House Sitting in Hillside, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Blythe R.
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Sitter Profile Image: Blythe R.
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1. Blythe R.

Star Sitter
Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
4.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
143 reviews
64 repeat clients
from
$55
per night

Blythe was great! She took care of our girls while we were away for a quick weekend trip and when we arrived home they were very happy and content and the house was clean and neat. There’s no doubt we’ll be booking with her again!

Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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2. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
98 reviews
33 repeat clients
from
$59
per night

Jessica Z stayed in my house with my 14 y/o blind Boston Terrier. She was wonderful. I received daily updates and photos, she clearly took excellent care of my pup. She left my place spotless and I would highly recommend her. She is excellent and I will definitely use her again.

Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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3. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$50
per night

This was Lily’s first time house sitting Kai and she exceeded my expectations. She clearly developed a great connection with Kai, did a really nice job keeping me connected/informed, and overall left the house looking like it did when I left. I so much enjoyed her texts, pictures and video clips. Thank you Lily!

Sitter Profile Image: Payton R.
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Sitter Profile Image: Payton R.
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4. Payton R.

making tails wag one walk at a time
Milwaukee, WI, 53211
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
2 repeat clients
from
$40
per night

She was the best! Very flexible, great At communication and great with our pup. Highly recommend!

Sitter Profile Image: Ali M.
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Sitter Profile Image: Ali M.
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5. Ali M.

I love dogs, cats, and herptiles !
Milwaukee, WI, 53211
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
36 reviews
18 repeat clients
from
$65
per night

I would absolutely book with Ali again! We did a meet and greet before and my dog absolutely loved Ali. I got text updates and photos while I was away too which was awesome. Ali is great - highly recommend!

Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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6. Jackie C.

Looking forward to meet your pet!
Brewer's Hill, Milwaukee, WI, 53212
0.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
69 reviews
22 repeat clients
from
$65
per night

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.

Sitter Profile Image: Micaela B.
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Sitter Profile Image: Micaela B.
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7. Micaela B.

Star Sitter
Pet lover looking for new friends!
Riverwest, Milwaukee, WI, 53212
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
29 reviews
7 repeat clients
from
$50
per night

Micaela put us at ease when my husband & I left our dog with someone other than family for the first time. She sent regular updates & her communication was wonderful overall. Would absolutely book Micaela again.

Sitter Profile Image: Emily R.
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Sitter Profile Image: Emily R.
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8. Emily R.

Rover 101
Star Sitter
Pawsitively excellent pet sitter!
Milwaukee, WI, 53204
2.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
54 reviews
17 repeat clients
from
$72
per night

Emily is incredible with my senior dog, Bernie. She's gentle and patient and is understanding of the unfortunate accident or 2 requiring clean up on some visits. I have peace of mind knowing she will be there for Bernie!

Sitter Profile Image: Daniela & Michael P.
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Sitter Profile Image: Daniela & Michael P.
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9. Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
282 reviews
160 repeat clients
from
$65
per night

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.

Sitter Profile Image: Annabelle L.
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Sitter Profile Image: Annabelle L.
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10. Annabelle L.

lifelong animal lover!
Milwaukee, WI, 53212
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$35
per night

Annabelle is incredibly kind, gentle and passionate! Her love of animals is clear upon meeting her and this shows in her care for her own pets. Along with being passionate about animals, she works well with people, making them feel comfortable in her presence.

Sitter Profile Image: Becca S.
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Sitter Profile Image: Becca S.
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11. Becca S.

Rover 101
Walkies in Milwaukees!
Historic Third Ward, Milwaukee, WI, 53202
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
6 repeat clients
from
$60
per night

Becca was super nice,sent updates her whole stay with my puppy Abril. I highly recommend her. I will keep using her services. Thanks Becca for being understanding of my puppy with separation anxiety and made her happy until I got home.

Sitter Profile Image: Beth P.
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Sitter Profile Image: Beth P.
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12. Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53212
1.5 mi. away
House Sitting
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$60
per night

Beth is a Godsend! She stayed at our home for five days and took exceptional care of our many animals: our dog, cats, rabbits, Guinea pig and fish. We came back to a tidy house and relaxed animals. She took our dog on two mile walks and sent photos and updates regularly. We couldn’t have asked for a better sitter. She is kind and considerate. We highly recommend Beth!

