House Sitting in Kaupo

Find a loving dog sitter to watch your dog overnight in your home.

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Top rated Kaupo house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Crystal B.
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Crystal B.
from
$50
per night
22 years of experience
Makena, HI, 96753

About: I have cared for many animals over the years horses dogs cats goats fish racoon turtle rabbits. I am an animal lover! And they love me also! Open to about any situation and any time. It is all negotiable. I am very flexible and easy going. I prefer ocean settings or very natural settings I do love exploring the ocean and nature. And walking alot so I can offer plenty of activities if your pet is up to it. I am also a Rieki master so I can provide healing emotional and enetgentically for animals, people and environments.

Sitter Profile Image: Grace B.
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Grace B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
20 reviews
2 repeat clients
20 years of experience
Pukalani, HI, 96768

About: I'm a 43-year-old woman who is a full-time pet care and home care provider. About 10 years ago I made the decision to leave professional kitchens in search of a more fulfilling lifestyle. I chose to follow my heart and my dreams of traveling the world. I have a Bachelor's degree in Psychology, a Professional Culinary Degree from NYC and a TEFL certification from Bangkok. I set up my life to be able to go anywhere and do anything! I have been traveling full-time for the last 10 years as a pet sitter, but have over 20 years of experience as a pet sitter and dog walker. I have recently done long-term sits in Ecuador, Peru, Mexico, and Maui. I have an enormous amount of pet care experience. It ranges from dogs and cats to tropical birds and even a few axolotls! I have a lot of experience with geriatric and end-of-life pet care as well. You can see even more references from past homeowners and pet owners on my website, just search Grace's Buddies. You can be assured, that not only will I treat your pets like my own, but I will spoil them with love and affection. It's my passion. I currently work from home part-time, so I have plenty of time to play and exercise your pets! Your pets will get one-of-a-kind care and tons of hugs and kisses! I will always keep your dog on a lead. Even if you, as the dog owner, have them off of a lead, I will keep them on a lead because of other unknown dog interactions and it is my utmost responsibility to make sure your animals are safe and unharmed in my care.

Sitter Profile Image: Johnathan W.
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Johnathan W.
from
$58
per night
5.0 out of 5 stars
46 reviews
19 repeat clients
35 years of experience
Wailuku, HI, 96793

Jonathan was really great! Punctual, reliable and very communicative. You can tell he really loves and cares for the pets he watches. He sent lots of pictures of our dog every day, which we very much appreciated. Would love to use him again in the future.

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Tia P.
Sitter Profile Image: Nicole B.
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Nicole B.
from
$70
per night
5.0 out of 5 stars
4 reviews
1 repeat client
10 years of experience
Makawao, HI, 96768

About: Aloha :) My dogs and I would love to have your dog stay at our house in Olinda! We have a fenced yard and a few (partially fenced) acres of land beyond that for the pups to play and fetch the ball (depending on your comfort level with that, of course). Delilah is a sweet 4 year old golden retriever who loves equally to play and chill. Bear is a 2 year old golden Aussie who *always* loves to play and love on other pups! We live 10 minutes from both Olinda forest and Makawao forest so we usually go for morning walks there 4-5 days week. We would love to bring your pup along with us! I work from home during the day. I’m never gone for more than a 5-6 hour time frame at a time and on top of that, we have a doggy door for the dogs to go in and out freely in our fenced yard. I have a fenced yard for the dogs to hang out in and a few acres beyond that (partially fenced) for them to run around and get their energy out in. I’m always watching the dogs when they are beyond the fully fenced yard. I will also make sure you are comfortable with your dog in this situation before doing so.

Sitter Profile Image: Madilyn V.
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Madilyn V.
from
$85
per night
4.9 out of 5 stars
25 reviews
15 repeat clients
25 years of experience
Haiku, HI, 96708

About: I am a dog fanatic, they are very special to me. I have had many dogs growing up of all breeds and sizes. I will love them whole heartedly, I have a 2 year old furry baby and I understand how much love and care they need while you're away. I do have a 5 year old who is dog crazy as well, he has lived with dogs of all sizes and personalities. Animals have a very special place in my heart (especially dogs) and I would love to be the one to take care of your special friend. I know the importance of trust with your loved ones. I would like to bring good energy into you and your pets life with a whole lot of love. Mahalo I am flexible, I don't mind traveling around the island to take care of animals. I have been fortunate to work with animals all over Maui for the last 10 years. I am very open to any specific instructions your special friend will need; first timers, allergies, high energy, separation anxiety and any extra care your pet may need

Sitter Profile Image: Giovanna A.
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Giovanna A.
from
$50
per night
5.0 out of 5 stars
1 review
3 years of experience
Haiku-Pauwela, HI, 96708

About: So you just have to find help caring for your furry friend, and unsure who to trust? I get it! I’ve been in your shoes and it’s not easy, bios and reviews can only reveal so much. I can assure you, boarding will be a breeeze, with pick up and drop off available. I’ll send pic and updates to your hearts content. Basic training daily to reinforce positive behavior. If you choose, and is appropriate for your pets current health, visits to giggle hill / pukalani park, iao river and beach are the norm in our home. Miki, my fur baby is 1.5 years old and is very sweet and friendly. Bath and nail filling for maintenance available for extended stays and needed. Feel free to reach out for a meet up and plan ahead. Not need wait for emergency to happen, I’m here to become an extension of your pets care and comfort. I work from home most of the time, and travel for work all over the island. When going on errands I take Miki with me, and your pet, if allowed by you, can join us into town. Miki is on a leash outside as fenced yard cutter has some pukas. Indoor she’s free to roam, and is crate trained. You can expect your pet to have 24/7 care most of the time or be in crate 1-2 hours if needed, or up to 4 hrs when I’m working. I have a big yard and your pet will be on a leash when outdoors.

