Pet Sitting & Drop Ins In Uptown Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Uptown pet sitters

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: Kathy S.
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Kathy S.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
212 reviews
57 repeat clients
40 years of experience
Wauwatosa, WI, 53213

Kathy is very friendly and communicates well. She stopped in to feed my cat for a few days and things went very well. I would recommend Kathy to anyone who needs an attentive and friendly pet sitter!

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Elizabeth C.
Sitter Profile Image: Elizabeth B.
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Elizabeth B.
from
$12
per visit
5.0 out of 5 stars
12 reviews
3 repeat clients
15 years of experience
Milwaukee, WI, 53208

Liz was great!! She sent so many videos, was so responsive, and made sure my puppy was happy!

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Kira M.
Sitter Profile Image: Lexi K.
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Lexi K.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
133 reviews
40 repeat clients
10 years of experience
Cannon Park, Milwaukee, WI, 53214

A true cat sitter and full emotional support sitter for our furry family in Wisconsin. We love Lexi and highly recommend her for anyone who has high maintenance cats or special instructions. Thank you Lexi!

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John A.
Sitter Profile Image: Jessica B.
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Jessica B.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
16 years of experience
Borchert Field, Milwaukee, WI, 53206

About: I have hands-on experience caring for dogs of all sizes, ages, and energy levels. I'm comfortable managing multiple dogs at once, maintaining routines, and ensuring each dog feels safe, exercised, and cared for. I prioritize calm, structured walks, positive reinforcement, and clear communication with pet parents. I can take the on potty breaks as often as needed as I work from home. I also have experience with overnight boarding, feeding schedules, leash manners, and providing companionship throughout the day. I have a small friendly dog named Bob who gets along well with other dogs. With owner permission, Bob can join walks to provide socialization and companionship which is especially helpful for dogs with anxiety or who enjoy gentle interaction. Safety, cleanliness, and individualized care are always my top priorities. My daily routine balances client care with my own dog's needs. I schedule every morning, midday, and evening walks, ensuring every dog receives attention, exercise, and socialization while my small, friendly pup joins safely when appropriate. I provide attentive, loving care for pets in my home including feeding, walks, playtime, and safe socialization. My small, friendly dog can join walks for companionship and comfort with owner's permission.

Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
96 reviews
26 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

Emily took great care of my three kitties while I was gone. She was wonderful at communicating and following the instructions I left. The litter area is clean and she watered my plants! I highly recommend her for your pet care. A+++

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Virginia I.
Sitter Profile Image: Michelle Y.
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Michelle Y.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
98 reviews
29 repeat clients
16 years of experience
Cooper Park, Milwaukee, WI, 53222

Michelle is so kind and patient with my very energetic puppy. She’s punctual and follows directions! Bailey loves when she comes by! We will continue to use her!

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Kelly H.
Sitter Profile Image: Leilani W.
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Leilani W.
from
$15
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
2 years of experience
Wauwatosa, WI, 53213

Very timely and responsive

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Sarrah O.
Sitter Profile Image: Mary N.
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Mary N.
from
$14
per visit
5.0 out of 5 stars
13 reviews
2 repeat clients
6 years of experience
Wauwatosa, WI, 53213

About: I have a diverse experience of taking care of dogs. One of my previous jobs was working in a dog daycare/kennel where I took care of dogs of all sizes and temperaments. I have been a dog walker and sitter for many years now, and have been around dogs my whole life! I currently own a mini poodle puppy! I am currently a full time student and can help walk your dog on weekends, holidays, and some odd days throughout the week. My schedule does change, so I can’t provide consistent care, but would love to help out when I can! I take dog walking very seriously, and make sure that the dog’s safety is prioritized. It make sure to be very observant of the dog’s surroundings and temperament, and will be ready to pivot whenever necessary. Communication is very important to me, so I am as prepared as possible for every situation.

Sitter Profile Image: Cindy H.
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Cindy H.
from
$25
per visit
5.0 out of 5 stars
51 reviews
14 repeat clients
45 years of experience
Martin Drive, Milwaukee, WI, 53208

Cyndi has been kind and professional. She has experience with dogs that need medication and is warm and friendly. We have rescues with medicine needs and social issues. She’s already been helpful with our newest rescue giving us a great tip to use while walking. We’re thankful for her and finding her through Rover was easy and a good experience.

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Erin S.
Sitter Profile Image: Ivy G.
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Ivy G.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
35 reviews
11 repeat clients
20 years of experience
Uptown, Milwaukee, WI, 53210

Initially, Ivy came over for a meet and greet and our dogs took to her quickly, which is always a huge sign for me! Since then she’s been accommodating, personable, easy to communicate with and great with our dogs! I’d highly recommend her!

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Trista B.
Sitter Profile Image: McKenna D.
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McKenna D.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
2 years of experience
Wauwatosa, WI, 53213

McKenna helped us out with a last minute request. She is reliable and Hazel seemed to have a great time with her!

