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

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As many of you know, housesitting 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!

Housesitting
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 a housesitting experience 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:

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.

housesit Tuscany

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.

Housesit Santiago

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! 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!

Housesit Tucson

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:

Housesit Mexico

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 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

Housesit New York City

How to get started housesitting:

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.

We have a detailed listing of 20+ housesitting websites on our dedicated housesitting website UltimateHousesittingGuide.com, and recommend choosing a couple of sites that offer housesits in the region(s) you’re looking to housesit in.

Our top three housesitting membership websites are:

  1. Housecarers.com
  2. Trustedhousesitters.com
  3. Mindmyhouse.com

Read our tips on how to set up the perfect housesitting profile here and we share more tips on how to actually get chosen for a housesit here.

Housesitting
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, 2nd edition at special price!

We want you to start housesitting.

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.

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. Both the Kindle and the PDF have the 25% membership discount to TrustedHousesitters.com, one of the biggest housesitting websites. This makes both ebooks practically free, considering the discount is more $$ than the books, themselves!

You can download the colorful Break Free eBook directly right here for our special introductory price of only $8.99!

Find out more about Break Free – The Ultimate Guide To Housesitting.

Break Free 2.0

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Tags : Housesitting

33 Comments

    1. Megan, that would be awesome! Housesitting is the perfect way to travel slowly 🙂 And believe me, a furry companion makes the whole experience even better 😀

    1. Thanks, Sam! I hope you’ll be able to find some housesitting gigs in Europe next year – ours will be in North America (it’s confirmed now, yay!) 🙂

  1. I’ve just decided that housesitting might be worth looking into. I’ve always wanted to move abroad for a bit, and rentfree? Yes, please. Mandatory catcuddles are also not an issue for me 🙂

    1. Definitely something worth looking into 🙂 There are a ton of 3 to 6-month housesits in Spain and France, and in the U.S. – you’ll have to let us know if you end up giving housesitting a try!

  2. I have used The Caretaker Gazette to find rent-free living opportunities for decades, and have saved thousands of dollars on the rent I used to pay. I recommend the Gazette to anyone who can take care of homes as a housesitter or property caretaker.

    Sincerely. Karen Wright

  3. Love housesitting! Another perk is making friends with some of the homeowners. We’re going to Morocco in January to spend a month with one of our first housesitting clients who have become terrific friends. It’s funny that they have to get housesitters so they can go vacation with their housesitters. 🙂

    Can’t wait to get a look at your shiny updated book…what a great resource!
    Betsy Talbot recently posted..How We Found Paradise…and Then Got Kicked Out

    1. That’s amazing – vacationing with someone you housesat for!! Love it 🙂 That’s another thing we love about housesitting though: the people we get to meet! It’s usually very unlikely that our paths would’ve crossed had it not been for a housesitting assignment, but we made some great friends and are still in touch with most of the homeowners 🙂 Enjoy Morocco!

  4. Wow you’ve had some great house sitting experiences! We purchased your first book which has inspired us to pursue some house sits ourselves. We’re still waiting to land our first sit but we’ve made it to the top three applicants five times so we know we’re doing something right and I’m sure we’ll be celebrating our first soon! Thanks for all the great tips, looking forward to reading the second edition.

    1. Thanks, Sarah! That’s great news about making it in the top 3 applicants five times!! We’re keeping our fingers crossed for you that you’ll be able to land your first housesitting gig soon! Please let us know when it happens, we’d love to hear from you!

  5. It’s really fantastic tour but for me the best are your photos like a gallery. Sunshine in Mexico is absolutely
    outstanding. Only sunshines on polish seaside can compete with this… This is also my favourite region – polishseaside, one of the most beautifull in the world I’m sure. You can think about visitting polish beaches…

    1. Jeff – um, yes, we’re not the greatest people with plants but we’ve gotten better with every housesit, I think 🙂 We’ve looked after three houses with pools – it’s actually not uncommon! 🙂

  6. 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)
    Ann Coughlan recently posted..Welcome!

    1. 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.

    1. 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.

  7. 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

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