Dog Sitting South Milwaukee

Book a South Milwaukee dog sitter to watch your dog in your sitter’s home or yours.

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Over 109
pet parents in South Milwaukee have booked dog sitting

South Milwaukee, Find top rated dog sitting

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Lauren F.
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Lauren F.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
13 reviews
5 repeat clients
16 years of experience
Oak Creek, WI, 53154

Lauren was absolutely amazing. She was adaptive to our animals. This was my first rover experience and I wouldn’t think twice of using the service again; hoping for Lauren. She was amazing, responsive and professional!

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Sarah B.
Sitter Profile Image: Kayla J.
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Kayla J.
from
$14
per visit
2 years of experience
Oak Creek, WI, 53154

About: As a teacher, patience, responsibility, and building trust are part of who I am every day. I naturally create calm, positive relationships and understand that every dog, just like every child, has a unique personality and deserves individualized care. Since I'm on summer break, I have a flexible schedule and can give your pet the time and attention they deserve rather than rushing through visits. Whether it's an energetic walk, extra playtime, or simply providing companionship, I strive to make every dog feel safe, loved, and comfortable. I know that trusting someone with your pet is a big decision, and my goal is to give you peace of mind by treating your dog like family. 🐾 As a teacher on summer break, I have a flexible daily and weekly schedule, allowing me to prioritize consistent, reliable pet care, walks, and check-ins throughout the day. I care for pets with patience, attention, and love—ensuring they are safe, comfortable, and happy through reliable walks, playtime, feeding routines, and gentle companionship.

Sitter Profile Image: Lynette F.
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Lynette F.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
86 reviews
13 repeat clients
11 years of experience
Milwaukee, WI, 53207

Wonderful, sent the best photos and the cats were always excited to see her! Would definitely love to have her over again!! I’m always nervous leaving my high maintenance and high attitude sphinx alone but this weekend was a breeze thanks to Lynette!

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Alexis S.
Sitter Profile Image: Jamie A.
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Jamie A.
from
$13
per visit
6 years of experience
Saint Francis, WI, 53235

About: Hi! My name is Jamie and I have been a dog mom for 6 years, but a pet lover for my whole life. I personally know how difficult it can be to leave your pets alone and I want to give people peace of mind that their best friends are loved and cared for while they are away. I am available for dog walking, drop-in visits, and house sitting. I love to take my own dogs for walks and adventures around the neighborhood. I also enjoy playing catch with them and cuddling at the end of the day. I have experience taking care of large and small dogs, as well as high energy and low-maintenance dogs. I look forward to giving your animals the care and attention they deserve!

Sitter Profile Image: Joseph F.
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Joseph F.
Star Sitter
from
$17
per visit
4.9 out of 5 stars
49 reviews
9 repeat clients
25 years of experience
Oak Creek, WI, 53154

I wasn't sure what to expect from my two.. but everything was great! I love the pics and the "bathroom" updates. Joe is great with the "big one..Seamus" and the "little one" warmed up after she realized Joe had food...lol!

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Jodie N.
Sitter Profile Image: Teri B.
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Teri B.
Star Sitter
from
$35
per visit
5.0 out of 5 stars
110 reviews
42 repeat clients
16 years of experience
St. Francis, WI, 53235

Terri sent check in photos every day. Left out enough wet food bowls that she didn't have to wash them, but was pleasantly surprised to come home to a clean stack. She's obviously a pet lover and one can feel confident your fur babies are well cared for.

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Dana B.
Sitter Profile Image: Shawn J.
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Shawn J.
from
$15
per visit
5.0 out of 5 stars
28 reviews
11 repeat clients
10 years of experience
Oak Creek, WI, 53154

Thank you Shawn! You were easy to work with and I felt Sonny would be very well cared for, I was very happy to find someone close by who was good with large dogs. I would definitely book with Shawn again :)

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Daniel P.
Sitter Profile Image: Lucia H.
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Lucia H.
from
$25
per visit
5.0 out of 5 stars
5 reviews
4 years of experience
Milwaukee, WI, 53207