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Brian H.
Sitter Profile Image: Sydney P.
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Sydney P.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
18 reviews
10 repeat clients
12 years of experience
Wauwatosa, WI, 53213

Sydney is great! She was able to check in on my two pups multiple times. Sydney always leaves a detailed report and makes sure we get pics of the pups during her visits. We highly recommend her!

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Zach M.
Sitter Profile Image: Krystal D.
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Krystal D.
from
$20
per visit
5.0 out of 5 stars
43 reviews
12 repeat clients
26 years of experience
Milwaukee, WI, 53210

About: 👋🏼 Hello! My name is Krystal and I am a dog lover who has taken care of dogs for 25+ years. I have 2 male poodle mixes, Adobo and Charley.💙 They’re social boys who love company, but respect boundaries if their furry friends don’t want to play. I work from home and walk my dogs 2 times a day (or 1 long walk) and we also enjoy hiking or playing in our fenced-in backyard. Your furry friend will have activity, company, and love while under my care! ☺️ 👩🏻‍💻 Working from home full time gives me the flexibility to easily fit pet care into my day, allowing me to provide regular attention, walks, playtime, and companionship. Please feel free to send a message to check on my availability! 🐕‍🦺 I have a large fenced in yard and friendly dogs, Adobo and Charley, that can keep your furry friend company with play or lounging. I can crate if needed.

Sitter Profile Image: Gretchen S.
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Gretchen S.
from
$20
per visit
5.0 out of 5 stars
2 reviews
1 repeat client
10 years of experience
Wauwatosa, WI, 53213

Flexible and communicative! Available on a short timeline. Would hire again!

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Alivia M.
Sitter Profile Image: Jennifer B.
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Jennifer B.
from
$20
per visit
5.0 out of 5 stars
4 reviews
1 repeat client
20 years of experience
Wauwatosa, WI, 53213

About: I have grown up with Golden Retrievers my whole life as my dad hunted with them and trained them for Field trials. We always had three in our home. Once we even had a litter of puppies and there is nothing better than puppy kisses. I personally have had two Black labs, one that was so content to lounge and be a couch potato and my current lab at 8 years old fools everyone into thinking she is 2 or 3 with how active she is. Because of her I understand the importance of walks and her needing lots of exercise, new sights and smells. I have a flexible work schedule and typically only work 3 days a week so I can be there to ensure your pup gets what they need. Happy to play in the yard or walk as needed to make sure your pup is content. Just let me know what their rules are and I'm happy to follow to ensure they are happy and healthy.

Sitter Profile Image: Elizabeth C.
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Elizabeth C.
from
$15
per visit
5.0 out of 5 stars
15 reviews
7 repeat clients
7 years of experience
Wauwatosa, WI, 53213

Elizabeth did a great job with our pup! She kept us updated the entire time with lots of details and pictures. It was comforting knowing Elizabeth was treating Bo like her own while we were away. She approached separation anxiety with nothing but compassion and patience. Thank you Elizabeth for such a great experience!! :)

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Olivia W.
Sitter Profile Image: Maggie S.
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Maggie S.
from
$15
per visit
5.0 out of 5 stars
32 reviews
7 repeat clients
40 years of experience
Milwaukee, WI, 53213

About: I recently lost both of my dogs and while I'm not ready for a new dog, I'd love to take care of yours. I'm very active and love taking walks. I cared for my own very senior dog for several years. I work 10-6 Monday through Friday. I can walk morning and evenings and if required I'm close to my job to stop home mid day. I have a fairly large back yard with a tie up but will more likely take the dog for walks. I live in a safe neighborhood by myself and I have no other pets at this time.

Sitter Profile Image: Michelle M.
Verified Background Check
Michelle M.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
61 reviews
24 repeat clients
15 years of experience
Washington Heights, Milwaukee, WI, 53208

About: Hi, my name is Missy I've had a great deal of experience with all different kinds of animals. I worked with a local vet helping place feral cats in homes and providing excellent care for them. Including helping pregnant feral cats with delivery and maternal care. I have volunteered at the Wisconsin Humane Society. There I worked in the Wildlife rehabilitation center as well as the dog care center. I currently own dogs and cats of my own and I recognize how important it is to provide excellent care as well as exercise and playtime. I have past experience in boarding and dog sitting in my home which has always been a great experience. Can't wait to give the love and care your dog(s) deserve!

Sitter Profile Image: Ariana B.
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Ariana B.
from
$17
per visit
6 years of experience
Sunset Heights, Milwaukee, WI, 53216

About: I’ve taking care of pets since I was 13. I currently have a blind senior german shepherd, and guide him when needed, giving him lots of treats and love. I also have a 1 year puppy and give her frequent time out. I’m planning on working weekends whenever needed to play with doggies and give them the care they need! I can feed them, give medicine, and care for blind and senior dogs. I put my dogs before anything and make sure they have everything they need. Treats, water, food, play time, medicine, supplements, nap time and love.

Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$25
per visit
5.0 out of 5 stars
51 reviews
19 repeat clients
5 years of experience
Dineen Park, Milwaukee, WI, 53216

Stephen and Amelie are the best! They take excellent care of our babies and our home when we’re away and make us feel completely comfortable when we need to travel without the pups. Our dogs love them too!

