5 Luxurious House Sits That Transformed Our Travels

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House sitting changed our lives. Ever since the very first sit we did on the tiny Caribbean Island of Grenada back in 2014, we’ve always been amazed at how luxurious some of these homes are and we still pinch ourselves that we not only stayed for free, but in some cases, were sometimes even paid to house sit.

I really can’t stress enough just how perfect I think house sitting is for people who want to travel more, who want to stop wasting money on expensive accommodation, or those who travel so much that they can’t have a pet in their normal lives.

The latter is us, and over the years we’ve made some amazing friends (both human and animal!) around the world thanks to house sitting.

In this article, I’m going to share the 5 most amazing, luxurious house sits we’ve had all around the world. Keep reading until the end because we’re going to show you how you can land a dream house sit for yourself.

SEE ALSO: 8 Expert Tips for Landing a House Sitting Job

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Our Top 5 Most Luxurious House Sits

Let’s get into this list. While we’ve done many sits around the world, and even had to turn down quite a few, these are some of the most stunning homes we’ve had the opportunity to stay in around the world thanks to house sitting.

1. A Beautiful House in Barbados

remote work visa countries living in barbados

This was the third house sit we landed from our favorite house sitting website, Trusted Housesitters.

The owner of this lovely home in paradise had 2 big golden retrievers named Honey and Hesus and she actually contacted us when she saw our profile on the site.

Hesus & Honey

We had a quick interview with her on Skype, which is a standard part of the procedure before getting hired for any sit, and within a couple of months, we were in Barbados with Hesus and Honey where we’d be living for 6 weeks over Chrismas and New Years!

The owner left us with her car for the entire time and we spent our days driving around the island, laying on beautiful white sand beaches, working at local cafes, and walking Hesus and Honey through sugarcane fields. It was a blast.

2. A Jungle House in Costa Rica

house sitting in costa rica

This was a really serendipitous one. We had just started house sitting about a year before this and our good friends knew we were house sitting because we were posting about it on our social media.

They reached out to us and asked us if we wanted to watch their beautiful jungle house and their little puppy, Jack, while they were away on vacation for a few weeks.

They were already on the same house sitting website that we always use, so we had them hire us through the platform so that we could get an official review from them, and within a couple of weeks, we were in Costa Rica hanging out with Jack and watching their house.

waterfall in costa rica

They lived right in the jungle, so aside from one tarantula that we saw on the day we arrived, we spent the time enjoying nature surrounded by wildlife that we loved.

Our morning coffees were spent spotting toucans and monkeys in the treetops just off the back patio, and we would walk Jack twice a day to a beautiful waterfall that was just a few kilometers from their property.

They also left us with a motorbike while we were there. Every house sit we’ve ever done has given us a vehicle to use for free while we are sitting, and this was the first one to only give us a motorbike. 

pet sitting in costa rica
Us heading out for a day on the bike with Jack!

It was a lot of fun ripping around on the bike and exploring the nearby beaches and surfing villages up and down the west coast of Costa Rica.

It was extra fun when we took Jack with us. While he may have been a puppy when we first accepted the job, he grew extremely quickly while his mom and dad were away. It was clear that he had outgrown the motorbike, especially with three of us, and groceries, trying to fit on the little bike.

3. Stunning Beach Huts in Grenada

This was the first house sit we ever did and it is still one of our favorite places in the world.

We had just created our profile, uploaded some photos, and had some character references from our friends, family, and colleagues on our account. Within a couple of weeks, a kind woman and her husband who are still our very close friends to this day, invited us to come and take care of their beloved dog named Spare.

pet sitting and house sitting

Sometimes in life, you have these moments where you just have to pinch yourself and ask if what’s happening is actually real, and this is how we felt when we checked in to this gorgeous beach bungalow in the Caribbean.

First of all, the owners were the loveliest people you could meet, but what made this sit even more amazing is that there wasn’t even a house to mind… just the coolest little dog in the world.

pet sitting in grenada
The diving dog, Spare. So many adventures with this sweet boy.

The “sit” was on a rustic luxury beach resort which comprised of 5 bungalows that sat on a perfectly manicured property right on the beach.

Each of these little bungalows was once rented out at over 250 GBP per night … and this was 7 years ago so it would likely be well over 500 today (around $600/night). 

The owners had since shut the place down to the public, so aside from a few “in the know” guests who came and went for a week or so, we had the entire place to ourselves.

Because it was once a resort, we still had a weekly cleaning from the housekeeper who lived on the property, there was security there and a landscaper who became a friend of ours, and who kept the place tidy while the owners were away.

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Working on The Beautiful Property

These are some of the chores that would typically be left to the house sitters during a house sit. But on this one, they were all taken care of. All we had to do was look after Spare Dog.… for around 6 months.

That’s right, the owners were gone for about 6 months every year. They left us with not just one, but two vehicles to use for the entire time and they introduced us to a lot of their friends around the island, which meant we instantly felt like locals.

sailing in grenada as a digital nomad

As this was our first pet sit ever, we just couldn’t believe how lucky we were.

But what honestly made this sit one of the best experiences in our lives was that it introduced us to Spare Dog. Spare showed us around the island on this sit and for the next 5 years we kept returning to Grenada until the little guy passed away in 2019.

Spare Dog will be loved and missed

While I might be mentioning quite a bit about how wonderful the accommodations have been, the best part of house sitting is when you get to have a pet, and as far as pets go, Spare Dog was one of the most special little guys you could ever ask for. Rest in peace little buddy.

4. A Huge House on a Cliff in Grenada

Spare Dog’s owners introduced us to their friends around the island, and this sit was thanks to them as we met the owner through friends of their friends – it’s all about who you meet!

