House Sitting in 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
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Sitter Profile Image: Blythe R.
Verified Background Check
Sitter Profile Image: Blythe R.
Verified Background Check

1. Blythe R.

Star Sitter
Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
3.6 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

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!

Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check

2. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
0.8 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 was great! Our emotionally needy animals soaked up her attention and loved on her right back. Super great communication throughout the stay, and lots of great photos. Thanks again, Jessica!

Sitter Profile Image: Lily S.
Verified Enhanced Background Check
Sitter Profile Image: Lily S.
Verified Enhanced Background Check

3. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
1.5 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.
Verified Enhanced Background Check
Sitter Profile Image: Payton R.
Verified Enhanced Background Check

4. Payton R.

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

Payton did a great job with Izzy!

Sitter Profile Image: Alexy & Dylan G.
Verified Enhanced Background Check
Sitter Profile Image: Alexy & Dylan G.
Verified Enhanced Background Check

5. Alexy & Dylan G.

Star Sitter
Animals are my passion and joy!
Bay View, Milwaukee, WI, 53207
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$28
per night

Alexy watched my puppy and cat for a few days and gave him constant attention and activity while keeping me updated with frequent pictures. My puppy is very energetic and still going through training and Alexy was accomdating and understanding. Returned home to the house in great shape. I would definitely have Alexy watch my pets again.

Sitter Profile Image: Micaela B.
Verified Background Check
Sitter Profile Image: Micaela B.
Verified Background Check

6. Micaela B.

Star Sitter
Pet lover looking for new friends!
Riverwest, Milwaukee, WI, 53212
1.9 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: Jackie C.
Verified Enhanced Background Check
Sitter Profile Image: Jackie C.
Verified Enhanced Background Check

7. Jackie C.

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

Jackie is incredible! Great communication, she is punctual, sent so many pictures, and best part was my pup was so happy. I definitely recommend! Thanks again Jackie!!

Sitter Profile Image: Ali M.
Verified Background Check
Sitter Profile Image: Ali M.
Verified Background Check

8. Ali M.

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

Ali gave me such peace of mind when she watched my cat for the weekend. I’ve never used any pet sitting or boarding services prior to meeting Ali, so I really didn’t know what to expect. She was very professional, friendly, and helpful with the entire process. She sent me photo updates of my cat when she stopped in and she took such good care of everything I asked her to do. I will definitely be using her again.

Sitter Profile Image: Megan M.
Verified Enhanced Background Check
Sitter Profile Image: Megan M.
Verified Enhanced Background Check

9. Megan M.

Star Sitter
Passionate pet sitter
Milwaukee, WI, 53215
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
5 repeat clients
from
$28
per night

Megan did a great job with bella. She was attentive to her needs, mande sure she got pain medications if she needed it, and was diligent about timely bathroom breaks. Bella was happy and healthy when we returned. She was also worn-out enough to not be too crazy. I would happily use Megan again

Sitter Profile Image: Emily R.
Verified Enhanced Background Check
Sitter Profile Image: Emily R.
Verified Enhanced Background Check

10. Emily R.

Rover 101
Star Sitter
Pawsitively excellent pet sitter!
Milwaukee, WI, 53204
1.2 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.
Verified Background Check
Sitter Profile Image: Daniela & Michael P.
Verified Background Check

11. Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
1.8 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 is the perfect pet sitter and can handle our great dane! Our dog was on medications while we were away and she did a great job with his extra needs. We will keep booking wjth Daniela!

Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check
Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check

12. Leandrea R.

Rover 101
Star Sitter
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
2.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
106 reviews
37 repeat clients
from
$60
per night

Leandrea mananged to even get through trustful my shy cat. She sent many pictures and updates throughout they stay. I was even a little worried my dog and cat were going to like her more than me. Haha.

Sitter Profile Image: Becca S.
Verified Background Check
Sitter Profile Image: Becca S.
Verified Background Check

13. Becca S.

Rover 101
Walkies in Milwaukees!
Historic Third Ward, Milwaukee, WI, 53202
0.6 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: Anna L.
Verified Background Check
Sitter Profile Image: Anna L.
Verified Background Check

14. Anna L.

Seeking furry friends!
Historic Third Ward, Milwaukee, WI, 53202
0.4 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 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: Beth P.
Verified Enhanced Background Check
Sitter Profile Image: Beth P.
Verified Enhanced Background Check

15. Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53212
2.2 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: Jordanne H.
Verified Background Check
Sitter Profile Image: Jordanne H.
Verified Background Check

16. Jordanne H.

I’m a teacher with all summer off!!
Riverwest, Milwaukee, WI, 53212
2.2 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: Teana G.
Verified Enhanced Background Check
Sitter Profile Image: Teana G.
Verified Enhanced Background Check

17. Teana G.

Love to spend time with animals!
Milwaukee, WI, 53202
1.1 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: Kimberly B.
Verified Enhanced Background Check
Sitter Profile Image: Kimberly B.
Verified Enhanced Background Check

18. Kimberly B.

Your pets are my new BFFs!!
Lower East Side, Milwaukee, WI, 53202
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
from
$50
per night

Kimberly did a great job taking care of my two dogs for a week! Just the right amount of communication and updates throughout the time she was house sitting. Lilo and Stitch were very content and well taken care of!

Sitter Profile Image: Talor G.
Verified Background Check
Sitter Profile Image: Talor G.
Verified Background Check

19. Talor G.

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

Talor dogsat our 2 pups over our first long weekend out of town away from them. Our two dogs have really different personalities and Talor was patient with them both and kept them comfortable for the weekend. They are a handful but she handled everything very professionally and kept me in the loop the entire time.

Sitter Profile Image: Laurie P.
Verified Enhanced Background Check
Sitter Profile Image: Laurie P.
Verified Enhanced Background Check

20. Laurie P.

Rover 101
Experienced, reliable, retired!!!!!
Historic Third Ward, Milwaukee, WI, 53202
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
89 reviews
40 repeat clients
from
$75
per night

This is our second time using Laurie and she is fabulous. She shows up on time, keeps the dogs on their schedule, sends lots of updates, is very attentive to their needs, and the house is always super clean when we get back. I hate leaving my dogs and typically worry about them while away, but with Laurie I don't worry at all. We've already got her scheduled again next month!

Search Map

Milwaukee House Sitting ratings

Overall Rating:
4.9 out of 5 stars

House sitters in Milwaukee are rated on average 4.9 out of 5 stars based on 2,110 reviews.

Check out the House Sitting in your neighborhood:

Rover also offers House Sitting in:

Rover also offers other services in Milwaukee:


Rover.com is the simple, savvy way to find and book Cold Spring Park, Milwaukee 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 Cold Spring Park 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 the Rover Guarantee, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a 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 Cold Spring Park, Milwaukee, WI house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

House Sitting