Sitter Profile Image: Marie H.
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Sitter Profile Image: Marie H.
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13. Marie H.

Star Sitter
Your Pets New Favorite Sitter :)
Martin Drive, Milwaukee, WI, 53208
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$45
per night

We recently adopted a dog and this was our first time using Rover. Marie always communicated quick and kept us updated the whole time she was with our pets. She entertained our pets and took good care of our new dog during the potty training phase. She stayed overnight and we felt like our home was respected. Would recommend Marie!

Sitter Profile Image: Anna L.
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Sitter Profile Image: Anna L.
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14. Anna L.

Seeking furry friends!
Historic Third Ward, Milwaukee, WI, 53202
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$50
per night

Ms. Anna treated Ruby like her own puppy. It was so fabulous to travel to Chicago for the day and know Ruby was in competent hands. We highly recommend Ms. Anna.

Sitter Profile Image: Riley N.
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Sitter Profile Image: Riley N.
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15. Riley N.

Star Sitter
Animal lover since birth! PETS=FAM
Milwaukee, WI, 53212
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
4 repeat clients
from
$60
per night

Riley was great with our little anxious dogs. They immediately loved her and seemed very content when we got home! We’ll definitely book with her again!!

Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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16. Erica L.

Rover 101
Pro. Dog Handler with WFH job!
Park West, Milwaukee, WI, 53206
1.8 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
84 reviews
29 repeat clients
from
$75
per night

Erica was thorough in her communication, notes, and care of our dog, Sheba. I appreciated all the messages and clarifications on the details. It certainly gave us peace of mind having Erica care for Sheba for the first time! She provided many wonderful pictures and video, as well as clear reports as to how the visit was going. We are very happy and grateful for the service Erica provided. We would hire her again and also recommend her.

Sitter Profile Image: Teana G.
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Sitter Profile Image: Teana G.
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17. Teana G.

Love to spend time with animals!
Milwaukee, WI, 53202
1.2 mi. away
House Sitting, Dog Walking
1 review
from
$35
per night

Teana has been our go-to pet sitter for our 5 furbabies. We trust her more than anyone to care for our dogs, cats and rabbit. She goes above and beyond always giving them tons of attention and making sure they have everything they need. She is dependable and friendly. I highly recommend her for anyone looking for a reliable and trustworthy petsitter.

Sitter Profile Image: Jordanne H.
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Sitter Profile Image: Jordanne H.
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18. Jordanne H.

I’m a teacher with all summer off!!
Riverwest, Milwaukee, WI, 53212
1.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
18 reviews
5 repeat clients
from
$75
per night

We were happy to re-connect with Jordanne for dog sitting this summer. She is prompt, attentive and responsible, and so we are very comfortable with her caring for our senior dog Connor. We have already booked her for another visit!

Sitter Profile Image: Allison S.
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Sitter Profile Image: Allison S.
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19. Allison S.

Star Sitter
Guaranteed tail wags!
Avenues West, Milwaukee, WI, 53233
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
7 repeat clients
from
$30
per night

Allison did a great job taking care of our 2 fur kids while we were on a weekend getaway. And she kept our house in great condition. Thank you!

Sitter Profile Image: Talor G.
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Sitter Profile Image: Talor G.
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20. Talor G.

Star Sitter
I <3 furry friends & miss my fam’s
Lower East Side, Milwaukee, WI, 53202
0.8 mi. away
Boarding, House Sitting
5.0 out of 5 stars
35 reviews
9 repeat clients
from
$75
per night

Taylor watched our shy pitty for a long weekend while we were away getting married! She was wonderful, sent pictures, assured us Lucy was doing great and took care of our home. Would absolutely book Taylor again. ?

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Pet parents in Hillside, Milwaukee, WI love dog sitters on Rover.com. 1089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Hillside house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Hillside, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Hillside house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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