Pet Sitting & Drop Ins in Williamsburg, 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.

Search Results

Sitter Profile Image: Carole & Shannon C.
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Sitter Profile Image: Carole & Shannon C.
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1. Carole & Shannon C.

Star Sitter
east side dog-whisperers
Murray Hill, Milwaukee, WI, 53211
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
50 reviews
20 repeat clients
from
$25
per visit
Profile image

I can’t say it enough! Carole is an absolute dream! Miss Oaklei hurt her leg and she was so sensitive to the issue. She even got so excited when Oaklei was starting to show signs of improvement! She is AMAZING!!

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
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
98 reviews
34 repeat clients
from
$20
per visit
Profile image

Jessica took such good care of my cat. She gave me updates each time and took photos. I am happy to have Jessica care for my cat and would book with her again.

Sitter Profile Image: Emily Z.
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Sitter Profile Image: Emily Z.
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3. Emily Z.

Star Sitter
Help me help you help your pet
Milwaukee, WI, 53211
2.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
20 repeat clients
from
$20
per visit
Profile image

Emily was so great with my kittens!

Sitter Profile Image: Kim S.
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Sitter Profile Image: Kim S.
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4. Kim S.

Star Sitter
Never lived a day without a pet
Glendale, WI, 53217
1.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
65 reviews
21 repeat clients
from
$23
per visit
Profile image

Kim has great communication and attention to detail. She clearly cares for animals dearly so I felt very comfortable having her check in on my cats. She gave nice updates and pictures.

Sitter Profile Image: Emily V.
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Sitter Profile Image: Emily V.
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5. Emily V.

Star Sitter
Caring, active, & attentive sitter
Brewer's Hill, Milwaukee, WI, 53212
2.2 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
29 reviews
3 repeat clients
from
$14
per visit
Profile image

Emily was wonderful during our drop in visit! She took Pickles for a walk and played with Brownie! We look forward to her next drop in visit and appreciate her help taking care of our little ones!

Sitter Profile Image: Marilia D.
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Sitter Profile Image: Marilia D.
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6. Marilia D.

Star Sitter
I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
31 reviews
8 repeat clients
from
$22
per visit
Profile image

Marilia is very responsible and I could tell at our meet and greet she takes caring for pets seriously. I felt really comfortable knowing she’d be helping walk and play with our dog while we were out.

Sitter Profile Image: Liz P.
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Sitter Profile Image: Liz P.
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7. Liz P.

Star Sitter
Pet Lover who works from home!
Riverwest, Milwaukee, WI, 53212
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
58 reviews
19 repeat clients
from
$18
per visit
Profile image

Junior had a great time playing with Liz! Liz was also flexible when I asked to switch the time for a day. The feedback on how Junior was doing was also helpful!

Sitter Profile Image: Alec B.
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Sitter Profile Image: Alec B.
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8. Alec B.

Third generation dog lover
Milwaukee, WI, 53211
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$16
per visit

Alec is a responsible young man who absolutely loves dogs, and he's cared for dogs in our neighborhood on numerous occasions over the years. He's also had a lot of experience with children, working in an after-school program, supervising on field trips, and such. His sister and aunt are both experienced dog-sitters with outstanding reputations, so he has good role models in this field. Our dogs have always LOVED Alec.

Sitter Profile Image: Angela S.
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Sitter Profile Image: Angela S.
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9. Angela S.

Cat mom and teacher on summer break
Murray Hill, Milwaukee, WI, 53211
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
5 repeat clients
from
$12
per visit
Profile image

We have hired Angela twice, and would love to have her again. We have 2 very shy cats and they actually come out and play with her. Angela is very thorough and gives us updates with pictures during every visit.

Sitter Profile Image: Jenna M.
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Sitter Profile Image: Jenna M.
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10. Jenna M.

Caring and attentive pet sitter
Milwaukee, WI, 53202
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
1 repeat client
from
$15
per visit
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Jenna did an amazing job taking care of Ace! She responded quick, sent plenty of details on her drop in, and lots of good photos! Will definitely book again!

Sitter Profile Image: Alexandra D.
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Sitter Profile Image: Alexandra D.
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11. Alexandra D.

Rover 101
Quality pet care you can trust.
Milwaukee, WI, 53212
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
95 reviews
10 repeat clients
from
$23
per visit
Profile image

Alexandra is a wonderful pet sitter. She is quick to respond to requests and any questions. She made a point of meeting myself and my lab prior to her first drop in visit. I truly appreciated her walking my dog for the requested 30 minutes and hanging out. She seems very comfortable with my 11 year old lab. I look forward to utilizing her services in the future.

