House Sitting in Headingley
Find a loving house sitter to watch over your pets and your home.

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Top rated Headingley house sitters
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“We loved having Kristin dog-sit for us! Kristin truly went above & beyond from buying our dog Odin a special toy to cleaning our oven! It made our holiday even more enjoyable having the peace of mind that Odin & our home were being so well looked after!”

About: I have been taken care of dogs since I was a baby and have had 9 puppers in my life time. My dog Beau is my companion who is full of life! Taking care of her includes administering her medication on a daily basis. I have trained Beau since she was a puppy, this includes simple commands such as sit or shake but also includes more complex training including “place” “heel” and other tricks! I also have experience with senior dogs who often require more care. I am a full time University Student with time during the day, evenings, and weekends to care for pets with all levels of needs. I often have breaks in classes that allows me time to care for animals during the day when most people are at work n I create a safe and comforting environment for all animals in my own home or theirs. I do my best to revolve my schedule around the animals daily routines to make the transition more seamless.

“We used RP while we were away for 3+ weeks to care for our “zoo” consisting of two dogs and two cats. He met us twice beforehand to ensure it was a good fit and he asked thoughtful questions. Our animals were in great hands while we were away: he sent pictures, told us how everyone was doing, and generally left us with peace of mind. We would highly recommend RP to others!”

“Another fantastic job. Really took care of my dog like he was hers. Communication was good. Even though I was several time zones away. Always ready to do right by my dog. If you really want someone that will care for your pet and has great communication skills, Shayleece is fantastic.”

“I feel so lucky to have found Amelie! From the moment we met, I could tell how much she truly loved the work she does and that gave me so much peace of mind. She took such amazing care of Otis. The week prior to us leaving Otis had a bout of pancreatitis - Amelie continued medication and caregiving sending me updates and photos that made me smile and able to enjoy myself while I was away. When I came home, Otis was healthy, happy, calm, and clearly well-loved the whole time. My home was very clean and even my garbage/recycling were already outside for pick-up. It’s such a relief to know that I can trust someone who treats my dog and home like their own. Amelie went above and beyond, and I couldn’t be more grateful. I wouldn’t hesitate to book her again and would highly recommend her to anyone who wants their animal cared for with love, attention, and lots of cuddles. Thank you Amelie for your help you are very special and very appreciated! Brian, Juanita and Otis ❤️🐾”

About: I had a Yorkie for 13 years before adopting my cat Pawl last year. I will be happy to take care of your babies too! I can do boarding for dogs only and drop-in visits for both cats and dogs. I work from home most days of the week and will also be happy to take care of your pet in the evenings and during weekends. I live in a house with a fenced yard and my indoor only cat is allowed anywhere he likes. My priority is your pet’s safety and happiness and your peace of mind. I will follow your care instructions and make sure to always keep you updated!
“Ruth was absolutely amazing!! She sent constant pictures of our girls and kept us in the loop if anything happened! We will definitely be rebooking with her🥰 highly recommend to anyone looking to book!”

