Pet Sitting & Drop Ins in Oakwood Village, Madison, WI
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 Oakwood Village pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Hannah was great! She agreed to do 2 meet and greets since we were moving and came in to feed our kitten (16 year old prissy cat) and got her to take all her meds, no problem! Thank you, Hannah!”

“Kaitlyn was wonderful! She took care of our cat while we were out of town and she did the job well and sent photos. We were happy with the service Kaitlyn provided, would highly recommend and we will book again with her in the future.”

About: I have taken care of pets since I was ten years old. Family members and neighbors have counted on me to take care of their pets for years, including pets of all ages and with medical needs. I have an incredible attention to detail and will treat your pets as my own. I am also willing to care for pets other than cats and dogs. I specifically have experience with leopard geckos, guinea pigs, and parrots, and my experience volunteering in wildlife rehabilitation would allow me to assist with any exotic. I'm currently self-employed, so I have plenty of time to dedicate to your precious pets. I am available for house sitting, drop-in visits, and walking every day of the week. I will care for your pets as if they were my own, and I will be sure to follow all instructions given to me. Keeping your pets safe will be my priority. You can trust that your pets will be safe and happy while they are in my care. If I am staying in your home, I will do my best to make sure my impact on the space is as minor as possible and the only evidence that I was there will be a happy pet!
“Jess was sincere, flexible, and very accomodating to my variable travel plans and respective changes to our scheduling to watch my boy. I would recommend her as a trusting sitter and would be thankful to utilize her care and services in the future.”

About: Hi, I’m Kaitlyn and I’ve lived with dogs for almost 20 years! I’ve helped family, neighbors and friends with pets of all ages, sizes and personalities. My experience has provided insight into how to comfortably care for most pets! I’m currently working at a dental clinic in the Madison area from Monday - Thursday. While work days can be busy, I can be readily available for drop-ins and walks over the lunch hour if needed. There is a large open field behind my apartment that is used by many dog owners to let their fur babies have some freedom throughout the day
“Mandi was great when she stopped by to meet Rosie and I. She took a lot of notes, and did great with Rosie, which made me feel much better about leaving for my out of town work gig knowing that Rosie would be well cared for.”

“Cleta did an amazing job taking care of our 3 cats while we were gone. She left thorough updates after each visit and took lots of pictures. It made me appreciate our vacation even more knowing our pets were in excellent care!”

“Hannah was awesome with our 11 yo rescue dog, very caring and spent quality time with her. Hannah is very responsible, showed up promptly, and Luna was very happy with her visit (we were too)!”

“This was my first time using Rover and Laura made the process very easy. She was very responsive, sent us notes and pictures from her visits and did a great job trying to engage our particularly skittish cat. I would not hesitate to rebook with Laura the next time we are out of town.”


“My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!”

“Was very quick and easy set up, especially with the key swap and her flexibility with everything. Appreciated her reaching out about pets concerns to be on the safe side. She also was very good about pricing.”

“Watching my old cat isn’t very glamorous and I always hire a little nervously. Annie was so responsive and clearly has a lot of experience with pets of all kinds. My kitty had an accident at home and Annie was kind enough to send pictures and update me right away. Best rover ever. Thank you!!!”


“Whitney has visited my 4 year old cat Clark on multiple occasions. On the most recent, I had to go away for the weekend, and Clark had gotten sick a few times earlier in the week. Needless to say, I was nervous to leave him. But Whitney was so responsive to all of my concerns and requests, and took really good care of him. Luckily there were no issues, but Whitney’s notes and care really helped put all my concerns at ease. Will definitely be requesting her services again!”

“Kim was wonderful and sent detailed messages about the drop-in visits. The pictures were great to see that our cat was happy. She watered our plants too which was amazing! She cared for the wellbeing of our cat which made it that much easier to leave him. Highly recommend!!”

“Went with Sabrina again! She does such a great job with my picky, old toy poodle lol. Chewy takes a while to warm up to people so I'm glad he is in good hands with Sabrina. Was a no-brainer going with her and I recommend her!”

About: I’ve grown up with dogs since I was born, and adopted my own puppy as soon as I moved away to college. I’ve trained my dog since she was a puppy, and love teaching her new tricks in her old(er) age! I’ve cared for dogs in all stages of life and health. I’m medically trained in human health care, and have experience working with animals with healthcare needs as well. Advocating for our furry friends who can’t talk is what I aim to do every day! During this semester of graduate school I am available at various times throughout the day to check in on your pet, go for walks or play outside, and spend time caring for them in the ways they need. I care for all animals as if they were my own, and I tailor my visits to your pets needs. During all walks, entrances/exits from the home, and interactions throughout my visits I am focused on keeping the environment safe for our furry friend.
Oakwood Village pet parents share their Rover experiences
Ann was absolutely excellent! Our babies were so well taken care of and they felt secure and safe. Her updates were thorough and consistent with pictures and comments and she tracked their walks and how many potty breaks they had. Ann was incredibly kind and our babies loved their time together. I will be requesting Ann again in the future ❤️

Courtney did a wonderful job with my two cats. Both my kitties warmed up quickly to her! She took lots of pictures and videos of them which helped me miss them a little less. I am glad that I chose Courtney to watch over them and I will for sure be choosing her again and recommending her to friends and family!

Kally was amazing! She watched my cat for almost two weeks over the holidays and I have nothing but great things to say. Kally was super responsive and sent the most adorable videos of my cat, which I loved seeing. She even shoveled my driveway after a heavy snowfall. Thanks so much, Kally!

Janay was great with my two cats! They both warmed up to her very quickly and she sent me a ton of pictures each day. She did everything asked and even managed to make sure my cat with asthma got his inhaler everyday without issue. I came home to two happy and well cared for kitties

Jesse does a great job caring for our two timid kitties. We are repeat customers of hers because she is reliable, trustworthy and responsible and the cats are getting to know her. The less social kitty is even warming up to Jesse; I was very pleased to see the photo of her greeting Jesse. While we were traveling our area got some snow. Jesse offered to shovel our driveway. It was very nice coming home after a long day of traveling to a clear driveway! Thank you, Jesse!
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 pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your 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!
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 Oakwood Village.
Rover makes it easy to find Oakwood Village 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.
Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.















