House Sitting in Headingley

Find a loving house sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Brena D.
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Sitter Profile Image: Brena D.
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1. Brena D.

Rover 101
PAWSITIVELY GREAT PET CARE
Winnipeg, MB, R3A
19.0 km. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
77 reviews
27 repeat clients
from
$45
per night

I was very happy with Brena’s care of my cat and house during the ten days while I was away. I liked her as soon as I met her, as did my cat. She’s definitely an animal/pet person. I received daily updates on how Ollie was doing as well as photos and videos. She kept in touch and reached out if she had any questions. I came home to a content kitty and a maintained home. I would definitely hire her again. Thanks so much Brena!

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Sitter Profile Image: Rp S.
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Sitter Profile Image: Rp S.
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2. Rp S.

Rover 101
Your pets & home are in good hands.
Winnipeg, MB, R2L
21.5 km. away
House Sitting, Dog Walking
5.0 out of 5 stars
66 reviews
23 repeat clients
from
$40
per night

Rp is incredible! He is extremely thorough in following instructions and goes above and beyond to ensure the right care is provided to your pet! We really appreciate how accommodating he was in taking care of pupper, who definitely enjoyed his evening with RP. Would highly recommend!

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Sitter Profile Image: Sara M.
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Sitter Profile Image: Sara M.
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3. Sara M.

Caring and Dedicated Pet Sitter 🐾
Winnipeg, MB, R3K
8.6 km. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$65
per night

I would highly recommend my sister Sara as a pet caregiver. She loves animals and has such responsible qualities. With our pets, she is always playing with them, cleaning for them, and caring for them. She gives as much attention as she can to them all the time. She methodically plans when the pet should be fed, let outside, or cleaned up. With pets of family and friends, she loves and cares for them like they are her own, always doing what is best for them, playing with them, and interacting with them. Sara loves snuggles, giving pets, playing games, and also knows when the pet needs their own space or to be left alone. I would highly recommend Sara for your pet caregiver needs.

Confirmed availability: Victoria Day Weekend
Sitter Profile Image: Varsha T.
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Sitter Profile Image: Varsha T.
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4. Varsha T.

When I Need A Friend, I Find A Paw.
Winnipeg, MB, R2R
16.0 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
4 reviews
from
$50
per night

I was thrilled to encounter Varsha; she is a true dog lover who takes excellent care of my dog. I have no concerns about Varsha. Lacee wags her tail and travels with her without complaint. Varsha will text me a picture, leave me information on the finest treats for my pets, and care for each of them like I would. I never worry about Lacee when Varsh is present. Thank you so much for giving me "peace of mind" while I work. The Best Ever for Dog Lovers!!

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Sitter Profile Image: Aambika S.
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Sitter Profile Image: Aambika S.
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5. Aambika S.

Tail-Wagging Pet Care
Winnipeg, MB, R3L
18.9 km. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night

Aambika is one of the kindest people I know. She is very easy to get along with and has a vibrant energy that lights up any room. As a nurse, she’s very patient and smart and genuinely loves taking care of people, pets and her plant babies, too! She is the perfect person to take care of your pet as I know she will care for them as if they were her own.

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Sitter Profile Image: Jessa J.
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Sitter Profile Image: Jessa J.
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6. Jessa J.

ex puppy foster mom
Winnipeg, MB, R3G
24.2 km. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
8 repeat clients
from
$50
per night

Great communication with Jessa beginning to end. She sent us updates and pictures. Felt comfortable and confident leaving Maggie in Jessa’s care in my home while we were on a weeks vacation: would recommend and will definitely be in touch for our next trip!

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Sitter Profile Image: Megan G.
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Sitter Profile Image: Megan G.
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7. Megan G.

Animal lover, attention to detail!
Winnipeg, MB, R3J
11.4 km. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night

Megan is simply amazing with pets. She's caring, responsible, and goes above and beyond to ensure every animal in her care is happy and healthy. From toys to dietary needs, she covers it all, making sure each furry friend feels right at home. Megan takes the time to understand each pet's quirks and preferences, providing tailored care that truly sets her apart. Plus, she keeps pet owners in the loop with regular updates, giving them peace of mind. With Megan, you know your pets are in the best possible hands.

