Pet Sitting in Headingley

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Headingley pet sitters

Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.

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Sitter Profile Image: Kristin C.
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Kristin C.
Star Sitter
$28
total per visit
5.0 out of 5 stars
46 reviews
16 repeat clients
15 years of experience
Winnipeg, MB, R2Y

This is our second time to have Kristin visit our apartment fur baby cat while we are away. Kristin has been great working with us and communicating to us and keeping us informed on how things are going. We are planning her for our next trip too!

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Robert S.
Sitter Profile Image: Kirsten M.
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Kirsten M.
$28
total per visit
23 years of experience
Cartier, MB, R4K

About: I have been taken care of dogs since I was a baby and have had 9 puppers in my life time. My dog Beau is my companion who is full of life! Taking care of her includes administering her medication on a daily basis. I have trained Beau since she was a puppy, this includes simple commands such as sit or shake but also includes more complex training including “place” “heel” and other tricks! I also have experience with senior dogs who often require more care. I am a full time University Student with time during the day, evenings, and weekends to care for pets with all levels of needs. I often have breaks in classes that allows me time to care for animals during the day when most people are at work n I create a safe and comforting environment for all animals in my own home or theirs. I do my best to revolve my schedule around the animals daily routines to make the transition more seamless.

Sitter Profile Image: Shayleece R.
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Shayleece R.
$24
total per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
10 years of experience
Winnipeg, MB, R2Y

About: I have a huge heart for animals of all kinds. With years of experience caring for a variety of pets, I understand the deep bond people share with their animals and the trust required to care for them while you are unable. I can provide walks, feeding on time, play time, giving medication if needed. It brings me joy caring for furry friends! I am available whenever throughout the week weekends, anytime after 8am. Except Wednesdays, and Thursday evenings. So please feel free to ask me about availability I have a big backyard that is fully fenced in. Also lots of room to roam around inside of the house. Please let me know any accommodations as needed

Sitter Profile Image: Anna P.
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Anna P.
$28
total per visit
5.0 out of 5 stars
4 reviews
1 repeat client
14 years of experience
Winnipeg, MB, R3R

I had a great experience with Anna during the first time watching my cat. She was reliable, caring, and attentive to all details and instructions I provided. Highly recommend Anna.

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Irina S.
Sitter Profile Image: Lucie Y.
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Lucie Y.
Star Sitter
$24
total per visit
5.0 out of 5 stars
13 reviews
3 repeat clients
5 years of experience
Winnipeg, MB, R3P

Lucie goes above and beyond! She’s amazing with our little goldendoodle puppy, Pip, who feel in love with Lucie immediately! Shes calm and playful with our pup. I would highly recommend Lucie.

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Holly L.
Sitter Profile Image: Whit R.
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Whit R.
$28
total per visit
5.0 out of 5 stars
70 reviews
27 repeat clients
11 years of experience
Cartier, MB, R4K

Accommodating and friendly! Thanks so much for checking in on our cat Biggie! He was a lot less lonely and the photos Whitney sent put our mind at ease on our trip. We’d love to use her services again for our next trip!!

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Victoria S.
Sitter Profile Image: Amanda B.
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Amanda B.
$28
total per visit
5.0 out of 5 stars
1 review
24 years of experience
Winnipeg, MB, R3J

About: I have taken care of animals since I can remember. Between caring for my dogs and cat at home or my grandma’s horses, I have always been around animals. As my dog is high energy, I have taken numerous courses on how to help train and guide her through life. These courses has extended my knowledge on how to take care of dogs and love them even more! I am currently working full time however, due to the flexibility in my schedule, I am able to take care of your furry loved ones round the clock! I am able to adapt to your routine to make sure that your pet(s) aren’t thrown off by a new routine created by a new person. This allows for a smoother transition while you are away. I am also comfortable walking dogs of all ages and reactivity as I have well versed experience with reactive dogs.

