Pet Sitting & Drop Ins in Hillside, 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)?

Search Results

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

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

Little Miss Oaks get so excited when Carole comes over and it just melts my heart! I’m so happy to have found someone who loves my little just as much as I do.

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Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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2. Jessica Z.

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

Jessica did has looked after our cat a few times and always has done a great job. She always provides great updates and lots of photos and does a great job engaging with our shy kitty

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Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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3. Leandrea R.

Rover 101
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
2.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
104 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!

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Sitter Profile Image: Karsyn R.
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Sitter Profile Image: Karsyn R.
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4. Karsyn R.

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

Karsyn is great! She put up with our mischievous cats, sent lots of pictures and was super responsive! Definitely have her watch your fur babies :)

Sitter Profile Image: Emily Z.
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Sitter Profile Image: Emily Z.
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5. Emily Z.

Help me help you help your pet
Milwaukee, WI, 53211
1.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
33 reviews
19 repeat clients
from
$20
per visit

Emily is the best thing to happen to Ellie since arriving in MKE! Great communication. Great service. Highly recommend!

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Sitter Profile Image: Kennedy K.
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Sitter Profile Image: Kennedy K.
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6. Kennedy K.

Ready to be your pet’s assistant!
Milwaukee, WI, 53212
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
19 reviews
9 repeat clients
from
$20
per visit

Kennedy is a lovely human and a great sitter— very responsive, communicative, kind, and dependable. I’ve rebooked once and will plan to again :) Highly recommend!

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Sitter Profile Image: Emily V.
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Sitter Profile Image: Emily V.
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7. Emily V.

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

Emily is your best choice as a dog walker. She is very reliable, timely and most importantly a dog lover! She'd walk your dog all day if you'd let her. You dog will be in great hands.

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Sitter Profile Image: Olivia G.
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Sitter Profile Image: Olivia G.
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8. Olivia G.

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

Olivia is so amazing!! What a way to take the nerves away as this was our first time using rover. She was able to do everything we asked while we were gone. Thank you Olivia!

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Sitter Profile Image: Lillith L.
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Sitter Profile Image: Lillith L.
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9. Lillith L.

ABC VA Certified and ❤️ all animals
Milwaukee, WI, 53208
2.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 reviews
7 repeat clients
from
$19
per visit

I recently adopted my dog so I was nervous to introduce more humans so soon. But I didn’t have to worry with Lillith. She’s knowledgable and you can tell how much she loves dogs. Maverick can’t wait to see you again!

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Sitter Profile Image: Becca S.
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Sitter Profile Image: Becca S.
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10. Becca S.

Rover 101
Walkies in Milwaukees!
Historic Third Ward, Milwaukee, WI, 53202
1.8 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!

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Sitter Profile Image: Hannah R.
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Sitter Profile Image: Hannah R.
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11. Hannah R.

Lover of furry friends!
Riverwest, Milwaukee, WI, 53212
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
76 reviews
17 repeat clients
from
$20
per visit

Hannah was amazing and very flexible! She was very courteous, prompt and caring heart for the fur butts! I plan on using her in the future!!

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Sitter Profile Image: Kristine K.
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Sitter Profile Image: Kristine K.
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12. Kristine K.

Experienced dog & cat mom
Merrill Park, Milwaukee, WI, 53208
2.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
17 reviews
13 repeat clients
from
$16
per visit

We are so glad Kristine was available on Christmas Day to check on our cat. She came a few days prior on late notice for a meet and greet and provided a nice update!

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Sitter Profile Image: Stephanie M.
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Sitter Profile Image: Stephanie M.
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13. Stephanie M.

Excited to meet your pet!
Lower East Side, Milwaukee, WI, 53202
0.9 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
1 repeat client
from
$18
per visit

I've used Stephanie a couple times now to watch two of our dogs (Dolly & Zoe) and she has always done a fantastic job! She sends frequent pictures throughout the visit and is a fast communicator. I haven't found another sitter yet that I trust this much with my pets.

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

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

Amazing. Honestly amazing!! Thank you🥰

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Sitter Profile Image: Allison S.
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Sitter Profile Image: Allison S.
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15. Allison S.

Guaranteed tail wags!
Avenues West, Milwaukee, WI, 53233
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
21 reviews
7 repeat clients
from
$14
per visit

Allison was so laid back and easy going. We got married and I had so much going on I couldn’t give her the full run down or layout of the house and she was fine with it. I left notes for Allison, she fed and provided our dogs with their meds. She updated me with photos which I enjoy.

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Sitter Profile Image: Maddy H.
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Sitter Profile Image: Maddy H.
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16. Maddy H.

I love the pitter patter of paws.🐾
Milwaukee, WI, 53202
1.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
2 repeat clients
from
$18
per visit

Maddy was great! Showed up on time and was good in communication. Would highly recommend!

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Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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17. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
4 repeat clients
from
$25
per visit

About: I grew up in a household that fostered many animals! Starting at age 12, I started training bloodhounds with my mother for Search & Rescue. Over the years, I've served as the default dog sitter and trainer in my social circle. With tons of patience and research I also rehabilitated our two rescue dogs, who were human/dog aggressive when my husband adopted them. I have nursed our dog Molly back to health after numerous surgeries and I have extensive experience with geriatric dogs and cats. I'm pursuing my college degree late in life, and fully online. Other than a few random appointments here and there, I have full-time flexibility in my schedule. As long as you have wifi, I can do my work! We can't currently host animals at our house, but I'm happy to follow all guidelines you may have, strictly and with zero judgement. I'm happy to crate, keep dogs off furniture, or let them be laps dogs. The important thing is consistency, so I will follow your lead 100% unless you ask for my advice!

Sitter Profile Image: Sophia Y.
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Sitter Profile Image: Sophia Y.
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18. Sophia Y.

Friendly Pet Lover
Lower East Side, Milwaukee, WI, 53202
1.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
3 repeat clients
from
$15
per visit

Sophia was such a great sitter for Seymour! She came over prior to her drop ins with Seymour to meet him and and pick up our keys. She was super responsive and continued to send updates on how he was doing. We definitely recommend her!

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Sitter Profile Image: Sydney Z.
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Sitter Profile Image: Sydney Z.
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19. Sydney Z.

Your pet will be in great hands 🤍
Juneau Town, Milwaukee, WI, 53202
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
2 repeat clients
from
$18
per visit

Sydney took wonderful care of my dog Morty while I was away! I will definitely contact her again

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Sitter Profile Image: Paula O.
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Sitter Profile Image: Paula O.
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20. Paula O.

Your best friend’s next friend
Brewer's Hill, Milwaukee, WI, 53212
0.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
5 repeat clients
from
$15
per visit

Paula kept me in the loop as I requested when she picked up trooper for the first time. She sent pictures and reassured me! Trooper was very comfortable with her. Would absolutely rebook! :)

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When it comes to pet sitting, dog owners in Hillside, 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 Hillside 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.

Rover.com is the simple, savvy way to find and book Hillside, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Hillside, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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