Confirmed availability: Victoria Day Weekend
Sitter Profile Image: Nate M.
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Sitter Profile Image: Nate M.
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8. Nate M.

Tony's doggy play care! 🐾🦈
Winnipeg, MB, R3T
21.4 km. away
Boarding, House Sitting, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
from
$50
per night

my boyfriend and I got a little (lol) Bernese Moutaimn dog puppy and needed someone to board for a few days while we were moving. Aspen was in a little fenced area (that we brought) while they were inside house and he got a lot of playtime with Nate. They took Aspen on cute walks to the lakes and let him have first great social interactions with adult dogs. His dogs are super friendly and great puppy trainer 😍 We already had used Nates service again and would definitely book him anytime 😊

Sitter Profile Image: Joshua F.
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Sitter Profile Image: Joshua F.
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9. Joshua F.

Loyal trusting loves dogs
Winnipeg, MB, R3M
17.9 km. away
House Sitting, Dog Walking
from
$40
per night

For as long as I’ve known him, josh has always been great with dogs. He’s been a reliable dog sitter, with many friends and family trusting him with their fur babies. He is patient, reliable and kind- always willing to go above and beyond. He’s active and never sitting still! He would make an excellent friend for your furry companion!

Sitter Profile Image: Morin B.
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Sitter Profile Image: Morin B.
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10. Morin B.

Momo & Miki
Winnipeg, MB, R3Y
19.1 km. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
from
$35
per night

We invited Morin and Miki to stay with Loka while we travelled this month. This was our first time using someone from the Rover app and we were initially a little nervous. However, all anxiety fell aside the second we met them. We instantly felt so comfortable with them! We could tell they genuinely were so excited to care for Loka. They asked all the right questions about her routine/schedule and preferences… And if I’m being honest, they may have done a better job caring for Loka than us!! Loka was spoiled with attention, frequent potty breaks/walks and so many snuggles. We really enjoyed the check ins and photo updates too! Our home was spotless when we returned! Absolutely would not hesitate to use them again in the future! Highly recommend!

Confirmed availability: Victoria Day Weekend
Sitter Profile Image: Holly E.
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Sitter Profile Image: Holly E.
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11. Holly E.

Eat. Play. Love.
Winnipeg, MB, R3L
19.3 km. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
3 repeat clients
from
$38
per night

Holly was punctual and polite. Holly communicated quickly and clearly. Our home was clean with a good vibe, upon return. Our pets were peaceful, and calm upon our return

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Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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12. Ashley B.

Last minute bookings welcome!
Winnipeg, MB, R3C
18.9 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
3 repeat clients
from
$60
per night

Ashley was great! We booked last minute and she was very accommodating. Our bullies seemed to really like her. Will definitely book her again

Confirmed availability: Victoria Day Weekend
Sitter Profile Image: Rebecca K.
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Sitter Profile Image: Rebecca K.
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13. Rebecca K.

Anything for your dog
Winnipeg, MB, R2M
22.9 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
17 reviews
10 repeat clients
from
$73
per night

I can't say enough wonderful things about Rebecca. She loved on our dogs while we were away just like I would. Sent photos and videos, and was just so dang sweet and lovely. Your pets are in SUCH good care with her.

Sitter Profile Image: Lisa S.
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Sitter Profile Image: Lisa S.
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14. Lisa S.

