Pet Sitting & Drop Ins in Jackson Park, Milwaukee, 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 Jackson Park pet sitters
“Mallory did a great job checking in on our cat Marvin while we were away on vacation. She provided great updates with photos every visit, and was very professional & communicative overall. Thank you Mallory!”

“I enjoyed the photo updates everyday showing Merlin doing his favorite thing, people watching on the porch. I wasn’t worried about my kitty while away.”

“Lisandra has been wonderful withy puppy. She has been reliable and willing to change her schedule last minute for me which I can't say how much I appreciate. My puppy is always happy and relaxed when I get home from work, which again is everything I could ask for!”

“Sarah did it again! We have a whole herd at our house between resident and foster dogs and she gave great care to everyone. We just feel so much better having her stop by when we are gone for a long day.”
“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.”

“Jenn cared for our cats just as if they were her own. She clearly loves cats, as evidenced by the meticulous details she communicated to me about her daily visits with them. We came home to happy cats! I will definitely ask Jenn to care for our cats again in the future.”

“Linsey did an awesome job taking care of Pearl! She sent great pictures and videos and made sure to keep me updated on how she was doing every day. Thank you so much, Linsey!”

About: My unconditional love for all animals. Every cat or dog that I meet I treat and cherish as if they were my own fur baby. I do work a full time job, 8-4 Mon-Fri. However, I am looking to use some of my free time taking care of your fur baby! I do my best to maintain whatever routine you have with your fur baby. I am willing to go the extra mile to make your pup feel safe and comfortable while you are away.
“Lilly was amazing with our two cats while we were gone for a week! Both of our girls absolutely loved her (even our shy kitty) and warmed up to her instantly. She is very communicative and goes above and beyond. Do yourself a favor and hire her! ?”

“Hannah was and continues to be great with my puppy Ivy!! She has been instrumental in getting Ivy adjusted to her new life with us and getting her on a schedule when we’re at work. We plan on continuing to use Hannah for as long as she’ll let us! Thanks Hannah!! 😊”

“This was our first booking with Lauren and she was absolutely wonderful. She took great care of our cat and we will definitely rebook with her. We were so happy to receive the photos and messages from her. It is such a pleasure to know he was safe and sound with her.”

“Stephanie was great with our two boys! She took lots of pictures, took them on walks, and played with them tons. Our dogs loved having her stop by while we were away!”

About: I've been around animals my whole life and currently share my home with three cats and one dog - it's a full house! I have hands-on experience caring for senior dogs, including my own 13-year-old who needs daily medication. I also grew up with huskies, so I'm no stranger to high-energy breeds and the active care they require. On the flip side, I'm just comfortable with laid-back pus - my pug keeps things goofy and fun. Whether it's administering meds, going for long walks, or just providing companionship, I bring patience, energy, and love to every pet I care for. I work full-time remotely, which gives me the flexibility to offer morning and afternoon drop-ins and walks during the week. On weekends, I'm fully available for all listed services and can accommodate a wider range of times. My home has a partially fenced yard and system of tall gates inside to safely separate cats and dogs when needed, so every pet can feel secure and relaxed. I'm happy to kennel your pup if that's part of their routine or needed for comfort. Your pet's safety and peace of mind are always my top priority.
About: I've always had pets in the house since I was little, dogs and cats mostly. I have two of my own dogs, trained them both when they were puppies. I also volunteered at the Wisconsin Humane Society for 8 years, I was a dog walker, which entailed cleaning rooms, walking them, feeding them, playing with them, etc. Always had so much fun seeing all the types of dogs coming in. I'm currently working full time but I normally work the same days, shifts varies from week to week. But I would like to add more fun to my life and not so strict with work work work. So I would love to add more Rover days to my weeks as time goes on. I have a fully fenced yard, plenty of space in the yard and in the house. I have baby gates to rooms that don't need to be entered and at the top of some of our steps to prevent falls. Always pay attention any unusual signs that the pet might be in distressed. Also aware of little things as I come across them with the fur babies.
“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.”

“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!”

“Hailey is truly the best! She gives awesome play by plays of her visits and provides the cutest pictures. My pup loves her! Can’t recommend her enough!!”

Over 6 pet parents in Jackson Park have booked pet sitting
Jackson Park pet parents share their Rover experiences
Caitlyn is an amazing cat sitter! I hired her while I was away for a work trip and she dropped in multiple times a day and medicated one of my cats (who gets several meds throughout the day). On top of that, her updates were phenomenal! She gave me up descriptions of my cats activities that were very consistent with their personalities, so I could tell she was really paying attention to their moods and needs. One of the best cat sitters on here and I would easily hire her again! So flexible to work with, sends amazing photos, and responds quickly.

Nicole was excellent! When she came for the meet and greet, she asked excellent questions to really get to know our girls and set expectations. She was calm and let our girls come to her. Then, when she came for the visit, she took excellent care of our kitties and was able to pill our calico successfully! Throughout the whole experience she communicated super well, which is something that we value. We will absolutely recommend and rebook!! Thanks Nicole!

This is our second time booking with Emily, and we’ve loved her so much that we’ve referred friends to her who confirm the same sentiment: She is just fantastic at what she does. Her experience with young children as an elementary school teacher certainly translates to being phenomenal with furry friends! We were concerned that our shy calico would hide, but she was happily making friends within a few visits. Rover reports were detailed (and so sweet!) each day. Cannot continue recommending Emily enough!

Rusha is the best when it comes to nervous cats. My cat is so shy around people but loves Rusha. She even let Rusha pick her up and cuddle. I am always so comfortable leaving my cat in Rusha’s knowing that she will not only be taken care of but given all the attention.

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1. Search
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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
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The median cost per night for pet sitting in Jackson Park is $20
Why Choose Rover?
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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 Dec 2025 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.
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 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
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.



















