House Sitting in Jackson Park, Milwaukee, WI

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Top rated Jackson Park house sitters

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

Keisha was amazing! She helped us out when another sitter cancelled. She took amazing care of our 2 dogs while we were away! She was very responsive, sent lots of pictures, and kept us posted the whole weekend! She truly understood and embraced my dog’s personalities! I would highly recommend her and will be using her again in the future!

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Janine P.
Sitter Profile Image: Rachel H.
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Rachel H.
Star Sitter
from
$30
per night
5.0 out of 5.0 stars
95 reviews
24 repeat clients
11 years of experience
West Allis, WI, 53214

Rachel was wonderful! She kept us updated the whole time and our boy was so happy! She took him to the dog park every day and made sure she had a great time while we were gone. We’ll use her every time we can if she’s free!

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Melissa Z.
Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$59
per night
5.0 out of 5.0 stars
15 reviews
3 repeat clients
30 years of experience
Milwaukee, WI, 53213

Emily did a great job watching my pups, and chickens. Easy and quick communication, she took the pups on some adventures as well. Highly recommend her and would use her again.

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Lauren S.
Sitter Profile Image: Sonia E.
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Sonia E.
from
$49
per night
5.0 out of 5.0 stars
7 reviews
18 years of experience
Harder's Oaks, Milwaukee, WI, 53215

About: I LOVE DOGS. Their lives are short, and I want to help them enjoy those years with comfort, care, and fun. I have had a dog companion in my life since I was five years old. I especially enjoy caring for high-energy dogs who need regular exercise—I’m always up for long walks, playtime, or outdoor adventures. I also have experience with senior dogs, and I understand the importance of patience, gentle handling, and keeping routines consistent. I’ve successfully trained dogs to potty outside, sit on command, and even walk off-leash. Whether your pup is young and active or older and needs a slower pace, I’ll make sure they’re well cared for while you’re away. I function better with a dog at my side. Dogs help me start my day with purpose—there’s nothing like a good morning walk to get us both moving and ready for breakfast and whatever the day brings. I love building routines that keep dogs active, happy, and well cared for. I work remotely, so my schedule is very flexible and allows me to be fully present for pet care throughout the day. With cats, I understand how much they value consistency. I’m attentive to their morning and evening routines—feeding, cleaning the litter box, and giving them space or affection depending on their mood. I also make time for play and interaction throughout the day, based on each cat’s personality. Communication is everything. I try to make sure I understand each animal's boundaries and needs before providing care, this includes list of allergies and medications.

Sitter Profile Image: Liz B.
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Liz B.
Star Sitter
from
$50
per night
4.9 out of 5.0 stars
40 reviews
14 repeat clients
7 years of experience
West Allis, WI, 53214

Liz was wonderful! Excellent communication. This was my first time using Rover and she made for an amazing first experience. I will definitely use her services again.

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Stacy J.
Sitter Profile Image: Emily S.
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Emily S.
Star Sitter
from
$45
per night
4.9 out of 5.0 stars
44 reviews
24 repeat clients
6 years of experience
West Allis, WI, 53227

Emily did a great job with our older dog. She communicated any concerns she had with him. The house was left in pristine condition. We were thankful to have her staying with Louie.

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Cheryl D.
Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$62
per night
5.0 out of 5.0 stars
98 reviews
27 repeat clients
40 years of experience
West Allis, WI, 53227

Jenn was awesome with our pets, we had no worries or anything while we were away. She made us feel very comfortable and took great care of our babies! We would definitely use her again, and would highly recommend!

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Brianna J.
Sitter Profile Image: Daniela & Michael P.
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Daniela & Michael P.
from
$65
per night
4.9 out of 5.0 stars
291 reviews
166 repeat clients
11 years of experience
Bay View, Milwaukee, WI, 53207

Daniela did a wonderful job watching Chewie. When we were feeling anxious, she was so quick to respond with a photo of our happy pup. Highly recommend.

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Tracy H.
Sitter Profile Image: Elizabeth C.
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Elizabeth C.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
9 reviews
4 repeat clients
7 years of experience
Wauwatosa, WI, 53213

Elizabeth went above and beyond to take care of our pup and our home during her stay. She provided multiple updates and photos throughout the day and kept our dog safe and happy while we were away. Can’t recommend her enough!