Pawsitive pet care
Winnipeg, MB, R3T
19.8 km. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$60
per night

Lisa has been an absolute life safer for Sadie and I! When the day care that I took Sadie to shut down, she agreed to watch Sadie in my home. I work long varying hours, and Lisa has always been flexible with that. Sadie is very high energy, and she’s always pooped when I come home from work! Lisa takes her for all the walks she needs, and spends time playing/cuddling with her too. Sadie absolutely loves her! I would absolutely recommend Lisa to look after your furry friend :)

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Sitter Profile Image: Alyssa D.
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Sitter Profile Image: Alyssa D.
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15. Alyssa D.

supplying love, care and fun always
Winnipeg, MB, R3P
15.8 km. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
2 repeat clients
from
$65
per night

Alyssa stayed with our pup Louis for a week while we were traveling and we are so thankful for her help! We were able to relax and enjoy our holiday away without having to worry about Louis because we knew he was in good hands. From start to finish Alyssa was thorough and professional, and she made everything so easy. She went absolutely above and beyond and we are so grateful to have met her. ❤️

Sitter Profile Image: Adam M.
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Sitter Profile Image: Adam M.
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16. Adam M.

Here to care for your friends!
Winnipeg, MB, R3G
17.7 km. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night

This guy has been pet sitting for me for years- he's consistent, kind, has the biggest heart, and gives my special guy extra love and cookies when I'm away. I know my pet is in good hands when A is here, and it takes alot of worry off my plate.

Confirmed availability: Victoria Day Weekend
Sitter Profile Image: Jaeda G.
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Sitter Profile Image: Jaeda G.
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17. Jaeda G.

Eat. Play. Love🩵
Winnipeg, MB, R3J
11.1 km. away
House Sitting, Drop-In Visits, Dog Walking
5 years of experience
from
$25
per night

About: I’ve been taking care of animals since I was 16! I love the outdoors and long walks! I have great references as well:) I hope to meet your furry loved ones soon! Im currently working part time, no more than 4 hours! So I am available Monday to Sunday at whatever times. If you’re gone for One day or even 3 weeks I’d be happy to help you out! I care for them by loving them every second and playing with them when needed! I love to go for walks or will be happy to play in your back yard!

Sitter Profile Image: Christelaine G.
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Sitter Profile Image: Christelaine G.
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18. Christelaine G.

your furry friend's bestfriend!
Winnipeg, MB, R3Y
18.0 km. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night

Elaine has helped take care of our cat, our dog, and our bird on multiple occasions. She is great with all types of animals, and especially adores dogs (they adore her too!). Biggest animal lover I know!

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Sitter Profile Image: Gabrielle W.
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Sitter Profile Image: Gabrielle W.
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19. Gabrielle W.

Rover 101
Dog Sitting/Boarding/Walking
Winnipeg, MB, R3L
18.3 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
3 years of experience
from
$25
per night

About: I have taken care of friend’s and family’s pets while they were away travelling for the last couple of years. I also have a year of experience working at a dog shelter in Montreal. I make my own schedule during the week and have access to my work vehicle so I have lots of time to spend with the dogs I board/sit. Please note I am only able to board small dogs due to the rules of my condo building. If I board a pet at my home, there will be plenty of other dogs in my building to meet and play in the yard. If I dog sit at someone’s home, I do my best to keep them as comfortable as possible. I know it can be stressful when owners leave.

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Sitter Profile Image: Hannah H.
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Sitter Profile Image: Hannah H.
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20. Hannah H.

Experienced. Here to help.
Winnipeg, MB, R3P
14.1 km. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
1 repeat clients
from
$70
per night

Hannah has walked our sensitive and hesitant Spaniel many times and our dog loves her. Hannah is on time is very reliable and has very good skills with our dog. I highly recommend her.

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Rover also offers House Sitting in:

Rover also offers other services in Headingley:

Book reliable house sitting in Headingley with Rover. The house sitters you’ll find on Rover provide services that let your pet relax in the environment they like best when you’re away—your home. It doesn’t matter if you’ll be gone for a night or several weeks, there’s a sitter right in your neighborhood who can’t wait to watch your dog. Other house sitting websites don’t offer the same level of ease, security, and friendliness you’ll find on Rover. Plus, booking with Rover gives you plenty of peace-of-mind protections, like pet insurance and a round-the-clock support team.

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