House Sitting Kaupo
Find a loving dog sitter to watch your dog overnight in your home.
Kaupo, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Thank you so much for taking care of my cats while I was away! I really appreciate your time, effort, and responsiveness throughout the booking. It gave me great peace of mind knowing someone was there to check in on them. Thanks again for your help!”
“5 stars! We have a high maintenance border collie and an anxious rescue pointer-mix. They bonded with Johnathan who sent daily photos of walks, frisbee, etc. Johnathan telecommutes so he could work while house sitting and hanging out with our dogs, which is what they're used to. Highly recommend; friendly, reliable, and responsible.”
“Chris took wonderful care of my puppy, May! She kept in close contact with me and answered all of my questions while I was gone at work. I greatly appreciate Chris and I'll definitely be contacting her again for her awesome service! May was a happy pup when I got home :)”
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 understand how much love and care they need while you're away. I do have a 9 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 11 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
“Angie was an absolute dream for us! She stayed and watched our 2 cats and 4 month old puppy while we were away for almost a week. She kept us updated daily on all 3 of our fur babies with detailed recaps and tons of pictures. It made this worried fur mama feel so at ease about being away from our pets. Angie left not only our pets perfectly spoiled and happy, but she even left our home in pristine condition. Not to mention she is such a sweet person. Highly recommend Angie to anyone and everyone. We will definitely request her again!”
About: I’ve spent my life around dogs, from raising my own senior pup to pet-sitting for friends and neighbors. I’m comfortable with everything from high-energy dogs to gentle senior care, including administering oral medications. I also use a patient training method for dogs that pull on the leash, and I always keep things clean—whether that's wiping muddy paws or keeping their play area tidy! My schedule is highly flexible! Since my daily routine already revolves around caring for my dog, Lily, I can easily fit in your pet's needs. For house-sitting, I can bring Lily along as a built-in playmate. If you prefer solo walks or drop-in visits, I’ll gladly leave her at home to give your pet my undivided attention I have a fully fenced yard for safe playtime and a friendly 12-year-old dog who gets along great with other pups. Plus, having lived on Maui for 16 years, I know all the best quiet trails, parks, and safe outdoor spots to take your dog for some fun adventures
About: Hi there, I’m Brooklen! Animals have always been a huge part of my life, and caring for them comes as naturally to me as caring for people. With years of experience as both a veterinary technician and pet sitter, I bring not only love and compassion but also the skills to keep pets safe, comfortable, and happy. Whether it’s walks, belly rubs, medication administration, or simply keeping your furry family member company, I approach every pet as if they were my own. I understand how important it is to have peace of mind while you’re away, so I make communication a priority—sending updates, photos, and little stories from our time together. From energetic pups who need adventure to senior pets who need gentle patience, I adapt my care to each animal’s unique personality and needs. Your pets deserve someone who’s reliable, responsible, and genuinely devoted to their well-being—I’d love to be that person for you. 🐾 I work part-time and home fairly early in the afternoon. I have some freedom with my schedule and am eager to plan around your pup/kits schedule. Whether your pet is staying with me or I’m caring for them in your home, my goal is to keep them safe, comfortable, and loved—just like family. 🏡 In My Home: I create a cozy, pet-friendly space where your furry friend can relax and feel secure. I follow their normal feeding, potty, and exercise routines so they feel right at home. Fresh water is always available, and I provide plenty of toys, walks, and snuggles to keep them happy and engaged. Safety is a top priority, so I make sure all hazards are out of reach and each pet has their own comfortable spot to rest. 🚗 In Your Home: I respect your space while giving your pet the care and attention they deserve. I’ll follow your instructions carefully—from feeding and walks to medications and house rules. I also keep your home secure, tidy up after meals or litter changes, and make sure your pet feels loved with playtime and companionship. 📸 Communication: You’ll always feel connected while you’re away! I send regular updates with photos and notes so you know how your pet is doing. My goal is for you to have total peace of mind, knowing your pet is happy, healthy, and cared for.
“Natalie is a amazing! I have an extremely high maintenance, elderly, not always friendly, sassy bulldog who is about as stubborn as they come. Natalie adhered to all of my many requests and suggestions about how to best handle Lana as well she went above and beyond by watering all of my plants (both indoor and outdoor) AND I returned to a house cleaner than I had left it!! Not to mention she texted with photos, videos, and updates daily to put my mind at ease. It was such an Incredible experience that I immediately booked her again. Such a relief to have a competent sitter close to home!”
About: I've been surrounded by animals all of my life, with a wild assortment of pets including dogs, cats, horses, goats, pigeons, an African Grey, hamsters, rats, chickens, and even an iguana! I grew up in the Midwest with parents who were talented breeders and trainers of German Shorthaired Pointers and Vizslas, as well as master gardeners. In my adult life I've lived with dogs, cats, and chickens, though currently have no pets of my own as I travel too much to provide consistent care. I am seeking longer in-home sits (1+ weeks) and am available to chat ahead of booking. I'm a semi-retired professional, and very much appreciating the flexibility therein! I am mainly interested in longer-term, in-home sits, and offer discounts depending on length of stay, number/ages/types of animals, and if use of car is included. The care I provide varies depending on the needs your animals! The flexibility of my schedule allows me to easily adapt to yours, making transition into caring for your pets as seamless as possible.
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.
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.
The median cost per night for house sitting in Kaupo is $65
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local sitters who will treat your pets like family
1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for house sitting - Kaupo
Select a filter and find qualifying sitters offering house sitting.Sitters in Kaupo average 2 repeat house sitting clients
FAQs for House Sitting - Kaupo
Frequently asked questions about Rover
As of October 2026, there are 131 sitters on Rover offering House Sitting across Kaupo. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Kaupo walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Kaupo maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
<b>Tip:</b> Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Kaupo choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to 25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to 25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet .
sitters on Rover set their own cancellation policy , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Kaupo. On Rover:
- 95% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 100% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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.
Connect anywhere with the Rover app
