Dog Sitting Winnipeg

Book a Winnipeg dog sitter to watch your dog in your sitter’s home or yours.

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Over 377
pet parents in Winnipeg have booked dog sitting

Winnipeg, Find top rated dog 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: Hayley B.
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Hayley B.
Star Sitter
$28
total per visit
5.0 out of 5 stars
4 reviews
3 repeat clients
10 years of experience
Winnipeg, MB, R2M

About: I currently work at a doggy daycare and am in school to become a veterinary assistant, so I have experience caring for all different kinds of dogs and animals! I have 2 dogs of my own, one is a puppy I’m raising, and they are just the sweetest things. I work 1 day a week, so other than that all of my time is free and flexible to work around your schedule and your needs! I promise to take as good of care of your fur babies as I do of my own! I care for them in the comfort of your own home! So they don’t need to get used to a whole different environment. I do daily drop-ins, dog walks, and overnight pet sitting.

Sitter Profile Image: Melissa F.
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Melissa F.
Star Sitter
$35
total per visit
5.0 out of 5 stars
28 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: Mary Anne R.
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Mary Anne R.
Star Sitter
$36
total per visit
5.0 out of 5 stars
46 reviews
14 repeat clients
50 years of experience
Winnipeg, MB, R3J

Appreciate your ability to come short notice

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Shauna M.
Sitter Profile Image: Billie-Lyn M.
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Billie-Lyn M.
Star Sitter
$28
total per visit
5.0 out of 5 stars
18 reviews
7 repeat clients
15 years of experience
Winnipeg, MB, R3L

Billie-lyn was terrific and cat Avocato was well looked after, I highly recommend her!

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Stephen J.
Sitter Profile Image: Cassandra C.
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Cassandra C.
Star Sitter
$18
total per visit
5.0 out of 5 stars
18 reviews
10 repeat clients
20 years of experience
Winnipeg, MB, R3C

I was really happy with the care you gave my cats. You were very proactive and attentive and I really appreciated all the pictures and updates. The only thing I wanted to mention was the situation with the keys. I unfortunately don’t drive so I wasn’t able to drop them off as early as I would have liked, and I did feel bad about the inconvenience. When you asked if you were expected to stay the full hour, I also felt a bit uncomfortable saying yes because I was worried about inconveniencing you even more. For the key return I had originally planned to pick up the keys myself and only asked if I could pick them up later today. You offered to drop them off after another appointment, which I really appreciated and thanked you for. So I was a little surprised to later feel like I had asked you to make that last-minute arrangement, if you had said no I would’ve been there at the time we had discussed I really do appreciate your flexibility but I wanted to be honest that I felt a little uncomfortable with the communication around the keys. That said, I really appreciated the care you gave my pets and all the updates you sent 😊

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Catalina L.
Sitter Profile Image: Nicole T.
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Nicole T.
Star Sitter
$23
total per visit
5.0 out of 5 stars
10 reviews
15 repeat clients
3 years of experience
Winnipeg, MB, R2J

Nicole was thankfully available at the last minute and did a great job taking care of our cat, Wall-E. She was reliable, responsive, and made us feel confident that he was in good hands. We really appreciated her help and would gladly book with her again.

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Marcel B.
Sitter Profile Image: Nerissa M.
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Nerissa M.
Star Sitter
$26
total per visit
4.9 out of 5 stars
99 reviews
29 repeat clients
20 years of experience
Winnipeg, MB, R2J

Nerissa is great! Very reliable and the dogs love her!

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Ben S.
Sitter Profile Image: Jonathan D.
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Jonathan D.
$24
total per visit
5.0 out of 5 stars
3 reviews
2 repeat clients
2 years of experience
Winnipeg, MB, R3C

