Pet Sitting & Drop Ins in Rolling Green, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Sitter Profile Image: Karsyn R.
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Sitter Profile Image: Karsyn R.
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1. Karsyn R.

Rover 101
Star Sitter
Dog Buddy & Reliable Care
Milwaukee, WI, 53207
5.6 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
157 reviews
53 repeat clients
from
$18
per visit

Karsyn was a great friend to Simba while we were away for a few hours! She was super responsive when we reached out for the initial visit and was very kind. Simba warmed up to her friendly personality right away, so we felt relieved when leaving him. Will definitely be using Karsyn again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lexi K.
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Sitter Profile Image: Lexi K.
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2. Lexi K.

Star Sitter
Lover of all animals big and small
Cannon Park, Milwaukee, WI, 53214
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
44 reviews
12 repeat clients
from
$16
per visit

She did so good with my evil cat and even brought in a package and put my robot camera back on the charger. We met up before my vacation and did a quick review of what was needed. I felt comfortable knowing she was there for my cat :)

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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3. Leandrea R.

Rover 101
Star Sitter
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
4.5 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
$15
per visit

Leandrea did a superb job with my kitty Sunny! I was anxious about leaving him due to him just having surgery a couple of days prior, but I was immediately put at ease with her quality of care! I would recommend her to anyone looking for care for their pet! I will definitely be booking for all my pet needs in the future! Thank you for being so wonderful!

Sitter Profile Image: Michele M.
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Sitter Profile Image: Michele M.
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4. Michele M.

Star Sitter
15+ yr pet owner & dog foster
Milwaukee, WI, 53221
3.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
10 repeat clients
from
$20
per visit

Michele is so kind and so helpful and Samson is always so happy to have had a visitor in the middle of my long days at work! Thanks Michele :)

Sitter Profile Image: Danielle S.
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Sitter Profile Image: Danielle S.
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5. Danielle S.

Puppy-lover and kitty-cuddler.
West Allis, WI, 53227
2.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
58 reviews
13 repeat clients
from
$18
per visit

Danielle watched our two small dogs in our home recently and she was fantastic. I received updates on how they were doing and eating as well as a few photos. Danielle is very caring and made us feel so much better about going on vacation and leaving our pups at home.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Katie N.
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Sitter Profile Image: Katie N.
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6. Katie N.

Star Sitter
Here kitty kitty (and doggies too!)
Greendale, WI, 53129
2.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
40 reviews
10 repeat clients
from
$20
per visit

Katie was so nice to our dog Maggie who is very protective but loved Katie right a way. Katie was great and we would highly recommend her and will definitely use her again.

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Sitter Profile Image: Melissa H.
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Sitter Profile Image: Melissa H.
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7. Melissa H.

I will love your pet like my own!
New Berlin, WI, 53151
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
68 reviews
20 repeat clients
from
$18
per visit

Melissa took care of our cats while we were away and gave one of them insulin. She constantly kept me updated with pics and what was going on! She left the house clean and made it easy to be away from them. Will definitely be using her again!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sarah J.
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Sitter Profile Image: Sarah J.
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8. Sarah J.

I’m awkward with humans.
West allis, WI, 53219
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
121 reviews
39 repeat clients
from
$13
per visit

Sarah, was fantastic. Our dog was very well taken care of. Sarah took care of Odie as if he was her own dog, she played with and sent picture of the interactions between them.. she went way past our expectations. We will be calling on her again.

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Sitter Profile Image: Hillery F.
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Sitter Profile Image: Hillery F.
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9. Hillery F.

Happy to help!
West Allis, WI, 53214
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
84 reviews
35 repeat clients
from
$19
per visit

Hillery did an excellent job taking care of my cat while I was gone for a week! I so enjoyed her daily picture updates, and she was able to get my cat to warm up to her after a few days - quite a feat! She even straightened up my apartment a little bit before I returned home :) would absolutely rebook.

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Sitter Profile Image: Allie S.
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Sitter Profile Image: Allie S.
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10. Allie S.

Teacher with a fenced-in yard here!
West Allis, WI, 53219
1.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$18
per visit

Allie was fantastic! We booked her last minute and she was super accommodating to us. As nervous pup parents we were super unsure about leaving him, but she was so sweet, took extra good care of him, sent us tons of report cards and photos and made us feel as though he was in great hands! We will definitely book with her again in the future. He misses you already!

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Sitter Profile Image: Amanda B.
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Sitter Profile Image: Amanda B.
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11. Amanda B.

