level of professionalism and honesty, which I have found to be true across the board with people everywhere. There have been no hard feelings, as far as I know!

      October 30, 2013 at 7:55 pm Reply
  5. Love your blog Josie, and I agree with all you say. I would sent as many as I could find in the country of my choice at the time. I have literally applied to 1000’s of sits, certainly didn’t get 1000’s replies though. But certainly got the sits I was meant to have and were absolutely perfect.
    I love this quote from the Bible
    Do Not Worry
    …26″Look at the birds of the air, that they do not sow, nor reap nor gather into barns, and yet your heavenly Father feeds them. Are you not worth much more than they? 27″And who of you by being worried can add a single hour to his life?
    I don’t sit and wait for sits to come to me, I am pro active, I am open to another way to live and I have found my niche in Home and Pet Sitting whilst experiencing this amazing world.
    Francien Daniels-Webb recently posted..Comment on scheduled_subscription_end_of_prepaid_term by ActionSchedulerMy Profile

    July 15, 2014 at 8:59 am Reply
  6. Hi Josie, great post with sound advice. Because we’ve been housesitting since 2009 we’re in the fortunate position where homeowners often contact us. Unfortunately we’re not always available as it’s impossible to be in two places at once. Turning down an assignment saddens us as we love the lifestyle as much as you! Our application process is similar to yours. We read the daily homeowner’s lists and consider a combination of things before we apply. This includes our availability, the location of the sit, number of pets, time or year, etc. We find corresponding by email is a good start, followed by a Skype or FaceTime chat. Both really help give us a good feel for the situation and the bottom line is it has to feel ‘right’ for us AS WELL AS the homeowners. We’ve also learned to listen to that little voice inside our head. If warning bells go off we discuss it privately and then back away because we’re obviously not the right people for that particular homeowner.
    Dianne Burns recently posted..To France to HousesitMy Profile

    March 16, 2015 at 3:56 am Reply
    • Hi Dianne,
      I couldn’t agree more — to every point you make here in your fantastic comment. House sitting is an art form and a lovely one for all involved. So glad you’ve reaped the benefits!
      Thank you so much for your insightful views,

      March 16, 2015 at 8:41 am Reply

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