About: Your pets deserve more than just someone to feed them and let them outside, they deserve someone who genuinely enjoys spending time with them. Whether your pet loves long walks, playtime, cuddles on the couch, or simply having a calm and caring companion nearby, I'll make sure they feel safe, comfortable, and loved while you're away. I understand that every pet has a unique personality and routine, and I take the time to learn what makes your pet happiest. I have experience walking dogs at the Humane Society for around two years and I grew up with a dog for 18 years. My goal is simple: to treat your pets with the same care, patience, and attention I'd want for my own. My schedule is very flexible, which allows me to provide reliable and consistent care throughout the week. I'm available for morning, afternoon, evening, and weekend visits, and I can often accommodate last-minute bookings when needed. I understand that pets thrive on routine, so I make every effort to work around their normal schedule for feeding, walks, playtime, medication, and bedtime. Whether you need regular care while you're at work or someone to look after your pet while you're away, I'm committed to providing dependable care and keeping you updated every step of the way. The safety, comfort, and well-being of every pet in my care is my top priority. I take the time to learn each pet's routine, personality, and any special instructions so they can feel as comfortable as possible while you're away. I provide a calm, supervised environment and always pay close attention during walks, playtime, feeding, and outdoor activities. I follow all owner instructions carefully, including medication schedules, dietary needs, and behavioral preferences. I also believe that communication is an important part of pet care. You'll receive regular updates and photos so you can feel confident that your pet is safe, happy, and receiving the attention they deserve. My goal is to create a positive, stress-free experience for both pets and their owners.

Sitter Profile Image: Kristin C.
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Kristin C.
Star Sitter
$28
total per visit
5.0 out of 5 stars
60 reviews
23 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: Ellen P.
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Ellen P.
Star Sitter
$28
total per visit
5.0 out of 5 stars
202 reviews
84 repeat clients
15 years of experience
Winnipeg, MB, R2M

Ellen was amazing! Provided great communication and made sure to send pictures each visit so I knew Dixie was doing OK. Thanks so much for your help Ellen! Would definitely book again ☺

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Jarrett M.
Sitter Profile Image: Emma B.
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Emma B.
$23
total per visit
5.0 out of 5 stars
9 reviews
5 repeat clients
10 years of experience
Winnipeg, MB, R3G

About: Located in beautiful Wolseley, but can travel nearby. I am Fear Free Shelter certified and I volunteer with two animal shelters. I have completed all required training to understand body language, temperament and behaviour and can connect with both friendly and timid dogs. We foster dogs, and have lots of experience with shy or injury-recovering ones who need special attention. Our own dog is a beautiful shepherd who we rescued from a shelter in Morden and we have had the absolute privilege of watching her learn the world isn't so scary. Our second is a little French bulldog who we foster-failed and decided to keep. I love all dogs and would love to spend time with yours! I work full time, but my schedule is flexible. I work from home Monday and Thursday and can pop over to hang out during the day, and am free every day after 4:30. My weekends are usually wide open as well. We have a fenced yard, and one of us is home Mondays, Thursdays, and Fridays so the only time our animals are alone all day are Tuesday-Wednesday. We love to walk and have two dogs and a cat who all love other animals. We have foster animals here often so they are used to revolving animals in the house. Our frenchie is a little excitable at first which can freak some dogs out, but he settles down within an hour and then acts like nothing has changed.

Sitter Profile Image: Janice R.
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Janice R.
$28
total per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
30 years of experience
Winnipeg, MB, R3E

Janice took great care of my cat when I was away. Great communication.

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Eli C.
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: Misilyna W.
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Misilyna W.
$28
total per visit
5.0 out of 5 stars
11 reviews
3 repeat clients
16 years of experience
Winnipeg, MB, R2H

Appreciate Misilyna’s punctuality, great communication and patience with my puppy!

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Carolyn S.
Sitter Profile Image: Julianna M.
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Julianna M.
$23
total per visit
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Winnipeg, MB, R3L

About: I have grown up with dogs and cats my whole life. And recently I have started pet sitting for my neighbors and family friends and I would like to continue to pet sit for more people. I typically work in the mornings and have afternoons or evenings free. I do not work a consistent schedule so I will be updating my availability to pet sit frequently. I have a fenced backyard perfect for a small or medium dog to play in. I also live near a dog park if more exercise is needed. I will be working a fairly consistent schedule, I will be available weekdays at 4:00pm. I am able to house sit and have pets board at my house most weekends. Drop off would need to be Friday afternoons at or after 4:00pm. I will update my availability as soon as I get my schedule from work. I have a fenced in yard and baby gates to ensure the pets don't go roaming far away from me. There is a dog park near my house that I can walk them on leash any time of the day multiple times if needed.

