Pet Sitting & Drop Ins in Harbor View, 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: 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
1.0 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.

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
2.9 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.

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

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

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: Leandrea R.
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Sitter Profile Image: Leandrea R.
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4. Leandrea R.

Rover 101
Star Sitter
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
1.6 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.

Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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5. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
2.2 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! :)

Sitter Profile Image: Emily V.
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Sitter Profile Image: Emily V.
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6. Emily V.

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

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: Elaine P.
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Sitter Profile Image: Elaine P.
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7. Elaine P.

☀️Experienced & loving pet owner
Milwaukee, WI, 53207
1.7 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. 😊

Sitter Profile Image: Alexy & Dylan G.
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Sitter Profile Image: Alexy & Dylan G.
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8. Alexy & Dylan G.

Star Sitter
Animals are my passion and joy!
Bay View, Milwaukee, WI, 53207
2.1 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. 💜

Sitter Profile Image: Olivia G.
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Sitter Profile Image: Olivia G.
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9. Olivia G.

Star Sitter
I will love your pet like my own :)
Lower East Side, Milwaukee, WI, 53202
2.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
34 reviews
11 repeat clients
from
$18
per visit

Olivia did a wonderful job taking care of my kitties! She was prompt and very communicative. I loved the pictures she shared daily and the anecdotes about how they were doing. Olivia also came over ahead of time for a meet and greet so I could show her around. She was very personable and warm. I highly recommend her!

Sitter Profile Image: Jessica H.
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Sitter Profile Image: Jessica H.
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10. Jessica H.

Star Sitter
The best care in Bay View!
Bay View, Milwaukee, WI, 53207
1.8 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
43 reviews
12 repeat clients
from
$20
per visit

Jessica is always so quick to respond, thoughtful and is great with Catdog! Goes above and beyond, giving him time to sit on the porch (his favorite) and is super communicative with me. Highly recommend

Sitter Profile Image: Becca S.
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Sitter Profile Image: Becca S.
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11. Becca S.

Rover 101
Walkies in Milwaukees!
Historic Third Ward, Milwaukee, WI, 53202
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 reviews
6 repeat clients
from
$20
per visit

Becca did great and she was fun to chat with! Would recommend!

Sitter Profile Image: Emily R.
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Sitter Profile Image: Emily R.
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12. Emily R.

Rover 101
Star Sitter
Pawsitively excellent pet sitter!
Milwaukee, WI, 53204
0.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
54 reviews
17 repeat clients
from
$25
per visit

Emily took great care of my three kitties while I was gone. She was wonderful at communicating and following the instructions I left. The litter area is clean and she watered my plants! I highly recommend her for your pet care. A+++

Sitter Profile Image: Amanda & Cody T.
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Sitter Profile Image: Amanda & Cody T.
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13. Amanda & Cody T.

We love dogs! Come meet us!
Historic Third Ward, Milwaukee, WI, 53202
0.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
45 reviews
13 repeat clients
from
$20
per visit

Amazing. Honestly amazing!! Thank you🥰

Sitter Profile Image: Megan M.
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Sitter Profile Image: Megan M.
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14. Megan M.

Star Sitter
Passionate pet sitter
Milwaukee, WI, 53215
1.9 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 !!!

Sitter Profile Image: Lisa W.
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Sitter Profile Image: Lisa W.
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15. Lisa W.

Here to be kind to your pets!
Bay View, MILWAUKEE, WI, 53207
1.5 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!

Sitter Profile Image: Anna L.
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Sitter Profile Image: Anna L.
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16. Anna L.

Seeking furry friends!
Historic Third Ward, Milwaukee, WI, 53202
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$25
per visit

She helped me with a last minute drop-in. She was really friendly and helpful! I’ll definitely rebook with Anna in the future!

Sitter Profile Image: Natalie W.
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Sitter Profile Image: Natalie W.
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17. Natalie W.

Friendly Petsitter in Milwaukee!
Walker's Point, Milwaukee, WI, 53204
0.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
5 repeat clients
from
$16
per visit

About: I have experience taking care of and training puppies to seniors. I have a dog and two cats of my own and grew up around a lot of animals. I can’t wait to meet your pet! I am currently work from home Tuesday through Thursday. I am available during the day as long as I have notice. I am home most nights and during the weekend. Care for the pet in the clients home is preferred.Making sure your pet is safe is my top priority. Please share any additional information that is important to know about your pet!

Sitter Profile Image: Berenice B.
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Sitter Profile Image: Berenice B.
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18. Berenice B.

Rover 101
I walk to keep their tails waggin’
Bay View, Milwaukee, WI, 53207
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
57 reviews
22 repeat clients
from
$20
per visit

Bernice was always prompt, kept us informed, sent pictures, and met all of our / our pet's needs.

Sitter Profile Image: Katarina N.
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Sitter Profile Image: Katarina N.
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19. Katarina N.

The best care for your best friend
Walker's Point, Milwaukee, WI, 53204
0.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
5 repeat clients
from
$15
per visit

Kat was great! She took the time to get to know Lily. She was punctual, great communication, and she sent pictures. I would use her again for sure.

Sitter Profile Image: Lora L.
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Sitter Profile Image: Lora L.
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20. Lora L.

Need to meet all the dogs!
Harbor View, Milwaukee, WI, 53204
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
30 years of experience
from
$14
per visit

About: I have loved dogs and taken care of them since I was in my 20s. Believe me, that is a long time with dogs! Thanks I work a full time 9-5 during the week, which is great because I know when I can schedule and when I can't. It's dependable. I would rather be a guest in a dogs home instead of the added stress when they stay with me. Meet them where they are.

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When it comes to pet sitting, dog owners in Harbor View, 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 Harbor View 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.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Harbor View pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Harbor View, Milwaukee, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Harbor View pet sitters and avoid the kennel.

Drop-In Visits