House Sitting Milwaukee
Find a loving house sitter to watch over your pets and your home.
Over 878 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.
“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!!”
“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!”
“This was our first time using a dog sitting service and we couldn’t have been more lucky to have Lily watch our dogs. She met with us multiple times to meet our pups and walk through our routine. During our trip she sent plenty of updates and pictures to keep us up to date. We couldn’t have asked for a better sitter for our pups and will definitely book Lily in the future!”
About: I have taken care of dogs and cats of all ages and sizes, even dogs that can be leash, collar, and dog aggressive when walking. I am mostly available later in the week and weekends due to being a full time student, but have breaks in between my school days! There is a green area for dogs down the street from me and a quick 15 minute walk towards the lake for more walking paths!
About: I trained my own dog growing up and bought a beagle at the age of 22. At 30 I rescued another hound who loves his life. We take two walks daily and spend a few days a week at the dog park. Your dog will receive the same treatment! Morning walk. Lunch date in the yard. Afternoon walk or dog park. Potty breaks every two hours unless it's a Wednesday when I’m in the office. I live in a condo so I can't board right now. I do continue to offer walks, drop ins, and can dog sit at your home!
“I’m a full on dog mom, I worry about my pup and miss her when I’m away but this trip I was able to rest assured that she was safe and happy with Nikki! She was quick to respond when a hurricane was headed our way with me out of town, she gave me daily updates and pictures of my dog, took her to the park, on car rides, played fetch, and gave snuggles. Nikki was exactly what every traveling dog mom needs in a doggy sitter!”
“Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.”
“Joe was great with our Fifi, he was really a lifesaver! He stayed at our house as our rescue dog can be a little clingy. I received the cutest pictures and was really able to enjoy myself on vacation knowing she was at home!”
“Chelsea stayed at my place and took excellent care of my fur babies. She took care of all of their needs and loved them as if they were her own. I would definitely recommend Chelsea for all your pet sitting needs!”
“I am very very protective over my dog who is a pitbull mix. Jenna is amazing. From day one she made it clear she was confident in working with my dog. My dog is like my child and I wouldn't even trust family to watch him. She gained a relationship with him first starting with weekly walks and he warmed up to her. The updates she provided allowed for a worry free trip out of state knowing my dog was in great hands. Couldn't have asked for a better person to trust with my doggos care!”
About: I promise to treat your pet like family! I currently have one cat, but I love dogs as well. *FYI: I am unable to watch dogs over 30 pounds. Rover sometimes allow these requests to come through. Please understand that I will likely decline. Ty 🙂 I currently work from home and have a very flexible schedule. My availability is pretty open, unless I am out of town. I am available to book both weekdays and weekends. I have a spacious 1600 square foot apartment with an enclosed balcony. I will frequently walk your dog if you choose to board with me and your dog is also welcome to step out onto the balcony for fresh air and people watching. I have one cat, who gets along well with dogs. He is a bit more tempermental with other cats, so I would prefer to watch cats in their own space. In my experience with cats, this is also often more comfortable for them.
“Alexy & Kayla were great with my senior dog and two cats while I was away for a 4-day weekend. They were in constant communication and sent a ton of pictures! I knew my pets were well cared for! Thank you, Alexy & Kayla!”
“Fatima was amazing to work with. I booked her on short notice before the holiday when my original plans fell through. She offered and made it a priority to come do a meet & greet on days notice. I’m always a little nervous when using a new sitter especially when they stay at mine, but my mind was at ease immediately when I met her. I could tell she has a big heart and really cares for animals. She followed all instructions and she went above and beyond spending time with Diesel doing his favorite activities (walks, playing fetch, swimming, etc.). She was incredibly communicative and sent a lot of pictures and videos which was much appreciated. As a former Rover sitter and a frequent user of Rover’s services, I can confidently say that Fatima is one of the best sitters I’ve come across. I will definitely be using her in the future and have already recommended her to others looking for sitters. Thank you Fatima!!!”
“Madeline is a great and responsive sitter. She took great care of our boys, and she charmed our skittish boy. He even crawled on her lap... amazing while he is a lovebug he does not usually warm up that quickly.”
About: I have had pets all of my life, dogs when I was younger and until I moved up to Milwaukee, and I've had a cat for the last 3 years. I do my best to make sure pets feel cared for and loved. I have spent a lot of time getting my cat Sybil to "sit", "stand up", and "lay down". So I at the very least I have a lot of patience I currently work 9-5 but I work from home on Thursday and Fridays! So I have a pretty flexible schedule to take care of your pets. I make sure to follow your instructions to a T. I will likely not let them out of my sight for the duration of my stay with your pet.
The median cost per night for house sitting in Milwaukee is $50
Pet parents share their Rover experiences - Milwaukee
Samantha is so wonderful, I want to keep her all to myself, but that wouldn’t be fair. She took such great care of my dogs that I felt completely comfortable leaving them in her competent and loving care so I could visit my son out of state. I’m so pleased to have found Samantha; now I will be able to fulfill my obligations to care for my family and know that my beloved dogs are well looked after. She loves them as her own.
Ray was a wonderful sitter for our senior dog who is going through some health challenges. She spent several hours in our home with Scooby and took excellent care of him. She’s a true dog-lover. Ray was also very flexible with some late changes to our plans, and she was respectful of our home and it’s contents. Thanks, Ray!
This was our first time using Rover and having someone pet sit (outside of family), and it could not have gone better. Jessica provided lots of pictures and updates, made sure the dogs had food and water and gave my senior dog his medication. I would absolutely recommend!
Hannah was absolutely wonderful! She took such amazing care of my pets and my home, and I truly couldn’t have asked for a better experience. The little pet “report cards” were such a thoughtful and personal touch that made me smile! It was clear how much care and attention she gave them. Most importantly, I had complete peace of mind knowing my pets were safe, happy, and in loving hands while I was away. That kind of reassurance is priceless. I would wholeheartedly recommend Hannah to anyone looking for someone they can truly trust with their furry family members! ❤️
This is the second time Keisha has taken care of our dog Frankie at our house and she will absolutely be our go to if she is available the next time we travel. Our house was also in perfect shape after arriving home Exhausted after our trip. Our dog Frankie was perfectly taken care of! Thanks for everything you do Keisha!!!
Mika was so amazing! I knew my dog was in great hands and felt at ease our whole trip. They asked us how many daily updates we wanted and kept us in the loop with what was going on. I never felt the need to reach out to check in, I knew things were going smoothly.
Sara and Ethan were excellent. They swooped to the rescue to cover a full week just a few days before we left (a different sitter canceled last minute). Our pup Bailey adored them, but more importantly, we could tell how genuinely they adored him. He was in great spirits when we returned and had been well looked after. They followed all our guidance and were consistent in providing daily updates. Our house was in great shape too, having watched Bailey here. We will be booking them again soon!
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.
How to book house sitting
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 of House Sitting in Milwaukee is $50 per night as of November 2026. Most bookings cost between $29 and $84 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 1,236 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
sitters on Rover set their own cancellation policy, which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Milwaukee. On Rover:
- 87% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 96% 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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