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: Melissa F.
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Melissa F.
Star Sitter
$35
total per visit
5.0 out of 5 stars
27 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: Burgess M.
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Burgess M.
$23
total per visit
5.0 out of 5 stars
5 reviews
1 repeat client
6 years of experience
Winnipeg, MB, R3G

About: I have over 7 years experience working with dogs. 4 years experience full-time dog walking and worked at a pet rescue shelter for 2 years. Your furry family member will be in good hands with me! I am currently working dog walking and am away 3 to 4 hours on weekdays. Otherwise I'm home with my dogs and yours. Dogs can be left out in home or crated depending on their training. I have a fully fenced in yard with room for your pup to play or relax with my 2 dogs. Your dog will be part of our family while staying in our home and treated as such.

Sitter Profile Image: Kristin C.
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Kristin C.
Star Sitter
$28
total per visit
5.0 out of 5 stars
56 reviews
19 repeat clients
15 years of experience
Winnipeg, MB, R3J

Kristin was excellent with my cat! There were some last minute changes to my cat’s care, and Kristin handled them perfectly! The care was top notch

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Nicole N.
Sitter Profile Image: Maggie D.
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Maggie D.
$23
total per visit
5.0 out of 5 stars
7 reviews
3 years of experience
Winnipeg, MB, R3C

About: I have experience caring for fish, painted turtles, salamanders, guinea pigs, parrots, dogs, and cats. Most of which are from childhood family pet care experience. My most extensive pet care experience is with dogs, as I have experience working at dog daycare and overnight kenneling. I love all pets as my own! Downtown Evening Walker & Overnight Housesitter Because I work a stable early-morning schedule (6:00 AM – 2:30 PM), your pets get my full attention all evening and all night long. I have full-day availability every Tuesday and Wednesday, and I am ready for walks or drop-ins any evening after 3:00 PM. For overnight stays, I happily base myself out of your home to ensure your pets follow their exact morning and evening routines seamlessly. Based right in West Broadway, I primarily serve Downtown, the Exchange District, and Broadway, but I am happy to travel across Winnipeg for the right match. Let's connect for a quick evening Meet & Greet! I live in an apartment building that does not allow pets, so I strictly work in your home and/or walks. I have trusted references to provide upon request and I am more than happy to send updates throughout housesitting pet care that I provide. I am flexible and will follow your instructions and methods in order to provide the best care for your pet.

Sitter Profile Image: Misilyna W.
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Misilyna W.
$23
total per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
16 years of experience
Winnipeg, MB, R2H

About: I have been taking care of dogs and cats of various ages since I’ve been in high school. I have always felt comfortable around animals and instantly bond with animals that I meet! I currently have one dog, Terra, and one cat, Momo, who I love more than anything in the world. I have worked with Terra on her reactivity and recall for 6 years, and I’m so proud of how far she has come. I am currently unemployed and spend all day with my pets. I typically walk my dog Terra once in the morning after breakfast, and again after dinner in the evening. She likes to do her zoomies in the backyard in the afternoons and I enjoy cuddling with her on the couch throughout the day. At least once a week, I try to take her on longer walks that are around 1 hour long. I cuddle and spend time with Momo during the days, and typically change her litter every couple days. I have taken care of pets in other people’s homes since high school. I am very flexible and can accommodate almost any request that the pet or owner needs.

Sitter Profile Image: Nerissa M.
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Nerissa M.
Star Sitter
$26
total per visit
4.9 out of 5 stars
95 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: Lise D.
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Lise D.
$28
total per visit
5.0 out of 5 stars
14 reviews
2 repeat clients
18 years of experience
Winnipeg, MB, R2H

About: I have fostered several rescue dogs. I have also owned 3 dogs over my life. I currently have a beautiful playful friendly 70lb female dog.. We walk daily - about 2 hours or more every day. We love going to the dog park, and go almost daily. My house is small and dog friendly. My yard is fairly big. I am retired and have time to care for my dog and others. I live alone with my girl, and when I’m not fostering a rescue, I am happy to care for another dog. I have a fenced yard to keep your dog safe and a female dog to keep your dog active. I also go for long walks a few times a day.

Sitter Profile Image: Aalisha P.
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Aalisha P.
$24
total per visit
10 years of experience
Winnipeg, MB, R2M

About: I grew up with birds and cats! My kitty is a year younger than me. I have 10+ years in experience with pet and babysitting x My availability is quite flexible! I prefer working in the afternoon or evening. However I don’t mind mornings! I am usually free on weekends x I have a 21 year old cat! She cannot eat dry food. Due to her age she most likely has dementia.. in order to make it easier for her we have two litterboxes x

Sitter Profile Image: Ryan H.
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Ryan H.
$24
total per visit
6 years of experience
Winnipeg, MB, R3G

About: I've cared for dogs through dog-sitting and have lived with and become close to several cats. I have research and experience 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 your home. My home is clean, safe and has room for pets to play and relax. I have lots of toys for dogs, and depending on the pet, we can also spend time in the yard or go for walks.