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Laura B.
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Uptown pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Grateful for Aiden and all she did for us while we were out of town. It was a relief to know my cat was so well cared for and I wouldn't hesitate to recommend Aiden to anyone. I'm not even sure my cat is happy we're back - I think she misses Aiden 😊.

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Stacey M.
Drop-In Visits
5.0 out of 5 stars

Kathy is amazing!! Communication throughout was wonderful and genuinely cared for our 2 cats and our home. Kathy checked in and out daily and provided a great summary of the visit... even brought in an unexpected delivery - thank you! Kathy is highly reliable and trustworthy, looking forward to future in-home care☺️

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David O.
Drop-In Visits
5.0 out of 5 stars

Cindy had been wonderful! She asked questions about Vladimir’s schedule, behaviors, even where he likes to sleep. She pays close attention to directions and details and is an excellent communicator! I feel very comfortable leaving Vladimir in her care. I know he will be loved on, cared for, and is safe. Vladimir loved her immediately and we’re lucky to have found her!

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Marie W.
Drop-In Visits
5.0 out of 5 stars

Thank you so much Sydney! Great communication and super attentiveness to our little buddies! Highly recommend Sydney!

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

Kristine was awesome with my cat Winnie. She can get scared with new faces but Kristine was kind and gentle with her. 10/10 would book with her again!

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Jordan S.
Drop-In Visits
5.0 out of 5 stars

Wonderful experience! I appreciate her flexibility and willingness to come back more than once, so helpful for me!

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Jennifer R.
Drop-In Visits
5.0 out of 5 stars

Elizabeth always goes above and beyond to care for our dogs. You can tell this is her priority above all else, and always ensures they are safe and taken care of. 10/5 would recommend

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Chris K.
Drop-In Visits
5.0 out of 5 stars

Esterah is wonderful! She was able to do a last minute same-day drop-in visit. She always sends pictures and takes great care of my dog.

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Autumn M.
Drop-In Visits
5.0 out of 5 stars

Erica was a huge help and accepted my request on very short notice! She did a great job taking care of my cat, Ladybug, and provided updates after every visit. Thanks, Erica!

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Devin D.
Drop-In Visits
5.0 out of 5 stars

Michelle takes excellent care of our two dogs. We have fairly detailed instructions and she follows them to a tee! I feel confident leaving her in charge of our pets while traveling abroad. Thank you, Michelle!

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Sara H.
Drop-In Visits
5.0 out of 5 stars

Danielle is amazing with our puppy, Boomer. She makes sure he is played with, and handled with care. She is very trust worthy and passionate. She keeps the house cared for as well. We look forward to continued bookings with her!

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Kyle T.
Drop-In Visits
5.0 out of 5 stars

Jill was extremely kind and professional. My cat is honestly pretty rude to sitters. Jill was great at noticing her body language, giving my cat her space, and even finding her when she managed to get into an unusual hiding space. She's a great and reliable caregiver for your pets!

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

Kaitlin was amazing! She took great care of our kitties while we were out of town. Her communication was stellar. She took the initiative to bring in some mail and a package that snuck through before we asked her to. Highly recommended! We would definitely book with Kaitlin again!

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Elizabeth J.
Drop-In Visits
5.0 out of 5 stars

Ivy was absolutely AMAZING! Our dog is sometimes timid and shy of other people but he quickly warmed up to her. I would highly recommend having her help with your furry friends :)

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

Michelle did great drop in visits for our dog while out of town for a couple of nights, and provided us with lots of updates and reassurance.

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Nicole L.
Drop-In Visits
5.0 out of 5 stars

Leesa was so wonderful with our cat! Our cat was initially unsure of a stranger but they quickly became best friends! I couldn’t recommend Leesa enough :)

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Bella N.
Drop-In Visits
5.0 out of 5 stars

Repeat booking with Julia! We appreciate her updates and communication. She is reliable and professional - highly recommend!

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

Nicole was excellent! When she came for the meet and greet, she asked excellent questions to really get to know our girls and set expectations. She was calm and let our girls come to her. Then, when she came for the visit, she took excellent care of our kitties and was able to pill our calico successfully! Throughout the whole experience she communicated super well, which is something that we value. We will absolutely recommend and rebook!! Thanks Nicole!

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Amy S.
Drop-In Visits
5.0 out of 5 stars

I have had Kristin three times now to take care of my diabetic cat twice a day for a week at a time. She has to feed and inject her with insulin at each visit. She is kind, detail oriented and professional. I highly recommend her to care for your pet.

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Mary O.
Drop-In Visits
5.0 out of 5 stars

Excellent communication and does a great job with our pets! This is the 3rd time we’ve used her and she does a fantastic job.

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Veronica Z.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
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  3. 3. Book & Pay

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The median cost per night for pet sitting in Uptown is $16

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Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Uptown on Rover as of Apr 2026 was about $16 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Uptown pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Uptown.

Rover makes it easy to find Uptown pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.