Pet Sitting & Drop Ins in Oakland-Winchell, Kalamazoo, MI
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Oakland-Winchell pet sitters

“Jaime is such a gift! She took great care of both my dogs during her check in with them, taking them for a walk, sending pictures and giving me an update. I appreciate her communication and quick responses. I’ll definitely rebook with her in the future!”


“Kathleen does a great job taking care of my Standard Poodle Cairro. I highly recommend her to anyone who feels guilty about leaving their furry family member at home while they go on vacation... like me! Excellent communication, trustworthy, and reliable”


“Grace was a wonderful cat sitter! She was punctual, respectful, kind, and very patient with my shy cat. She sent sweet photos of my cat and gave helpful, detailed updates. I’d book with Grace again anytime!”


“My dog had a wonderful time with Dominique while I was away for thanksgiving! I knew she was in good hands. Thank you for playing and snuggling my pup and making her a happy girl!”


“Jess was a perfect for our dogs & situation. Excellent communication & care. She went above & beyond to deal with one of them who was sick. Appreciated her kindness & understanding. My dogs Jellee & Finn took right to her. I highly recommend her for your pet care & will seek her out first for the next time we need help!”


“This was my Husband and I’s first time using Rover and Carly was such an amazing find. From the moment we met Carly we knew our Kitty Fur Babies would be in good hands. She made sure she had their daily num num routine down along with their other personal care needs. Carly put us at ease being away from our Fur Babies Gala and Floki. We looked forward to getting our Rover Report Card everyday. It had an update with how they were doing along with pictures. She was also very quick with responding to messages. We were so beyond happy with how she took care of our Fur Babies. You will not go wrong with Carly.”


“Petra is awesome! She is attentive and detailed. I appreciate her flexibility with my ever-changing schedule. My dogs love her and that's a challenge with my husky because he's very stubborn.”



“Teresa is always so amazing and goes above and beyond to care for our cat. I have never booked with anybody else because I know that I will not be stressed during my travels, knowing that I have Teresa coming. We enjoy and trust her so much and it truly feels like she is family!”


“Lynn has been phenomenal to work with! In her summary of each visit, you can tell that she is invested in your pet and is enjoying spending time with them. Before our vacation, she alsp set up a meet & greet to ensure that she was fully prepared. I can't recommend her enough!”


“Dean was incredible taking care of my cats while I was on vacation. He was diligent on making sure they were taken care of and having fun. Highly recommend!”


About: I’ve had several years of experience with pets of all different kinds. I used to work for a professional pet sitting company, a dog day care, and currently work at a vet clinic. I have experience with puppies, senior dogs, reactive dogs, shy dogs, and hyperarousal behavior. I am currently working full time at a local veterinary clinic, and I am pet sitting part time on my days off! I am available on Friday's, some Tuesday's, and some weekends. I do not offer services in my own home as I have two dogs of my own, however I do drop in visits/walks at your home!

“As always Katey goes above and beyond to make sure the time she spends with my Oakley wears her out! I love that she takes so many pictures and sneaks in extra cuddle time 🥰”


About: Hi! My name is Anna and I live in Kalamazoo Michigan. Throughout my whole life I have always been surrounded by animals. From 2 years old, to 20 years old, my family has had 3 dogs, 2 cats, 1 bearded dragon, a Guinea pig, and 2 bunnies (the bunnies are all mine though and my pride and joy). I’ve had lots of experience with all kids of pet care such as bathing, grooming, feeding, giving medicine, and more! I love all animals and do everything I can to make sure they are healthy and happy. I am currently in my Sophomore year at Western Michigan University studying Early Education. I also work part-time at a daycare. I originally started doing rover last year for a summer job but have really enjoyed it so have kept continuing with it! At my home my pets have access to food and water when they need it, and always gets lots of play time and of course love. My backyard is not fenced but I have lines that my dogs go on that are very long and prevent them from running out of the yard. My pets are also in a safe environment in my home 24/7. If I were to be in a clients home I of course 100% would give their animal(s) the best care that I can. Pets are welcome to my house if needed but with my littler dog being a very jealous little thing when other dogs get attention, it can bring him on the edge with his barking but it wouldn’t be a problem.

