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
Profile image

I booked house sitting with Blythe because pet hotels stress my senior baby out. Blythe went above and beyond taking care of my senior baby. She did everything I asked and more. She updated me with pictures and my baby looked very comfy and happy. The whole process was very smooth and stress free. I will definitely be booking with Blythe again and recommend you do as well!

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
Profile image

Jessica was amazing! She communicated with us every day and sent us pictures/videos of the dogs, which my daughters really enjoyed. She took extra special care of our geriatric dog, making and feeding him human food, per our request. We will definitely be hiring Jessica again! Thank you for taking care of our fur babies! Brandy

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

3. Lily S.

All-Day in Home Care For Critters
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
$60
per night
Profile image

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
Profile image

Payton did a great job with Izzy!

Sitter Profile Image: Bret H.
Verified Enhanced Background Check
Sitter Profile Image: Bret H.
Verified Enhanced Background Check

5. Bret H.

Star Sitter
Work from home and reliable
Bay View, Milwaukee, WI, 53207
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$55
per night
Profile image

Our usual dog sitter was unable to stay at our house so I decided to check Rover. It's a leap of faith to have someone who you don't know staying in your house with your dogs, so I spent a lot of time searching Rover and Bret ended up being our #1 choice. I am thrilled that we chose Bret - he was fantastic! He was great with communication, sent photos, and took impeccable care of our house and dogs. I highly recommend Bret!

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

6. 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
7 repeat clients
from
$28
per night
Profile image

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

7. 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
Profile image

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

8. 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
14 reviews
5 repeat clients
from
$28
per night
Profile image

Megan came over for the most part of our vacation to catsit our fur baby. She was reliable, caring and punctual. She was able to form a beautiful bond with our cat in the time she took care of him. She sent us pictures everyday and maintained constant communication with us while we were so far away. We would highly recommend her for anyone who is looking for a caring companion to look after their baby.

Sitter Profile Image: Jackie C.
Verified Enhanced Background Check
Sitter Profile Image: Jackie C.
Verified Enhanced Background Check

9. 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
Profile image

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

10. 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
Profile image

Ali was so great with both our house and our dog while we were away from home for 6 days! It was obvious from the Meet & Greet that Ali is very comfortable around dogs and a great presence for them - ours is a bit anxious around strangers but immediately warmed up to Ali and seemed very comfortable with her! She was very responsive/communicative (and sent us plenty of pics :)) and did all our house tasks as expected. Will absolutely book Ali again, thanks for taking such good care of our Tito!

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

11. 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
55 reviews
17 repeat clients
from
$72
per night
Profile image

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

12. Brynn R.

Your pet's new bestfriend!
Lower East Side, Milwaukee, WI, 53202
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
2 repeat clients
from
$40
per night
Profile image

Brynn was amazing with our 3 pups! This was our first time having someone new help us out and they all got to be very comfortable with her. She worked with our youngest a lot to help his reactivity, especially when we were leaving which was really hard for him. She was so patient with him and provided us with many pictures and updates.

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

13. 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
Profile image

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: 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
7 reviews
2 repeat clients
from
$50
per night
Profile image

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

15. 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
108 reviews
37 repeat clients
from
$60
per night
Profile image

Leandrea exceeded our expectations! She stayed at our house with our two dogs and cat while we were out of the country for our destination wedding. She communicated with us everyday by sending updates and pictures of all the pets. Our dogs loved her and Crista!!! We will definitely rehire!

Sitter Profile Image: Mary L.
Verified Enhanced Background Check
Sitter Profile Image: Mary L.
Verified Enhanced Background Check

16. Mary L.

Your pet’s new best friend!
Kilbourn Town, Milwaukee, WI, 53203
0.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
3 reviews
from
$32
per night

Mary has always been an animal lover and instantly connects with the animals she meets. She understands that every animal has different needs and approaches them in a calm, gentle manner to give them the attention they need. She has experience working with both cats and dogs, and understands that pets are a part of the family and treats them as if they’re her own. If you’re looking for a responsible animal lover with great attention to detail, Mary is your girl!

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

17. 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
21 reviews
7 repeat clients
from
$60
per night
Profile image

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: Sarah N.
Verified Enhanced Background Check
Sitter Profile Image: Sarah N.
Verified Enhanced Background Check

18. Sarah N.

Love dogs of all shapes and sizes!!
Lower East Side, Milwaukee, WI, 53202
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$28
per night

Sarah is wonderful with pets, she watched my families dog (who is crazy) a few fine and it was great!! She is a pet owner herself, and it’s so warming seeing how much love she has for her fur babies.

Sitter Profile Image: Kimberly B.
Verified Enhanced Background Check
Sitter Profile Image: Kimberly B.
Verified Enhanced Background Check

19. 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
Profile image

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: 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
91 reviews
40 repeat clients
from
$75
per night
Profile image

I am so happy to have found Laurie when I needed someone to take care of my cat Harley while I was gone on an extended vacation. First she explained how Rover works as I was new to the app and helped me fix up a couple things. While away she spent time with Harley as agreed. She worked with him wonderfully where he was snuggling with her by the end. I got pictures every day of their different interactions. Upon return, Harley was in good spirits. He missed me but having someone spend the time she did was perfect for him. The house was in excellent order also. I highly recommend Laurie if you need a pet sitter.

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