Pet Sitting & Drop Ins in Oakbridge Community, 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 Oakbridge Community pet sitters

“Amiya was great! Dealt with my crazy group - 4 cats, 3 different foods, 1 old man needing daily medication. She sent an update and pictures every single morning and brought in all my mail. Communication was prompt and professional and I’d definitely hire her again!”


“Julie was great! Communication was easy and timely, and she was very attentive and thorough in caring for our kitty and our place. She went above and beyond and we’ll be contacting her again for sure! Highly recommended.”


“Kim was so easy to work with - she responds to messages very quickly, sent written and picture updates, and had a simple set-up for key drop off and pick up. I could tell my cat was very well cared for while I was gone!”


“Krista did a fantastic job watching our cat. I would highly recommend her to anyone looking for someone to watch over their pet. She went above and beyond what we asked of her, and our cat loved her!”


“Laura was great with our new puppy! She was easy to get in touch with on the app and was such a joy to work with. We definitely hope to use her services again in the future!”


“Anna does such a good job! She sends a ton of pictures of all the girls and they all look happy and are having fun. She makes sure they have food, water, and receive a treat! Best dog sitter we've ever had!”


“Always super reliable! We know we can count on Cleda to do great drop ins with our cats when out of town. Very communicative and goes beyond to make sure the cats are taken care of”



“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!”


“I was a little nervous since this was the first time I left my little guy, but Annie made me feel at ease, knowing he was in good hands. I received many pictures and a note of what they did that day! Thanks Annie!”



“I messaged Whitney at the absolute last minute because I realized I forgot to get someone to check in on my kitty while we were out of town for Thanksgiving. Whitney replied quickly and said she’d be happy to help while we were away— what a relief! She was great and my skittish cat was happy to come out and get some pets from her. Will definitely book Whitney again!”


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

“Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!”


“Sydney was great—very helpful, communicative, and professional. Would love to book her again; the whole process was painless and I never felt anything less than confidence and trust.”


“Sidney is very understanding and patient with our nervous and reactive pup. Halla isn’t the easiest dog, he needs a sitter who will give him time, space and lots of treats but also he needs strict boundaries and discipline. We are so happy to have found Sidney!”


About: I’ve been caring for my own cats since I was in 3rd grade, learning the importance of caring for them in many aspects through feeding them, cleaning their litter boxes, and respecting their needs of play time vs needing space. I started caring for my friends animals in college and that’s when I learned more about dogs and how to tell what dogs are friendly, when they need space, etc. Respecting animals and giving them the love and care they deserve is of utmost importance to me. I have a fairly flexible job, so I’m able to fit in visits almost any time of day. The only day I’m not flexible is Sunday, I work a mandatory 12 hour, so could stop in after my shift but not before or during. Respecting people’s space and privacy is important to me, if I’m walking your dog and caring for your cats, you can trust me to do the job at hand and leave your space in one piece. Keeping a clean home is important to me, so you can rest assured that if your pet makes a little mess, it will be cleaned up for you and you’ll never know it happened.

“Austin is a dream walker! I got about 20 adorable pictures a day, all wallpaper and insta worthy ? He looked after my boisterous boy with enthusiasm, care and diligence. I cannot wait to plan my next vacation only so that newton and Austin can have more time together! ❤️ thank you so much, Austin!”


“Azaria was great! Always showed up on time, sent pictures and communicated well. Very trustworthy and kind. Will definitely reach out again when needed. Thank you!!”



“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)!”


About: I have grown up with a dog in my household for my whole life and i was responsible for bathing, walking, feeding, and playing with the dog. I also regularly dog sit for friends and family. :) I am pretty flexible with my schedule, I am free most days, especially the weekends. I work during the day usually from 10am-4:30pm monday-friday, but my schedule varies week to week. Every pet is different and how I will care for them will depend on the owners directions and the pets needs. I love playing with pets and taking them for walks, and of course I will do what is needed in terms of giving them medicine, cleaning, feeding, etc.

About: Hi, my name is Ava! I am looking to provide dog walking & check in services in the West Madison area. I am committed to providing individualized care, strong attention to detail, and genuine interest and compassion for animals. I grew up in a family that took in a variety of pets to provide a safe home. I am a strong believer in your fuzzy friends being your best friends! They deserve to be treated with care and love while you're away, just as I would want for my dog. I rescued my miniature pinscher 6 years ago and she is now 15 years old! She is both an old lady and still my little baby. I love all animals and I'm so excited to meet yours! I have experience working with children and youth with diverse needs, and that level of care and patience extends naturally to animals with anxiety, behavioral challenges, or special routines. My background in caregiving and support work has taught me to be highly responsible, communicative, and reliable. I’m organized, dependable, and quick to respond — qualities that give pet owners peace of mind. I also go the extra mile with photo updates, customized activities, and keeping pets happy and stress-free while their humans are away. I’m active and love outdoor time — whether it’s long walks, playing fetch, or trail adventures, I’m happy to match your dog’s energy level. I work from home so I have a flexible schedule from 7am-5pm, but it is not consistent every day. I am able to work my schedule around visits and walks if I have enough time to plan. Just message me with details! I could board pets during the day if it's a small dog with no aggression. I have a 15 year old miniature pinscher that gets anxious around medium-large dogs that have anxiety as well and/or some aggression. I am happy to do drop ins and walks throughout the day!
Loving pet sitters in your neighborhood
Search Results


