House Sitting Jackson Park

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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
$45
per night
4.9 out of 5 stars
47 reviews
21 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha took such great care of our two French bulldogs that are not exactly the easiest. She also did a great job trouble shooting some unanticipated situations like transportation issues and getting locked out — we will 100% use her again.

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Brock P.
Sitter Profile Image: Emily M.
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Emily M.
Star Sitter
from
$59
per night
5.0 out of 5 stars
38 reviews
9 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: Daniela & Michael P.
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Daniela & Michael P.
from
$65
per night
4.9 out of 5 stars
295 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: Maiah D.
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Maiah D.
Star Sitter
from
$100
per night
5.0 out of 5 stars
91 reviews
28 repeat clients
16 years of experience
West Allis, WI, 53214

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: Jenn S.
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Jenn S.
Star Sitter
from
$70
per night
5.0 out of 5 stars
124 reviews
34 repeat clients
40 years of experience
West Allis, WI, 53227

Jenn is amazing!! I have 2 cats and an anxious dog. She treated them all with so much love and cared for them while I was out of town.Updates and pictures every day!!

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Carrie L.
Sitter Profile Image: Alexandra I.
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Alexandra I.
Star Sitter
from
$70
per night
5.0 out of 5 stars
22 reviews
4 repeat clients
11 years of experience
Juneau Town, Milwaukee, WI, 53202

Alex did a great job with Tucker. She bonded with him immediately, he was feed, walked and pampered. Communication was excellent, we got lots of photos and updates. We will definitely use Alex again

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Phil S.
Sitter Profile Image: Brianna B.
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Brianna B.
from
$50
per night
5.0 out of 5 stars
11 reviews
1 repeat client
10 years of experience
Wilson Park, Milwaukee, WI, 53221

Brianna was a very attentive dog sitter to our high energy pup! She was also very good about letting us know when Sloane acted up so that we could help her handle the situation! Such a great house guest! She even stripped the bed!

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Georgia H.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
17 reviews
8 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: Samantha B.
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Samantha B.
from
$60
per night
4.9 out of 5 stars
14 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: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
101 reviews
28 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: Sarah J.
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Sarah J.
from
$50
per night
5.0 out of 5 stars
515 reviews
93 repeat clients
5 years of experience
West allis, WI, 53219

Sarah is amazing. Happy and safe pups, and she was flexible and worked with us gracefully through some scheduling changes. There was also a bad storm during her stay and she sent pictures and cleaned up some water, which is above and beyond. She sent great pictures and updates of our dogs, made us laugh, and was professional. Highly recommend Sarah.

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Claire L.
Sitter Profile Image: Rebecca M.
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Rebecca M.
from
$28
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

About: I’ve been caring for dogs for over 5 years, and I truly love getting to know each pet’s personality and routine. Friends, neighbors, and family have trusted me to walk, feed, play with, and stay with their pets while they’re away. I especially enjoy longer stays because it gives dogs time to feel comfortable and settled, and I love being able to build that trust with them. One of my favorite parts is taking dogs on enriching walks, keeping them active, engaged, and happy, and making sure they feel safe, loved, and well cared for while their owners are away. I work remotely, which gives me a flexible schedule and allows me to give pets plenty of attention throughout the day. I’m able to keep up with walks, feeding schedules, playtime, potty breaks, and companionship, especially during longer stays when consistency and routine are important. I always try to make pets feel as comfortable and relaxed as possible by sticking closely to their normal routine and giving them lots of attention and care. I pay close attention to each dog’s personality, energy level, and needs to make sure they feel safe, happy, and comfortable while their owners are away. I’m attentive on walks, respectful of clients’ homes, and committed to providing reliable communication and updates throughout each stay.

Sitter Profile Image: Fatima B.
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Fatima B.
from
$35
per night
2 years of experience
West Allis, WI, 53214

About: I am a dedicated pet caregiver committed to keeping your furry friend happy, healthy, and safe. I will strictly follow your pet's specific daily feeding and medication schedules to maintain their comforting routine. As an experienced and enthusiastic walker, I ensure they get plenty of exercise, fresh air, and fun outdoor adventures. Your pet will receive attentive, loving care and the absolute highest quality companionship every single day. In July I will have open availability. Please refer to my calendar or feel welcome to send me a message. I am also very accommodating. I will always follow the instructions that the pet owner gives me. Hiring me your pet will always be fed on schedule, enjoy play time, and treats. Every home I visit will be respected and well taken care of.

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

Our pup Banzo loved having Lynette care for him. She was very communicative, great with our dog and a super respectful house guest. We will definitely want to use her in the future!

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Samantha & Malcolm K.
Sitter Profile Image: Alena H.
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Alena H.
from
$55
per night
4.9 out of 5 stars
7 reviews
16 years of experience
Milwaukee, WI, 53233

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

Marilia took outstanding care of our older cat and young dog while we were gone! She was communicative, flexible, thorough, and kind. She handled medicating our pup and let us know immediately when there was a small problem. We loved getting her updates and photos, which showed how happy, relaxed and comfortable our pets were with her. Will very much look forward to working with her again!

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Julia M.
Sitter Profile Image: Jordanne H.
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Jordanne H.
from
$75
per night
4.9 out of 5 stars
19 reviews
6 repeat clients
5 years of experience
West Allis, WI, 53214

Jordanne was absolutely incredible. She was prompt and an excellent communicator. She took excellent care of my pup and kept my apartment clean. I highly recommend and will use Jordanne again in the future.