About: I have owned dogs, cats, and other animals in the past. I have also volunteered at veterinary clinic. I enjoy spending time animals and look forward to caring for yours. Let me know all the information I need to care for your pet(s). Can care for dogs that are house trained. I can care for dogs in my home and cats in yours. I enjoy spending time with animals and I look forward to hearing from you to care for your fur baby. I have considered my dogs to be a member of my family. I have a fenced back yard. I can care for dogs in my home and can pet sit cats in your home. I can offer drop in pet services also.
About: Hi :) I am someone who treats every pet like they're my own - not just cared for, but genuinely understood. I know how important it is to trust the person looking after your fur-babies, because they're family. I pay close attention to each animal's personality, routines and little quirks so they feel safe, relaxed and happy while you're away. Whether your dog needs long, energy burning walks or they prefer quiet company and gentle care, I adjust to them - not the other way around. What sets me apart is the level of attention and communications I provide. You'll always know how your pup is doing with regular updates, photos and honest check-ins. I'm reliable, patient and calm under pressure, which helps even anxious or shy dogs feel comfortable. I's also experienced with: 1. different energy levels (from playful pups to senior dogs.) 2. Administering basic medications if needed 3. Maintaining routines (feeding, walks, etc) 4. Giving lots of affection while still respecting boundaries At the end of the day, my goal is simple: your pet feels safe, loved and stress-free - and you have complete peace of mind. Pet care is my full-time focus, which means I've built my daily and weekly routine entirely around the needs of the pets I care for. I schedule my days to allow for consistent walks, check-ins, playtime and companionship, ensuring every pet gets reliable, unrushed attention. Your pet won't be "fit-in" - they'll be a priority in my day. When caring for pets in your home, I aim to keep everything as close to their normal routine as possible. I follow feeding schedules, walk routines, and household guidelines carefully so your pet feels secure and stress-free in their own environment. I treat your home with the same respect I would my own - clean, tidy and secure at all times. I'm mindful of details like locking up properly, keeping things organized, and maintaining a calm environment for your pet. You can also expect regular updates, photos, and honest communication so you always feel connected and at ease while you're away. I understand that inviting someone into your home requires trust, and I take that responsibility seriously.
About: I’ve had dogs as pets my whole life, and I have about 10 years of experience pet sitting for friends - both cats and dogs! I also have some experience caring for pets who require regular medications. I’m currently working full time in downtown Winnipeg, with my day typically ending between 3-4pm! This makes it easy for me to stop by your place for mid-afternoon walks and potty breaks for your pets! I am also comfortable staying overnight if you go out of town and can’t bring your pets with you :) I have many years of experience walking dogs of varying sizes on leash, and some experience with leash training! I am comfortable crating animals who require it as well.
About: Having grown up in a family with 3 cats and a dog, I've always had a strong love and interest in animals. I feel that I can really relate to the animal and get a sense of their soul. I looked after both dogs and cats while travelling in Europe. (During this time, I was working remotely as a freelance translator.) I have experience with various breeds, in particular, greyhounds, as I had an extended sit caring for a senior Spanish greyhound for 6 weeks. I have also cared for multiple cats and dogs at the same time, as I looked after 2 dogs and 2 cats at a house sit in England. I am based in Winnipeg and have a car to get to your location. I am a self-employed freelancer with plenty of spare time for pet care. At the moment, I am devoting most of my time to animal care. I always treat my clients' home and property with the upmost respect and I pay particular attention to the hand-over procedure and any special details or information about your home and/or your pets. I love animals and will look after your pets as if they were my own.
About: I’ve been a lifelong dog lover and have had the privilege of raising both rescue dogs and a purebred Golden Retriever over the years. Each one has shaped how I care for animals—with patience, understanding, and a lot of love. In our home, pets truly are family. Their happiness, comfort, and well-being are always a top priority, just as if they were children. I understand how important it is to trust someone with your dog, and I take that responsibility seriously. I’m known for being kind, conscientious, and reliable—not just with dogs, but with people too. I’ll always communicate clearly, show up when I say I will, and make sure you feel confident your pet is in good hands. I’m currently working part-time, which allows me to dedicate quality time and attention to the pets in my care. My approach is simple—I care for every pet as if they were my own. That means plenty of exercise tailored to your dog’s individual needs, along with a strong focus on mental stimulation through enrichment, play, and engagement—not just walks. In a client’s home, I respect your pet’s routine and environment, keeping things as consistent as possible to reduce stress. I make sure they receive plenty of attention, exercise, and mental stimulation, while also giving them the patience and calm presence they need to feel at ease. I care for every pet as if they were my own—prioritizing their comfort, happiness, and well-being at all times.
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.
“Michelle is an amazing pet sitter. We found her for a last-minute booking and couldn’t have been happier. She is friendly, responsible, and seems to love dogs as much as we do! Highly recommended.”

About: I’ve been caring for dogs since I was 12, and it’s truly one of my favorite things to do! I love spending time with furry friends—feeding them, playing with them, and making sure they feel happy and safe. Since moving to Winnipeg four years ago, I’ve been the go‑to pet sitter for friends whenever they travel. They trust me because I follow their instructions carefully and treat their pets like part of my own family. I’d be happy to give your beloved companion the same loving care while you’re away! I’m working from home right now, so I’d really enjoy hanging out with a furry friend. I have plenty of experience caring for pets, and I’m flexible with my hours to make sure they get all the attention and walks they need. I’ll make sure your pet feels safe and comfy. With a balcony for fresh air, your furry friend will be happy. I follow instructions carefully and give lots of love and care.
About: I bring a unique blend of experience, reliability, and genuine love for animals that truly sets me apart from other sitters. I have hands-on experience with dogs of all ages, including specialized care for energetic puppies and gentle support for senior pets with mobility or medical needs. I’m patient, detail-oriented, and fully committed to keeping pets safe, happy, and comfortable in their own environment. Whether it's administering medication, reinforcing training routines, or just providing plenty of affection and playtime, I treat every pet like they’re my own. My goal is to build lasting trust with both pets and their owners. I have background as a caregiver for cats, rodents, reptiles and fish as well. I freelance in media production, this gives me the benefit of planning and controlling my own schedule. The benefit is that your pet is given the priority it deserves when called upon. I currently do not have the space available at my own home to house a pet but my vehicle is available to travel with pets if required.
“Julia's love for animals was apparent from our initial meet and greet. She did a great job caring for our dog, cat, and house well we were away. We came home to a clean house and happy pets.”
“We are so grateful for the amazing care that Arissa provided our two kitties. She went above and beyond caring for them and ensuring we received regular updates. Arissa was truly amazing and our kitties had the best time with her. It was sweet knowing that she truly got to know our two kitties and cared for the comforts they love. Arissa also went above and beyond in the way she left our home and we can’t recommend her enough. She truly loves pets and has a heart of gold!”

Over 4 pet parents in Headingley have booked house sitting
Headingley pet parents share their Rover experiences
We had Eleni watch our dog (Jack) and cat (Morty) and she was absolutely wonderful! She was so kind and helpful, very communicative throughout the entire stay, and kept us well-informed with updates. Both pets were happy and well cared for when we returned, and it gave us real peace of mind knowing they were in such good hands. Eleni went above and beyond, and we’ll definitely be booking her again in the future. Highly recommend!

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Headingley is $50
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 house 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.
Sitters in Headingley average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Headingley on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 239 house sitters in Headingley. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Headingley house sitters respond in under an hour.
House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Headingley.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Headingley house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.


