Pet Sitting & Drop Ins in Mount Olivet, 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
3.2 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

Great communication and takes good care of our dog during drop-ins. Follows instructions for taking our dog out, and engages with our dog for fun playtime and training during the visit.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Devon W.
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Sitter Profile Image: Devon W.
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2. Devon W.

Rover 101
Star Sitter
Lover of all creatures!
Milwaukee, WI, 53207
4.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
50 reviews
23 repeat clients
from
$15
per visit

Devon did a great job dropping in on our dogs while we were on vacation. They had very good communication, promptness, and even though our pups can be a handful Devon had no problem taking care of them.

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
2.6 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
$15
per visit

Great communication always on time if there were any questions she asked. Very friendly and very good with the dog. Would highly recommend her for taking care of your dogs. Always sent pictures and an update on what was going on.

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Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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4. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
5.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
98 reviews
33 repeat clients
from
$20
per visit

Jessica took wonderful care of our cats while we were on a long trip! She went above and beyond helping us with taking care of the house too. Her communication and response is excellent. I am so grateful for her help and I really hope she’ll come help us again when we need it! :)

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Sitter Profile Image: Elaine P.
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Sitter Profile Image: Elaine P.
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5. Elaine P.

☀️Experienced & loving pet owner
Milwaukee, WI, 53207
3.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
15 reviews
6 repeat clients
from
$16
per visit

As always, very dependable and my girls love her! Kaia and Pepper were well taken care of and I looked forward to reading the check in notes and seeing their pictures. I can appreciate the thoughtfulness and care Elaine provides. I will continue to use Elaine whenever she is available. 😊

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Sitter Profile Image: Michele M.
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Sitter Profile Image: Michele M.
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6. Michele M.

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

Michele did an AMAZING JOB, she took care of my dogs at the last minute while I underwent a minor emergency procedure at the hospital. She fed them, played with them and took them out 3 times a day. I am so appreciative of her help and look forward to rebooking her, I definitely recommend her!

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Sitter Profile Image: Julia R.
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Sitter Profile Image: Julia R.
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7. Julia R.

I have experience for dogs
Cudahy, WI, 53110
4.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
11 reviews
4 repeat clients
from
$20
per visit

Julia has been SUCH a huge help to me with my dog Payton. She’s very responsive, reliable, kind, sends the cutest pics while I’m away at work and takes amazing care of P. I would recommend her for any service you may need :)

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

Star Sitter
Here kitty kitty (and doggies too!)
Greendale, WI, 53129
2.8 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: Alexy & Dylan G.
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Sitter Profile Image: Alexy & Dylan G.
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9. Alexy & Dylan G.

Star Sitter
Animals are my passion and joy!
Bay View, Milwaukee, WI, 53207
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$15
per visit

Alexy & Dylan are sweet! they took great care of my girl’s needs while I was away & sent plenty of pictures. I will contact them for future needs. 💜

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

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

Sarah has been an absolute life saver! I can go to work without worrying about my little guy. After a couple of false starts with Rover I was able to fi d Sarah! She is responsive, reliable, and flexible. And she takes the BEST pictures of my sweet guy on his walks. Thank you Sarah!!!

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Sitter Profile Image: Allie S.
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Sitter Profile Image: Allie S.
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11. Allie S.

Teacher with a fenced-in yard here!
West Allis, WI, 53219
2.9 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!

Sitter Profile Image: Christine H.
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Sitter Profile Image: Christine H.
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12. Christine H.

Experienced Dog Foster
Greenfield, WI, 53221
2.2 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
28 reviews
9 repeat clients
from
$20
per visit

Came on short notice and did a great job!

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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
2.6 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: Jennifer F.
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Sitter Profile Image: Jennifer F.
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14. Jennifer F.

Lots of Love & Care from Jenn
Jackson Park, Milwaukee, WI, 53215
0.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
2 repeat clients
from
$15
per visit

Jennifer was amazing. My dogs were very well taken care of and she was patient with them and their accidents/separation anxiety. I really appreciated her help over the holidays and highly recommend.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Megan M.
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Sitter Profile Image: Megan M.
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15. Megan M.

Star Sitter
Passionate pet sitter
Milwaukee, WI, 53215
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
5 repeat clients
from
$14
per visit

Megan did an excellent job looking after my cats, while I went out of town for a quick weekend away, all was really good. Would tell anyone needing someone to do drop in visits to use her. Would absolutely use again, Thanks !!!

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Sitter Profile Image: Jessica E.
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Sitter Profile Image: Jessica E.
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16. Jessica E.

Loving Sitter With a Fenced In Yard
West Allis, WI, 53227
3.4 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!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lisa W.
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Sitter Profile Image: Lisa W.
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17. Lisa W.

Here to be kind to your pets!
Bay View, MILWAUKEE, WI, 53207
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
52 reviews
20 repeat clients
from
$13
per visit

Lisa gave me such peace of mind while I traveled. My elderly dog (with 5 different medications!) looked healthy and happy when I returned. Lisa also took great care of my two cats, sending great pictures after each visit. Each time I texted, Lisa would promptly text back and she handled my anxiety like a pro ;) I’d love for Lisa to come back the next time I need pet care!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Rebecca S.
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Sitter Profile Image: Rebecca S.
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18. Rebecca S.

PAWSitively the Best!
Town Of Lake, Milwaukee, WI, 53207
3.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
12 reviews
3 repeat clients
from
$15
per visit

I was in a bind a couple months ago. My dog sitter canceled out on me at the last moment. Luckily a friend told me about Rebecca. I was able to schedule a meet and greet with my Dods. My dogs loved her. I decided to have her watch dogs while was out of town. Things turned out better than I expected my pups were happy when I picked them up. I would definitely recommend her she did a great job!

Sitter Profile Image: Mary C.
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Sitter Profile Image: Mary C.
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19. Mary C.

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

Mary is wonderful. I am so glad to have come across her service and connected. Her service is exactly what I needed. Also, she is very prompt with communication which I really appreciate.

Sitter Profile Image: Kevin H.
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Sitter Profile Image: Kevin H.
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20. Kevin H.

Star Sitter
Your best friend's new best friend
Fairview, Milwaukee, WI, 53219
1.9 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!

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When it comes to pet sitting, dog owners in Mount Olivet, Milwaukee, WI love Rover.com. Over 1089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of pet sitting in Mount Olivet may surprise you - in a good way. That's because there's a pet sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for pet sitting on Rover? Check out our average pet sitting rates to get an idea before you start a conversation with a sitter.

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 Mount Olivet 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 Mount Olivet, 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.

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