House Sitting in Williamsburg, Milwaukee

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

I'm looking for service for my:
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.

Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
133 reviews
60 repeat clients
from
$55
per night

We can’t say enough good things here. We had a really bad boarding experience and needed to do something different. We were a little hesitant with having someone in our home but Blythe was awesome. We have a large dog who is pretty needy and a little old man. She took pics, gave us updates and did everything we asked and our home looked the exact way we left it. Would highly recommend!

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

Jessica Z.

Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking
5.0
78 reviews
26 repeat clients
from
$55
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: Daniela & Michael P.
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Sitter Profile Image: Daniela & Michael P.
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3.

Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
House Sitting, Drop-In Visits, Dog Walking
5.0
275 reviews
158 repeat clients
from
$65
per night

Daniela was fantastic! Sent lots of pictures, videos and updates of Moose so that we knew he was happy and in great hands while we were gone. We definitely plan to have her watch Moose again!

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Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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4.

Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
18 reviews
3 repeat clients
from
$55
per night

Outstanding! Cindy is a natural with animals. I have a dog that gets very anxious when we leave the house, and she was calm as a cucumber when we returned from an evening out. We also have three cats - siblings from a feral litter - who generally go into hiding when a stranger comes into our home. Cindy got to playing with two of them, and was even allowed to pet one of them! I would happily have Cindy watch my babies in the future, and am very glad to have found her.

Sitter Profile Image: Kira W.
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Sitter Profile Image: Kira W.
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5.

Kira W.

Flexible Scheduling, Cats and Dogs
Lenox Heights, Milwaukee, WI, 53210
House Sitting
5.0
3 reviews
1 repeat client
from
$35
per night

Kira was amazing with our quirky doggo. We couldn't have asked for a better experience. She provided daily updates and loved on our pup while we were away for a long weekend. Upon returning home, we could tell puppers was anxiety free and our home was in excellent order. 1000% would use Kira again.

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Sitter Profile Image: Casey R.
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Sitter Profile Image: Casey R.
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6.

Casey R.

Let me love your pet!
Murray Hill, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking
5.0
19 reviews
7 repeat clients
from
$30
per night

Casey was just lovely and the fur babies enjoyed having her here every day & night I was gone. She was respectful of my home and to my landlords. I hope to book with her again for future dates.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Micaela B.
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Sitter Profile Image: Micaela B.
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7.

Micaela B.

Pet lover looking for new friends!
Riverwest, Milwaukee, WI, 53212
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
28 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.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Mackenzie A.
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Sitter Profile Image: Mackenzie A.
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8.

Mackenzie A.

Animal Lover
Juneau Town, Milwaukee, WI, 53202
House Sitting, Drop-In Visits
5.0
10 reviews
3 repeat clients
from
$40
per night

Mackenzie did great with taking care of Violet! She was so nice and took plenty of time to hang out with her, and make sure she was having fun. Would definitely recommend her to a friend!

Sitter Profile Image: Jordanne H.
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Sitter Profile Image: Jordanne H.
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9.

Jordanne H.

I’m a teacher with all summer off!!
Riverwest, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking
5.0
18 reviews
5 repeat clients
from
$50
per night

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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Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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10.

Jackie C.

Looking forward to meet your pet!
Brewer's Hill, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking
5.0
44 reviews
14 repeat clients
from
$65
per night

Jackie was great sitter! Our dogs seemed to love her and she was respectful, responsive and reliable for an overnight stay. We look forward to using Jackie again in the future!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Brianna T.
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Sitter Profile Image: Brianna T.
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11.

Brianna T.

Lover of all animals! <3
Lower East Side, milwaukee, WI, 53202
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
12 reviews
5 repeat clients
from
$50
per night

About: I currently have 13 guinea pigs, 2 rabbits and a small yorkie. I have such a passion and love for caring for animals. Ive been taking care of a variety of animals since I was 10, ranging from small cats and gerbils to large dogs, snakes, and birds! Im currently working virtually as a disability teacher so I have a very flexible schedule and will easily be able to meet you and your animals needs! I have a fenced yard and dog gates in my house. I am open to making changes that fit best for you and your dog :)

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Sitter Profile Image: Payton R.
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Sitter Profile Image: Payton R.
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12.

Payton R.

making tails wag one walk at a time
Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$40
per night

Payton is such an amazing dog sitter! She stayed at our house for a weekend while we were out of town and she watched my 3 y.o Aussie as well as my parents 1 y.o Border Collie. She did a great job following our routine with the dogs & took them on lots of walks. Even when my dog got sick overnight she communicated with me & did what was best to clean my house & help my dog feel safe and comforted. Payton is a very trustworthy person and does her best to give dogs the care they deserve! Thanks P :-)

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Sitter Profile Image: Danielle A.
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Sitter Profile Image: Danielle A.
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13.