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: Mary Anne R.
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Mary Anne R.
Star Sitter
$36
total per visit
5.0 out of 5 stars
43 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: John A.
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John A.
$23
total per visit
5.0 out of 5 stars
4 reviews
6 years of experience
Winnipeg, MB, R3E

About: I provide reliable, attentive care for active and playful dogs, making every walk, drop-in, or play session safe, fun, and tailored to their needs. I’m experienced with puppies and high-energy adult dogs, ensuring plenty of exercise, play, and mental stimulation, while also offering calm, structured attention. Detail-oriented and dependable, I follow each dog’s routine and provide love, care, and regular photo updates so you always know your pet is happy and safe 🐶 I have a flexible schedule and am happy to accommodate walks, drop-ins, and play sessions at times that work best for you and your dog 🎾 Whether it’s a morning stroll, an afternoon visit, or a quick play session, I can adjust my day to make sure your furry friend gets the attention and care they need 🐾 When caring for pets, their safety and comfort are my top priorities. During walks, I keep dogs on secure leashes, watch for hazards, and make sure they get exercise in a safe and controlled way. During drop-ins, I follow each pet’s routine, provide food, water, and attention, and ensure they are happy and secure in their own home environment. I always treat your home with respect and make sure pets feel calm, comfortable and cared for 🏠

Sitter Profile Image: Sarah M.
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Sarah M.
$23
total per visit
5.0 out of 5 stars
13 reviews
5 repeat clients
20 years of experience
Winnipeg, MB, R3M

Sarah took real good care of our pet Inigo while we were away for a few days! Also watered the plants for us and was good communicator. I’d ask her to watch our pet again!

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Harshil T.
Sitter Profile Image: Polina B.
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Polina B.
Star Sitter
$39
total per visit
5.0 out of 5 stars
54 reviews
19 repeat clients
12 years of experience
Winnipeg, MB, R3C

Thanks to Polina again for watching Shaytan! Polina is a great communicator during the drop in visits and does a great job looking after my cat!

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Brian D.
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: Chloe T.
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Chloe T.
$28
total per visit
4.5 out of 5 stars
4 reviews
10 years of experience
Winnipeg, MB, R3B

About: I have a range of experience working with dogs who are senior, and have a range of temperaments. I am also experienced in the basics of training and house breaking puppies. I also have several tricks up my sleeve for providing meds for dogs with good noses! Flexible, open to weekends and weekdays. Always up for a good walk, playing around in the yard, practicing commands, and completing enriching activities with your pet! I am a vigilant dog walker, with experience specifically with reactive dogs. I have an understanding of assessing the behaviour exhibited by nearby dogs, and the dog I am walking to determine if a situation would fall into a safe and appropriate opportunity for socialization between dogs. I also remain cognizant of litter and avoiding anything a pup might try to pick up that they’re not supposed to!

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

Great experience working with Amanda! She bonded well with my cat and I felt confident he was well-cared for in my absence. She provided very sweet visit updates and pictures. Highly recommend!

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Margot K.
Sitter Profile Image: Joy C.
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Joy C.
$23
total per visit
4.9 out of 5 stars
12 reviews
3 repeat clients
40 years of experience
Winnipeg, MB, R3G

About: I love all dogs- big and small! I have a medium sized (aprox. 60 lb) female mutt who is really easy going. She gets along really well with other dogs and people. We go to Maple Grove dog park every day, and would love to have your dog join us. I have had many different dogs over the years, big and small. During your dog’s stay at my home I can help to to train your dog to behave, teach them tricks, and - of course - love them to bits! Really, in my opinion, dogs are the best! I am home full time to take care of your fur baby. When your dog is in my care, my focus is on them alone. I have a fully fenced yard and a very easy going pup to play with (or help train) your pup. Your dog can sleep on a dog bed, couch, or in bed with me!

Sitter Profile Image: Jessa J.
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Jessa J.
$28
total per visit
5.0 out of 5 stars
21 reviews
9 repeat clients
6 years of experience
Winnipeg, MB, R3C

About: BOOKS OPEN NOVEMBER + DECEMBER. I have been on rover since the first few months of the pandemic, working with families mostly in Calgary, AB. I gave been back in Winnipeg and working with various regulars since 2023. I am currently transitioning out of a career in live music and am a returning university student studying to create community programming for musicians and artists. Currently all my studies are online/by distance so I can offer a work from home vibe for your pets are used to having their humans around. Very active and love to walk/run/hike on a regular basis around my studying. Books are currently closed for the fall - booking christmas 2026. Happy to answer any questions tot might have for your future travel needs. As mentioned all my studies at this time are by distance - I volunteer once a week and attend regular activities however am not typically out of the house for longer than 2/3 hours at a time a few days a week. I always treat your home and your pets as if they were my own. Pride myself in often leaving a space better then I found it and will care for your pets as they were my own. Catering to specific needs in any way that I can and always asking questions if I am unsure.

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

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
5.0 out of 5 stars

Our boys love to see Rylee. She takes such good care of them and makes sure they have fun! She always provides detailed information about her visits and lots of photos so we know about their adventures.

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

Autumn was amazing. I was in need of a dog sitter last minute and she was able to accommodate me so fast. She was so sweet and my puppy adored her. Will definitely be booking with her again in the future. Thank you autumn!

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Leah B.
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
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Why Choose Rover?

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Meet local sitters who will treat your dogs like family

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Popular requests for dog sitting - Winnipeg

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Sitters in Winnipeg average 5
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FAQs for Drop-In Visits - 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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