Pet Sitting 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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Over 33
pet parents in Headingley have booked pet sitting

Headingley, Find top rated pet sitting

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
• 63 reviews
24 repeat clients
15 years of experience
Winnipeg, MB, R3J

“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: Payton B.
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Payton B.
$28
total per visit
12 years of experience
Winnipeg, MB, R3K

About: I’ve been caring for large farm dogs since I was 14, so I’m comfortable around bigger breeds. I love animals and enjoy making sure they feel safe, happy, and loved! My schedule is flexible and allows me to dedicate plenty of time to caring for animals. I’m available for walks, visits, feeding, playtime, and companionship throughout the day. As well as boarding on week days and weekends. I follow each owner’s instructions carefully, maintain routines, provide feeding, walks, playtime, companionship, and attention, while keeping their home clean and fur baby safe, comfortable, and happy.

Sitter Profile Image: Shayleece R.
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Shayleece R.
$28
total per visit
5.0 out of 5 stars
• 9 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: Ann N.
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Ann N.
Star Sitter
$23
total per visit
5.0 out of 5 stars
• 9 reviews
2 repeat clients
15 years of experience
Winnipeg, MB, R3H

“Ann was amazing. She was very responsive and easy to communicate with. My dog loved her. Thanks Ann”

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Trevor G.
Sitter Profile Image: Ryan H.
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Ryan H.
Star Sitter
$24
total per visit
5.0 out of 5 stars
• 11 reviews
5 repeat clients
6 years of experience
Winnipeg, MB, R3G

About: I've cared for a bunch of dogs through dog-sitting and have lived with, cared for, and become close to several dogs and cats. I've also done a lot of research regarding cats & dogs - but I'm very respectful of owners’ beliefs and instructions. I have a pretty flexible schedule right now, because I'm self-employed with another business as well. I'm generally available 7 days a week, depending on my other work and plans. I can care for pets in my home or at yours. My place is clean, safe and has room for pets to play and run around. I have lots of great toys for dogs and cats, and depending on the pet, we can also spend time in the yard or go for walks.

Sitter Profile Image: Blair P.
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Blair P.
$19
total per visit
5.0 out of 5 stars
• 3 reviews
11 years of experience
Winnipeg, MB, R2P

“Incredible to have over and watch my girls. It’s especially hard finding someone comfortable with Great Danes. Follows all care instructions and checks in during the visit.”

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stefon i.
Sitter Profile Image: Melissa C.
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Melissa C.
$17
total per visit
20 years of experience
Winnipeg, MB, R3J

About: I have had cats my entire life - my childhood family cat is currently 17 years old! I have cat-sat for senior cats, mature cats, and young cats before, including administering medication and applying eye ointment. I have cared for anxious, shy cats before, as well as cats on special diets, and cats who need extra grooming due to their coats. My profile photo is me with one of the cats I have cat-sat! I have a 13 year old cat myself who takes medication in the form of pills. I adopted him last year - I have a soft spot for older kitties, but love cats of all ages! I love dogs too and research to stay up-to-date on how to care for them, but it has been many years since I have cared for a dog. I have flexible availability as a university student who works part-time. I am available many evenings and mornings, and some afternoons. I have my own vehicle for transportation. I am very respectful of others' homes. I scoop litter boxes daily. I wash used food dishes and food scoops. I ensure any messes are cleaned up. I respect your pet's body language and verbal communication.

Sitter Profile Image: Melanie A.
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Melanie A.
$84
total per visit
5.0 out of 5 stars
• 10 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: Angela S.
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Angela S.
$24
total per visit
30 years of experience
Winnipeg, MB, R3G

About: I've been a cat owner for most of my adult life and have also done cat sitting, dog walking/sitting for friends and family over the years. Starting at the end of August I'll be working part-time (4 days per week) and can do early morning visits/walks or late afternoon early evenings. I treat all my own and other's pets with lots of love. I generally prefer animals to people and most people would say I'm a natural with animals.

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.

Sitter Profile Image: Bree H.
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Bree H.
$23
total per visit
10 years of experience
Winnipeg, MB, R3T

About: I have grown up with pets my entire life both dogs and cats and love it so much. When I moved to the city I started fostering cats through the humane society and that has taught me many things especially with cats/kittens with medical needs or behaviour issues. I also have helped raise my dogs from puppies. I locally dog/cat sit consistently over the summer and have dealt with kittens, puppies, cats, dogs and seniors and love every single one of them. My priority is making sure your pet is happy and giving them lots of love! I am in school and work. I am able to always make time in mornings or after/in between school or work to see pets whenever possible. I am able to follow any instructions needed for your pet. If there is any medical or behaviour issues, I am comfortable doing whatever is needed. My goal is to make your pets as happy and comfortable as possible.

Sitter Profile Image: Denae E.
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Denae E.
$25
total per visit
5.0 out of 5 stars
• 16 reviews
3 repeat clients
9 years of experience
Winnipeg, MB, R2J

About: I have only recently begun expanding who's animals I take care of but have been taking care of my personal pets all my life. I have experience with cats, dogs, small mammals and amphibians. I have cared for all ages of pets including newborns and geriatric. I can handle administering medications of different sorts. I have first aid training, human and animal. If you have a specific way of doing things that you'd like continued I am more then happy to do so. My main concern is that your family member is well taken care of whether it be for an hour, a day or several days at a time. I have a schedule that is constantly changing. I am doing a training program come early 2025 so my schedule will be tighter than it is now but I will still try to arrange you to fit in. Keeping your pet safe is a big concern. I always check collars and leashes prior to use to ensure their functionality. I do have a dog who loves playing with others if yours needs a companion.