Sitter Profile Image: Carl & Shayele B.
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Carl & Shayele B.
from
$75
per night
15 years of experience
Haiku, HI, 96708

About: Hi there! We’re Shayele and Carl — a pet-loving couple who truly understand that animals are family. Between us, we have two amazing dogs of our own: a playful 3-year-old Boston Terrier and a sweet 13-year-old Cavalier King Charles mix who’s taught us the art of gentle, patient care for senior pets. Shayele works hands-on with animals every day at a local farm, caring for everything from donkeys and alpacas to goats, sheep, cows, chickens, and horses. From feeding to administering medications, you can trust that your pets are in experienced, capable hands. Carl brings a calm, steady presence and a big heart for animals of all kinds. Together, we’re reliable, responsible, and genuinely love spending time with furry (and sometimes feathered!) friends. Whether your pet needs a fun walk, some cuddle time, or consistent, compassionate care while you’re away, we’ll make sure they feel safe, loved, and right at home. 🐶 Reliable. Caring. Animal-loving. Always treating your pets like our own. 🐾 Pet care is a big part of our daily routine. Our schedule is flexible, and someone is usually home to watch the dogs. On the rare occasion we can t be home, we re happy to work with owners to meet each pet s specific needs. We love taking dogs along on outings and make sure they get plenty of attention, exercise, and companionship throughout the day. "We live in a safe, gated community with a large yard and a spacious field behind our house, perfect for pets to run, explore, and play under supervision. Inside, pets enjoy plenty of cuddle time on the couch, interactive toy play, and attention from us throughout the day. Our dogs often accompany us on walks, to the park, or on other adventures, helping your furry family member feel included and socialized. We carefully follow all instructions, including administering medications and accommodating any special care or routines your pet may require, ensuring they are safe, happy, and loved while in our care."

Sitter Profile Image: Natalie G.
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Natalie G.
from
$150
per night
5.0 out of 5 stars
47 reviews
12 repeat clients
26 years of experience
Wailuku, HI, 96793

Natalie watched our two pups while we were out of town for our wedding. Having a 6 month old puppy as well as a 4 year old dog was no easy feat, but we could not have been happier with their care! While we were busy with wedding events, Natalie was amazing at updating us and sending daily pictures and report cards. We came home to a clean house and happy dogs! Can’t wait to have her back:)

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Amanda R.
Sitter Profile Image: Jennifer A.
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Jennifer A.
from
$133
per night
5.0 out of 5 stars
12 reviews
2 repeat clients
44 years of experience
Wailuku, HI, 96793

Jennifer was so wonderful with our Harry. We were so apprehensive about leaving him for our European vacation for 10 days, but right from the start we received updates and pictures of how he was doing. She was so very patient and kind with him, taking him for walks on a regular basis, and attending to his needs for reassurance. We would not have enjoyed our trip if not for Jennifer's care of our Harry. She also took care of the house and left it clean as when we left it. Would definitely recommend Jennifer to anyone and plan to call upon her services in the future.

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Audrey B.
Sitter Profile Image: Maiya D.
Verified Enhanced Background Check
Maiya D.
from
$15
per night
1 year of experience
Makawao, HI, 96768

About: In the past I volunteered at Maui Humane Society. That experience has taught me skills in animal care, responsibility and taking on challenges in a fast paced environment. I’m currently working full time my work hours are 7:45am - 4:30pm. I would love to be able to walk dogs after work and/or pet sit if needed. I currently do not own any pets of my own has they are not allowed where I live. I always follow the instructions left for me by the owner of the pet to ensure that the animals schedule doesn’t change causing them any stress.

Sitter Profile Image: Sofia R.
Verified Enhanced Background Check
Sofia R.
from
$30
per night
5.0 out of 5 stars
2 reviews
10 years of experience
Wailuku, HI, 96793

Sofia was great with our girls. The girls really enjoyed her company and were taken care of. She stayed in our home and left it clean so when we returned all we had to do was relax from our trip. We will rebook with Sofia without hesitation.

Profile image
Jack V.
Sitter Profile Image: Elishia D.
Verified Enhanced Background Check
Elishia D.
from
$15
per night
5.0 out of 5 stars
3 reviews
3 repeat clients
12 years of experience
Kihei, HI, 96790

About: Hi there! My name is Elishia and I am a Veterinarian from Australia! Before I moved to Oahu I had my own full time dog walking/pet sitting business for the last 6 years. I have plenty of experience looking after pets, dog walking and providing the best care possible for your pooch! Animals have always played such a huge role in my life from a very young age which led me to study Veterinary Medicine. I am currently working as a vet in a small GP clinic and really enjoying it! I am confident with a large variety of breeds and medical needs. I am currently on holiday for the next 2 months prior to starting work so I have full availability. From there I work 4 days a week so will continue dog walking on my days off. I have a large amount of experience dog walking and very comfortable with all sizes and breeds. I have a vast knowledge and education regarding pet behavior and medical needs and can easily recognise symptoms of illness or know when something is wrong.

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  2. 2. Meet & Greet

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  3. 3. Book & Pay

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The median cost per night for house sitting in Kaupo is $65

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  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Kaupo average 2
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Kaupo on Rover as of Jun 2026 was about $65 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Kaupo house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 112 house sitters in Kaupo. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 88% of Kaupo house sitters respond in under an hour.

House sitters in Kaupo have an average of 15 years of experience. House sitters with repeat customers have an average of 2 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Kaupo.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Kaupo house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Kaupo house sitting needs. On Rover, it's easy to find a loving dog sitter in Kaupo who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Kaupo house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Kaupo for your dog — people who'll treat him like family.

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