Maiya W.Star Sitter

“Amiya was great! Dealt with my crazy group - 4 cats, 3 different foods, 1 old man needing daily medication. She sent an update and pictures every single morning and brought in all my mail. Communication was prompt and professional and I’d definitely hire her again!”


Julie A.Star Sitter

“Julie was great! Communication was easy and timely, and she was very attentive and thorough in caring for our kitty and our place. She went above and beyond and we’ll be contacting her again for sure! Highly recommended.”


Kim M.

“Kim was so easy to work with - she responds to messages very quickly, sent written and picture updates, and had a simple set-up for key drop off and pick up. I could tell my cat was very well cared for while I was gone!”


Krista C.Star Sitter

“Krista did a fantastic job watching our cat. I would highly recommend her to anyone looking for someone to watch over their pet. She went above and beyond what we asked of her, and our cat loved her!”


Laura D.Star Sitter

“Laura was great with our new puppy! She was easy to get in touch with on the app and was such a joy to work with. We definitely hope to use her services again in the future!”


Anna O.Star Sitter

“Anna does such a good job! She sends a ton of pictures of all the girls and they all look happy and are having fun. She makes sure they have food, water, and receive a treat! Best dog sitter we've ever had!”


Cleda W.
Star Sitter


“Always super reliable! We know we can count on Cleda to do great drop ins with our cats when out of town. Very communicative and goes beyond to make sure the cats are taken care of”




Allegra R.
Star Sitter


“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!”


Annie J.
Star Sitter


“I was a little nervous since this was the first time I left my little guy, but Annie made me feel at ease, knowing he was in good hands. I received many pictures and a note of what they did that day! Thanks Annie!”




Whitney H.


“I messaged Whitney at the absolute last minute because I realized I forgot to get someone to check in on my kitty while we were out of town for Thanksgiving. Whitney replied quickly and said she’d be happy to help while we were away— what a relief! She was great and my skittish cat was happy to come out and get some pets from her. Will definitely book Whitney again!”


Kaitlyn B.Star Sitter
“Kaitlyn is very responsible and always takes great care of my two cattle dog mixes! They’re very high energy, but Kaitlyn always does a great job keeping up with them. Each time they stay with her, regardless of the amount of time, I get great pictures and updates, keeping me up to date on what they are up to!”


Anna H.

“Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!”


Sydney R.Star Sitter

“Sydney was great—very helpful, communicative, and professional. Would love to book her again; the whole process was painless and I never felt anything less than confidence and trust.”


Sidney R.Star Sitter

“Sidney is very understanding and patient with our nervous and reactive pup. Halla isn’t the easiest dog, he needs a sitter who will give him time, space and lots of treats but also he needs strict boundaries and discipline. We are so happy to have found Sidney!”


Megan B.
“Megan is fantastic with our pets! She has watched them over weekends when we’re gone, and checked in while we’re at work during the day. She always makes sure they are comfortable and safe when she leaves which is huge because we have a little escape artist! I would hire Megan to watch our babies again and again!”


Austin C.Star Sitter

“Austin is a dream walker! I got about 20 adorable pictures a day, all wallpaper and insta worthy ? He looked after my boisterous boy with enthusiasm, care and diligence. I cannot wait to plan my next vacation only so that newton and Austin can have more time together! ❤️ thank you so much, Austin!”


Azaria O.

“Azaria was great! Always showed up on time, sent pictures and communicated well. Very trustworthy and kind. Will definitely reach out again when needed. Thank you!!”




Hannah I.
Star Sitter


“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)!”


Chase M.
“Chase is incredible, incredible! He was adored by our pup at first sight! 🤩 He has been such delight (not to mention a lifesaver) to have as our pet’s caregiver. Chase’s dependability, responsiveness, and trustworthiness has been out of this world! He goes the extra mile to ensure our pup is cared for like his very own. He is super accommodating and a happy, welcome part of our pup’s day. 🐕 10 out of 10 all the way! 🌟🌟🌟🌟🌟🌟🌟🌟🌟🌟”


Ava H.
“Ava is a compassionate, loving, caring, and responsible pet sitter and I would hire her in a heartbeat to care for my babies! She always gives endless love and affection to every animal she encounters. 10/10 recommend her for any pet sitting endeavor!”
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 Oakbridge Community.
Rover makes it easy to find Oakbridge Community 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.
