House Sitting Milwaukee
Find a loving house sitter to watch over your pets and your home.
Over 839 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!!”
“Keisha was amazing!! She sent lots of updates on our dog and spent really good time with her the whole 5 day trip. She was in such good hands and we would DEFINITELY use her again! Thank you!!”
“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!”
“Elizabeth did the most fantastic job with our dog Annie. She was always fast to respond and sent multiple updates with pictures! Annie can be reactive and has grudges against many of our neighbors dogs so leaving her with someone new for neighborhood walks can be daunting. I felt completely confident in Elizabeth after one walk with her and Annie. We will absolutely be reaching back out to Elizabeth the next time we are looking for a rover! Thank you so much for the best first rover experience.”
“We were so happy to have Carole staying at our house and taking care of our puppy! We were sent many updates and assured that our dog had been well taken care of. Thank you!”
“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.”
“Julianna Stayed in my house for five nights/six days and took excellent care of my large, high-energy Siberian Husky. It can be hard to find a trustworthy house/dog sitter sitter outside of personal friends and family, but I couldn’t have been more satisfied.”
“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.”
“Our family had recently experienced a loss of our other pet. It was a tough time for travel but Jessica supported our other pet while we were away. She kept us informed and made the world of difference being away during such a difficult time.”
“Cathy was fantastic! She was very easy to work with, and very friendly to our dog, Joey. You can tell she has plenty of experience with pets. We definitely plan on hiring her again!”
“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!”
“Laurie was fantastic!! During her stay with Bella my air conditioner went out. She was extremely knowledgeable about the problem and spoke with the repair tech . This was far beyond the dog sitting duties. Bella loved her as well. When I returned home Bella was in excellent spirits and the house perfectly clean - Laurie even washed the bedding that she had used. She sent pictures - very cute ones - throughout the time she was with Bella. I cannot thank Laurie enough for all she had done. This was my first booking with Laurie - and it most certainly will not be the last . I sincerely cannot speak highly enough about the excellent care she gave Bella - and my house :-)”
“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.”
“Emily did a fantastic job watching Tuukka while we were traveling to India for a wedding. She sent daily updates with lots of photos and we knew our pup was well take care of when we were away!”
“Berenice was absolutely fantastic. She watched our 2 year old dog and young puppy in a pinch over a weekend and we came home to happy, healthy pups. The house was clean and exactly as we left it. This was our first time using Rover and she helped me feel comfortable and informed. She was prompt and great at communicating. She sent updates and pictures. Highly recommend Berenice. Very trustworthy with our dogs and our home.”
About: From tables to tails: this former restaurateur turned full-time pet enthusiast wants to meet your fur baby! Truly love meeting all the silly kitties and playful doggies on this app. I have two cats and a pitbull puppy myself so I know how important routine, love, and attention is. I specialize in giving insulin if needed, medication/pills, and telling your cat/dog how pretty they are. Feel free to ask me to water your plants, feed your fishies, or bring in the mail/packages while you’re gone! I’m living a very flexible life right now. I make my own schedule and there’s always space for cats and dogs each week. Last minute bookings are absolutely welcome. Dogs and cats both get the same attention from me. Making sure they have food and water with potty breaks and exercise! Love having couch time at the end of the visit to give them some snuggle time.
“The best Rover sitter I have had. Communicative, clean, great with Gertie, and an all around kind, responsible, and trustworthy person. Thank you Acacia! It means the world to me 🥰”
“I am a first time user of Rover.com and was nervous about leaving my dogs with someone the dogs and I didn't know. The meet and greet with Jackie helped put my mind at ease. Jackie did an amazing job taking care of my 2 dogs at my house for a little over 2 weeks. One the dogs does not trust people. It did not take him long to warm up to her, which says that she has good, calm energy. It was great that the dogs could be at home and she would come to them. I think this made the dogs less anxious. She sent us great pictures and promptly responded to texts. I would highly recommend Jackie and I would definitely use her again.”
“Catherine did a great job house sitting and pet sitting my golden retriever for 5 nights. She was extremely professional throughout the entire process and left my home clean and tidy. I would not hesitate to book with her again!”
The median cost per night for house sitting in Milwaukee is $50
Pet parents share their Rover experiences - Milwaukee
I highly recommend Laurie for a dog sitter. I have had her twice this summer watch our dog at our house and I can’t say enough about how good she is. My dog doesn’t do well with strangers and will hide under the table. He now snuggles and lays on the couch with her. I do not worry about our dog at all with her. She’s really good with him. She sends lots of updates and pics which we all enjoy seeing. She leaves our house just like when you left. You would never know she was there. We plan our vacation dates around her availability. Highly recommend Laurie!!
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.
This was our second time having Nikki watch our dog for a three night stay, and everything went great as usual. My dog was expertly cared for, walked twice/day, fed and loved. My house was cleaner than we left it! Will definitely hire Nikki again she was great and kept in communication with us during our trip. Thanks again, Nikki!
Alex stayed at our house with our dog and cat for 3 nights and she was amazing. Super communicative, I loved all of her updates and pictures. I was never once worried about them! She was very respectful of our home - it looked just like we left it. We will definitely request Alex again for our next trip!
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 $49.95 per night (as of August 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 August 2026, there are 1,288 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:
- 90% 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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