This house was perched on a cliff overlooking the sea in Grenada and it was so beautiful, we had a hard time leaving. We would spend our mornings having coffee and watching the sun come up behind us, and in the evenings, we’d make a cocktail and watch as the sun dipped into the sea right in front of us.

The pooches here were Pumpkin and Macy, and our tasks were to walk them once or twice a day, keep them fed, and give them lots of love.

living in grenada

As with our previous house sit in Grenada, there was staff on property for a few hours during the week – a housekeeper, landscaper, and pool keeper. The owner left us with her brand-new Subaru SUV, which we used to explore the island. Like with all of our sits, we became close with the owner and she introduced us to some of her friends. 

She also paid us pretty well for this pet sit. It was something we weren’t expecting at all, so when she handed us an envelope full of cash after we had just stayed in her house for the past 3 months, we were blown away and incredibly grateful.

5. A Luxury Villa With an Infinity Pool in Grenada

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You’ll notice that these last 3 sits are all in Grenada. For one, we fell in love with the island and we didn’t want to leave, but also something happened to us that I feel happens (or can happen) to many house sitters.

Once you get one house sit in a place you love, the owner of that first place will ask you to return year after year. On top of that, they introduce you to your friends who also want house sitters, and then you meet other people who are looking for sitters.

Whether you’re on a tropical Caribbean island, or a cool city 30 minutes from your hometown, there always seems to be an endless stream of house sits coming up once you get started.

That’s how we found this sit. The owners were friends we had met through other friends on the island and we had already been at their house a couple of times for catered parties that they would throw during US Independence Day and New Year’s.

money saving tips on accommodation
What a view!! this is one of our favourite homes, anywhere

This house is so luxurious that it could probably rent for $4,000 per night if it was on Airbnb or something. But the owners are super kind and generous people who were just so excited to have us take care of their adorable pups Winslow and Mia.

They gave us a list of things to do for the dogs, which mostly included how to feed them, medications to take, etc, and they asked that we walk them near the house once per day. Having an itemized list makes remembering daily tasks much easier.

luxury pet sitting and house sitting with two dogs
Good morning! We’re ready for breakfast please!

This home didn’t have a housekeeper, but there were two groundskeepers on staff. They left us with their new SUV again and set us up in their guest unit, which is like a villa in itself.

This house is perched on a cliff and the infinity pool looks over the sea. There’s always a perfect breeze running through the house and the open kitchen.

That’s what made this sit so perfect for us at the time. Dariece and I had just decided that we wanted to start eating healthy and we were talking about how amazing it would be to have a modern kitchen.

living in grenada as a digital nomad
A massive fridge full of healthy food in Grenada

Well, the kitchen at this house is like a professional kitchen that you’d find in a top Michelin-star restaurant. The owners had every kitchen appliance and gadget you could think of and we’d cook our healthy dinners while looking out at sunset over the Caribbean Sea.

Winslow and Mia took to us and because we spent so much time in the house, they loved having us around. We would work at a table on the deck overlooking the ocean and one of them would always be lying at our feet.

top new years resolution ideas start pet sitting and house sitting
Walking Mia and Winslow in the evening

To this day, we’re still close friends with Winslow and Mia’s parents, and we’d gladly return to take care of those two sweet pups.

How Did We Get House Sits?

Every one of these house sits was found on the same website. We used this site for years and ended up staying at beautiful accommodations with adorable pets all around the Caribbean and in Costa Rica…with offers that we turned down in places like Italy, New York, and Mexico.

luxury house sitting jobs in the caribbean
One of the luxury house sitting jobs we’ve had

Every one of our sits had a dog (or two), but there are some house sits on the platform that are just houses with no pets, or are cat sits, or horse sits, or goat sits… or even owl sits… seriously… one of our friends took care of an owl.

Obviously, you can choose which animals you’re comfortable with and also add that preference to your profile.

If you’re interested in getting house sits like the ones in this post, check the links below. We have a free resource to get you started in house sitting. It’ll show you the best house sitting sites to sign up for depending on where you live and where you want to house sit. 

Download Our House Sitting Roadmap (+20% Off)

Everything you need to land your first luxury house sit anywhere in the world. We’ll show you:

✓ How To Make Your Profile Irresistible
✓ On The Job Hacks To Get Hired Back
✓ How To Nail The Interview
✓ 20% Off The House Sitting Subscription

how to get a house sitting job and free accommodation

It also includes the exact methods we used to set up our profile, plus some example profiles for you to get inspiration from. If you don’t set up your profile properly, you’ll never get hired for sits. Our profile outline will ensure that you get offers from homeowners, and we also share on-the-job hacks to make sure the owners love you and will hire you year after year.

In Conclusion

Over the years, we have saved tens of thousands of dollars on accommodation costs thanks to house sitting. Our sits have ranged from a few days to 6 months at a time and we’ve made some amazing friends around the world, both furry and human, thanks to house sitting.

It has literally changed our lives and it allowed us to stay in lovely homes for free while we were just starting out with our digital nomad life

At that time, we had just started our blog and we were freelance writing to earn a living and having free accommodation made it easy to support ourselves while living in luxurious accommodations around the world.

If you want the same, we’d love to help. I hope you enjoyed this article. Make sure to click here for our free roadmap and discount code for house and pet sitting.

Nick Wharton Author Bio Picture

Written by

Nick Wharton

Nick is the co-founder, editor and author of Goats On The Road. He contributes to numerous other media sites regularly and shares his expert knowledge of travel, online entrepreneurship and blogging with the world whenever he can. He has been travelling and working abroad since 2008 and has more than 10 years of experience in online business, finance, travel and entrepreneurship.

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