First Time House Sitting: It’s Like You’ve Won

First Time House Sitting

When you find out you’re going to be house sitting for the first time you feel a rush of exhilaration. It’s like winning a contest. As a first-timer you have no experience, yet the homeowners chose you. They trust you.

That’s how Heather and I felt when – with no house sitting experience – we scored a once-featured house sit on TrustedHousesitters.

We were enduring a persistent maritime winter in April. There was snow. Lots of snow. And it was getting us down. Then (after two short Skype conversations with the homeowners) we were going to Mexico to care for a beach front villa. And a pair of sweet rescue dogs. We had ‘won’.

We knew we should pay to stay here. The villa had a private beach, reef snorkeling, kayaks, and fast WiFi. Any other tourist would pay to stay. Yet for 2 months we’d be house sitting in paradise for FREE.

Is this for you banner susrise

How did we decide house sitting was right for us?

As we worked to get our own blog up-to-snuff we looked for blogging mentors. We subscribed to the best travel blogs. At some point we stumbled on Hecktic Travels and their house sitting stories.

If Pete + Dalene Heck could travel and housesit for free, couldn’t we? Couldn’t you?

  • Flexible travel plans. We are passionate when it comes to lists and schedules; our year is already planned in Excel. But change happens. The reality is, we don’t have fixed plans. Accommodating a homeowner’s travel dates isn’t a problem.
  • Slow-paced travel. Experiencing more is better than seeing more. Home-share services (like Airbnb) let us unpack, use the kitchen, and experience the culture from a “home base”. House sitting is like Airbnb… with chores & pets.
  • Work online. We work from our computers. So any location is OK if we have electricity and internet access. House sitting lets us work AND enjoy a new location.
  • Caring for pets. House sitting & pet setting are like cherries connected at the stem. Good thing we enjoy pets: I grew up with dogs and have experience raising farm animals. Heather never had a dog or cat as a child, but saved up all her unspent affection and now adores the shit out of any loving animal.
  • Easygoing personality. Getting a job over the internet (even house sitting) means accepting the unexpected. No matter how good the house sitting description is, your perception will be different from the reality. Adventure and uncertainty is good for us.

We considered the facts above, and decided house sitting was right for us.

Then we signed up to TrustedHousesitters, created a profile (with a video introduction), and opted to get house sitting email updates. It was our first time house sitting, and to gain an edge we wanted to be the first house sitters to apply.

Everything is Awesome Beach Walk

How is our first house sit working out?

We look after a remote beach villa in Xcalak, Mexico. It is off-grid and powered by solar. Fresh water comes by large cisterns that collect rainwater. The beach is steps away, the water is turquoise, and there’s coral reefs. It’s beautiful.

We look after the villa while the owners are away in exchange for accommodation in the caretaker’s house. Our presence deters petty theft while the owners are away. We do light work 3 hours a day.

Work includes walking the dogs, cleaning the pool, watering plants, clearing palm tree detritus, and oiling surfaces to protect them from the salt air. It is easy work. We are enjoying our first time house sitting.

House and Burning Fronds

House sitter skills for newbies

Caring for someone’s house – and pets – is a hefty responsibility. As beginners we didn’t feel adequate to compete against experienced house sitters. Applying was intimidating. Then we started listing our skills and realized even though it’s our first time house sitting, we are skilled.

  • Travel experience. We proved our resourcefulness by referencing our travels. We’ve worked where English is not spoken. We’ve studied on a small island where supplies weren’t always available. Travel makes you adaptable.
  • Career responsibility. We never house sit but we have taken on responsibility. Use your work experience to prove your reliability.
  • Being relatable. We talked in the interview about how we became Divemasters, after discovering the home owner was a diver. We discussed Wisconsin, after learning their daughter is going to Madison U. Find a way for the owner to see a little bit of themselves in you.
  • Enthusiasm (for the house sit). Get the owners excited about having you house sit. Talk about the personalities of the pets, what the owner like about the house, how they have fun.
  • Pets. If you had a pet growing up you have a skill. All the better if you’ve looked after someone else’s pet. Show that you have a heart by hyping your relationship with animals.
  • Handy Skills. I grew up in the country and know how to use a chainsaw. Which is not the most in-demand skill for a house sitter. Yet people assume I’m good with most tools when they hear about my pathetic prowess with a chainsaw. Who am I to tell them differently?
  • House ownership. Why is this last? Because we never owned a house. We’re renters. Being a former house owner is a killer skill for your house sitting profile. But it isn’t essential.

Surprise! Our first house sit had a few…

Do you remember how I mentioned to ‘accept the unexpected’ when getting a house sitting job over the internet? We encountered these surprises:

Preconception: White sand beaches. Maybe Jimmy Buffet playing.

