How to do Housesitting in Hawaii and Get Free Accommodations

Anyone who has traveled to Hawaii knows how special this part of the US is—and how expensive it is. That is what makes housesitting in Hawaii so wonderful. You get to experience island paradise without having to pay for somewhere to stay, and sometimes you even get paid for doing it!

Over the past year my husband Josh and I have completed six housesits with TrustedHousesitters, and our most recent was on the island of Oahu, Hawaii.

We started housesitting initially to save money during our year of digital nomading (and searching for a home base). We always worked remotely while caring for pets while housesitting, but we decided to take time off in Hawaii and treat it as a vacation. We weren’t sure if it would really feel like a vacation since we’d still have responsibilities, but actually turned out to be our favorite vacation of all time.

We had such a great time during our Oahu housesit that we’ve decided to add a Hawaii housesit trip into our travel plans every single year.

If you’re curious about doing the same, you’ve come to the right place. In this guide to housesitting in Hawaii I cover everything you need to know about the topic—how housesitting works, how housesitting compares to normal vacations, and how to land the best Hawaii housesits.

Housesitting in Hawaii

How Housesitting in Hawaii Works

There are several types of housesitting opportunities available in Hawaii and elsewhere, including both paid and unpaid housesits.

Unpaid housesits are the most easy type of housesit to find if you don’t have personal connections in Hawaii, and its the type of housesitting I do in Hawaii. With an unpaid sit, you provide care for the owner’s home and pets in exchange for a free place to stay.

With most hotels costing a minimum of $200 a night in Hawaii and the lack of Airbnb options on the islands, being able to stay in an entire house for free is certainly appealing, even if you have to do some work in exchange.

Every single house is different, though. Some homes are small condos with very little room, while others are large mansions right on the beach.

Likewise, the requirements and responsibilities vary from sit to sit. Some home owners are looking for a sitter who will be able to stay at home with their pets throughout the day, while others may have no pets to look after.

So, depending on the type of sits you do, you might end up in a small condo with dogs that need to be taken out several times at day. Or you might end up in a beautiful five bedroom home with a cat that requires very little care. Who knows, you might even end up on a large property caring for farm animals!

The best platform for finding Hawaii housesits

While you can find Hawaii housesits through Facebook groups or personal connections, my personal favorite way is through TrustedHousesitters. Everyone on their online platform must go through a background check, and they have a review system similar to Airbnb so you can see what past sitters said about their experience.

You do have to pay an annual fee to join TrustedHousesitters (use this link to save 30% and check current prices), but the annual fee is comparable to the price of one night in a hotel in Hawaii. To me, joining TrustedHousesitters is absolutely worth it, as long as you end up using your membership and you understand what you’re getting yourself into as a sitter.

The membership fee covers the costs to operate the online platform and a background check, and it includes unlimited house sits for one year. Depending on the membership tier, the fee can also cover a 24/7 vet support line, insurance, and even airport lounge passes. The fee also weeds out both sitters and home owners who are not fully serious about using the platform.

My Experience Housesitting in Oahu, Hawaii

How much money I saved by housesitting in Hawaii

Most hotel rooms in Oahu cost a minimum of $200 a night, and have extra costs and parking fees as well. We stayed in a very basic hotel for $236 on our first night in Oahu, and paid $50 extra for parking. If we were to pay this everyday during our 8-night trip, we would paid paid $2288 for accommodations alone. And that is with a basic Waikiki hotel with no pool or special amenities.

Meanwhile, we got to stay seven nights in a five bedroom, three bathroom house that was located on the edge of a gorgeous nature preserve. It was a family house, so it felt like a home and we had everything we needed to cook food in their large kitchen.

My responsibilities as a pet sitter in Hawaii

While housesitting on Oahu, my husband and I watched two elderly dogs who were too old to go on walks. They had their own doggy door and were accustomed to staying at home for up to 11 hours a day while their owners were at work.

As sitters, we were encouraged to explore island during the day, but were responsible for feeding the dogs twice a day, refilling their water, and giving them plenty of love. We also watered a few plants and kept their house clean and safe.