Sitter Profile Image: Sara v.
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Sara v.
$28
total per visit
5.0 out of 5 stars
• 11 reviews
6 repeat clients
6 years of experience
East Saint Paul, MB, R2E

About: I’ve been pet sitting for just over 6 years and have fallen in love with the work. I specialize in multi pet homes and furry friends that may have specialized diets and/or medication needs. I recently have relocated to the city after graduating school for aviation! I’m on a job hunt currently but for the time being my schedule is clear and open for your little one! Your pets safety and comfort is my top priority! My goals are to try and disrupt routines the least when you’re away from your pet as well as send regular updates and photos!

Sitter Profile Image: Daryna H.
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Daryna H.
$24
total per visit
5.0 out of 5 stars
• 1 review
10 years of experience
Winnipeg, MB, R2H

About: I grew up around animals and have years of hands-on experience with both dogs and cats. I’m patient, reliable, and understand how to care for pets of all ages — from playful puppies to gentle seniors. I offer loving, safe walks and drop-in visits with full attention to your pet’s needs. I usually take care of pet walks after 4 PM and am available for walks or visits then. My schedule is flexible in the afternoons and evenings to fit your pet’s needs. I prioritize creating a safe, calm, and loving environment for every pet, whether in my home or the client’s. I follow all care instructions carefully, keep hazardous items out of reach, and supervise pets closely during walks and playtime. Trust and open communication with pet owners are very important to me to ensure pets feel comfortable and well cared for at all times.

Sitter Profile Image: Julia B.
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Julia B.
$39
total per visit
5.0 out of 5 stars
• 9 reviews
2 repeat clients
7 years of experience
Winnipeg, MB, R3C

“Julia did such a good job looking after our Kitty!”

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Pamela L.
Sitter Profile Image: Zoe H.
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Zoe H.
$34
total per visit
1 repeat client
3 years of experience
Winnipeg, MB, R3X

About: Experienced in caring for dogs from playful pups to wise seniors (8 weeks to 14+ years), I tailor my pet sitting and training services to meet your dog's specific needs. Whether it's positive reinforcement, leash training, or specialized commands, I ensure every pup receives the personalized attention and training they deserve. Rest easy knowing your furry friend is in skilled hands, receiving the care they need at every stage of life! As I navigate my job search, pet sitting offers a flexible and rewarding opportunity that seamlessly fits into my week. With my existing experience caring for various animals, I can provide loving and attentive care to your pets while earning an income. As a reliable pet sitter, I maintain open communication with you before, during, and after the pet sitting period. You can count on regular updates and check-ins, so you never have to worry about your furry family members. I respect and maintain your pets routines to keep them comfortable and reduce stress. This includes sticking to their feeding, playtime, and walking schedule. I’m mindful of your pets preferences and behaviors, adapting my care approach to fit their unique needs. This includes any specific training or care requirements you may have.

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

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.

How to book pet sitting

  1. 1. Search

    Browse profiles of sitters near you who offer pet sitting.
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit.
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform.

Popular requests for pet sitting - Headingley

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Sitters in Headingley average 5
repeat pet sitting clients

FAQs for Pet Sitting - Headingley

Frequently asked questions about Rover

The average cost of Pet Sitting in Headingley is $26 per visit as of November 2026. Most bookings cost between $16 and $31 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.

There are 376 sitters on Rover for Pet Sitting in Headingley. About 87% of Headingley sitters can respond to requests in under 60 minutes. Whether you’re planning ahead for holidays, need last-minute care, or need same-day coverage for an urgent trip, you can message multiple sitters at once to find available care.

Once you find the right match, you can arrange a Meet & Greet to ensure they are a perfect fit for your pet’s personality before confirming.

You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.

Before booking, confirm:

  • the timing, length, and frequency of visits;
  • the care instructions the sitter should follow;
  • which parts of your pet’s usual routine should be prioritized;
  • how often you would like to receive messages, photos, or other updates.

Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.

You can coordinate how much supervision you want directly with your sitter. While every sitter’s schedule varies, here are some examples of supervision by pet care service:

  • Boarding or doggy day care: Many sitters can provide frequent companionship because they design their day specifically around the pets in their care or work from home.
  • House sitting: Your sitter generally stays in your home for the requested duration, which may include overnight care. They may step out briefly to visit other pet clients, but your home remains their primary base.
  • Drop-in visits or dog walking: These can be scheduled in 30- or 60-minute windows (and can be shorter or longer at your request) to help your pet receive dedicated attention and care during those specific times.

Interested in constant or 24/7 care? This service often incurs an additional fee but many sitters are happy to discuss this option with you.

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 Headingley 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!

Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they do not have any disqualifying offences.

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.

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.

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.

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.

Payment is handled securely through Rover. For a one-time booking, your payment method is charged at the time of checkout when you submit your booking request. This charge will include fees payable to Rover. Your booking is confirmed once the sitter accepts it.

If the request is not accepted, the pending charge is released in 1-7 days. How long it takes to disappear from your account depends on your payment provider.

For eligible recurring weekly services, you are charged for the first week when you book and then each Monday for the upcoming week. You’ll see the full price before you confirm. Always pay through Rover so your booking remains eligible for the Rover Guarantee and support.

Yes, you can find sitters who have experience administering medication or managing dietary requirements. On Rover:

  • 87% of sitters can help with special care needs
  • 90% can help with giving oral medications or injections
  • 94% 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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