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Jimmie H.
Sitter Profile Image: Samantha S.
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Samantha S.
from
$30
per night
10 years of experience
Bay View, Milwaukee, WI, 53207

About: No kids or pets of my own and a big Jeep means my outdoorsy lifestyle is open and flexible for your fur babies. I'm experienced with dogs from all walks of life, from your social butterflies to your shy guys, your runners fetchers swimmers and wrestlers, you name it, I'm down for it. I have calm and confident experience with reactive dogs and big breeds especially. I'm a part time barista, working mostly evenings, so morning and mid-day walks work best for me. I am available for night walks after work as well, if that works for your schedule. Weekend boarding is best with advance notice, as I occasionally pick up Friday and Saturday shifts at the coffee shop. I live on the second floor with access to a fenced in backyard. Hardwood floors in home. No kids or other pets of my own. I do have houseplants if your dog is sensitive to soils, fungus, or has a history of plant eating. Crating is an option I'm comfortable with if that's what helps your furry friend feel safe, though my ideal set up is to share my whole space and enriching lifestyle with your pup, or to visit them in their home where they're already comfortable. I'm mobile with the Jeep as well, so we don't have to stick to my neighborhood if your dog is reactive and needs some extra space.

Sitter Profile Image: Scott S.
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Scott S.
from
$40
per night
5.0 out of 5 stars
20 reviews
5 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: Kelli H.
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Kelli H.
Star Sitter
from
$50
per night
5.0 out of 5 stars
25 reviews
5 repeat clients
20 years of experience
Bay View, Milwaukee, WI, 53207

Kelli was absolutely AMAZING!!! She was a great communicator and provided the perfect amount of updates for us. We will 1000% be using her in the future!

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Benjamin K.
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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

I have nothing but great things to say about Scott! From arranging our initial meet and greet to caring for our dog while we vacationed for a week, he was nothing short of amazing. Scott proved himself professional, kind, flexible, communicative with us, and patient with our reactive dog. Though our dog was thrilled to see us when we came to pick her up, she seemed equally sad to leave Scott which is a VERY big deal for her. I would not hesitate to rehire Scott or recommend him to others!

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Deb D.
House Sitting
5.0 out of 5 stars

Wow! What can I say? Margaret exceeded every expectation I had for Uecker’s care today! As a new puppy mom who’s only had him for three weeks, leaving him with someone for the first time was a little nerve-wracking. But Margaret made me feel completely at ease. She didn’t just watch him—she played with him, loved on him, reinforced the commands we’ve been working on, and treated him like he was her own. The best part? Walking through the door and finding Uecker snuggled up right next to her. My heart absolutely melted. It was obvious he felt safe, loved, and completely comfortable. I truly couldn’t be happier with the care Margaret provided. Book her before I do, because with my busy schedule, I’ll definitely be calling her again! Thank you so much, Margaret. Uecker already adores you, and so do I!

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Jackie G.
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

Mallory was very kind and amazing with our dogs. She was reliable and sent frequent updates while away. I would highly reccomend her!

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Rebekah J.
House Sitting
5.0 out of 5 stars

As always, Megan was amazing with our fur babies! I could tell they felt happy and safe while we were away which is the best feeling! Thank you!!

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Emily H.
House Sitting
5.0 out of 5 stars

Stephany was great! She updated us when she arrived and kept us updated with pictures throughout. The dogs were happy when we got home and the house was clean. Highly recommend.

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Lyndsay Z.
House Sitting
5.0 out of 5 stars

I can’t recommend Nicole highly enough! She takes wonderful care of my senior cat, who’s gotten a bit needier in his older years, and she goes above and beyond every time. Her communication is fantastic — she sends regular photo updates, so I always know my cat (and home) are in good hands. You can tell she’s genuinely bonded with him and enjoys their time together, which gives me so much peace of mind while I’m away. Her communication is fantastic — she sends regular photo updates, so I always know my cat (and home) are in good hands. She’s trustworthy, reliable, and treats my house with real care and respect. I’d absolutely recommend her to anyone looking for cat sitter!!

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Shelby L.
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

Keisha was great! She was very communicative and took great care of our pup while we were out of town :)

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Kate W.
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

She did an amazing job with our boy, Koda! We were nervous being away from him for a whole week, but she did such a good job of being with him, communicating with us of updates as well! We will definitely be using her again in the future!

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Brittney R.
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
5.0 out of 5 stars

Tarah did great, took excellent care of my pups, even when one of them tried to test the waters. Super appreciative of her care for them.

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Christy J.
House Sitting
5.0 out of 5 stars

Alexis saved the day when we had a last-minute cancellation for a long trip. She was wonderful and spent lots of time with our pets, sending updates and giving them lots of love!

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Cassandra D.
House Sitting
5.0 out of 5 stars

Elizabeth was wonderful! She arrived on time, kept the housing looking neat, and took excellent care of our sweet dog! We would gladly have her come back!

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Kristen A.
House Sitting
5.0 out of 5 stars

Caitlyn checks in once a day with pictures, which I really appreciate, and is super communicative. She’s catsit for me twice now and does a great job - I will absolutely continue to schedule with her!

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Tressa S.
House Sitting
5.0 out of 5 stars

Samantha was great. The dogs loved her from the meet and greet and she was in constant communication sending lots of pictures. Had complete piece of mind with her watching them.

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Scott B.
House Sitting
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Sitters in Jackson Park average 4
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