House Sitting Wailea Makena
Find a loving house sitter to watch over your pets and your home.
Wailea Makena, 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.
“Victoria is terrific! She took very good care of my pup and my home while I was out of town. She was very patient, caring and conscientious and she updated me daily with pictures and messages. It was reassuring know that my little bulldog was in good hands.”
“Casey took care of our pup while we were off island for a weekend; he even brought him his new favorite toy. Casey is very pleasant and we felt very comfortable with him after our meet and greet. He sent updates with pictures and left our place just as we left it. Our dog had a great time with him and we would definitely work with him again!”
“Jonathan was amazing! Very friendly, obviously loves and understands dogs, kept our place in great shape and our pets happy! The frequent photos helped us overcome our guilt and anxiety about leaving our elder, very attached pooch behind for a quick trip off island. Will definitely use him again and highly recommend to others!”
About: I've been an animal lover my whole life, caring for pets of all sizes and personalities. Living a plant-based lifestyle, I bring the same compassion to pets as I do to all animals. I'm available most of everyday, except if I have an appointment. I'll keep your pet healthy, happy, and loved. I treat your pet like my own! Let's connect! I'm available full-time, working remote so I'm always home with the pets. I'll have plenty of time to play, walks, and snug cuddles. I have a fenced yard, so pets can play safely outdoors. Since my dog's currently staying with my sister, your pet will get my full focus. I'll give them all the love and attention they deserve.
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 .
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!
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
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.
“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.”
About: I started off at a large animal vet hospital as a teen and since then I have taken care of coworkers' and friends dogs, even my chiropractor. I recently retired from the Department of Education and have plenty of time on my hands. Would love to do more with animals now that my time has freed up. I only offer in home care as I am not allowed to have pets at my own place. Preferably, I would like to remain outside of the home when coming to pick up your baby but it is not necessary.
About: I communicate with animals very well & have cared for & regularly research a variety of creatures, both with domestic & farm lifestyle to constantly improve my knowledge of different situations. My Reiki practice is run from home & I have the flexibility in my schedule to be fully present with your animal & to will also offer Reiki treatments for your anxious / blue pet. I have a huge property with a security gate & fencing that allows lots of space for outdoor play & clean, comfy, & safe indoor quarters that can allow room for your crated pet. (*Owner to provide crate.)
About: I can care for your pups as well as horses and cats. I have a nice fenced in yard and lots of love to give. I currently work part time, and have a pretty flexible schedule. You can drop off your pet or I can pick them up. Thank you I have an older beagle mix and one cat. I have a nice fenced yard and lots of room for pets to run and play.
About: Aloha ! My name is Ronda and I’d love to be your fur baby’s friend! I’ve been caring for animals my whole life- as a child my family and I rescued/rehabilitated dogs and cats, at 13 I started my first dog walking business, at 15 I started petsitting, and I’ve been dog walking and petsitting ever since 🐾 I love dog walking, pet sitting, a drop ins! I gear my care towards the specific needs/preferences of the pet and their owner, but I do everything! Walks, play time, fetch, couch cuddles, you name it! I have experience with elderly animals, large dogs, and puppies. Tell me about your pet and I will listen! What are their likes/ dislikes/ schedule/ sensitivities/ favorite toy? I will make note of their needs so that our time together is comfortable and fun. I work a part time job, but am pretty flexible otherwise. My references will speak highly of my reliability, caring and friendly nature, and my trustworthiness. I want to accommodate your pet’s regular schedule! I work part time (my shifts are midday to early evening, two or three days per week ), so I have lots of free time to walk/ drop in/ stay with your pet! My morning’s are wide open, as well as most afternoons/evenings. For petsitting clients, I can let you know my exact work schedule and adjust my shifts if needed. Your pet’s safety and your home’s security is my highest priority. I pride myself on leaving every space better than I found it; For petsitting clients I clean up after myself so you’ll always come home to an empty sink, clean sheets/towels, and a vacuumed floor!
About: Hi! I’m an experienced pet sitter who has been dog sitting and boarding for returning clients over the past three years. Caring for dogs has become one of my favorite ways to spend my time, and I love getting to know each pup’s unique personality. Whether your dog is energetic, shy, anxious, or loves attention, I’m comfortable adapting to their individual needs and routine. I have experience caring for dogs with a variety of temperaments and always prioritize making them feel safe, loved, and at home. I’m very active and love being outdoors, so your dog can expect plenty of walks, playtime, exercise, and affection. I live in a pet-friendly apartment and offer both boarding and house sitting. I also have experience with basic training and reinforcing good habits, so I’ll happily stick to your dog’s routine and any instructions you provide. My goal is simple: to give you peace of mind while you’re away and make sure your dog has a fun, safe, and loving experience from start to finish. I can’t wait to meet you and your pet! I am available to care for your pet everyday of the week. I work as a surf instructor 3 days a week (8am–1pm), which leaves me very flexible and home the majority of the time. On work days, I provide early morning walks and care before I leave, plus afternoon/evening walks and attention when I’m back. On my off days, I’m fully available for plenty of walks, playtime, and company. Your dog will always get a consistent routine, lots of exercise, and plenty of love based on their individual needs. Whether in my home or yours, your pet’s safety, comfort, and routine are my top priorities. My apartment is dog-friendly, clean, cozy, and smoke-free, with easy access to safe outdoor areas for walks, potty breaks, and exercise. I keep my space tidy and calm so pets feel relaxed and at home right away. For house sitting, I treat your home with the same respect and care as my own.
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
About: Hi! I’m Taylor 🤍 I’d love to care for your dog like part of our family. We have a calm, loving home where dogs can relax and roam freely. They’re never left alone for long periods. I have a one-year-old who is my world, so I only accept gentle, very friendly dogs, and everything is closely supervised. Your pup will get daily walks, plenty of potty breaks, and lots of love—no crates unless you prefer. Dogs must be comfortable on leash when on walks and not aggressive or reactive. Thank you so much! My daily routine is flexible and built around your dog’s needs, including: • Morning, afternoon, and evening walks • Frequent potty breaks (as often as every hour, if needed) • Playtime, rest, feeding following your current schedule Your dog’s safety and comfort are my top priorities. I’m home and present at all times, so your dog will never be left alone. Our home is calm and family oriented, and we only accept baby-friendly, gentle dogs due to our one-year-old. Dogs receive frequent potty breaks, outdoor time, and personalized care, and must be well-mannered on a leash for walks with my child.
“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!”
The median cost per night for house sitting in Wailea Makena 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 - Wailea Makena
Select a filter and find qualifying sitters offering house sitting.Sitters in Wailea Makena average 2 repeat house sitting clients
FAQs for House Sitting - Wailea Makena
Frequently asked questions about Rover
As of August 2026, there are 166 sitters on Rover offering House Sitting across Wailea Makena. 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 Wailea Makena 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 Wailea Makena 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.
Tip: 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 Wailea Makena 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Wailea Makena. On Rover:
- 97% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 97% 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.
Connect anywhere with the Rover app