About: I have 3 cats & a dog who I treat as if they were my biological children. One of my cats & my dog are medically “blessed,” so I have experience giving meds & sticking to dietary restrictions. They are also anxious creatures, so I’m more than experienced in the world of patience. I foster for a cat rescue who saves stray cats & have experience with getting cats/kittens to trust me. I work full-time but am available weekday evenings for drop-ins & walks. I am available for boarding & house-sitting on weekends or over holidays. My weekends are flexible, so I can also accommodate medication schedules easily With a fenced in yard, dogs can enjoy time outdoors safely. I live in a quiet neighborhood that allows for nice walks. My dog & cats are very laidback. For other dogs, after a proper introduction, my dog loves playing with other dogs & is cat savvy. Since I foster, I also have a separate room where I could keep any cat guests.

Sitter Profile Image: Brittany M.
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Brittany M.
from
$25
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
25 years of experience
Cudahy, WI, 53110

About: Hi, I’m Brittany! I’m a lifelong animal lover, foster volunteer, and proud dog mom who understands how important it is to find someone you trust with your pet. I have experience caring for dogs of all ages, sizes, and personalities, including: • Reactive and fearful dogs • Senior dogs • Dogs with medical needs • Multi-dog households • Newly adopted and foster dogs One of my own dogs is reactive and fear-based, so I understand that every dog is different. Some pups are ready to make a new friend immediately, while others need patience, consistency, and space to feel comfortable. I’m happy to meet your dog where they are. Whether I’m stopping by for a drop-in visit or taking your dog for a walk, my goal is to keep their routine as normal and stress-free as possible. I’ll make sure they receive plenty of attention, exercise, potty breaks, playtime, and of course, belly rubs if they’re interested. I’m comfortable administering medications and following detailed care instructions. The little things matter, and I always appreciate learning about your pet’s preferences, routines, quirks, and boundaries before we get started. My schedule is flexible, and I’m generally available for morning, evening, and weekend visits. I’ll always communicate clearly, send updates and photos, and care for your pet as if they were my own. I look forward to meeting you and your pup! My schedule is very flexible, allowing me to accommodate morning, midday, evening, and weekend visits. Whether you need a regular walker, drop-in visits, or occasional help, I’m happy to work with you to find a schedule that fits your pet’s needs. I’m committed to caring for your pet in the way that makes them feel most comfortable. I’ve cared for dogs with a wide range of routines, personalities, and needs, and I know how important it is to stick with what works best for them. Every pet is unique, and I always appreciate a heads-up about any quirks, preferences, or boundaries—those little details make all the difference. Routine is especially important when a new person enters a pet’s space, so I do my best to keep things calm, familiar, and stress-free. At home, my dogs are separated during meals and when given chews. I use gates or kennels when needed to provide structure, downtime, or simply give everyone a break. Otherwise, you’ll usually find them snuggled up on the couch or playing together, with plenty of belly rubs, of course.

Sitter Profile Image: Kimberly H.
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Kimberly H.
from
$18
per visit
4.8 out of 5 stars
49 reviews
14 repeat clients
20 years of experience
Oak Creek, WI, 53154

Kim was Fantastic! Loved getting updates from her and she spent good quality time with my little kitties! We will be using her time and time again!

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Robert T.
Sitter Profile Image: Sean T.
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Sean T.
from
$13
per visit
15 years of experience
Oak Creek, WI, 53154

About: I have been taking care of dogs almost my whole life. Whether it was my family dog or checking in on others dogs while their family went on vacation. I do work full time M-F 7:30am till 6pm at night. I am typically free on the weekends outside of schooling which is only a couple hours a day. By caring for pets in my clients home, I first take them outside to do their business right away and stretch their legs. I always make sure there is water in their bowl and food as explained by my client. If taking on walks I try to stay local unless the family has a preferred route the dog likes.

Sitter Profile Image: Lucy K.
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Lucy K.
from
$14
per visit
3 years of experience
Cudahy, WI, 53110

About: I’ve been doing pet sitting since I was 13, whether it was just stopping by to feed and play with them to spending nights keeping watch on them and my neighbors home. I work part time as a hairdresser in Kenosha so my schedule is very flexible and free to spend time and take good care of your fur babies. I have a 5 month old cat who stays inside my apartment and has plenty of scratching posts and toys. I’m working on getting her to wear a collar just incase she runs out but she seems to know how to take it off herself.

