House Sitting Jackson Park

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

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Over 2
pet parents in Jackson Park have booked house sitting

Jackson Park, 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.

1 / 1
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
• 56 reviews
25 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

“Keisha was great! She watched our 2 doodles, one with a bit of an attitude! She sent texts when she had questions and sent us pictures. Will definitely book with her again!”

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Marie G.
Sitter Profile Image: Samantha B.
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Samantha B.
from
$60
per night
4.9 out of 5 stars
• 15 reviews
4 repeat clients
13 years of experience
Milwaukee, WI, 53215

“Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.”

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Alyssa T.
Sitter Profile Image: Emily M.
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Emily M.
from
$59
per night
5.0 out of 5 stars
• 45 reviews
12 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: Alexis G.
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Alexis G.
from
$47
per night
5.0 out of 5 stars
• 13 reviews
9 repeat clients
6 years of experience
Greenfield, WI, 53221

“Alexis was super communicative and took great care of our dog while we were away!”

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K M.
Sitter Profile Image: Evita E.
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Evita E.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 22 reviews
4 repeat clients
10 years of experience
Sunset Heights, Milwaukee, WI, 53216

“While Evita watched our pup Molly overnight at our house, she was punctual and communicated well. She also took Molly on a nice long walk each day that pleasantly tuckered her out. Molly seemed calm and happy when we returned home.”

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Alia E.
Sitter Profile Image: Rebecca M.
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Rebecca M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
• 16 reviews
8 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

“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!”

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Kristina P.
Sitter Profile Image: Lynette F.
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Lynette F.
Star Sitter
from
$60
per night
5.0 out of 5 stars
• 93 reviews
16 repeat clients
11 years of experience
Milwaukee, WI, 53207

“Lynette was terrific with our dogs. One of our dogs is blind and the other one had been turned down from a doggy daycare for not being friendly enough. She spent time with them and sent us pictures of both of them in her lap sleeping. We have already talked with her about watching them again in March. Great job!! and great service.”

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Bill B.
Sitter Profile Image: Fatima B.
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Fatima B.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 9 reviews
2 repeat clients
2 years of experience
West Allis, WI, 53214

“Fatima was amazing to work with. I booked her on short notice before the holiday when my original plans fell through. She offered and made it a priority to come do a meet & greet on days notice. I’m always a little nervous when using a new sitter especially when they stay at mine, but my mind was at ease immediately when I met her. I could tell she has a big heart and really cares for animals. She followed all instructions and she went above and beyond spending time with Diesel doing his favorite activities (walks, playing fetch, swimming, etc.). She was incredibly communicative and sent a lot of pictures and videos which was much appreciated. As a former Rover sitter and a frequent user of Rover’s services, I can confidently say that Fatima is one of the best sitters I’ve come across. I will definitely be using her in the future and have already recommended her to others looking for sitters. Thank you Fatima!!!”

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Alex S.
Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$68
per night
5.0 out of 5 stars
• 132 reviews
35 repeat clients
40 years of experience
West Allis, WI, 53227

“Another great experience with Jenn!! Came home to a happy pup and tiddy home. In addition, I was out of town and a snow storm hit! My flight was cancelled. Jen was a saint for being able to take care of my dog with my extended leave.”

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Jenna Z.
Sitter Profile Image: Berenice B.
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Berenice B.
Star Sitter
from
$70
per night
4.9 out of 5 stars
• 293 reviews
121 repeat clients
15 years of experience
Bay View, Milwaukee, WI, 53207

“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.”

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Claire L.
Sitter Profile Image: Angela R.
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Angela R.
Star Sitter
from
$64
per night
5.0 out of 5 stars
• 141 reviews
40 repeat clients
30 years of experience
Bay View, Milwaukee, WI, 53207

“Angela was amazing!!! We had never left our dog with anyone overnight and she helped me feel comfortable and at ease. She sent lots of pics and updates and loved on our guy all weekend. So grateful!”

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Braelyn G.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$64
per night
5.0 out of 5 stars
• 226 reviews
67 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

“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.”

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Carlie V.
Sitter Profile Image: Joseph D.
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Joseph D.
from
$28
per night
4.9 out of 5 stars
• 9 reviews
2 repeat clients
10 years of experience
Wauwatosa, WI, 53213

“Joe is great. He stayed with our Chihuahua for a couple days and nights. He's responsive, sends great photos and Fiona seems relaxed and well cared for now that we are home.”

