Our five favorite housesitting experiences (and the 2nd edition of the Break Free housesitting book!)

Last Updated on February 16, 2021

As many of you know, housesitting worldwide has become an unexpected passion of ours – and an integral part of how we maintain a comfortable nomadic lifestyle. Saving thousands of dollars in accommodation costs over the last three years hasn’t hurt, either!

In fact, we are in the process of negotiating another dream housesit right now for next spring. We’re not revealing any details until everything is set in stone, but it feels like the absolute perfect fit!

Clockwise: Housesitting in Chiang Mai, Thailand; Los Angeles; Chicago; Ontario, Canada and Costa Rica

To celebrate today’s launch of the brand new color PDF version of Break Free: The Ultimate Guide To Housesitting, we put together a list of our own top five housesits and we also included our top tips for how to get started with housesitting yourself.

A while ago we rounded up a bunch of our housesitting friends and put together an epic post about dream housesits around the world.

Today’s post about our own top five is to help you better visualize what housesitting worldwide can be like, and show how different they all are. Jump into our memories with us as we show you what our top five housesits (so far!) have been like.

Table of Contents

Housesitting worldwide: our five favorite sits

5. A Bed & Breakfast in Tuscany, Italy

It was a rainy Sunday morning in January back in 2010 when we read an article in the Guardian about a journalist who had an entire Bed & Breakfast in Italy to herself with her boyfriend, ‘housesitting’ for a couple of months while the owners went away. This was the first time we’d heard of housesitting but even so, something this romantic seemed like a crazy long-shot.

Cut to 14 months and four housesits later and we would be doing just that: housesitting a B&B in Tuscany, where we cared for five outdoor cats, a centuries-old farmhouse and stared out at the beautiful Tuscan landscape.

4. A luxury condo in Santiago, Chile

We had no idea how lucky we were scoring a housesit in Vitacura, one of Santiago’s finest neighborhoods. The owners were expats and looking to spend the holidays in Europe. They needed us to care for their two Scottie dogs and we happily accepted. We ended up falling head over heels for these two dogs and spend eight weeks living in and exploring Santiago. We had a blast in the city and it felt amazing to return home to our luxury condo and two adorable dogs every night.

3. An adobe desert home in Tucson, Arizona

This was our first ever official housesit that we found through one of the housesitting websites (Housecarers.com) in 2010, and it was the reason we decided to keep housesitting worldwide! The beautiful home, surrounded by the Sonoran desert, wonderful owners, lovable dog, great neighbors and perfect summer weather in Tucson charmed us so much that we have returned twice to look after Miss Millie again – and probably will return for another housesit!

2. Our own Caribbean beach, Mexico

Entirely off-the-grid, no cell reception and miles away from civilization outside a town you’ve never heard of: having our own private Caribbean beach was an experience we will never forget. We were there to care for the house alongside our ‘guard dog’ Loba. Loba turned out to be our best friend; her larger than life personality playing and hopping through the water chasing fish kept us entertained for hours a day. There was a hurricane during the housesit and we packed up the entire house and escaped with Loba, thankfully there was no serious damage upon our return. Even with that adventure, those eight incredible weeks living the Robinson Crusoe life were magic – sunbathing, snorkeling in the crystal clear water right in our backyard and endless Mexican food. Although we would miss the beach, the hardest part was saying goodbye to Loba at the end of our stay.

You can read more about this housesit here:

1. A condo in New York City

Living in New York City has always been a dream of ours, but to do it rent-free? That was something we never imagined possible. We couldn’t believe our luck when we were asked to care for two indoor cats in a posh Brooklyn Heights condo just five minutes from the Brooklyn Bridge. We spent just under two months in New York in the late spring, exploring way beyond the tourist trails and coming home every day to two cuddly cats. This was, by far, the ultimate housesitting worldwide experience for us. Can you imagine how much a vacation rental would have cost for two months – average rate $149 a night x 60 nights = impossible. This was the absolute best way to live in New York City.

