House Sitting In Uptown Milwaukee

Find a loving house sitter to watch over your pets and your home.

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Top rated Uptown house sitters

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

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Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
99 reviews
27 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

Emily was wonderful - communicative, friendly, and our dog and cat clearly loved her. She sent amazing pictures and updates and allowed us to feel completely relaxed about being away. Thanks, Emily!!!

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Kathleen P.
Sitter Profile Image: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
32 reviews
6 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

It was our second time hiring Elizabeth, another positive experience. My pooch likes his walks and we are grateful she is ok with taking him. She is great with giving updates and sending photos. Upon return the house was just as we left it.

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Carol M.
Sitter Profile Image: Joseph D.
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Joseph D.
from
$28
per night
4.7 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Wauwatosa, WI, 53213

About: I’ve been looking after fluffy frens of all shapes and sizes from a young age. My time doing a full house/dog sitting gig was for my grandparents and their French bulldog, Sugar (miss you, Sugs!). Since then I have been the go-to for my friends and family for taking care of their for legged family. I make sure your fury family gets the love and care they need, whether you just have one smol dog or a pack of greyhounds. I currently had a stretch of rough health luck, but my ails are your pups gain! I’m currently on the mend, and it’s going well, but between jobs, so my schedule is wide open. I’ll have the time to give your pups the TLC they deserve! Currently unavailable to board pets at my house, but I will make sure to treat all pets in a safe and caring way. I’ll treat them like a newborn baby, because hey, in a way they are!

Sitter Profile Image: Scott S.
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Scott S.
from
$40
per night
5.0 out of 5 stars
17 reviews
4 repeat clients
15 years of experience
Honey Creek Parkway, Milwaukee, WI, 53214

Scott was our first introduction to Rover. We really appreciated that he could come on short notice to sit with our 22-week old puppy. We loved Scott's relaxed and gentle way with our dog who is so excited to meet someone new, but is still in manners training in how to greet people. Scott quickly picked up on what we were trying to teach and went along with that routine. Scott arrived on the dot of our agreed time and we plan to ask him to come again!

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Maree E.
Sitter Profile Image: Molly O.
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Molly O.
from
$65
per night
5.0 out of 5 stars
64 reviews
20 repeat clients
18 years of experience
Wick Field, Milwaukee, WI, 53208

Molly absolutely crushed it- I can’t say enough good things. Our dogs have huge personalities, some bizarre behaviors, and special needs (and so does our weird old rental house) and she handled all of it with aplomb. Our resident canine klutz tore his paw pad the night before we left, and even though we totally sprung this development on Molly at the last minute, pro that she is, she jumped in and changed his dressings, kept the area clean, AND kept the dog calm to prevent further injury. He was basically fully healed upon our return. Thanks, Molly! We will be back if you’ll have us- with fewer surprises next time, we hope!

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Lily S.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$64
per night
5.0 out of 5 stars
204 reviews
63 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica was amazing! She communicated with us every day and sent us pictures/videos of the dogs, which my daughters really enjoyed. She took extra special care of our geriatric dog, making and feeding him human food, per our request. We will definitely be hiring Jessica again! Thank you for taking care of our fur babies! Brandy

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Brandy F.
Sitter Profile Image: Keisha P.
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Keisha P.
from
$45
per night
5.0 out of 5 stars
43 reviews
19 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha is wonderful! Our pups are very shy but Keisha did a great job helping them warm up. She is sweet, communicative and flexible, and even sent us pics of the girls while she was watching them!

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Julianne S.
Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$59
per night
5.0 out of 5 stars
30 reviews
8 repeat clients
30 years of experience
Milwaukee, WI, 53213

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!

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Creighton B.
Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$95
per night
5.0 out of 5 stars
51 reviews
19 repeat clients
5 years of experience
Dineen Park, Milwaukee, WI, 53216

Stephen and Wipawee watched our dog for the second time. They took excellent care of him. They kept us informed with pictures and updates throughout our trip. They were very respectful of our home and even brought in our mail and took our trash out to the curb. 100% recommend them and will definitely ask them to dog sit again in the future!

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Kristin L.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$90
per night
5.0 out of 5 stars
145 reviews
50 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

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.

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Christine H.
Sitter Profile Image: Catherine R.
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Catherine R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
24 reviews
10 repeat clients
1 year of experience
Murray Hill, Milwaukee, WI, 53211

We could not have asked for a better dog sitter. Catherine stayed at our home with our dog for 12 days and took exceptional care the entire time. She sent daily updates with photos, which gave us peace of mind. Our dog was happy and healthy when we returned. We would absolutely book Catherine again and recommend her to family and friends.

