House Sitting in Kaanapali

Find a loving house sitter to watch over your pets and your home.

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Top rated Kaanapali 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: Kevin & Ashley L.
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Kevin & Ashley L.
from
$65
per night
5.0 out of 5 stars
13 reviews
5 repeat clients
16 years of experience
Lahaina, HI, 96761

We love Kevin & Ashley! Our pup is always nurtured with lots of attention and snuggles. He looks so happy in the pictures we receive. I'm confident leaving island for any amount of time when he's in Kevin & Ashley's hands. They're super flexible and respectful of our home as well. I look forward to having them housesit knowing our pup loves them so much.

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Brogan C.
Sitter Profile Image: Crystal A.
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Crystal A.
from
$60
per night
5.0 out of 5 stars
28 reviews
3 repeat clients
18 years of experience
Lahaina, HI, 96761

Crystal was an amazing dog sitter! She took great care of our 60 lb dog Sunny and our two cats. She sent us pictures each day, took Sunny for walks and took amazing care of our house while we were gone. We highly recommend her!

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Ryan M.
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

We got tons of pictures and updates from Johnathan and our pup was the most calm he has been after being away from us for a few days. Will definitely rebook!

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Kelli M.
Sitter Profile Image: Courtney C.
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Courtney C.
from
$30
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Kihei, HI, 96753

Courtney was amazing while I was away. She took great care of my pets and my home and sent me updates each day, which I really appreciated. Coming home was so nice, the house was all set and she even left me flowers. I felt at ease knowing everything was in good hands and will definitely be booking with her again in the future.

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Katelyn T.
Sitter Profile Image: Emma L.
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Emma L.
from
$60
per night
5.0 out of 5 stars
16 reviews
1 repeat client
15 years of experience
Lahaina, HI, 96761

About: I grew up with a dog and have watched many different types of dogs since I was a teenager. I routinely walk and feed my roommates dogs when they are at work. Walking dogs is a great way for me to get daily exercise too. I’m only working part time so I am available throughout the week and have a very flexible schedule right now. Especially in the afternoon and at night There is a fenced in backyard the dog can play in. There are also two other friendly dogs in the downstairs unit who love to play. The street i live on is a great dog walking street with a sidewalk.

Sitter Profile Image: Laurel S.
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Laurel S.
from
$40
per night
5.0 out of 5 stars
35 reviews
7 repeat clients
20 years of experience
Kihei, HI, 96753

About: Hi! My name is Laurel, but my friends call me Lolo. I have been caring for animals since I could walk. No, seriously, I have! I was blessed with the opportunity to grow up with all kinds of animals to care for daily. If you have grown up on a ranch or a farm, you know what I am talking about. We had two Australian Shepherds, horses, a donkey, barn cats, you name it! Those days sparked the passion I have for animals and taught me how to work my booty off. We were taught to NEVER leave the gate open, always clean up after ourselves (and the animals), and to show love to every living being. As an adult, I worked at multiple doggy daycares, adventured with some really amazing horses (and riders) at a Girl Scout camp in California, and have taken every opportunity I have found to spend time with animals. My dream is to one day open a ranch for rescue animals of all species and breeds. Until then, I am elated to be offering my pet care services to YOU and your furry friends (or scaly, I don't judge). Follow our Instagram to see what we are up to. I can't wait to hear from you! I can definitely handle young crazy puppies that jump, chew, pee everywhere, etc. as well as older (more fragile) dogs that need specialized care. I also have experience giving medications. I don't mind having dogs in my car and will happily bathe your dogs upon request. I am passionate about caring for all animals, especially dogs, and I am not intimidated easily! If you have other pets in your home, I will feed them and give them some love as well. I look forward to meeting your fur/feather/scaly babies and will treat them as they are my own! I work remotely Monday-Friday for a small company and I have a very flexible schedule. I can tailor my day to fit your pets needs, and I will be with them most of the day! **I absolutely update all of my clients with photos and updates! I give you my direct cell phone number so you can contact me at any time if you want to know how your babies are doing. Safety of your pet is my number one priority. I never leave your home until your dog is properly leashed and wearing protective footwear when necessary. Please understand that I will not be able to provide a dog walk without proper safety equipment such as a collar with updated tags, a secure leash, etc. I operate my own pet care business out of my home, caring for your pets IS my weekly routine. I have a very flexible schedule. Safety of your pet is my number one priority. I never leave your home until your dog is properly leashed and wearing protective footwear when necessary. Please understand that I will not be able to provide a dog walk without proper protection for their paw pads due to the high heat in the summer. My own house has multiple baby gates to ensure no dog escapes through any entry point as clients are coming and going. Our backyard is fenced and we keep a lock on our gate at all times. We have a shaded area for dogs to go potty even on the hottest of days and keep our AC set to 78 or lower at all times.