Read more about this housesit here: Housesitting in New York City: A dream come true

How to get started housesitting worldwide:

Housesitting used to be much more word-of-mouth, a friend-of-a-friend kind of thing. Today, there are plenty of housesitting websites that connect homeowners with housesitters, and the process is much more professional, almost like a job interview of sorts.

Our top three housesitting membership websites are:

Clockwise: Exploring Malaysian food during our housesit in Kuala Lumpur; beach fun with fellow housesitters in Mexico; homemade food in Bavaria; one of the monkeys that swung by daily during our housesit in Costa Rica

Break Free: The Ultimate Guide To Housesitting Worldwide, 2nd edition at special price!

We want you to start housesitting worldwide, or just in your backyard!

We want you to get chosen for the housesits you really want.

We want you to have success while you housesit so you do it again and again.

We wrote this book specifically to help you get housesits and to help homeowners find the absolute perfect housesitters for them.

That is why Break Free – The Ultimate Guide To Housesitting is packed with over 120 pages of everything housesitters and homeowners will both ever need to know about housesitting worldwide.

The Kindle version on Amazon has also been updated and is better than ever. It’s a great book to have with you on the go for $9.99.

This brand new direct download version is packed with pictures, a beautiful layout makes it easy to read and search, plus we include a bonus package of practical housesitting print-outs to print again and again for each housesit. The book includes a 25% membership discount to TrustedHousesitters.com, one of the biggest housesitting websites. This makes the book practically free, considering the discount is more $$ than the book!

Jacky

Saturday 13th of September 2014

Hi Girls Just come across your site. This is amazing information and a fabulous way to travel and save some money. I am selling up everything in Australia and my son and I (53 & 29) are going to travel the world around December this year starting in SE Asia. Would this be something available to us as it would save us heaps in accommodation. This is a huge step for me so any advice would be appreciated

Marteen

Monday 4th of August 2014

Thanks for the info! We are thinking of house sitting for the first time this year. Are there any sites that don't have membership fees?

Dany

Hi Marteen, even if there was a website that was free, I would probably not recommend signing up for it. The membership fees make the sites much more legit, only having people sign up for them who really want to housesit, which is why an annual membership fee makes sense. I just renewed the three memberships with my favorite sites (about $150 for a year) and made my money back within two days of housesitting here in New York City. If you don't want to invest right now at this point, I'd recommend signing up for Mindmyhouse which is only $20.

Jordan

Wednesday 26th of March 2014

Hey there! Do you guys have an email address? I would love to ask you guys a few questions! Thanks!

Dani

Wednesday 2nd of April 2014

Hi Jordan, you should have our email address now :)

Nadia vs. the World

Tuesday 21st of January 2014

Amazing resource for housesitting. I am going to take it slow this year :)

Ann Coughlan

Saturday 4th of January 2014

Hello, I've just come across your stuff on housesitting. Informative. Thank you! I have two questions: 1. Do you see many options that do not involve the care of animals. (It's not that I don't like animals but unfortunately I'm allergic!!) 2. Do you think it's an option for solo travellers? Maybe you've answered these questions in your guide. If so, apologies. I'm bookmarking your site and will come back to explore further. Regards, Ann (Ireland)

Sunday 5th of January 2014

Thanks, Ann! As for your questions: About 80 per cent of the housesitting ads involve pet care. We've only had 1 housesit without pet care (in Canada) but I have to say that we're usually looking for sits with pet care involved. Most of the major housesitting websites have a filter though that let you search specifically for gigs without pet care. As for solo travelers - YES, absolutely! Most housesitters are actually solo housesitters. We're sharing some tips on how to make the most of a housesit (esp. when you're by yourself) here. Our fellow nomad Nora, the Professional Hobo, has done a lot of solo housesits - you can check out some of her articles on that here.