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Amy W.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
• 27 reviews
11 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: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$100
per night
5.0 out of 5 stars
• 51 reviews
19 repeat clients
6 years of experience
West Allis, WI, 53227

“We couldn't have asked for a better experience! Stephen and Amilie were very communicative to us about how our animals are doing. We felt very comfortable with them and they took great care of our animals! We would no doubt use their services again!”

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Rebekah J.
Sitter Profile Image: Marilia D.
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Marilia D.
from
$75
per night
5.0 out of 5 stars
• 84 reviews
28 repeat clients
15 years of experience
Wilson Park, Milwaukee, WI, 53221

“Marilia is fantastic! We felt very comfortable leaving our two dogs overnight in our home with Marilia even after meeting her for the first time. Our girls were happy and healthy when we returned, and we feel even better about having Marilia take care of Rae and Frankie sometime in the future! Thanks Marilia!!!”

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Mark M.
Sitter Profile Image: Simon K.
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Simon K.
from
$40
per night
5.0 out of 5 stars
• 6 reviews
2 repeat clients
10 years of experience
Yankee Hill, Milwaukee, WI, 53202

“Simon was great. I appreciated all the communication ahead of time and while he was dogsitting.”

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Kristin S.
Sitter Profile Image: Carolyn G.
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Carolyn G.
from
$35
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
17 years of experience
West Allis, WI, 53214

“Cary was an excellent dog sitter! She cared for my dog for 7 days while I was out of the country, and this was my first time being away from my dog. She was very thoughtful about sending regular updates throughout the day, which gave me so much peace of mind. Cary stayed at my home and took great care of both my dog and my space. She kept everything clean and even washed my sheets before I returned, which I truly appreciated after a long day of traveling. It’s clear she genuinely cares and treats your pet like her own. I highly recommend her to anyone looking for a reliable and caring dog sitter!”

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Seryna G.
Sitter Profile Image: Carolina G.
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Carolina G.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 41 reviews
9 repeat clients
9 years of experience
Cudahy, WI, 53110

“I have a couple challenging pets, including an anxious, blind senior dog but Carolina moved at their pace and took great care of them. She was communicative and I got pictures every day. We came home to the house exactly as we left it. She’s kind and respectful.”

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Megan S.
Sitter Profile Image: Emma G.
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Emma G.
Star Sitter
from
$95
per night
5.0 out of 5 stars
• 6 reviews
4 repeat clients
7 years of experience
Bay View, Milwaukee, WI, 53207

“Emma was so sweet with my little senior dog! My dog has various quirks and some chronic health and anxiety isssue and Emma was very accomadating with it all! She was also a great communicator and would check in and ask questions to clarify if she needed anything. I would definetely recommend her to anyonne and would trust her again with my furbabies <3 Thanks so much Emma!”

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Adriana S.
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The median cost per night for house sitting in Jackson Park is $50

Pet parents share their Rover experiences - Jackson Park

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5.0 out of 5 stars

Mallory is so great! My dog has never been so calm and content after we have been away. Mallory was responsive, shared great updates, and made him feel so comfortable while we were out of town. Would book with her again in a heartbeat!

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Anna K.
House Sitting
5.0 out of 5 stars

Alexis took great care of Zuzu. I was amazed at how quickly Zuzu warmed up to her at the initial meat and greet. I will absolutely book Alexis again.

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Douglas D.
House Sitting
5.0 out of 5 stars

Stephany did a phenomenal job watching my dogs overnight. I was nervous at first as it was my first time leaving them with someone besides family. However, stephany went above and beyond. Following their usual daily schedules, taking them for walks, and updating me regularly with photos and videos. I could tell that they were comfortable with her and really liked her! I will absolutely re book stephany again in the future, she will take wonderful care of your pets and home while you are away. Thank you Stephany!

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Erika R.
House Sitting
5.0 out of 5 stars

Margaret was great—took great care of our pup, was communicative, sent pictures, and the was immaculate when we returned.

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Tom And Mary H.
House Sitting
5.0 out of 5 stars

Super friendly and the pups clearly loved snuggling with her! Very smooth booking - even when we needed to add a night. Would absolutely ask her to sit with our babies again

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Kathi K.
House Sitting
5.0 out of 5 stars

Maiah was great to work with! She was quick to respond and communicate with. Our doggos enjoyed her company and she took great care of them! Would definitely rebook with her again!