Reality: Sargasso grass has inundated the coast of Xcalak this year. It’s smelly, heavy, and ugly.

Rescue Dogs house sitting dock
Xcalak sunrise over dock

Preconception: You can buy fresh fish from the local fisherman walking up the beach.

Reality: The fishermen are not there. They don’t like the grass either.

Preconception: Looking after a whole villa would be difficult.

Reality: The owner showed us how to do everything a few days before leaving. It was simple.

Tim Hirtle Cleaning Pool

Other surprises from our first house sit:

  • Coconuts are everywhere. We’ve learned to husk, crack, and make milk from coconuts.
  • Conch shells are everywhere. We’ve gone all Lord of the Flies, making & blowing conch trumpets to get each other’s attention.
  • There’s so little work. We prepared to bust our ass working this house sit. Instead we go snorkeling.
  • The heat made us lazy. I understand why the local Mexicans take a siesta. The heat zaps our energy. It makes us lazy. Yes… it’s the heat’s fault.
  • We’re meditating. Our first house sit is remote. It’s just us, the dogs, the beach, and the jungle. It gives us time to think. So we are practicing meditation and realizing the benefits. If you’re interested see our review of free guided meditation.

Interested in house sitting yet? Read our tips below or check out this awesome infographic for first-timers How to Start House Sitting (Infographic)

Coconut Family Become a House Sitter

Become a first-time house sitter (advice from a now not-first-timer):

Competing against experienced house sitters is mentally difficult. It is not impossible. You are responsible, interesting, and worthy of house sitting. Even if it is your first time.

  • Apply, even if you’re not qualified. People ask for more than they need, so if you like the description, apply. We got our first house sitting assignment because the owners like our age and personalities.
  • Look outside your own country. We wanted our first house sit to be in Canada. It seemed “safer” to house sit in the country we are from. Problem was, none of the house sits in Canada interested us. We scored big after considering Mexico.
  • Make your profile engaging. The homeowners liked the video we made for our house sitting profile. It pre-empted some of their questions & showed our personalities.
  • Consider carefully. We had to cancel our first potential house sit. The owner was not upfront about the requirements, work, or costs. If we showed up I’m sure she would have revealed more surprises. We pulled the plug because she wanted to use us.
  • Prepare your references. You need to prove that you are trustworthy. Coach your references before the homeowner calls them. Your references will give the best description of you if they expect the call from the homeowner.
  • Use work references. Our homeowners only called our former manager for a reference. They wanted someone who knew our level of responsibility.
  • Be fast. Reply to house sitting ads immediately. The owner doesn’t want 100 applicants. They will only do so much work before deciding on a house sitter. Being short listed means being good, fast.
Now What Man on Beach

You got your first house sit. Now what?

Ask why they selected you. When you apply to your next house sit, this information will be valuable. It is a strength that you can play to. Scoring another house sit will be easier when you know what makes you appealing to homeowners.

Email your travel itinerary. Showing the homeowner you are committed to the house sit will put them at ease. They have travel plans of their own and are worried you will cancel on them, ruining their travel plans.


If you have flexible travel dates, and exchanging work for accommodation interests you, consider house sitting. The first time house sitting is intimidating. You will question if you’re good enough. You are. As a responsible adult you have skills that traveling homeowners need. Make sure the house sit is right for you before accepting. And enjoy any surprises that come along. They make life interesting.

Coconut face & Pineapple

Think traveling is the best way to find yourself? Good, we already have something in common. Subscribe to our updates & you’ll never run out of motivation to go and find yourself.


  1. Sounds like a great experience and wonderful location for a first (or any) house sit. We do home exchange, so rather than having to care for pets, we have exchanged homes.

    • I think home exchange is perfect for traveling. You get to visit and get to know a place, and still have the comfort of home. Plus you’re able to be an ambassador helping others enjoy your part of the world. It’s win-win.

  2. Good Stuff guys! We have been kicking around house sitting next year after our commitments run out to ketchup on things. it will be nice after over-landing in Africa for 52 weeks.

    • Hi David, I think after 52 weeks in Africa you deserve a break! That’s what housesitting feels like for us (even though there are chores to do of course). I hope you really enjoy it, and get a chance to catch up like you want to. Probably going through photos is going to take up a lot of your time!

    • Sometimes it’s bothersome that we are tied to the property (looking after pets), but for the most part it is a great way to really experience the place long term.

  3. GREAT information—Thank you for your HONESTY! I recently applied to TrustedHosesitters—-fingers crossed for my first “job”.

What do you think?

Please enter your comment!
Please enter your name here

This site uses Akismet to reduce spam. Learn how your comment data is processed.