Sitter Profile Image: Camille R.
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Camille R.
from
$31
per visit
5.0 out of 5 stars
15 reviews
3 repeat clients
5 years of experience
Saint Francis, WI, 53235

I was traveling abroad and Camille was so easy to communicate with throughout my entire trip. She dropped in at my home at all agreed-upon times to feed and walk not just one, but two dogs (our 7 month bernedoodle puppy and senior German Shepherd)! She sent photos and thorough updates and I felt at ease knowing my dogs were in good hands while my partner and I were away. We’re so grateful for Camille and will definitely look to her again for our next trip out of town!

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Roseryn B.
Sitter Profile Image: Mia M.
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Mia M.
from
$20
per visit
5.0 out of 5 stars
23 reviews
6 repeat clients
15 years of experience
Avenues West, Saint Francis, WI, 53235

Mia dropped in to take care of my cats when I was out of town. She did a great job trying to make them feel comfortable and keep up their normal routine. It was also great to know that someone was there to check in with them. She sent check-in pictures of the cats and they even warmed up to her being there. It was wonderful to have Mia take care of the cats.

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Kelly F.
Sitter Profile Image: Evangeline M.
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Evangeline M.
from
$15
per visit
5.0 out of 5 stars
1 review
13 years of experience
Cudahy, WI, 53110

About: I’ve had dogs growing up and currently have one myself, I work at dog daycare/boarding facility and have been there for over 2 years now. I absolutely love dogs and have taken care of them my whole life I work part time in the afternoons but am available most days and am always available in the mornings. I’m also available full time on the weekends I would make sure to take care of any safety precautions necessary to keep your pup or pups safe in your home while you are away!

Sitter Profile Image: Mikeila F.
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Mikeila F.
from
$30
per visit
4.9 out of 5 stars
28 reviews
10 repeat clients
19 years of experience
Cudahy, WI, 53110

About: Married stay at home mom of 3 girls and 1 boy, who loves animals. Pre-covid I was a banquet cook for a living. I have always owned dogs( Pitts and huskys), cats, fish, rats, rabbits, turtles, bearded dragons, snakes, and other animals.. but currently have none of my own.. I'd love to watch others as a way for me to fill the void until I find another forever furpal. I live in a decent sized house with a nice yard so there is plenty of room for animals to roam and stretch their legs. I give animals all the attention they want and need. Couches and beds are free game as long as it's ok with you, I wouldn't want to upset what an animal is used to. At my place there are Treats walks and belly rubs galore. I am a stay at home mom so my schedule is open and my routine can be changed to fit what your pup or other animal needs. I have no animals of my own and usually only take one family at a time for boarding and 2 families for doggy daycare unless discussed ahead of time with clients so I can match your pets normal care schedule and routine.

Sitter Profile Image: Carolina G.
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Carolina G.
Star Sitter
from
$35
per visit
4.9 out of 5 stars
38 reviews
8 repeat clients
9 years of experience
Cudahy, WI, 53110

About: Welcome! With a passion for animals and years of experience, I have developed a strong connection with pets of all breeds, and the feedback from my clients speaks for itself. I offer affordable pricing without compromising on the quality of care, ensuring that your pet receives the love and attention they deserve. Regarding my availability, I do have a six-year-old son who will be with me occasionally, and prior to booking, it is important to consider accepting him as part of the agreement. This does not affect the quality of care, as I ensure both my son and your pet are happy and safe. Safety and trust are my top priorities. I am always mindful of your pet’s well-being, whether we’re out for a walk or spending time together at home. If we encounter other pets, I’ll ensure that the experience is positive and safe. I also respect the privacy of pet owners and follow all instructions carefully, making sure to create an environment where both pets and owners feel comfortable. Homes with cameras are always welcome, and I take great care in maintaining an open line of communication.

Sitter Profile Image: Rachel L.
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Rachel L.
from
$20
per visit
5.0 out of 5 stars
20 reviews
2 repeat clients
10 years of experience
Oak Creek, WI, 53154

Rachel does a great job taking care of our cats. Very easy to communicate with and can always count on her to have everything taken care of while we are gone.