Sitter Profile Image: Jeiana l.
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Jeiana l.
from
$75
per night
5.0 out of 5 stars
1 review
7 years of experience
Wailuku, HI, 96793

About: From the time I was born, I always had an animal in the household. My love for taking care of my four legged fuzzy friends continued into high school, when I started volunteering at Assistance Dogs of Hawaii. One thing I learned from my experience volunteering is that I enjoy making a positive impact on pet and owner relationships. I’m currently working part time so I will have down time that I can spend caring for your animals. I am also taking a few online classes which makes my day to day very flexible! My care for your animal/s will be based on your needs as routines are different depending on your pet and home life. I am very diligent and detail oriented. I will be able to follow your directions and ensure that your pet gets lots of love!

Sitter Profile Image: Hanna B.
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Hanna B.
from
$30
per night
15 years of experience
Kihei, HI, 96753

About: I’ve been taking care of the dogs since my childhood. Neighbors and friends rely on my help . I have my own dog - 8 years old Pomeranian . I cook the best food for dogs and would love to share with you healthy recipes and tips . I will get to know your dog personality and help you with training . Please ask me any questions. I look forward to meet your furry friend and take good care of them . I’m currently working part-time, so my schedule is flexible and I will have plenty of time to take good care of your dog . I’m available during the week and weekends as well . Each service will be different . I can take your dog for a walk in your preferred neighborhood or bring him/her to West Boca. We have a beautiful lake here and all pet owners take their dogs for a walk here .

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: 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: 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: 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: Christin S.
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Christin S.
from
$100
per night
5.0 out of 5 stars
2 reviews
1 repeat client
20 years of experience
Kaanapali, HI, 96761

About: I grew up around animals my entire life. I had a loved fur family for 10 years before crossing the rainbow Bridge. I have a soft spot for animals and have pursued animal reiki, gifting those special members of our family with calm and presence. I have also assisted other animals in healing from traumatic events. Animals in my neighborhood always seem to come by and say hello. :) I work part time a little out of the house but most of the time I'm home to be with your loved fur animals. I love being outside so taking them for walks fits perfectly! I make sure to love on your animals like they were my own. I respect your rules if they are not allowed on your furniture they will not be allowed on mine. I know how important consistency is to them so I stick to your routine as much as I can.

Sitter Profile Image: Jessica W.
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Jessica W.
from
$90
per night
5.0 out of 5 stars
4 reviews
18 years of experience
Lahaina, HI, 96761

Jessica took care of my mini-zoo while I was visiting family on the mainland. I had booked an aggressive travel schedule, visiting family in both east coast and west coast time zones. Jessica not only took exceptional care of my 2 large dogs and my 2 persnickety felines, but she also took great care to make sure I knew all was well back home. I never had to ask. Thank you Jessica! See you next time.

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Danny M.
Sitter Profile Image: Gail F.
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Gail F.
from
$100
per night
30 years of experience
Lahaina, HI, 96761

About: Aloha, I believe that our fur babies our genuinely part of the family. I was the kid that always managed to find the strays and bring them home...I still do:) My pup passed away last year. he was my constant companion for 11 years. I am now the mom of a very spicy kitty. I have done many walks and overnight stays for friends and family. I truly love being around all animals and look forward to meeting your fur baby! oh, I also enjoy the not so fury creatures...lizards, tortoise, fish!! I am fortunate to have a flexible schedule. I am available for drop in walks, sit ins to keep your pet company, overnight or extend stays. Because of my kitty, I would have to know your pet is cat friendly if needing to come to my space. If taking care of your pet in your space I can assure that they will be happy and safe.

Sitter Profile Image: Megan G.
Verified Enhanced Background Check
Megan G.
Star Sitter
from
$125
per night
5.0 out of 5 stars
159 reviews
14 repeat clients
20 years of experience
Kahului, HI, 96732

About: I have been a Rover sitter and dog walker since 2023 and have always had a lifelong love for all animals. Growing up on a farm in rural Nebraska, I was responsible for horses, cattle, pigs, chickens, goats, cats, dogs, and even fish. This hands-on experience honed my understanding of different pet needs and personalities. My cat, Milly, has been a part of my family for 9 years and counting. I have worked at a vet clinic and interned at the California Wildlife Center, which gave me veterinary medical knowledge and skills. I am comfortable with medication administration and special diets. With 20+ years of pet care experience, I'm dedicated to ensuring your fur family receives the utmost care and attention they deserve! I'm thrilled to offer my flexible availability to cater to your pet's needs! I am available on weekdays in the mornings and afternoons, and can schedule for midday as well depending on your location. Most weekends I am available to schedule for any time that suits you best. Based on the pet parent’s guidance, I tailor my care approach to match their pet’s personalities and preferences. I have experience working in veterinary medicine and can help administer any medications or give special diets. Safety, happiness, and well-being are my top priorities.