Sitter Profile Image: Kristy S.
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Kristy S.
$28
total per visit
35 years of experience
Winnipeg, MB, R3R

About: Hi :) I am someone who treats every pet like they're my own - not just cared for, but genuinely understood. I know how important it is to trust the person looking after your fur-babies, because they're family. I pay close attention to each animal's personality, routines and little quirks so they feel safe, relaxed and happy while you're away. Whether your dog needs long, energy burning walks or they prefer quiet company and gentle care, I adjust to them - not the other way around. What sets me apart is the level of attention and communications I provide. You'll always know how your pup is doing with regular updates, photos and honest check-ins. I'm reliable, patient and calm under pressure, which helps even anxious or shy dogs feel comfortable. I's also experienced with: 1. different energy levels (from playful pups to senior dogs.) 2. Administering basic medications if needed 3. Maintaining routines (feeding, walks, etc) 4. Giving lots of affection while still respecting boundaries At the end of the day, my goal is simple: your pet feels safe, loved and stress-free - and you have complete peace of mind. Pet care is my full-time focus, which means I've built my daily and weekly routine entirely around the needs of the pets I care for. I schedule my days to allow for consistent walks, check-ins, playtime and companionship, ensuring every pet gets reliable, unrushed attention. Your pet won't be "fit-in" - they'll be a priority in my day. When caring for pets in your home, I aim to keep everything as close to their normal routine as possible. I follow feeding schedules, walk routines, and household guidelines carefully so your pet feels secure and stress-free in their own environment. I treat your home with the same respect I would my own - clean, tidy and secure at all times. I'm mindful of details like locking up properly, keeping things organized, and maintaining a calm environment for your pet. You can also expect regular updates, photos, and honest communication so you always feel connected and at ease while you're away. I understand that inviting someone into your home requires trust, and I take that responsibility seriously.

Sitter Profile Image: Brena D.
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Brena D.
Star Sitter
$39
total per visit
5.0 out of 5 stars
128 reviews
43 repeat clients
20 years of experience
Winnipeg, MB, R3A

Brena went out of her way to take care of, and make our cat Cali, feel like she was loved while we were away. Brena was in contact with us daily and ensured we could rest easy by sending us pictures and videos. Our cat is very shy and tends to hide from strangers. You would never know that as it took Brena no time to establish a relationship and build trust. Thank you so much Brena and also thank you for bringing in the deliveries we forgot we ordered 🤣 Anyone that needs someone to take care of their pet should put Brena at the top of their list…we have! Thank you again Brena. You put our mind at ease while on our family vacation without our 1 family member 😺

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Cylina J.
Sitter Profile Image: Melissa F.
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Melissa F.
Star Sitter
$35
total per visit
5.0 out of 5 stars
25 reviews
8 repeat clients
20 years of experience
Winnipeg, MB, R3M

About: We’ve always been happiest with a dog in our home. With one of us working from home full-time, we’re able to give visiting dogs steady company throughout the day along with the walks, playtime, and routine they’re used to. After caring for our girl Nora for 17 wonderful years, my husband and I have lived through every stage of a dog’s life and still miss having that energy around. We already look after the pets of friends and family, and we’re excited to welcome a few more furry guests. We tailor each stay to your dog’s usual needs, whether that means long neighbourhood walks, extra exercise, or trips to the dog park. We’re big believers in keeping things consistent for the dogs we watch. If your pup has house rules, feeding schedules, training cues, or favourite spots to nap, we follow them closely so their stay feels familiar and comfortable. We reinforce the habits and boundaries you’ve already worked hard to build. Caring for our own dog through a few medical challenges taught us how to handle medications, mobility needs, and gentle support for older pets. If your dog needs special care or a bit of extra patience, we’re comfortable providing it. During the week, there is always someone at home, and weekends are usually spent together too. If your dog enjoys little outings, we’re happy to bring them along on pet-friendly errands or quiet park trips. If they prefer a slower pace, we’re just as happy to relax on the couch and keep things calm. We’re simply hoping to bring a bit of that tail-wagging joy back into our home and make your dog feel safe and loved while you are away. My husband works from home and I work 20% at home and 80% in office. We are both off evenings and weekends. We have a 17 year old teenager as well who is eager to help out. When it comes to your dog’s safety and comfort, we’re your people. We treat every dog like they’re part of our family—so much so, we’d probably share our snacks with them if they gave us that “sad puppy eyes” look. Hopefully we would make them do a trick first. Our yard is fully fenced, which means no escape artist dogs on our watch! While we love giving dogs the run of the yard, we also recognise that some dogs need to have their own space. If your dog has a special bed, crate, mat that brings them comfort bring it. This ensures they have a place they can feel comfortable in. For success we know following usual routines make your pup feel comfortable and safe as possible. Basically, your dog will be treated like royalty… but with more belly rubs.