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Megan B.
Sitter Profile Image: Brooke R.
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Brooke R.
from
$15
per visit
6 years of experience
South Milwaukee, WI, 53172

About: My name is Brooke and I work with animals in my current career. I have been house/pet sitting for many years, and grew up watching all of our neighbors pets! I have prior experience with animal training and care in my day to day life. Having grown up with multiple dogs, I quickly became interested in volunteering at my local humane society. I would love to get to know your furry friends! There’s nothing better than seeing happy and healthy pets feel good, whether that be with a great walk, a nice cuddle puddle, or even something as small as checking in and a belly rub. Whatever fits your pet’s personality, I’d be happy to accommodate! :) I work full time, but am often available on weekends, mornings, and after work hours. I am flexible, and open to short term check ins or longer visits. I do not currently have any pets in my home, and am not able to host dogs for the foreseeable future due to housing constraints. I absolutely love and respect the space and comfort levels of all animals, as empathy is a major component of my daily career. I would love to work with animals of all ages, needs, and personalities.

Sitter Profile Image: Amber E.
Verified Background Check
Amber E.
from
$14
per visit
4 years of experience
South Milwaukee, WI, 53172

About: I’ve taken care of my dogs my whole life and about 4 years ago I dog sat for other families who trusted me to take care of their pets. I love to go for long walks and hikes and have lots of playtime. I currently have a family who I dogsit for when they are on vacations or away for long hours. I’m currently going to college full time, so I can come throughout the day and I have extra free time to take your dog on long walks In my home, I do not have a fenced yard, so I am used to keeping dogs on leashes and making sure they are safely secured if going outside, if they need leashes.

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The median cost per visit for dog sitting in South Milwaukee is $20

Dog parents share their Rover experiences - South Milwaukee

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5.0 out of 5 stars

Anna takes great care of Sammy! She takes great photos of him too! I save all of them to my camera roll!

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Andy P.
Drop-In Visits
5.0 out of 5 stars

Julia has been helping me transition my new 5 month lab/boxer puppy to his new home with her drop in visits. She’s very eager to help practice basic commands, crate train, and get my pup comfortable walking around his new neighborhood. Julia asks great questions, communicates quickly, is flexible, and made me feel comfortable leaving my pup for the first time!

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Hailey C.
Drop-In Visits
5.0 out of 5 stars

Blythe is so patient with Miley! She’s very conscientious of Miley’s needs which is so important to me!

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Robin F.
Drop-In Visits
5.0 out of 5 stars

We have been using Stephanie for consistent visits with our new puppy. She has been flexible, is always very communicative, and does a great job with him. Highly recommend.

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John B.
Drop-In Visits
5.0 out of 5 stars

Thanks River, for your care of our boys! They are so calm and content when we get home when you've done drop-in visits when we're gone! It is such a relief!

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Bobbie G.
Drop-In Visits
5.0 out of 5 stars

Melana is an amazing caretaker for our dog :) She is timely, communicative, and responsible! We would highly recommend Melana to any dog owner.

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Lauren C.
Drop-In Visits
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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Meet local sitters who will treat your dogs like family

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Popular requests for dog sitting - South Milwaukee

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Sitters in South Milwaukee average 6
repeat dog sitting clients

FAQs for Drop-In Visits - South Milwaukee

Frequently asked questions about Rover

The average cost for Dog Sitting in South Milwaukee on Rover is $16.05 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog 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 Dog Sitting. For more information on service fees, click here .

As of July 2026, there are 2,223 sitters on Rover offering Dog Sitting across South Milwaukee. Enter your ZIP code to see which available sitters are closest to your home.

A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.

Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a South Milwaukee stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.

Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.

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 South 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!

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 .

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.

A Meet & Greet is a short introductory meeting between you, your dog, 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.

While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.

To find sitters in South Milwaukee with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.

Yes, you can find sitters who have experience with handling special pet needs in South Milwaukee. On Rover:

  • 92% of sitters can help with special care needs
  • 96% can help with giving oral medications or injections
  • 95% 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.

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.

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