House Sitting Milwaukee
Find a loving house sitter to watch over your pets and your home.
Over 907 pet parents in Milwaukee have booked house sitting
Milwaukee, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Keisha deserves a perfect rating for the great care she provided for our dog and the house was in absolutely perfect shape! I can’t say enough about how great she was! When we got home she left our pet with a soothing pet sounds screen saver on the TV. It was such a nice way to be welcomed home!!”
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!
“Jessica has taken care of our cats, pup, and home while we’re traveling multiple times. She is such a wonderful sitter, and we’re really grateful to have found her. We highly recommend her to anyone looking for someone reliable, communicative, and wonderful to work with!”
“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!!”
“Megan was so lovely! She was so great with my (big) dog and I felt really confident leaving my pup with her. She kept me updated the whole time and sent a lot of pics. I came home to my apartment the same way I left it and Megan even left a sweet card. Highly recommend Megan!”
“Julianna (and her partner Ed) were amazing with our anxious pup Winnie. She was communicative beforehand, organizing a meet and greet and asking great questions. She wanted to make sure Winnie was comfortable as possible, allowing us to walk Winnie together before entering our home. During the stay, she sent regular updates with photos. Asked some clarifying questions about our pup’s favorite activities, and ultimately let us relax and enjoy our vacation. She administered our pups meds and helped us have peace of mind. Would absolutely recommend Julianna and Ed!!!”
“Jasmine was a fantastic person to have house sit for our pets! She sent many updates and photos. I know that she took the best care of our Great Dane (and cat!). I would highly recommend her! Hope we can book 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.”
“This is our second time using Laurie and she is fabulous. She shows up on time, keeps the dogs on their schedule, sends lots of updates, is very attentive to their needs, and the house is always super clean when we get back. I hate leaving my dogs and typically worry about them while away, but with Laurie I don't worry at all. We've already got her scheduled again next month!”
“Rebecca was phenomenal with my little critters! Excellent communication throughout the week and she was able to adjust last minute to needing to give my dog extra TLC and medication. I highly recommend her for your pet-sitting needs!”
“Emily was great at communicating with us the entire stay, and we could tell from all her updates and pictures that our pups loved having her around. Our flight ended up getting delayed because of the blizzard rolling through Wisconsin this past weekend, and Emily was able to help make sure our pups were let out and fed while we figured out how to get back to Milwaukee. I would absolutely recommend Emily to anyone else looking for expert and friendly care for their pups on Rover. Thank you again!”
“Jackie stayed in our house with our dog for the weekend and she was great. Our husky Zero is our baby and a bit particular sometimes but she took it all in stride. She sent pictures throughout the weekend and reached out when she had questions. We also tried to make the house nice and neat for her time here and when she left we were wondering if she actually touched anything it was still so clean! We highly recommend Jackie and plan on booking her in the future when we're away for any extended amount of time.”
“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!”
“Berenice has a great heart for animals. Our dog has special needs and required hand feeding for meals. I think she would be a wonderful addition to your household, as an animal sitter. She has a kind disposition and will treat your pet with the utmost care. She left the house clean and played with our dog outside - he likes to sleep and can be lazy (so it was nice she provided enrichment playtime)! We got picture updates. She was on time for the meet and greet / when we left for our family trip to see relatives. Our dog seemed happy and content when we got home.”
“Angela was amazing!!! We had never left our dog with anyone overnight and she helped me feel comfortable and at ease. She sent lots of pics and updates and loved on our guy all weekend. So grateful!”
“Lyly was amazing with our 3 kitties while we were out of town. It's nerve-wracking to leave for 2 weeks, but the daily pics and updates helped tremendously. Having someone stay over really helped keep their mood and spirits up and we're thankful Lyly did such a great job with them. We're definitely booking with her again!”
“While Evita watched our pup Molly overnight at our house, she was punctual and communicated well. She also took Molly on a nice long walk each day that pleasantly tuckered her out. Molly seemed calm and happy when we returned home.”
The median cost per night for house sitting in Milwaukee is $50
Pet parents share their Rover experiences - Milwaukee
Lack of communication from another sitter left us scrambling for a pet sitter 1 week before we were leaving town. David answered my request within minutes and immediately set up a meet & greet. He did everything we asked him to do and kept us informed with notes. We recommend and would use him again.
Jessica is 100% reliable and cares for my dogs with love and attentiveness. I felt completely confident in leaving for five days with my dogs in her care. She sent me updates and pictures to put me at ease. When I returned home the dogs were happy and that makes me happy. I cannot recommend Jessica highly enough.
Wish we could leave more than 5 stars! Alex was an amazing Rover find. She came to us and stayed at our house, keeping our dog comfortable and house safe and clean while we were away. She was extremely responsive and communication was so great, we got tons of pics and she even let us know if she’d be leaving for short stretches and when she was back (which was above and beyond!). We were all over the place with our plans (travel with kids, IYKYK)- possibly leaving later than planned and ended up coming back earlier than planned, and she was super flexible and pivoted with everything. Our dog LOVED her and they cuddled and went for plenty of walks. We were so appreciative to find someone like her and it made our time away so much easier, will definitely book again! Thanks Alex!
Keisha is an absolute wonder sitter! Our little pup was very anxious about us leaving and Keisha was so very kind, patient and loving. She took extra special care to help our pup feel safe, loved and secure. We will always ask Keisha to come watch our pup anytime we leave or even just to hang out for an afternoon. Trust Keisha to be the best care giver!
I was out of the country and needed a reliable person to help care for Olive during the daytime hours as my partner works long hours. Becca took the best care of Olive and she's so incredibly reliable!! She was always on time, took Olive on her walks, played with her, fed her and I didn't have to worry about anything. She also sent pics and videos of Olive which made being away from her a little bit easier. I can also tell in all of the pictures that Olive loves Becca and there's nothing better than knowing your pup is happy while you're out of town! Highly recommend Becca!!!
Talor recently stayed at my home and watched my French bulldog while I was on a work trip. She was amazing and sent the cutest pictures and updates on how things were going back home. I would definitely recommend Talor for your housesitting needs. Hazel cannot wait for her to come over again. :)
Ashley took such great care of our cats while we were away! She sent us pictures and an update everyday. She even printed out some of the photos and left them for us which was so sweet and unexpected! We will definitely be booking with Ashley again in the future!
I liked Sam from the moment I met her. At the meet n greet, she came prepared with treats to offer my 2 dogs-after asking if they were allowed to have them. She had a calming personality, and took it slow the first time meeting them. During the stay, I enjoyed the updates, AM and PM. Along with pictures. She took the dogs for walks, and ended the day with snuggles and play time. It was hard to leave my babies with someone I didn’t really know, but I trusted Sam and I’d do it again.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 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.
Meet local sitters who will treat your pets like family
1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for house sitting - Milwaukee
Select a filter and find qualifying sitters offering house sitting.Sitters in Milwaukee average 4 repeat house sitting clients
FAQs for House Sitting - Milwaukee
Frequently asked questions about Rover
The average cost for House Sitting in Milwaukee on Rover is $53.28 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of September 2026, there are 1,246 sitters on Rover offering House Sitting across Milwaukee. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Milwaukee walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Milwaukee maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Milwaukee choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Milwaukee. On Rover:
- 89% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 97% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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