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Meghan M.
Sitter Profile Image: Julianna W.
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Julianna W.
from
$45
per night
5.0 out of 5 stars
10 reviews
1 repeat client
30 years of experience
Milwaukee, WI, 53202

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.

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Josh K.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
15 reviews
6 repeat clients
13 years of experience
Juneau Town, Milwaukee, WI, 53202

Ashley took absolutely excellent care of our cat while we were out of the country for a week! I knew from the moment she met our cat during our meet and greet that our little girl was going to be in great hands. Throughout the trip, Ashley reached out with check-ins and photos reflecting how well she was being taken care of. She also responded quickly to any messages and went above and beyond watching our place. We (and our cat) look forward to seeing her again in the future!

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Jeremiah W.
Sitter Profile Image: Cindy H.
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Cindy H.
from
$70
per night
5.0 out of 5 stars
54 reviews
14 repeat clients
45 years of experience
Martin Drive, Milwaukee, WI, 53208

Cindy took care of our dog Frankie and our house and is hands down the best Rover experience we have ever had!!! After our meet and greet we knew Frankie and our house were being left in good hands. We returned home without having anything to worry about thanks to Cindy! She is booked for our next trip! She is absolutely wonderful!

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Mark M.
Sitter Profile Image: Alena H.
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Alena H.
from
$55
per night
4.5 out of 5 stars
2 reviews
16 years of experience
Milwaukee, WI, 53233

About: Taking care of dogs is something I have enjoyed for much of my life, even a malanois can’t resist my affection! I’m very excited to have fun with your fur baby! I am currently working part time so my availability is open to help you and your lovely pet! I am able to easily balance your pet care with my own schedule. Figuring out your pets needs is crucial, then building a good routine around play, rest and bathroom breaks. Building a good routine is very important for me to develop a good relationship with your friend!

Sitter Profile Image: Maiah D.
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Maiah D.
Star Sitter
from
$100
per night
5.0 out of 5 stars
90 reviews
27 repeat clients
16 years of experience
Juneau Town, Milwaukee, WI, 53963

Maiah did a terrific job taking care of my dog. She gave us daily updates and photos, left the house clean and even stayed with my dog so she didn’t get lonely! Amazing!

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Will S.
Sitter Profile Image: Riley N.
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Riley N.
from
$60
per night
5.0 out of 5 stars
26 reviews
4 repeat clients
10 years of experience
Milwaukee, WI, 53212

Riley is great with our crabby old men and we appreciate all the pictures she sends! It was even their birthday on Monday and she sent a video of her singing happy birthday to them 🥺

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Josie H.
Sitter Profile Image: Ivy G.
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Ivy G.
from
$50
per night
5.0 out of 5 stars
37 reviews
13 repeat clients
20 years of experience
Uptown, Milwaukee, WI, 53210

Ivy was a fantastic sitter. Super communicative, thoughtful, and loving to our dogs. She made sure they were loved and cuddled while we were away. We look forward to having Ivy stay with them again in the future!

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Larissa B.
Sitter Profile Image: Evita E.
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Evita E.
from
$50
per night
5.0 out of 5 stars
7 reviews
1 repeat client
10 years of experience
Sunset Heights, Milwaukee, WI, 53216

Great to communicate with and our pups love her!

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Carley M.
Sitter Profile Image: Jamila M.
Verified Background Check
Jamila M.
Star Sitter
from
$65
per night
4.9 out of 5 stars
97 reviews
29 repeat clients
27 years of experience
Washington Heights, milwaukee, WI, 53208

Awesome job! Would highly recommend. Expert care of our needy, elderly Great Pyrenees, and pure wizardry with our little shepherd who can be tricky unless you’re in her pack.

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Jon G.
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Uptown pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

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!

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Mandy S.
House Sitting
5.0 out of 5 stars

Keisha did an amazing job! Kept the pets safe and happy! Very easy to communicate with. The house was clean and in order when we returned home. Highly recommend!

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Justine R.
House Sitting
5.0 out of 5 stars

I couldn’t have asked for a better dog sitter! She communicated wonderfully from the start and even met with me ahead of time to get to know my dog’s routine and feel comfortable with the space. While I was away, she sent daily updates with pictures of Stewart completely abandoning dad to cuddle with his new friend! 😂 I wholeheartedly recommend her to anyone looking for a trustworthy and caring sitter.

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Brad B.
House Sitting
5.0 out of 5 stars

Libby house sat and took great care of Jaq over the weekend. She was attentive to his separation anxiety and needs, making sure he felt comfortable while I was away.

