Pet Sitting & Drop Ins in Silver Spring, 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
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

Calendar Recently Updated
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check

1. Jessica Z.

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

Jessica was amazing!! She sent photos and updates, I knew my pup was having a great time. Really happy to meet her, I never have to worry about Russell being alone.

Calendar Recently Updated
Sitter Profile Image: Kim S.
Verified Enhanced Background Check
Sitter Profile Image: Kim S.
Verified Enhanced Background Check

2. Kim S.

Star Sitter
Never lived a day without a pet
Glendale, WI, 53217
4.6 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 was absolutely amazing with my dog. I needed a few drop in visits while I was out of town. She took the time to ensure he had everything he needed & was comfortable while I was away. She's great at communication and I didn't have to worry about a thing.

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

3. Tegra R.

Star Sitter
The right Mama to care 4 your baby
Milwaukee, WI, 53223
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
19 reviews
9 repeat clients
from
$18
per visit
Profile image

Tegra took great care of our dogs and was very easy to coordinate with. We look forward to using her services again in the future!

Calendar Recently Updated
Sitter Profile Image: Lindsey F.
Verified Enhanced Background Check
Sitter Profile Image: Lindsey F.
Verified Enhanced Background Check

4. Lindsey F.

Star Sitter
Your best friends new best friend!
Wauwatosa, WI, 53213
3.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
28 reviews
3 repeat clients
from
$15
per visit
Profile image

Lindsey is awesome! She gave us detailed updates with pictures of our dog, Kobe. She made our night away very easy and stress-free. Thank you, Lindsey!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Marilia D.
Verified Enhanced Background Check
Sitter Profile Image: Marilia D.
Verified Enhanced Background Check

5. Marilia D.

Star Sitter
I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 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.

Calendar Recently Updated
Sitter Profile Image: Anna L.
Verified Enhanced Background Check
Sitter Profile Image: Anna L.
Verified Enhanced Background Check

6. Anna L.

Star Sitter
Attentive & Caring - ♥️ Senior Pets
Wauwatosa, WI, 53213
4.0 mi. away
Drop-In Visits
5.0 out of 5 stars
60 reviews
18 repeat clients
from
$20
per visit
Profile image

Anna was absolutely amazing! She took great care of my cat maisel always sending pictures and a little blurb about how she was doing. It made me feel so much better being away to know she was being well taken care of. Anna was also super flexible and helped me figure out how to use Rover, I was using the browser at first which was causing all sorts of problems but Anna knew what I was trying to do and got it all sorted out. I cannot recommend Anna enough!

Calendar Recently Updated
Sitter Profile Image: Christina J.
Verified Background Check
Sitter Profile Image: Christina J.
Verified Background Check

7. Christina J.

Star Sitter
Experienced and attentive!
Wauwatosa, WI, 53226
5.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
54 reviews
20 repeat clients
from
$20
per visit
Profile image

Christina was great with our two pups for the drop in visit. Asked questions before hand so she knew exactly what we wanted. Would book with her again and highly recommend.

Calendar Recently Updated
Sitter Profile Image: Jen G.
Verified Background Check
Sitter Profile Image: Jen G.
Verified Background Check

8. Jen G.

Star Sitter
Experienced Dog & Cat Lover ❤️
Menomonee Falls, WI, 53051
4.1 mi. away
Drop-In Visits
5.0 out of 5 stars
64 reviews
25 repeat clients
from
$22
per visit
Profile image

Jen is very kind and very thorough. She clearly enjoys caring for animals. We felt comfortable the entire time we were gone because she sent us pictures of our cat enjoying her attention on each visit. We look forward to her help in the future because we know our cat will be happy and safe.

Sitter Profile Image: Katie K.
Verified Enhanced Background Check
Sitter Profile Image: Katie K.
Verified Enhanced Background Check

9. Katie K.

Friend to felines & all animals
Menomonee Falls, WI, 53051
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
4 repeat clients
from
$18
per visit
Profile image

Katie was great with my kitty. She put a lot of effort into making my cat feel safe and entertained while visiting. The pictures she shared were adorable, my cat was obviously having a great time with Katie!

Calendar Recently Updated
Sitter Profile Image: kiki A.
Verified Enhanced Background Check
Sitter Profile Image: kiki A.
Verified Enhanced Background Check

10. kiki A.

Star Sitter
Animal lover & nurturer
Silver Spring, Milwaukee, WI, 53218
0.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
18 reviews
7 repeat clients
from
$15
per visit
Profile image

Kiki did a terrific job with my dog. She showed up on time, did what I had asked of her, and sent me reassuring reports of her visits. I am very pleased.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lance C.
Verified Enhanced Background Check
Sitter Profile Image: Lance C.
Verified Enhanced Background Check

11. Lance C.

Coffee loving dog walker!
Enderis Park, Milwaukee, WI, 53210
3.5 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$14
per visit

I had an amazing experience with Lance as my dog sitter! He was incredibly attentive to my furry friend's needs and went above and beyond to ensure their comfort and happiness while I was away. Lance provided regular updates and even sent adorable photos of my pup enjoying their time together. I felt completely at ease knowing that my dog was in such capable and caring hands. I highly recommend Lance to anyone in need of a reliable and compassionate dog sitter.