“Hunter was great start to finish. Fantastic communication and we were able to see Hunter went above and beyond taking care of our cats. Hunter was even able to win over our Orange tabby Opal from the first meeting, which Opal rarely likes anyone besides her parents. Would absolutely recommend Hunter to anyone in need of a pet sitter!”


About: I will cuddle or walk for hours if that is what your pooch desires. I am happy to play inside or outside too. I am really a tune to what animals are trying to tell us when sick or needing more attention. My empathy for animals goes a long way. With my 8-5 job, I have flexible lunch hours. I don't have any pets living at home anymore and I am single with no kids. I have plenty of time to fulfill my yearning for companionship these days. I will always be sure to use a leash with a collar and a harness if needed. I will also be sure to be careful around other animals and walkers on trails.

“Cara was absolutely amazing from the first minute we met her! We did a meet and greet before booking and we knew right away our pups would be in the best hands. Cara had fantastic communication, sent pictures, and really bonded with our dogs. Our dogs have some weird quirks and she handled everything perfectly! We felt so good knowing our pups were in great hands and being taken care of with love. They loved her! Absolutely recommend Cara for your pet watching needs. She’s the best and will absolutely use her services again for our next vacation.”

Loving pet sitters in your neighborhood
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Jamie B.
Star Sitter


“Jaime is such a gift! She took great care of both my dogs during her check in with them, taking them for a walk, sending pictures and giving me an update. I appreciate her communication and quick responses. I’ll definitely rebook with her in the future!”


Kathleen W.Star Sitter

“Kathleen does a great job taking care of my Standard Poodle Cairro. I highly recommend her to anyone who feels guilty about leaving their furry family member at home while they go on vacation... like me! Excellent communication, trustworthy, and reliable”


Grace C.

“Grace was a wonderful cat sitter! She was punctual, respectful, kind, and very patient with my shy cat. She sent sweet photos of my cat and gave helpful, detailed updates. I’d book with Grace again anytime!”


Dominique Y.
Star Sitter


“My dog had a wonderful time with Dominique while I was away for thanksgiving! I knew she was in good hands. Thank you for playing and snuggling my pup and making her a happy girl!”


Jess P.Star Sitter

“Jess was a perfect for our dogs & situation. Excellent communication & care. She went above & beyond to deal with one of them who was sick. Appreciated her kindness & understanding. My dogs Jellee & Finn took right to her. I highly recommend her for your pet care & will seek her out first for the next time we need help!”


Carly B.Star Sitter

“This was my Husband and I’s first time using Rover and Carly was such an amazing find. From the moment we met Carly we knew our Kitty Fur Babies would be in good hands. She made sure she had their daily num num routine down along with their other personal care needs. Carly put us at ease being away from our Fur Babies Gala and Floki. We looked forward to getting our Rover Report Card everyday. It had an update with how they were doing along with pictures. She was also very quick with responding to messages. We were so beyond happy with how she took care of our Fur Babies. You will not go wrong with Carly.”


Petra P.Star Sitter

“Petra is awesome! She is attentive and detailed. I appreciate her flexibility with my ever-changing schedule. My dogs love her and that's a challenge with my husky because he's very stubborn.”


Dee M.Star Sitter

“Much appreciated on coming over with such short notice. Very impressive that Loki was receptive to you and your care. Very professional and respectful.”


Gina L.Star Sitter

“Total piece of mind when Gina is watching our boys! SUPER reliable and dependable and goes the extra mile to make friends with even the shyest of cats. Recommend 100%!”