Sitter Profile Image: Amelie P.
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Amelie P.
$28
total per visit
5.0 out of 5 stars
4 reviews
16 years of experience
Winnipeg, MB, R3K

About: Hi there ! My name is Aimee, I’m a 22 year old University of Manitoba student athlete and of course an animal lover. I grew up around cats and multiple dogs that provided me with crucial experience in caring for pets through feeding, bathing, training, walking, vet visits, and lots of love and affection. I would love the opportunity to care for and keep active with your pets throughout this summer, as well be a help to those with busier schedules! I’m currently a University student who has a lot of free time through the week. I just finished my summer classes and will be returning back to school at the beginning of September, leaving me with plenty of free time throughout the weeks for the rest of the summer! In my personal life at home we have a long gated back yard allowing for lots of room to run around. I care for my pets and others pets by playing with them outside or taking them for walks if a backyard is not available. I love to be active and bring along my pups on any adventures that is safe for them. I follow a routine feeding schedule and always have water available, except after extensive physical activity for about 15 minutes. I have no problem with the pets up on the couch to rest, but have beds for them to lounge on as well!

Sitter Profile Image: Tanya G.
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Tanya G.
$28
total per visit
5.0 out of 5 stars
2 reviews
15 years of experience
Winnipeg, MB, R3N

About: I have owned dogs, cats, and other animals in the past. I have also volunteered at veterinary clinic. I enjoy spending time animals and look forward to caring for yours. Let me know all the information I need to care for your pet(s). Can care for dogs that are house trained. I can care for dogs in my home and cats in yours. I enjoy spending time with animals and I look forward to hearing from you to care for your fur baby. I have considered my dogs to be a member of my family. I have a fenced back yard. I can care for dogs in my home and can pet sit cats in your home. I can offer drop in pet services also.

Sitter Profile Image: Gabrielle W.
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Gabrielle W.
$28
total per visit
5.0 out of 5 stars
9 reviews
3 repeat clients
3 years of experience
Winnipeg, MB, R3L

This is the second time Gabrielle took care of Birdie and both times were great! Gabrielle kept things very tidy and I loved the pictures I got every day :) thank you!

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Madeleine G.
Sitter Profile Image: Cara S.
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Cara S.
$24
total per visit
1 repeat client
15 years of experience
Winnipeg, MB, R3K

About: Ive loved animals my whole life and Ive had dogs in my life for around 15 years. I love to train, play, walk and love dogs and you can guarantee that your fur babies will be in the best hands possible. I am currently without a job so i am free to be able to entertain and love your fur babies while you are unable to! I have a fenced in yard that will keep all dogs safe. I have a 13 year old shitzu who spends her time on the couch, a 2 year old goldendoodle who is so friendly and sweet and would love to play and go for walks. He follows a schedule of training and walks that he would love a buddy to join him or he is happy to stay at home while i walk your dog!