Calendar Recently Updated
Sitter Profile Image: Rayanne N.
Verified Enhanced Background Check
Sitter Profile Image: Rayanne N.
Verified Enhanced Background Check

12. Rayanne N.

Animal lover! Happy to help!
Glendale, WI, 53209
2.8 mi. away
Drop-In Visits, Dog Walking
1 review
from
$15
per visit

Rayanne is a very caring animal lover! makes sure your animals needs are being met and no messes left behind! If you are looking for someone to put your animal first in every aspect, look no further 🫶🏽

Calendar Recently Updated
Sitter Profile Image: Krystal D.
Verified Enhanced Background Check
Sitter Profile Image: Krystal D.
Verified Enhanced Background Check

13. Krystal D.

Pawsitively Reliable Dog Sitter!
Milwaukee, WI, 53210
3.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
1 repeat client
from
$14
per visit
Profile image

Excellent communicator and did a great job with making sure Bo had everything he needed.

Calendar Recently Updated
Sitter Profile Image: Lizzy B.
Verified Enhanced Background Check
Sitter Profile Image: Lizzy B.
Verified Enhanced Background Check

14. Lizzy B.

Rover 101
Work from Home Dog Mom
Kops Park, Milwaukee, WI, 53222
3.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
from
$15
per visit
Profile image

Lizzy did a great job taking care of all three of our pups while we were out of town. Her communication was top notch and she went above and beyond during her visits. We loved seeing how happy the dogs looked in her updates and will definitely reach out to her the next time we need someone to care for our dogs!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Hannah E.
Verified Enhanced Background Check
Sitter Profile Image: Hannah E.
Verified Enhanced Background Check

15. Hannah E.

Star Sitter
Animal Lover Pet Sitter/Walker!
Wauwatosa, WI, 53225
3.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
3 repeat clients
from
$15
per visit
Profile image

Hired Hannah for my cats. She was always on time and left my house with clean dishes. My cats were also happy :) would love to recommend her.

Calendar Recently Updated
Sitter Profile Image: Cindy T.
Verified Background Check
Sitter Profile Image: Cindy T.
Verified Background Check

16. Cindy T.

TOTAL DOG LOVER :)
Wauwatosa, WI, 53222
2.7 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
559 reviews
343 repeat clients
from
$22
per visit
Profile image

Cindy is great with our dog that is very shy and likes to hide and has really bad separation anxiety. I always feel good when Cindy’s there to take care of them.

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

17. Susana P.

Loving pet owner
Fairfield, Mikwaukee, WI, 53209
2.0 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$18
per visit

Suzy is great with dogs. She has watched my dogs for extended periods in the past and my dog absolutely loves going back. She loves taking her dogs on long walks through the park, so your dog will fully enjoy themselves. She also has experience training an untrained rescue dog, so she has a lot of experience around dogs. She is a loving dog mom and will provide a great home for your dog while you're away.

Sitter Profile Image: Rachel G.
Verified Enhanced Background Check
Sitter Profile Image: Rachel G.
Verified Enhanced Background Check

18. Rachel G.

Love all animals like they are mine
Kops Park, Milwaukee, WI, 53222
3.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
15 repeat clients
from
$20
per visit
Profile image

We use Rachel whenever we can because she is so reliable and always goes above and beyond with our cats. She sends pictures every day and she genuinely seems to enjoy seeing our pets, which I appreciate!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Alana F.
Verified Enhanced Background Check
Sitter Profile Image: Alana F.
Verified Enhanced Background Check

19. Alana F.

Loving pets are always welcomed!
Long View, Milwaukee, WI, 53218
1.0 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
3 reviews
from
$25
per visit

Alana would be a great person for this job for a couple reasons c she not only make sure the dogs are fed and well taken care of , but they also feel loved in her presence. She is a very responsible person who knows how to really go up and above.

Calendar Recently Updated
Sitter Profile Image: Tiffani H.
Verified Background Check
Sitter Profile Image: Tiffani H.
Verified Background Check

20. Tiffani H.

Loving pet sitter,flexible schedule
Hampton Heights, Milwaukee, WI, 53218
1.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$13
per visit

She loves that crazy dog lol She"s amazing with dogs and ginuinely loves animal. Also as an individual shes a very responsible young lady. Give her a try

Search Map

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

Rover also offers other services in Silver Spring:

Dog lovers in Silver Spring, 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 Silver Spring 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 Silver Spring, 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