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Emily F.
Sitter Profile Image: Lisandra V.
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Lisandra V.
from
$40
per night
5.0 out of 5.0 stars
107 reviews
23 repeat clients
10 years of experience
West Allis, WI, 53227

Lisa was wonderful with our pups. I had a concern that there might be some anxiety with our new rescue, but they LOVED her right away. That says a lot. She sent lots of updates and photos- so appreciated!

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Ann S.
Sitter Profile Image: Maiah D.
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Maiah D.
Star Sitter
from
$80
per night
5.0 out of 5.0 stars
75 reviews
22 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: Sarah J.
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Sarah J.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
410 reviews
83 repeat clients
5 years of experience
West allis, WI, 53219

Sarah did a fabulous job with the Furry Herd! Five dogs is no small undertaking, much less having two with medical conditions requiring medication. She was very attentive, spending a good amount of time here when she came, and the dogs were super happy to see us, but not in a frantic way. What a wonderful way to come home! Loved the pictures, too!!!

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Cam H.
Sitter Profile Image: Alexy & Christian G.
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Alexy & Christian G.
Star Sitter
from
$40
per night
4.9 out of 5.0 stars
78 reviews
22 repeat clients
9 years of experience
Bay View, Milwaukee, WI, 53207

Alexy and Dylan took wonderful care of our dogs while we were out of town. We got lots of pics, videos and updates. They also left our apartment in great shape. We will be using them again.

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STEPHANIE R T.
Sitter Profile Image: Sarah A.
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Sarah A.
from
$50
per night
5.0 out of 5.0 stars
1 review
1 repeat client
4 years of experience
Avenues West, Milwaukee, WI, 53233

Sarah was great with Walter! She sent us daily updates and our house was left very clean – thank you!

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Livia A.
Sitter Profile Image: Ivy G.
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Ivy G.
Star Sitter
from
$45
per night
5.0 out of 5.0 stars
11 reviews
4 repeat clients
20 years of experience
Uptown, Milwaukee, WI, 53210

Ivy was a fantastic sitter for our dog! He can be fearful meeting new people, but Ivy was so patient with him and they were besties in no time. We received lots of updates and photos, our apartment was left in great condition and our dog’s needs were met above and beyond. Knowing he was in good hands made being away a lot easier. :)

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Nina L.
Sitter Profile Image: Samantha B.
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Samantha B.
from
$60
per night
4.9 out of 5.0 stars
12 reviews
4 repeat clients
13 years of experience
Milwaukee, WI, 53215

Ive had Sam over twice now to watch my fur baby. My dog loves her and I never worry about her while Im gone. Shes trustworthy and communicates well while im gone. I will definitely use her again

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Tia R.
Sitter Profile Image: Jamila M.
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Jamila M.
Star Sitter
from
$57
per night
4.9 out of 5.0 stars
90 reviews
25 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.
Sitter Profile Image: Lauren S.
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Lauren S.
Star Sitter
from
$75
per night
5.0 out of 5.0 stars
9 reviews
6 repeat clients
10 years of experience
Kilbourn Town, Milwaukee, WI, 53203

Lauren did a great job taking care of the boys while we were away. She gave them plenty of exercise and engagement as well as keeping them on their regular schedule. Very much appreciated and we hope to book again.

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Alex J.
Sitter Profile Image: Alissa A.
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Alissa A.
from
$70
per night
5.0 out of 5.0 stars
7 reviews
1 repeat client
20 years of experience
Greenfield, WI, 53221

Excellent communication from the start. Came for a greet and meet and easy to be with and obvious knew dogs well. Ended up a friend of mine knows Alissa so a double excellent reference. She communicated with me constantly throughout the stay. My dog is a senior and she did well with him and when I returned he kept roaming into where she was staying in my place. Would have back again as she is available.