Sitter Profile Image: Melanie A.
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Melanie A.
$84
total per visit
5.0 out of 5 stars
9 reviews
1 repeat client
40 years of experience
Winnipeg, MB, R3J

About: Welcome to The Elite Doggie House!!! Where your Doggie is treated like Royalty. If you’re seeking a luxury, personalized, and private Doggie retreat, read on to discover more! Your Doggie will receive one-on-one attention like no other place in town! I limit my care to NO more than 2 unrelated Doggies at one time. I can limit to just me and your Doggie alone, if that’s what your Doggie needs. With car rides, trips to the Doggie park and a walk through the Doggie friendly neighborhood throughout the day, your Doggie will for sure go home tired!!! Your Doggie will receive fresh water, treats, kibble, as no Doggie goes thirsty or hungry here. Constant attention, playing fetch, and belly rubs!! This is your Doggie’s day and it’s all about them! I have big comfy chair, couch, or my bed for your Doggie to sleep on. You are welcomed to bring your Doggie’s bed if they need the scent of home during their stay. If your Doggie enjoys a brushing or bath, I can do that too. Just bring the brush and shampoo!! I offer a small, cozy 900 sq ft, home, with a fenced in backyard, that backs onto a field for convenient walks. A safe space to play, relax and socialize. Your Doggie’s experience will be like no other, and one you’ve never seen, as I constantly send pics and videos throughout their stay for your own peace of mind. Check out the testimonials!! I guarantee you’ll never book anywhere else again. Pet care is a natural and meaningful part of my daily and weekly routine. I structure my schedule around the needs of the pets in my care, making sure they receive consistent attention, exercise, feeding, and companionship. Whether it’s morning walks, midday check-ins, playtime, or evening wind-down routines, I prioritize each doggie’s comfort and well-being as if they were my own. Because I intentionally keep my schedule balanced, I’m able to provide focused, one-on-one care rather than rushing between multiple commitments. This allows me to be fully present, attentive to their cues, and responsive to any special needs, ensuring every pet feels safe, happy, and loved while in my care. I’m committed to working closely with you to understand your dog’s unique needs, preferences, and any special concerns—offering a level of personalized care you won’t find just anywhere. My approach is truly one-on-one, meaning your dog receives my full attention, patience, and dedication, as if they were my own.

Sitter Profile Image: Brooke L.
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Brooke L.
$28
total per visit
5.0 out of 5 stars
1 review
7 years of experience
St Francois Xavier, MB, R4L

About: Hi I’m Brooke! I have worked at a doggy daycare for two years which then led to me doing my own dog daycare, walking and training on the side of this as well! I have had my business Dogs On The Block Co. for about a year and it is my full time job! You can check out all my clients to get a feel for what I do and who I am! I showcase a lot of the training and tricks I do with my dogs on their Instagram page, if you would like to get a feel for me as a dog owner. I believe what sets me apart is my enthusiasm for dogs. I am eager to teach your dog(s) new tricks, obedience and manners. I am also totally happy to play and give your dog a nice long walk (or run)! I will do my absolute best to accommodate to your schedule and work with you on your pet care needs! I am someone who enjoys being busy and am happy to work around my schedule to offer your pet the best care, and help you in any way possible:) I care for your dogs as if they were my own. My attention will be towards your dogs and providing them the best experience in my care. I love taking pictures and providing you with the details on your pets experience with me. I know it isn’t always easy leaving your fur baby with other people therefore I will give you as many updates as possible to ease your mind.

Sitter Profile Image: Ann N.
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Ann N.
$23
total per visit
5.0 out of 5 stars
2 reviews
15 years of experience
Winnipeg, MB, R3H

About: I’ve been a lifelong dog lover and have had the privilege of raising both rescue dogs and a purebred Golden Retriever over the years. Each one has shaped how I care for animals—with patience, understanding, and a lot of love. In our home, pets truly are family. Their happiness, comfort, and well-being are always a top priority, just as if they were children. I understand how important it is to trust someone with your dog, and I take that responsibility seriously. I’m known for being kind, conscientious, and reliable—not just with dogs, but with people too. I’ll always communicate clearly, show up when I say I will, and make sure you feel confident your pet is in good hands. I’m currently working part-time, which allows me to dedicate quality time and attention to the pets in my care. My approach is simple—I care for every pet as if they were my own. That means plenty of exercise tailored to your dog’s individual needs, along with a strong focus on mental stimulation through enrichment, play, and engagement—not just walks. In a client’s home, I respect your pet’s routine and environment, keeping things as consistent as possible to reduce stress. I make sure they receive plenty of attention, exercise, and mental stimulation, while also giving them the patience and calm presence they need to feel at ease. I care for every pet as if they were my own—prioritizing their comfort, happiness, and well-being at all times.

