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
79 reviews
28 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
67 reviews
23 repeat clients
from
$40
per night

This was our second time leaving our home and 2 dogs in the care of RP. He took the time to learn about the medical needs of one of our dogs and administered medication while we were away. RP was also willing to make adaptations to his schedule when we thought we may have a delay returning home. We came home to a clean house and happy, well-cared for dogs. We feel lucky to have found RP and would definitely recommend him to anyone who needs a dog sitter! Thank you RP!

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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

Sara has a sweet and gentle nature. She is professional and polite - making her lovely to work with. Sara is dedicated to the work she does, no matter what field. I would certainly trust her with my pets.

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
6 reviews
from
$50
per night

Hello, I just wanted to let you know how satisfied we were with your service. Brody was overjoyed and playful when we returned. It's wonderful to know that someone cares enough to look for them while we're away.

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Sitter Profile Image: Megan G.
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Sitter Profile Image: Megan G.
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5. Megan G.

Animal lover, attention to detail!
Winnipeg, MB, R3J
11.4 km. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$55
per night

Megan is great! She helped look after my 2 large dogs while I was away on vacation, and they both loved her. Took them for walks, made sure they had everything they need, and played with them loads. My dogs miss her, they love seeing her again!

Confirmed availability: Victoria Day Weekend
Sitter Profile Image: Aambika S.
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Sitter Profile Image: Aambika S.
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6. Aambika S.

Tail-Wagging Pet Care
Winnipeg, MB, R3L
18.9 km. away
House Sitting, Drop-In Visits, Dog Walking
1 reviews
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: Erika A.
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Sitter Profile Image: Erika A.
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7. Erika A.

Animal loving care taker
Winnipeg, MB, R2V
22.4 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
3 reviews
from
$65
per night

Erika is an animal lover at heart. She will go above and beyond to make any animal as happy as can be. She takes the best care of so many animals and her friends and family can always rely on her to take care of their pets because she does such a great job!

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Sitter Profile Image: Alyssa D.
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Sitter Profile Image: Alyssa D.
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8. 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. ❤️

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Sitter Profile Image: Asia D.
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Sitter Profile Image: Asia D.
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9. Asia D.

Life long pet lover and owner!
Winnipeg, MB, R3Y
19.6 km. away
House Sitting, Drop-In Visits, Dog Walking
12 years of experience
from
$40
per night

About: I have spent many hours volunteering at humane societies, I’ve had pets my entire life, when I lived in Hawaii where I took care of feral cat colonies (this included feeding them, enriching them, and making sure they were healthy), and I am planning on going to vet school I am currently attending school, so I have time before (7:30am) and after school (4:00pm) to be with you fur babies and I can be with them all day on weekends! I can snuggle with animals all day (I honestly have to be pulled away from them to not snuggle) and I also love playing with them! I am a very active person so I take my dog on walks at least once a day (usually twice a day) but I can do as many walks as needed!

Confirmed availability: Victoria Day Weekend
Sitter Profile Image: Nate M.
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Sitter Profile Image: Nate M.
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10. 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: Morin B.
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Sitter Profile Image: Morin B.
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11. 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!

Sitter Profile Image: Joshua F.
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Sitter Profile Image: Joshua F.
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12. Joshua F.

Loyal trusting loves dogs
Winnipeg, MB, R3M
17.9 km. away
House Sitting, Dog Walking
1 reviews
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!

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.

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Sitter Profile Image: Ashley B.
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Sitter Profile Image: Ashley B.
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14. 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

Sitter Profile Image: Holly E.
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Sitter Profile Image: Holly E.
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15. 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: Keegan B.
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Sitter Profile Image: Keegan B.
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16. Keegan B.

Student—Experienced Pet Care
Headingley, MB, R4J
1.4 km. away
House Sitting, Drop-In Visits
1 reviews
from
$65
per night

I was amazed with the dedication and passion Keegan showed caring for our beloved family dog! His attention to detail and willingness to go above and beyond was really appreciated. Keegan will definitely be the first person I ask whenever I need pet sitting services!

Sitter Profile Image: Lisa S.
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Sitter Profile Image: Lisa S.
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17. 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 devoted most of her lifetime to caring for animals escpecially dogs. Her connection with the furbabies is phenomenal. She puts them first and showers them with more love than they can handle. I won't lose any sleep if I left my pup was under her care.

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Sitter Profile Image: Jaeda G.
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Sitter Profile Image: Jaeda G.
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18. 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!

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Sitter Profile Image: Mikaela M.
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Sitter Profile Image: Mikaela M.
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19. Mikaela M.

Pet sitter- available all week
Winnipeg, MB, R2P
19.4 km. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
1 reviews
from
$80
per night

Mikaela is a wonderful dog owner, and would treat your doggo like her own! She is responsible and you can trust she would take good care of your pet.

Sitter Profile Image: Adam M.
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Sitter Profile Image: Adam M.
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20. Adam M.

Here to care for your friends!
Winnipeg, MB, R3G
17.7 km. away
House Sitting, Drop-In Visits, Dog Walking
1 reviews
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.

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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.

House Sitting