Have loved animals since birth.
Greenfield, WI, 53220
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
110 reviews
36 repeat clients
from
$14
per visit

Amanda is Wonderful with My 14 Year old Dog Shana and 15 Year Old Cat Simba. This is the 2nd time she cared for my Furbabies. So Happy how she takes care of them.

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Sitter Profile Image: Stephen & Wipawee D.
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Sitter Profile Image: Stephen & Wipawee D.
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12. Stephen & Wipawee D.

Pawfessional w/ Love & Care <3
West Allis, WI, 53227
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
46 reviews
17 repeat clients
from
$22
per visit

Stephen and Amelie are the best! They take excellent care of our babies and our home when we’re away and make us feel completely comfortable when we need to travel without the pups. Our dogs love them too!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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13. Katherine B.

Star Sitter
Dogs are happiness 😊
West Allis, WI, 53219
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
9 repeat clients
from
$25
per visit

I could tell our pup was very happy and comfortable with Katie. Katie was both friendly and professional. I was pleased with all of photos and regular updates we recieved. It was clear she gave our dog plenty of exercise as our dog was pooped. I will definitely be booking again.

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Sitter Profile Image: Jessica E.
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Sitter Profile Image: Jessica E.
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14. Jessica E.

Loving Sitter With a Fenced In Yard
West Allis, WI, 53227
1.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$14
per visit

Jessica did an incredible job with my furry baby :) Thank you for everything!

Sitter Profile Image: Kelly M.
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Sitter Profile Image: Kelly M.
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15. Kelly M.

Rover 101
Star Sitter
I love dogs and being outside!
Greenfield, WI, 53227
1.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
27 reviews
9 repeat clients
from
$20
per visit

It was a pleasure having Kelly watch after my puppy Stormi. I received many updates, pictures and videos during her time visiting Stormi. I will definitely be booking with her in the near future. Thank you Kelly!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jenn S.
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Sitter Profile Image: Jenn S.
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16. Jenn S.

Star Sitter
Animal lover and cat mom of 3 🐈
West Allis, WI, 53227
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
41 reviews
10 repeat clients
from
$23
per visit

Jenn was great! Came before hand to meet my dog and to get to know the usual routine. She sent pictures and updates and had great communication!

Sitter Profile Image: Kevin H.
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Sitter Profile Image: Kevin H.
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17. Kevin H.

Star Sitter
Your best friend's new best friend
Fairview, Milwaukee, WI, 53219
1.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$19
per visit

Kevin did a great job walking my not-so-easy to walk dog. He took some photos of my dog and updated me on how their walk and play time went. I really appreciated Kevin's thoroughness about the walk! I have already booked Kevin again for my fluffy boy!

Sitter Profile Image: Mary C.
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Sitter Profile Image: Mary C.
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18. Mary C.

Will care for pet your like my own!
GREENFIELD, WI, 53220
1.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
47 reviews
16 repeat clients
from
$15
per visit

Mary is our go-to for animal care when we travel, and we couldn’t feel more comfortable leaving our two dogs in her care. She’s so sweet and treats them like her own, gives individualized attention and truly cares about their experience -and ours- while we are away. Tanner and Wrigley can’t wait to see you again!

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Sitter Profile Image: Angie B.
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Sitter Profile Image: Angie B.
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19. Angie B.

Rover 101
Loving Family to Care for your Dog
West Allis, WI, 53219
0.8 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
7 repeat clients
from
$20
per visit

Angie was wonderful with communication and photos. I would highly recommend and would use again. Thank you!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Hannah W.
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Sitter Profile Image: Hannah W.
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20. Hannah W.

Full-time cuddler, part-time runner
Alcott Park, Milwaukee, WI, 53228
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
17 repeat clients
from
$15
per visit

Hannah did a great job watching our cat Diego. This was her second time caring for him while we were out of town. I cannot tell you what a relief it was to have her watch him again. He’s an older cat and usually very shy. She was able to make him comfortable enough to come out of hiding and spend time with her. I received adorable photos and updates that put me at ease the entire time.

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Rover also offers Pet Sitting & Drop Ins in these neighborhoods:

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Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 1089 owners have reviewed sitters in Rolling Green, Milwaukee, WI, giving them an average rating of 5.0/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect Rolling Green, Milwaukee pet sitter in seconds. Sitters on Rover are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters in Rolling Green, Milwaukee who can provide the care your pet needs, when they need it.

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