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Christina S.
House Sitting
5.0 out of 5 stars

Thomas did a great job taking care of our boys. The dogs got plenty of attention and exercise. He kept the boys on their regular schedule and checked in often with pictures and updates. We hope to book again in the future.

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Alex J.
House Sitting
5.0 out of 5 stars

Emily was great at following my instructions and requests while staying with my dogs. They have some health issues and she cared for them very well. Emily is reliable and cared for my dogs well in my absence.

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Amy N.
House Sitting
5.0 out of 5 stars

Nicole is awesome ! I felt more than comfortable leaving my baby in her care ! She sent me lots of pics a videos and kept me in the loop ! She was super nice and very professional !! You can tell she really cares about furrbabies !

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Emily Z.
House Sitting
5.0 out of 5 stars

Cindy took care of our dog Frankie and our house and is hands down the best Rover experience we have ever had!!! After our meet and greet we knew Frankie and our house were being left in good hands. We returned home without having anything to worry about thanks to Cindy! She is booked for our next trip! She is absolutely wonderful!

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Mark M.
House Sitting
5.0 out of 5 stars

Paige is an amazing, young woman and was so loving to my pups. We had a hard journey driving from FL to Milwaukee, and I wanted someone to hang with them while catching up with friends. I could not have picked anyone better. Within minutes, my little Elsa was in love with Paige and King had a new girl friend! I searched the night before and thank God, Paige was the answer :) Obviously, highly recommend Paige.

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Laura R.
House Sitting
5.0 out of 5 stars

Davina was truly incredible! I have a dog with many allergies, and is anxious and reactive. She sent me all the updates and he is pooped after her stay. I had such a peace of mind while I was gone, so I cannot recommend Davina enough!! 10/10

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Hailey Q.
House Sitting
5.0 out of 5 stars

Emily is reliable, quick to communicate, and our dog and cat love when she comes to stay with them! Thanks, Emily!

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Kathleen P.
House Sitting
5.0 out of 5 stars

Sofia again took great care of Athena as well as our house while we were on vacation. We always feel so comfortable with Sofia, love the pics and updates & our pup loves all the attention with her!

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Diane T.
House Sitting
5.0 out of 5 stars

Gretchen did a great job watching our anxious dog and two kitties. She kept me updated and always replied promptly when I would reach out. We came home to a well taken care of house. Would recommend her.

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Nikki P.
House Sitting
5.0 out of 5 stars

Ivy was great. Wizard, My Siberian Husky seemed to really like her and has spent a good part of the past 2 days looking for her. Would highly recommend. Came home to a clean house and a clean husky which is the real chore. You won't go wrong booking with Ivy

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Steve H.
House Sitting
5.0 out of 5 stars

Esterah was so great with our pets during the house sitting. Our dog is very nervous and she was patient with him when she first arrived. We got lots up updates. She asked questions during the meet and greet and the house sitting which was much appreciated. We came home to a clean house and happy pets!

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Todd S.
House Sitting
5.0 out of 5 stars

Bree did such an amazing job with Lulu while we were in Arizona. I came home to a happy and tired dog. Will definitely be using Bree again for dog sitting and recommend her!!

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Jessica F.
House Sitting
5.0 out of 5 stars

Jamila was amazing with my senior dog Vladimir! She’s helped with feedings and overnights at my house. She is kind, thoughtful, and Vlad loved her! She followed all my instructions and handled my old man with care. We will be asking her to watch Vlad again in the near future! I’m grateful to have found her!

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Marie W.
House Sitting
5.0 out of 5 stars

Nicole was simply fantastic. Walter is a new rescue, and has only been with me for about two weeks before I had to travel for work. Nicole kept all of my anxiety about leaving him at Bay, she was incredibly communicative, very patient with my anxious, crazy boy, and even left me a full page document of notes about her observations on him as I’m continuing to understand who he is. While I was away, I was telling some of the individuals I was with about everything she was doing for Walter and they all begged me to give them her information. Will absolutely be reaching out to Nicole in the future!

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Arianna C.
House Sitting
5.0 out of 5 stars

Brooke is easy to communicate with and a born dog whisperer too. She was thoughtful, didn’t hesitate to ask questions, and was helpful in every way.

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Beki L.
House Sitting
5.0 out of 5 stars

Did a wonderful job taking care of Bernie. Daily updates and pictures. Left the place just how we left it too. Thanks Enrique!!

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Courtney J.
House Sitting
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How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

Why Choose Rover?

  • Cashless payments

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  • Reservation protection

    It doesn’t happen often, but if your house 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.

House Sitting FAQs

Frequently asked questions about Rover

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

If you have an active request or have booked a service with a house 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 house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

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

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Uptown house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

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