Activities and excursions I did as a housesitter in Oahu

Although we could have left the dogs for longer, we were never gone for more than 6-8 hours a day, and we typically stayed at the house after sunset. We loved caring for these dogs and make sure they were not neglected. Even still, we were able to do so much on Oahu and never felt like our housesitting responsibilities got in our way of having fun. Some of our favorite Oahu activities included:

★ Visiting the Mermaid Caves on Oahu’s leeward side
★ Spending several days at Lanikai Beach (a ten minute drive from our housesit!)
★ Diving with sharks on the North Shore
★ Snorkeling with tropical fish at several beaches
★ Visiting the Byodo In Temple
★ Cliff jumping at the China Walls
★ Hiking the Lanikai Pillbox Trail at sunrise (its easy when you’re staying in the neighborhood!)
★ So much more… I cover many of the other activities we did in my other Oahu travel guides

How Housesitting is Different Than Normal Vacations

Of course it must be mentioned that you cannot show up to a Hawaii housesit expecting it to be an all inclusive resort.

Whether you use TrustedHousesitter or are a paid sitter, you’re providing a service for the home owner. Your number one priority must be to take care of their property and pets, even if that costs you the fun of a vacation.

You never know what could happen—the dog you’re watching could get sick and you might have to take them to the vet several times instead of going to the beach. The owner’s flight could be delayed and they might ask you to stay longer. Or worse, the owner might cancel their trip last minute, leaving you with nowhere to stay.

These circumstances are rare, but they can happen. You just have to remember that you are a service provider before you are a guest, and you have to be ready to do whatever needs to be done.

As long as your expectations are set properly, you’ll likely have a wonderful time housesitting in Hawaii. I know I did!

How to Visit Hawaii on a Budget by Housesitting

If you’re interested in traveling on a budget, housesitting in Hawaii is a great option, but you have to be careful not to spend too much on food and activities.

Nearly everything in Hawaii is expensive, but most of the best things to do in Hawaii are free. My favorite things to do always include beaches, hikes, snorkeling, and other free outdoor activities. Plus, many dog owners like to have housesitters take their dogs on hikes in the area. As long as you have transportation (some housesits include use of a car), you won’t run out of things to do!

It can be easy to spend a lot of money in Hawaii on food, so be sure to have your expectations set properly and plan ahead. Cooking your own meals will save you a lot, but groceries are expensive. You can ask the home owner about the best places to buy food in the area.

How to Land the Best Hawaii Housesits

You can certainly join TrustedHousesitters now (click here for 30% off) and apply to Hawaii housesits right away, but you will have a better chance of being invited to sit if you do a few things first.

First, make sure your profile is designed well. Include plenty of pictures that show who you are and ideally, your interactions with animals. When you share about why you want to do housesitting in Hawaii, focus on what you can offer the home owner, rather than what you want to get out of the situation. Think, why should they trust you out of all the other people with their home and their pets?

Next, I recommend doing some local housesits before applying to housesits out of state (in Hawaii). The truth is, housesitting in Hawaii is very competitive. Having a few positive reviews on your profile will go a long way. There are new housesits posted all the time, so apply to a few in your area and then get that experience (and review) under your belt.

Finally, I recommend turning on notifications for when new Hawaii housesits are posted. Only five people can apply at a time, so having your notifications on can help you apply fast enough and be one of the few whose applications actually go through.

TrustedHouseSitters Discount Code

If you’re new to TrustedHousesitters, use my discount link to save 25% off your membership.

Final Thoughts: Housesitting in Hawaii

Housesitting is a wonderful way to save money while traveling, while also meeting a genuine need in the community you’re visiting. Hawaii specifically is such a great place to housesit, since the cost of accommodations tends to be very high, but you can frequently find affordable flights from mainland US.

Of course, every house sit is completely unique and it is important to set the right expectations. However, if you have the ability, housesitting in Hawaii is certainly something I’d recommend to responsible, pet-loving travelers.