Sitter Profile Image: Laura N.
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Laura N.
from
$70
per night
5.0 out of 5 stars
8 reviews
3 repeat clients
10 years of experience
Kihei, HI, 96753

About: I’ve had two amazing dogs and cats in my lifetime, volunteered at an animal shelter since I was 13, and researched canine cognition at Duke University! I was also prevet in college, worked with many dogs and pups, and have experience training service puppies. I have most weekends off with occasional weekdays off from my full time job. Happy to house sit or dog walk outside of my work hours and commute! I have been a pet sitter for many people over the years and I’m extremely responsible, attentive, and comfortable around dogs and cats. I’ve had two dogs and two cats of my own and worked training service puppies in my free time. Very active and love being outside will give your pets lots of love and attention while you’re away!

Sitter Profile Image: Lauren K.
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Lauren K.
from
$100
per night
5 years of experience
Roseville, Lahaina, HI, 96761

About: Hi I'm Kam (a nickname)! I live in Point Loma but I’m originally from NH. I've lived here for about seven years. I had multiple dogs growing up and I’ve been an easy option for friends/acquaintances to help with their pets. I lost my Labrador in October (due to natural causes) and I’m not quite ready to take the leap again so this is the best of both worlds. I have worked with a professional pet sitting company in Summit County Colorado. I have been in property management/house sitting so I say I wear many hats! I’m comfortable with many breeds, ages, and sizes. Looking forward to helping you, your pet, and selfishly me too! I work in retail, so I don't have long hours. I’m typically up around 6/7 and in bed around 10/11. I also enjoy exercise and walks Safety and comfortability is of the utmost importance to me. I know each pet and home can come with certain quirks and/or specifications, which is totally understandable. Happy to accommodate!

Sitter Profile Image: Bryce R.
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Bryce R.
from
$70
per night
4.9 out of 5 stars
16 reviews
5 repeat clients
6 years of experience
Kihei, HI, 96753

About: I’ve always had a passion for dogs and recently loss my chocolate lab who lived 14 years. I do still have a 9 year old black lab who needs a playmate during the day. I’ve worked at the Boise zoo for 5 years and have experience in administering medicine. Im currently a full time BSU student and since most of my classes are online, I’m home all day to take care of dogs full time. I have a fenced in yard and I’m walking distance from several dog parks. I have a very friendly black Female lab who would love to have a playmate during the day. I’m a big guy (6’4”)so I can walk 3-4 dogs on a walk. Currently unemployed and looking for jobs in Kihei, Hawaii for now until I find either walk or until I figure out something just let me know and I’ll be there in a jiffy. I talk with the client and make sure to either give them a choice of daily or every other day updates on the dogs progress/mood if anything is out of the norm I will contact them immediately

Sitter Profile Image: Hideko A.
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Hideko A.
from
$100
per night
5.0 out of 5 stars
2 reviews
1 repeat client
16 years of experience
Lahaina, HI, 96761

About: Hello, my name is Hideko, thanks for checking my profile. After losing my beloved 16 year old lab mixed girl recently, I miss being around dogs. I used to have two cats too. It will be my honor to take care of your animal family and I will be doing it out of love. I'm here in Maui from San Francisco for several months while working remotely. I work in odd time zones so I have flexible schedule. I'm trusting, responsible, good communicator and will send pictures of your pets while sitting. I can also look after your plants and am available for house sitting too. I am fully vaccinated and practice covid safe protocol. Contact me with any questions. Looking forward to hearing from you.

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Kaanapali pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Crystal is fantastic! She is super responsive and felt so comfortable with her watching our 2 dogs. She sent us photos of our pups everyday and took them on walks. Definitely going to use her again.

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Robyn H.
House Sitting
5.0 out of 5 stars

Crystal was awesome, took excellent care of our pup and provided great updates and pictures every day.

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Tim N.
House Sitting
5.0 out of 5 stars

We love Kevin & Ashley! Our pup is always nurtured with lots of attention and snuggles. He looks so happy in the pictures we receive. I'm confident leaving island for any amount of time when he's in Kevin & Ashley's hands. They're super flexible and respectful of our home as well. I look forward to having them housesit knowing our pup loves them so much.

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Brogan C.
House Sitting
5.0 out of 5 stars

Kevin and Ashley are fantastic! We brought our dachshund out on vacation with us and he started to have an ivdd flare up unfortunately which requires meds and strict rest. Kevin came to keep him company and hang in our apartment with Benny while we went out on our last night out here. Kevin gave him lots of love and ensure he was safe and well taken care of! We are super thankful we got to enjoy our last evening here!

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Savannah K.
House Sitting
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  1. 1. Search

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  2. 2. Meet & Greet

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

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

Sitters in Kaanapali 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 Kaanapali 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 Kaanapali 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 158 house sitters in Kaanapali. 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, 85% of Kaanapali house sitters respond in under an hour.

House sitters in Kaanapali have an average of 17 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 Kaanapali.

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. Kaanapali 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.