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.
“Casey watched my 2 nuggets this past weekend while I was out of state- he sent photos while I was gone, kept me updated and responded right away when I reached out. He took them to the park, made sure they got their meds, and lots of cuddles. I highly recommend Casey to take care of your fur-babies anytime!”
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
“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!”
“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.”
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!
“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: 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: 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: 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.
About: I love all animals and they seem to love me too! I've been taking care of all kinds of animals since I was a child and have been pet and house sitting professionally for over 13 years. I have a calm and present personality which pets respond to well. I have many excellent reviews from pet and home owners both in the US and abroad which I would be happy to provide from other sites since I am new to Rover. I am in the process of relocating permanently to Hawaii and am currently available for overnight house and pet sitting preferably on Kauai or Maui. I am very responsible, clean and tidy, and lead a no-drama health conscious lifestyle. I am very detail oriented and enjoy connecting with each pet and providing loving care to them and the whole property. As my many referrals attest, I offer the utmost peace of mind to home owners when they travel.
“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.”
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: 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.
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.
“Emma was fantastic with Rico! She was great at communicating, always quick to answer questions and respond to messages, which gave me so much peace of mind while I was away. I had absolutely no worries knowing Rico was in her care. When I got home, the house looked great, and Rico was happy, healthy, and clearly well cared for. I would definitely book with Emma again. Thank you for giving me a worry-free vacation and for taking such wonderful care of my little guy! 🐾💙”
“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: Growing up in Hawaii, I was lucky enough to be surrounded by endless amounts of pets growing up. From the normal variety of cats and dogs, all the way to a pet pig and hamster. I understand cats and dogs at their core, and enjoy their company more than a normal dog walker or cat sitter. They add a lot of emotional value to my world, and I am grateful for any chance I get to hang and play with them! I do work other jobs, however I do have days completely free and also do tend to have morning, afternoon and evening availability scheduled throughout the week as well! So I am able to fit in walks and sits wherever they need to be! Obviously this all depends up to the owners discretion but I am always respectful of any home or environment I do enter into. Try to leave any space better than I found it and I find the same speaks to animal and pet care as well. I can do house cleaning/maintenance, plant care, and of course animal walking or sitting! Understanding what a pet is used to and where their familiar zones are is important to me in making sure they have the best experience!
The median cost per night for house sitting in Wailea Makena is $68
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?
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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
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Select a filter and find qualifying Wailea Makena sitters!Sitters in Wailea Makena average 2 repeat house sitting clients
FAQs for House Sitting - Wailea Makena
Frequently asked questions about Rover
As of July 2026, there are 158 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.
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