Sitter Profile Image: Joyce T.
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Joyce T.
$24
total per visit
2 years of experience
Winnipeg, MB, R3T

About: With over 2 years of pet care experience, I bring a wealth of expertise and a genuine passion for furry companions. What sets me apart from other sitters is my commitment to going the extra mile. Not only will I provide exceptional care for your pets, but I also offer house sitting services, ensuring that your home remains maintained and clean throughout your absence. From energetic puppies to playful younger dogs, I have ample experience and a deep understanding of their needs. I love taking pets for drives to parks, indulging in fun-filled play sessions, and creating memorable adventures. Additionally, I specialize in handling needy dogs, offering the patience, attention, and affection they require. Your beloved pets will receive top-notch care, companionship, and an abundance of tail-wagging joy in my capable and loving hands. While I may have obligations as a student, I make it a priority to allocate quality time and attention to each and every furry friend under my care. I devote myself entirely to the well-being and happiness of your beloved pets. Whether it's long walks, interactive play sessions, or simply providing them with the love and companionship they deserve, I ensure that they receive the utmost care and affection during our time together. Your lovely pets will never feel neglected or alone, as I strive to create a nurturing and engaging environment for them despite my schedule. Their happiness and comfort are always at the forefront of my mind, and I am dedicated to making every moment with them a joyful one. Safety, trust, and creating a secure environment are my top priorities when it comes to caring for pets, whether it's in my own home or at my clients' residences. I understand the importance of providing a nurturing and hazard-free space for our furry friends. In my home, I have taken extensive measures to ensure a safe and pet-friendly environment. I strive to create a space where pets can roam freely and play without worries. Additionally, I have a keen eye for maintaining a clean and sanitized environment, minimizing the risk of any allergies or infections. When caring for pets in their own homes, I treat their surroundings with the same level of care and respect. I make it a point to familiarize myself with their home setup, ensuring their safety by adhering to their specific routines and any instructions provided. I am dedicated to earning the trust of both the pets and their owners, providing regular updates and open communication to keep everyone informed and at ease. Rest assured that when your beloved pets are in my care, they will be surrounded by a secure, loving, and trustworthy environment where their well-being is my utmost priority.

Sitter Profile Image: Storey Alexander W.
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Storey Alexander W.
$24
total per visit
5.0 out of 5 stars
3 reviews
1 year of experience
Winnipeg, MB, R3M

About: I have had dogs my whole life from puppies to senior dogs. I love spending time with the furry friends, and making sure that they have someone there when needed. I work Monday-Friday until 5pm in downtown Winnipeg so I am relatively close to every area of the city, I’m free all weekends, long weekends. I make sure that I’m attentive to how they behave , I ask what is normal for your furry friends so that if they are not behaving as expected then I can notify you immediately.

Sitter Profile Image: Amanda C.
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Amanda C.
$40
total per visit
4.7 out of 5 stars
16 reviews
6 repeat clients
20 years of experience
Winnipeg, MB, R3C

Amanda’s reports immediately put us at ease as it was obvious she was spending time with and getting to know our two old cats in her visits. Such a comfort. We’d definitely book her again!

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Audra L.
Sitter Profile Image: Victor R.
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Victor R.
$28
total per visit
4.9 out of 5 stars
15 reviews
7 repeat clients
15 years of experience
Winnipeg, MB, R3L

About: Nothing is more precious than your pet’s safety and well being and so is your peace of mind when you are away. Let me provide a home for your pet or keep him/her at home. Safe and well looked after. I have the time, the love and will to keep your pet safe and well looked after. That’s is a commitment you can trust. I am a previous dog dad and I’m able to care for puppies as well as senior dogs. Experienced at house breaking puppies and providing schedule and structure to their day. Over the years, I have looked after friends and families pets. Both short and long term. Sometimes up to 6 weeks in a row. I am retired and free to go anywhere.

