Pet Sitting & Drop Ins in Jackson Park, Milwaukee
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

More resources
A focus on safety
Enjoy photo updates, easy messaging, and the knowledge that every sitter joining Rover needs to pass an enhanced background check. Learn more about RoverProtect
Loving pet sitters in your neighborhood
Search Results


1. Amanda T.

“Amanda has been so outstanding from her communication, updates and reliability; we are so happy with her! In addition to those things, when meeting Jax for the first time you can see just how much she loves and cares about animals. She is amazing!”


2. Vilma C.

“Vilma is fantastic! Attentive and good to sweet poppy!”


3. Sarah J.

“Sarah did a great job! She was quick to respond and communicate, really flexible, and very respectful of our space. Our kitty was well taken care of!”


4. Lilyia S.

“Liliya is great! I was setting up cat sitting for my relatives during a family emergency and from several states away, and she was so helpful and accommodating!”


5. Rebecca S.

“I would definitely book with Becky again, she is fantastic! My senior dog had a minor stroke on a Wednesday. I work from home during the week but I was worried about leaving him alone for my noon-8pm shift at my part-time job that coming weekend. A couple people had already declined my request for check-in because they weren't comfortable with the possibility of finding Briscoe in a critical state. But that's why I wanted the check-ins, the thought of him suffering alone was distressing. Luckily Becky was available & she lives right in our area. We arranged a meet & greet that Friday morning. Despite my anxiousness, Becky was so calm & professional, which helped put me at ease. Should the worst case scenario happen, we had a game plan in place for getting Briscoe emergency care. She was so easy to work with. Thankfully his condition improved. Becky provided very detailed updates on her visits & made sure Briscoe stayed hydrated. That was one of the Vet's concerns & she was on it. She also made me aware of a problem with my door lock that I hadn't noticed, it wasn't latching properly! Very happy with the service received.”


6. Berenice B.


“Berenice had great communication and was able to take a last minute l booking. She was also able to adjust the time she came. We appreciated her flexibility and attentiveness!”


7. Ashlee K.

“Ashlee was great at communicating and went above and beyond for my large dog with medical needs. She was able to assist him outside using a sling and adhere to his physical restrictions post surgery.”


8. Emily S.

“Emily has been wonderful with Heisenberg! I am so grateful for her help. I was nervous to have a stranger take care of him, but I couldn't be happier with how well it has worked out.”




9. Michele M.

“Michele did an AMAZING JOB, she took care of my dogs at the last minute while I underwent a minor emergency procedure at the hospital. She fed them, played with them and took them out 3 times a day. I am so appreciative of her help and look forward to rebooking her, I definitely recommend her!”


10. Leandrea R.


“Leandrea did a superb job with my kitty Sunny! I was anxious about leaving him due to him just having surgery a couple of days prior, but I was immediately put at ease with her quality of care! I would recommend her to anyone looking for care for their pet! I will definitely be booking for all my pet needs in the future! Thank you for being so wonderful!”


11. Keisha P.

“She is an amazing pet sitter! Very kind and our dog loves her!”


12. Katie N.

“Katie was fantastic! She was responsive, prompt, and attentive with our kitty. We really appreciated the photos and comments she sent and the cat/house were in great shape when we returned. Highly recommend Katie and would book her again!”


13. Mary C.

“Mary is amazing! My pup is my everything and he is in the best care with Mary. She gives a great update with how the visits go! We are beyond lucky to have her in our life!!”


14. Katherine B.

“I could tell our pup was very happy and comfortable with Katie. Katie was both friendly and professional. I was pleased with all of photos and regular updates we recieved. It was clear she gave our dog plenty of exercise as our dog was pooped. I will definitely be booking again.”


15. Holly J.
“Holly has been in a home with dogs her entire life. She has experience with very high energy dogs, elderly dogs requiring special attention, and multiple dogs at once. I would absolutely trust Holly with my dog or anyone else’s.”


16. Jaela W.
About: Hi! My name is Jaela I have had a dog most of my life, as well as constantly being surrounded by dogs my whole life. I love all animals and have always been the one to cuddle and play with them anytime I could. I additionally own 2 rabbits which are free roam in my home and take quite a bit of responsibility, as well as 3 fish. I have watched dogs with medical accommodations before and make sure they are all in check. I would love to spend time with your pet and make shire they are well taken care of! I am currently still a full-time student, but my work load is quite minor. I would be able to work after school from 3:30pm till whenever as well as sundays. I love spending time with pets as well as my own, I have an 11 year old dog, Bronx, 2 bunnies, Arlo and Zigi, and a couple fish. I primarily take care of all my pets and take responsibility for anything they need. I have previously taken care of pets as well.


17. Jaci L.
About: I have had all types of pets (dogs, cats, etc..) my whole life and have history of training different dog breeds. I have always babysat for pets (for jobs and for family friends) and am very good with animals I have completely open availability at the moment and can take care of any pets at any time. I can take them into my home or relocate. I make sure to give the dogs and/or cats all the attention they need and can deal with puppies that are not potty trained yet.


18. Laura C.
About: I’ve had cats since I was a child. I’m from Colombia, and Colombia is a very animal-friendly country. There, my mother has several cats, and I’ve learned to understand the different personalities of each cat. In the end, if you treat them with love, they will show love. I enjoy playing with them, pampering them, and making them feel safe. I work only from Friday to Sunday, 9 PM to 2:30 AM, so I have plenty of free time to take care of my cats and yours! 😺 If you want me to take care of them at my house, I live alone, have two gyms, and plenty of cat toys to create a harmonious environment for them! I also have several litter boxes to ensure the babies are comfortable! If you’d prefer me to go to your house, I can bring toys to keep them entertained! I know a lot about cats! My family loves cats, and we have cared for many cats from family and friends.


19. Tyler P.
“Tyler cared for my cat while I spent 5 days on vacation. He took excellent care of her - shes particularly shy, quiet, and untrusting. Tyler not only did exactly what I asked, he took time to help my cat feel more comfortable as she is not used to me being away. I work from home so my absence is particularly hard for her. He took the time to gain her trust and she noticeably warmed up to him in the video he sent. He definitely helped ease my worries about her being alone. I will be asking again for future pet sitting needs!”


20. Margaret K.

“Margaret watch three of my 50-60 lbs border collies for a week with complete ease. I am usually always worried how my dogs will react to people who don’t know how to handle them barking at you when you first come in. However, Margaret was able to quickly get them to calm down and was easily welcomed by the pack. She was great and on time for the scheduled drop in visits and followed all special instructions given for each dog. I’m extremely happy with Margaret and I will absolutely be continuing to book her for more drop in visits!”
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
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Jackson Park on Rover as of Jul 2024 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Jul 2024, there are 295 pet sitters in Jackson Park. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 85% of Jackson Park pet sitters respond in under an hour.
Pet sitters in Jackson Park have an average of 13 years of experience. Pet sitters with repeat customers have an average of 5 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Jackson Park.
Rover makes it easy to find Jackson Park 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
There are 295 pet sitters in Jackson Park on Rover, so you’re sure to find the perfect match for your pet! In Jackson Park, 100% of pet sitters offer daily exercise, 95% offer medication administration, and 95% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
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.