Theresa D.Star Sitter

“Teresa is always so amazing and goes above and beyond to care for our cat. I have never booked with anybody else because I know that I will not be stressed during my travels, knowing that I have Teresa coming. We enjoy and trust her so much and it truly feels like she is family!”


Lynn K.

“Lynn has been phenomenal to work with! In her summary of each visit, you can tell that she is invested in your pet and is enjoying spending time with them. Before our vacation, she alsp set up a meet & greet to ensure that she was fully prepared. I can't recommend her enough!”


Dean R.Star Sitter

“Dean was incredible taking care of my cats while I was on vacation. He was diligent on making sure they were taken care of and having fun. Highly recommend!”




Kristen F.
“Kristen was great. She sent me pictures of my cats which I always love! She was flexible and personable. Will use her services again and would definitely recommend!”


Nicole Z.
“I have used Nicole to check on my house cats for many years. Some were senior and required medicine. She has never been unable to meet my schedule even at last minute requests. She checks on them as agreed and always sends pictures of the cats getting their food or special treats she brings them. She takes care of their litter boxes and cleans up any ‘mistakes’ they make. She puts my mind at ease knowing that she takes such good care of them and always gives them love and attention.”


Katey M.


“As always Katey goes above and beyond to make sure the time she spends with my Oakley wears her out! I love that she takes so many pictures and sneaks in extra cuddle time 🥰”


Anna S.
About: Hi! My name is Anna and I live in Kalamazoo Michigan. Throughout my whole life I have always been surrounded by animals. From 2 years old, to 20 years old, my family has had 3 dogs, 2 cats, 1 bearded dragon, a Guinea pig, and 2 bunnies (the bunnies are all mine though and my pride and joy). I’ve had lots of experience with all kids of pet care such as bathing, grooming, feeding, giving medicine, and more! I love all animals and do everything I can to make sure they are healthy and happy. I am currently in my Sophomore year at Western Michigan University studying Early Education. I also work part-time at a daycare. I originally started doing rover last year for a summer job but have really enjoyed it so have kept continuing with it! At my home my pets have access to food and water when they need it, and always gets lots of play time and of course love. My backyard is not fenced but I have lines that my dogs go on that are very long and prevent them from running out of the yard. My pets are also in a safe environment in my home 24/7. If I were to be in a clients home I of course 100% would give their animal(s) the best care that I can. Pets are welcome to my house if needed but with my littler dog being a very jealous little thing when other dogs get attention, it can bring him on the edge with his barking but it wouldn’t be a problem.


Courtney C.

“Thank you!”


Hunter C.Star Sitter

“Hunter was great start to finish. Fantastic communication and we were able to see Hunter went above and beyond taking care of our cats. Hunter was even able to win over our Orange tabby Opal from the first meeting, which Opal rarely likes anyone besides her parents. Would absolutely recommend Hunter to anyone in need of a pet sitter!”


Nicole W.
About: I will cuddle or walk for hours if that is what your pooch desires. I am happy to play inside or outside too. I am really a tune to what animals are trying to tell us when sick or needing more attention. My empathy for animals goes a long way. With my 8-5 job, I have flexible lunch hours. I don't have any pets living at home anymore and I am single with no kids. I have plenty of time to fulfill my yearning for companionship these days. I will always be sure to use a leash with a collar and a harness if needed. I will also be sure to be careful around other animals and walkers on trails.


Cara V.Star Sitter

“Cara was absolutely amazing from the first minute we met her! We did a meet and greet before booking and we knew right away our pups would be in the best hands. Cara had fantastic communication, sent pictures, and really bonded with our dogs. Our dogs have some weird quirks and she handled everything perfectly! We felt so good knowing our pups were in great hands and being taken care of with love. They loved her! Absolutely recommend Cara for your pet watching needs. She’s the best and will absolutely use her services again for our next vacation.”
How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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 pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Oakland-Winchell.
Rover makes it easy to find Oakland-Winchell pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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.