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Cindy S.
Sitter Profile Image: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$38
per night
5.0 out of 5.0 stars
14 reviews
3 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

Jo is simply the best sitter out there! She takes care of my dog so well and treats him like a king. He has his own vacation when I’m gone and I could not recommend Jo enough to take care of your furry family. I know mine already misses her!

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Alli B.
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Jackson Park pet parents share their Rover experiences

1 / 1
5.0 out of 5.0 stars

Another great experience with Sarah! She house sat for me for three days/2 nights for my dog, Jimmy. She sent pictures, kept me updated on visit times and how everything was going, left the house looking great and even brought in the packages from the freezing cold outside! I came home to a happy pup!!

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Jenna Z.
House Sitting
5.0 out of 5.0 stars

Kaitlyn was a great sitter for my cat, Gus! She was proactive in asking any questions that came up and she sent me regular pictures/updates while I was gone. I would definitely recommend her to others and rebook with her!

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Tressa S.
House Sitting
5.0 out of 5.0 stars

Keisha was absolutely fantastic! I have 2 Pit mixes -1 who gets anxious when we're gone and my big guy who can be gregarious and at times stubborn,and a cat who rarely shows his face to a new person. She was wonderful with them all and they all were happy and comfortable with her. Even my cat let her pet him! She has a great energy and the house looked perfect when we returned home from the week. She kept in touch, was responsive, asked questions when necessary and was really kind. I will definitely book her again!

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Kelly G.
House Sitting
5.0 out of 5.0 stars

Emma did an amazing job watching my animals and housesitting!! I think my dog and cats probably love her more than me🤣

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Donna L.
House Sitting
5.0 out of 5.0 stars

Another fabulous visit - Hutch was happy, calm and well groomed when we came home. You’d never have known someone was in the house! Great communication and updates.

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Lisa W.
House Sitting
5.0 out of 5.0 stars

Mara watched our 2 pups for a week while my husband and I were on vacation. She sent us daily updates and cute pics of our pups, which put my anxious mind at ease while we were many miles away. I highly recommend he to others!

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Nicole W.
House Sitting
5.0 out of 5.0 stars

We can't speak highly enough of Katherine who has watched our house and pets numerous times. She is caring, thoughtful, and provides the pets (dog and 2 cats) with all the attention they need and then some. We came home to a spotless house and felt comfortable/like the pets were in good hands while we were abroad.

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Todd S.
House Sitting
5.0 out of 5.0 stars

This was our first time using Alex to watch our pets and it won’t be the last! He did a great job with our two dogs and three cats and taking care of our home. He kept us updated regularly and sent us photos. He was very respectful of our home! I would definitely recommend Alex and will be using him in the future!

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Kathryn E.
House Sitting
5.0 out of 5.0 stars

Liz was great with our two pups! She sent lots of photos and updated us throughout. The pups loved having her!

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Heather D.
House Sitting
5.0 out of 5.0 stars

Maria did a good job entertaining JoJo. You can tell right away that she is good with dogs. Kept me updated with JoJos activities. I felt very comfortable leaving JoJo in her care.

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Linda S.
House Sitting
5.0 out of 5.0 stars

Eleyna was absolutely wonderful with dexter! She listened to instructions throughly, was super responsive and sent plenty of pictures! i would absolutely use her again and would recommend to anyone looking for a dog sitter

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Alyssa F.
House Sitting
5.0 out of 5.0 stars

Holly was great! Took great care of our dogs and home. Put us at ease and allowed us to travel stress free!!! Highly recommend Holly & we will reach out to her again for sure!!!

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Kerry A.
House Sitting
5.0 out of 5.0 stars

Joely was amazing with Oakley, several pictures and mentions of each day was fantastic. She really is amazing with animals. Highly recommend.

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Josh D.
House Sitting
5.0 out of 5.0 stars

Grace was so great to work with! She was prompt to respond and set up a meet and greet. She asked insightful questions and took great care of Theo. He took to her immediately! She also left me the sweetest card. Would definitely love to work with her again.

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krupa s.
House Sitting
5.0 out of 5.0 stars

Thank you for taking great care of Henry & Emmy. The peace of mind you give us is so wonderful. You are appreciated Katie. David & Julie

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David C.
House Sitting
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