Danielle A.

Flexible, professional pet care
Upper East Side, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking
5.0
34 reviews
9 repeat clients
from
$75
per night

Danielle was fantastic. Great communicator and very personable. She was able to step in and help with my two dogs on a rather short notice, and I am truly grateful. I enjoyed receiving some photos and getting occasional updates. I will definitely have her to the house again and again! Thanks Danielle!

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Sitter Profile Image: Riley N.
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Sitter Profile Image: Riley N.
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14.

Riley N.

Animal lover since birth! PETS=FAM
Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking
5.0
6 reviews
1 repeat client
from
$60
per night

Riley was great overnight watching our dogs and cats. They all seemed happy and healthy when we got home, and the updates while we were gone was so appreciated.

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Sitter Profile Image: Morgan C.
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Sitter Profile Image: Morgan C.
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15.

Morgan C.

Loves all kinds of fur babies!
Shorewood, WI, 53211
House Sitting, Drop-In Visits, Dog Walking
5.0
16 reviews
3 repeat clients
from
$30
per night

Morgan was great and very flexible with the needs for my dog, Max! She did everything I asked her to do which helped calm my anxiety about leaving Max with someone I do not know. I would definitely recommend Morgan if you ever need a sitter!

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Sitter Profile Image: Jennifer T.
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Sitter Profile Image: Jennifer T.
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16.

Jennifer T.

Your dogs second best friend.
Milwaukee, WI, 53212
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
93 reviews
28 repeat clients
from
$45
per night

Jennifer did a wonderful job caring for my pups, one of whom has only been with us for 4 months and has some quirky behaviors. She adjusts to their needs (and ours), checks in daily with pictures and updates, and had them all packed up and ready to go at the door when I came to grab them after a day on the road. When we walked in for drop off, her living space truly looked like a legit dog vacay spot with lots of open space, soft things for lounging, and water bowls set out with treats sprinkled around them. She’s a total pro. We will definitely be using her again!

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Sitter Profile Image: Malissa N.
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Sitter Profile Image: Malissa N.
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17.

Malissa N.

Specialized in House/Dog Sitting
Upper East Side, Milwaukee, WI, 53211
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
45 reviews
21 repeat clients
from
$75
per night

Couldn’t ask for a better sitter. She takes care of our dogs with all the care and love youd hope for . You can just tell the dogs are happy when we get back home. We feel so comfortable leaving them with her. Thanks for everything Malissa! You rock!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Kait S.
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Sitter Profile Image: Kait S.
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18.

Kait S.

professional dog mama
Shorewood, WI, 53211
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
26 reviews
8 repeat clients
from
$60
per night

Kait was great with Wicket! We have a very large dog and she was able to play and walk him with no problems. We will definitely be using her again.

Sitter Profile Image: Maggie P.
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Sitter Profile Image: Maggie P.
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19.

Maggie P.

Will love your pet like my own :)
Riverwest, Milwaukee, WI, 53221
House Sitting, Drop-In Visits, Dog Walking
5.0
21 reviews
12 repeat clients
from
$50
per night

We were delighted to have Maggie housesit with Connor. Everything was thorough and efficient with his med schedule, and she is very experienced which we appreciated. We would definitely recommend Maggie to others, as well as have her back again ourselves.

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Sitter Profile Image: Marilia D.
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Sitter Profile Image: Marilia D.
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20.

Marilia D.

I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
House Sitting, Drop-In Visits, Dog Walking
5.0
22 reviews
4 repeat clients
from
$70
per night

Marilia did a great job staying with our pup and walking , feeding, playing and just being there for him. She spent 3 nights and fleas very responsive and respectful of our home . Was thankful she was available, Will hire again .

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Dog owners in Williamsburg, Milwaukee, WI love booking house sitting with sitters on Rover.com. Over 1,089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking house sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book house sitting with Rover? Check out our average house sitting rates to get an idea before reaching out and starting a conversation with a house sitter near you in Williamsburg.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Williamsburg house sitter in seconds on Rover.com. If you're looking for trusted dog sitters while you're away, whether it's for one night or a whole month, you can find a house sitter in Williamsburg, Milwaukee, WI who meets your and your dog's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your dog, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of dog lovers pet sitters and dog walkers.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Williamsburg, Milwaukee donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Milwaukee.

We're proud to support over 200 organizations across the nation, including:

House Sitting