Sitter Profile Image: Princess O.
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Princess O.
$43
total per visit
5.0 out of 5 stars
30 reviews
10 repeat clients
6 years of experience
Winnipeg, MB, R3C

Princess was a delight to meet and she really connected with Indie who is still a pup. Princess always arrived early so I could count on the fact that she was ready to sit with Indie. I would definitely recommend Princess and I know Indie will be looking forward to seeing her again.

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Genella M.
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The median cost per visit for dog sitting in Winnipeg is $25

Dog parents share their Rover experiences - Winnipeg

1 / 1
5.0 out of 5 stars

Carmelle has been excellent to work with, and our little puppy has taken very well to her in just a short time!

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Emily P.
Drop-In Visits
5.0 out of 5 stars

Nicolle was such a pleasure to connect with. Extremely communicative & kind. There was an inconvenience (I forgot to check that alarm was off for her) and she handled it so well - ensuring my pup was priority & comfortable while being resourceful and understanding with me. I 100% would recommend Nicolle & hope to use her again!

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Kelly S.
Drop-In Visits
5.0 out of 5 stars

Anne came over for some pop-ins for a weekend and we couldn’t be happier with how it went! Leaving your dogs in the care of someone else can be stressful but she put us at ease and the dogs thoroughly enjoyed their time with her. They were very well cared for and got lots of play time in while we were away. She was so so great! Very communicative and sent lots of pictures and detailed reports! Would absolutely trust her with our dogs any time!

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Robyn G.
Drop-In Visits
5.0 out of 5 stars

Meghan was fantastic. She came over and got the lay of the land. I have an older dog with health issues and she took very good care of him. Filled out the cards with photos, the dog is older and she took that into account. All I can say is excellent, really took the anxiety down for me.

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Aaron S.
Drop-In Visits
5.0 out of 5 stars

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

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Trevor G.
Drop-In Visits
5.0 out of 5 stars

Was awesome! Would definitely book again and she was so quick with communication and great with our pup :)

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Alex V.
Drop-In Visits
5.0 out of 5 stars

Grace did check-ins weekly with my puppy for several months! She was very organized, flexible with last minute appointment additions, and was great with my puppy and her quarks! A fantastic first experience with Rover and would recommend her to anyone!

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Megan G.
Drop-In Visits
5.0 out of 5 stars

Lucie has been wonderful with my little senior dog. I appreciate her patience and communication - It is nice to know she is in good hands!

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Susan M.
Drop-In Visits
5.0 out of 5 stars

Alicia has been a reliable sitter and I have appreciated her patience with my stubborn little senior terrier 🥰

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Susan M.
Drop-In Visits
5.0 out of 5 stars

Jacob has been for 2 meetings and greets before we go on vacation. Our dogs are very reactive but have reacted extremely well with Jacob. We are looking forward to our vacation knowing that Jacob is the right sitter for our pups. Thank you

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Roberta W.
Drop-In Visits
5.0 out of 5 stars

Perfect pet sitter who goes above and beyond for the little fur babies. I would recommend for anyone who is nervous their dog may be shy, he was great at getting goober to warm up to him so fast.

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Jake T.
Drop-In Visits
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  • 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.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your dogs like family

  1. 1. Search

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Popular requests for dog sitting - Winnipeg

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Sitters in Winnipeg average 5
repeat dog sitting clients

FAQs for Dog Sitting - Winnipeg

Frequently asked questions about Rover

The average cost for Dog Sitting in Winnipeg on Rover is $27.75 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .

There are 338 sitters on Rover for Dog Sitting in Winnipeg. About 87% of Winnipeg 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.

Rover makes it easy to find sitters who are available during your working hours. To find sitters who fit your schedule, select which days of the week and the time slots you'd like a sitter to visit. The search results will populate sitters whose calendars match your needs. You can also search for sitters by location, whether that’s a sitter near your office for day care drop-off or a sitter close to your home. Once you've found a sitter who you like, message them directly to schedule a Meet & Greet.

Tip: Doggy day care is another option for pet supervision while you're at work. Visit our doggy day care page for more information.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or travelling for a few nights, a pet sitter can offer poop breaks during a Winnipeg stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover based on what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.

The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.

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 Winnipeg 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.

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.

A Meet & Greet is a short introductory meeting between you, your dog, 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.

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