House Sitting in Milwaukee
Find a loving house sitter to watch over your pets and your home.
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Top rated Milwaukee house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Melissa is a great overnight dogsitter. She followed all the instructions for my dog and bullies have a lot of instructions. Ha! She provided updates everyday and you can tell she enjoys dogsitting. I came back to happy dog.”
“Jessica Z stayed in my house with my 14 y/o blind Boston Terrier. She was wonderful. I received daily updates and photos, she clearly took excellent care of my pup. She left my place spotless and I would highly recommend her. She is excellent and I will definitely use her again.”
“Elizabeth took amazing care of our dog Layla while we were away. She kept us updated with sweet messages and photos, and we could tell Layla was happy and well-loved the whole time. We came home to a relaxed, content pup — we couldn’t ask for more! Highly recommend Elizabeth and would absolutely book with her again.”
“Emily did a great job watching my pups, and chickens. Easy and quick communication, she took the pups on some adventures as well. Highly recommend her and would use her again.”
“I couldn’t have asked for a better dog sitter! She communicated wonderfully from the start and even met with me ahead of time to get to know my dog’s routine and feel comfortable with the space. While I was away, she sent daily updates with pictures of Stewart completely abandoning dad to cuddle with his new friend! 😂 I wholeheartedly recommend her to anyone looking for a trustworthy and caring sitter.”
“As always, Keisha did a wonderful job taking care of my little fur babies! She made sure my walk-crazy dog had many miles under his belt, snuggled my velcro cat, and sent many photos along the way! Not to mention, she did the dishes and made sure my home was clean :) will absolutely book again!”
“Jackie was amazing with the dogs and you could tell by how calm they were when I got home that they had a great weekend. I would recommend and will have her watch my dogs again.”
“Carole was nothing short of amazing! I have 2 senior dogs, one of whom is very “particular” as far as the people she likes. Carole was able to walk her and care for her without any issues. I received photos and updates and felt completely at ease knowing that they were in good hands.”
“Lauren did a great job taking care of the boys while we were away. She gave them plenty of exercise and engagement as well as keeping them on their regular schedule. Very much appreciated and we hope to book again.”
“Daniela & Michael did a fantastic job from start to finish. Talking with Daniela pre-sitting left me feeling confident in having her watch my dog. While she was here, she kept us updated with many photos of Ellie and it was clear Ellie was a huge fan of Daniela. We will definitely be reaching out in the future!”
“Catherine did a great job. She took great care of our dog and two cats. She asked a lot of great questions that I wouldn’t have even thought about. Very thoughtful and thorough. We will definitely be asking her to petsit again.”
About: I have taken care of dogs and was a dog walker around the neighborhood since I was 10. Neighbors and loved ones have relied on me to take care of their beloved pets. I have grown up with many dogs myself and I love to spend time with dogs and help them stay happy. I currently work a full time job, 9-5. I work in downtown Milwaukee and am more than willing to come let out any pets during lunch. I am available to stay at your house during the week or weekends. Whatever is required, I would certainly make it work! I would follow every precaution necessary for your pets. I have always adhered to the owners wishing in pet care. My family has a dog with some odd tendencies himself so I am ready for anything!
“Riley continues to be our first choice - our high maintenance and not super friendly boys love her, and we really appreciate the extra stuff she does for us like watering the plants!”
“Megan was friendly and super communicative the whole time she house sat for us! My dog got sick while I was away and Megan handled it like an absolute pro. I would definitely trust Megan to care for my dog again.”
“Ashley was So responsive and Wonderful with my boys! Thankful she was able to watch them in their house!! Will definitely book again if she is willing to watch them!!”
“We had a wonderful experience with Maiah and would absolutely recommend her. Our beagle can be a bit high-maintenance, but Maiah was so great with her. It gave us peace of mind knowing our pup was in trustworthy, kind, and capable hands. Maiah was also an excellent communicator--we received regular updates, photos, and quick responses, which made it easy to relax while we were away. We wouldn’t hesitate to book with her again!”
“Alex is great with animals, respectful, kind, caring and compassionate. She is great with communication and made me feel like my pets were being well cared for. Highly recommend!”
“Julianna was incredible! She stayed at my house for a week while we were gone to watch Sophia. She kept me updated on everything that was going on and gave her some extra love when she needed it. Sophia doesn’t love being away from us but Julianna made sure she was okay and did everything she could to make sure she was happy! Would definitely recommend her <3”
Over 3,941 pet parents in Milwaukee have booked house sitting
Milwaukee pet parents share their Rover experiences
Catherine gets 100 stars in our opinion! She was scheduled to house sit and take care of our dog Frankie for one day but the night before we were leaving for 4 days the second sitter, who was covering additional days, cancelled due to an emergency. Catherine saved us on a moment's notice.! Our house and Frankie were perfect upon our return. She is the absolute best sitter we've had! Your pet will be in the best of care if you put your trust in Catherine.
Elaina was great with our 11 week old Australian Shepherd. She watched her for 6 hours a day, took her on walks, played with her, had her stay in her routine of rules we have for her. Overall I would rebook and recommend Elaina to anyone she is kind, responsible, and respectful (and our puppy loved her)!
Alena did a great job taking care of my pup! I booked on short notice, and she was extremely gracious and accommodating, and even she made time for a meet and greet prior. She was prompt in responses when I reached out and sent check-in updates and photos as well. I would definitely recommend and will be rebooking if the need arises!
I couldn’t have asked for a better dog sitter! She communicated wonderfully from the start and even met with me ahead of time to get to know my dog’s routine and feel comfortable with the space. While I was away, she sent daily updates with pictures of Stewart completely abandoning dad to cuddle with his new friend! 😂 I wholeheartedly recommend her to anyone looking for a trustworthy and caring sitter.
Riley was such a relief for our first time using Rover for Willow since an unfortunate first experience with another pet. Not only did we have a short notice stay request but she also suggested to do a meet and greet prior to her stay to make sure both her and Willow weee comfortable. She was so flexible, great with communication and sent lots of pics! Will absolutely use Riley again when we need a sitter :)
Paige is an amazing, young woman and was so loving to my pups. We had a hard journey driving from FL to Milwaukee, and I wanted someone to hang with them while catching up with friends. I could not have picked anyone better. Within minutes, my little Elsa was in love with Paige and King had a new girl friend! I searched the night before and thank God, Paige was the answer :) Obviously, highly recommend Paige.
We had a wonderful experience with Maiah and would absolutely recommend her. Our beagle can be a bit high-maintenance, but Maiah was so great with her. It gave us peace of mind knowing our pup was in trustworthy, kind, and capable hands. Maiah was also an excellent communicator--we received regular updates, photos, and quick responses, which made it easy to relax while we were away. We wouldn’t hesitate to book with her again!
How Rover works
1. Search
Read verified reviews and choose a house 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 house and 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!
The median cost per night for house sitting in Milwaukee is $50
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 house 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.
Sitters in Milwaukee average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Milwaukee on Rover as of Jun 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 1,137 house sitters in Milwaukee. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 86% of Milwaukee house sitters respond in under an hour.
House sitters in Milwaukee have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Milwaukee.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Milwaukee house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.
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