Sitter Profile Image: Casey R.
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Sitter Profile Image: Casey R.
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12. Casey R.

Star Sitter
Let me love your pet!
Murray Hill, Milwaukee, WI, 53211
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
8 repeat clients
from
$15
per visit
Profile image

As always, Casey is a fabulous caretaker for Buttercup. She is attentive to her needs, super responsive and flexible, and even rolled with the punches when emergency construction happened on the house while I was away. Just the best!

Sitter Profile Image: Tressa F.
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Sitter Profile Image: Tressa F.
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13. Tressa F.

Star Sitter
An avid pet lover and owner💕
Shorewood, WI, 53211
1.3 mi. away
Drop-In Visits
5.0 out of 5 stars
26 reviews
5 repeat clients
from
$13
per visit
Profile image

Tressa cared for my elderly rabbit over a weekend. She gave him his arthritis medications and provided informative notes about how things were going as well as photos.

Sitter Profile Image: Danielle A.
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Sitter Profile Image: Danielle A.
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14. Danielle A.

Star Sitter
Flexible, professional pet care
Upper East Side, Milwaukee, WI, 53211
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
47 reviews
13 repeat clients
from
$25
per visit
Profile image

Danielle was wonderful and communicative. She even went out of her way to find and feed my very shy boy. Will definitely trust her for my future pet sitting needs!

Sitter Profile Image: Quinesha F.
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Sitter Profile Image: Quinesha F.
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15. Quinesha F.

Dogs are the best friends, EVER! 🐾
Riverwest, Milwaukee, WI, 53212
1.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
26 reviews
4 repeat clients
from
$18
per visit
Profile image

Quinn was great! She was thorough, thoughtful and communicative.

Sitter Profile Image: Rhonda G.
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Sitter Profile Image: Rhonda G.
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16. Rhonda G.

Star Sitter
Love to walk and cuddle.
Whitefish Bay, WI, 53217
1.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
87 reviews
42 repeat clients
from
$15
per visit
Profile image

Rhonda saved the day with a last minute service. She solved problems (getting in to our place) and went above and beyond to care for our two pups. We are very grateful for her flexibility and good care. Will definitely ask for her again!

Sitter Profile Image: Kathryn D.
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Sitter Profile Image: Kathryn D.
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17. Kathryn D.

Star Sitter
Excited to meet your furry friend!
Milwaukee, WI, 53211
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
9 repeat clients
from
$17
per visit
Profile image

Kathryn did a great job with my cats and went above and beyond when my flights got delayed, coming back for additional visits beyond our originally scheduled time frame.

Sitter Profile Image: Travis H.
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Sitter Profile Image: Travis H.
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18. Travis H.

Rover 101
Star Sitter
Love & Exercise for your dog or cat
Riverwest, Milwaukee, WI, 53212
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
190 reviews
77 repeat clients
from
$25
per visit
Profile image

Travis will treat your fur babies as if they were his own! This was our first experience using Rover & we were very satisfied. I would wholeheartedly recommend Travis to take care of your pets while you are away. We had 100% peace of mind & no worries or concerns. We will use him again!!!

Sitter Profile Image: Jessica F.
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Sitter Profile Image: Jessica F.
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19. Jessica F.

Work from home dog mom :)
Shorewood, WI, 53211
1.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
4 repeat clients
from
$25
per visit
Profile image

Thank you for taking such great care of our pups Jessica! We appreciate you coming to help out on a busy day!

Sitter Profile Image: Abigail L.
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Sitter Profile Image: Abigail L.
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20. Abigail L.

Rover 101
Communicative and flexible sitter!
Riverwest, Milwaukee, WI, 53212
1.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
247 reviews
82 repeat clients
from
$20
per visit
Profile image

Abigail was amazing!! I felt so comfortable and safe knowing she was caring for my cat. She sends great pictures and a lovely “report.” It was so fun to sit down and read while we I was away and gave me reassurance that our kitty was doing well!

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Dog lovers in Williamsburg, Milwaukee, WI love pet sitters on Rover.com. Over 1089 pet owners have reviewed pet sitters on Rover in Milwaukee, giving them an average rating of 5.0/5 stars. No matter what your price range is, you might be surprised to learn how affordable pet sitting in Milwaukee can be when you book with Rover. Wondering how much it might cost to book pet sitting? Check out our average pet sitting rates to get an idea before contacting a pet sitter near you.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Williamsburg pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Williamsburg, Milwaukee who meets your and your pet'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 pet, 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 pet sitters and dog walkers.

Drop-In Visits