Sitter Profile Image: Lindsey L.
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Lindsey L.
$28
total per visit
5.0 out of 5 stars
3 reviews
1 repeat client
27 years of experience
Winnipeg, MB, R3J

About: I have grown up with cats, dogs, and guinea pigs my entire life! I have two black lab crossed dogs and two cats that I love with all my heart, even though I only get to see them on my visits back to my home town. I also have a bengal cat of my own that I love very much despite her sassy attitude. Family gatherings don’t feel complete until there are half as many pets as there are people. Volunteering at the Pembina Valley Humane Society for two years in high school gave me lots of experience and enough responsibility to see what all goes into caring for the dogs and cats/kittens who were ready for adoption, as well as the confidence to deal with the excitable ones. I have always found it easy to relax around pets and connect with them. I work a full time job during the week but evenings and weekends I have full availability to watch the four legged family members :) My cat is free to wander wherever she would like to go and my dogs back home have a fenced back yard to play in I work a full time job Monday to Friday so my evenings and most weekends are free to take care of your very loved pets! I currently live in an apartment that only allows cats, which I have one. I am not able to take in any pets at this time.

Sitter Profile Image: Olly T.
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Olly T.
$23
total per visit
5.0 out of 5 stars
12 reviews
2 repeat clients
15 years of experience
Winnipeg, MB, R3R

About: i have had 3 dogs in my life, years of experience with them. my home has a big yard and its all fenced so great for dogs to play in. have 1 dog just now, 4yr old collie mix with shepherd. super friendly dog and regular at the dog park. i love dogs and am available most weekends and MOST evenings. would play with the dogs as much as is needed and give 100% attention, just getting started on rover and hoping to build a good clientelle, and get return customers. have trained my dog to do tricks like "bang", all the basics were very simple and he can turn off lights. willing to do work with ur dogs too. Have big house and yard so lots of space!!!!!

Sitter Profile Image: Hadas K.
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Hadas K.
$39
total per visit
5.0 out of 5 stars
2 reviews
16 years of experience
Winnipeg, MB, R3N

About: Hello! My name is Hadas and I am a dedicated pet sitter and dog walker based in Winnipeg. I am 26 years old and work full time from home during the week so my schedule is flexible. I have a passion for caring for animals, and I specialize in providing services for both cats and dogs. I am a big animal lover. I currently have three cats (one senior) and have experience with puppies and senior dogs. 🐶🐈‍⬛ I currently work home full time Monday to Friday 8-4:30. I am always home during the weekends as well. I have a very flexible schedule and can be with your pet all the time and give it all of the love and attention they need and deserve. My home is a very clean, organized and safe place. I have three cats who love dogs. Two of them are four years old and the other one is 11. They are all in great health condition, are fixed and have all their vaccines. We recently had our senior dog pass away and they all got along great. As long as your dog is cat friendly there won’t be an issue.

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The median cost per night for pet sitting in Headingley is $25

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Sitters in Headingley average 5
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Headingley on Rover as of Jun 2026 was about $25 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

As of Jun 2026, there are 364 pet sitters in Headingley. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 87% of Headingley pet sitters respond in under an hour.

Pet sitters in Headingley have an average of 13 years of experience. Pet sitters with repeat customers have an average of 5 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Headingley.

Rover makes it easy to find Headingley pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 364 pet sitters in Headingley on Rover, so you’re sure to find the perfect match for your pet! In Headingley, 100% of pet sitters offer daily exercise, 94% offer medication administration, and 88% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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.