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Rebekah J.
House Sitting
5.0 out of 5 stars

Keisha is an absolute wonder sitter! Our little pup was very anxious about us leaving and Keisha was so very kind, patient and loving. She took extra special care to help our pup feel safe, loved and secure. We will always ask Keisha to come watch our pup anytime we leave or even just to hang out for an afternoon. Trust Keisha to be the best care giver!

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Jamelyn H.
House Sitting
5.0 out of 5 stars

Katlynn followed my detailed instructions and I felt very comfortable with her caring for Mink. She watched him carefully to make sure he did not have a recurrence of his medical condition.

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Catherine K.
House Sitting
5.0 out of 5 stars

Sarah is an absolute star - we’re so lucky to have found her on Rover! Our dogs are so happy and comfortable with her, and we know we can rely on her 100%. Consistent photos and updates, and when we get home, the dogs are so chill that it’s like we never left.

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Hannah T.
House Sitting
5.0 out of 5 stars

Katherine is incredible! Our pets receive so much attention and she is so caring for each of their needs. We return home to an extremely clean house. Everything from the care of our pets and home, her attention to detail is above and beyond!

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Todd S.
House Sitting
5.0 out of 5 stars

Nicole is absolutely phenomenal! She took such great care of our Siberian kitten. Nicole is very professional, communicative, and you can tell how much she loves what she does! The whole time we were gone she sent us updates and photos. We would 110% recommend Nicole!

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Angela G.
House Sitting
5.0 out of 5 stars

Ryan was fantastic! He took great care of our very large dog, who can be reactive at times. I completely trusted him while we were away for a week. We received lots of updates like we asked. He gave our dog medicine without any issues. We came home to a very happy pup and a spotless house. Ryan even got our mail and watered our flowers while we were away, which was super nice. We highly recommend him and already have our next trips booked with him!

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Leah G.
House Sitting
5.0 out of 5 stars

Scott was FABULOUS with our dog, Rocket! Rocket is a bit picky, but he wholeheartedly loved Scott, too. Scott had wonderful communication--he gave enough so that I felt reassured that Rocket was doing well, but he also let me just relax while on our trip. He made me feel confident that Rocket was in good hands, and that means the world to me. Scott also took in our mail and watered our garden. Thanks for everything, Scott!

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Jen C.
House Sitting
5.0 out of 5 stars

As always, Caitlyn was amazing! Great updates of our pets, handles giving meds like a champ, and leaves our place nice and clean every time.

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Riley H.
House Sitting
5.0 out of 5 stars

Loved working with Marilia! We did a meet and greet beforehand and she was a pleasure. Our lil special-needs pittie mix loved her too and they shared many snuggles. She sent us lots of nice updates and photos and left our house spotless!

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Margaret M.
House Sitting
5.0 out of 5 stars

Rachel was great with Howie and I loved all the photo updates she provided. Really appreciated her patience with my puppy!

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Amanda K.
House Sitting
5.0 out of 5 stars

Amanda was wonderful. This was the first time we traveled without our puppy and we were a bit apprehensive. However, Amanda eased our concerns. She arrived a few minutes early which signaled a level of reliability that was very welcome. While we were away, Amanda provided regular updates and pictures. As a result, we were able to enjoy our vacation. And our puppy seemed to genuinely enjoy Amanda. We will definitely use Amanda again. We would feel very comfortable leaving our puppy with her.

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Kerry H.
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

Sonia and Alex did an absolutely excellent job caring for my dog. He is developmentally delayed, requires daily medication, and is incontinent, so his care takes extra attention and patience. Throughout the 6 days he was with them, they communicated promptly and openly about any challenges that came up, and together we were able to make simple adjustments to ensure his stay was comfortable and successful. They sent pictures frequently, which gave me great peace of mind while I was away. From every photo, it was clear that my dog was happy, well cared for, and comfortable in their care. I am incredibly grateful for the compassion, flexibility, and attentiveness Sonia and Alex showed, and I would wholeheartedly recommend them to anyone—especially those with pets who have special needs.

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Gwen P.
House Sitting
5.0 out of 5 stars

We use Amanda multiple times a year and she is great! I love the daily photos of our pup, and I know she with take great care of our big guy. Thanks, Amanda!

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Erin F.
House Sitting
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