Pet Sitting & Drop Ins in Roosevelt Grove, 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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What size are your dogs (lbs)?

Search Results

Sitter Profile Image: Kathy S.
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Sitter Profile Image: Kathy S.
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1. Kathy S.

Rover 101
Star Sitter
Patient walker and caregiver.
Wauwatosa, WI, 53213
2.4 mi. away
Drop-In Visits, Dog Walking
from
$16
per visit
5.0 out of 5 stars
74 reviews
25 repeat clients
Profile image

Kathy was our first experience with rover and I’m sure will be our best. She was extremely flexible with us as our schedule had some unexpected changes during our booking. She was great with the cats, communicated in a timely manner, and really went above and beyond in every aspect. We wish we found her sooner!

Availability updated today
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
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
118 reviews
37 repeat clients
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.

Availability updated today
Sitter Profile Image: Lindsey F.
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Sitter Profile Image: Lindsey F.
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3. Lindsey F.

Star Sitter
Your best friends new best friend!
Wauwatosa, WI, 53213
2.9 mi. away
Drop-In Visits, Dog Walking
from
$16
per visit
5.0 out of 5 stars
42 reviews
9 repeat clients
Profile image

I would recommend Lindsey to anyone. We hired her for three drop-in’s over the weekend and she was timely, respectful, had great communication throughout the process. It felt as though a family member was taking care of our dogs.

Availability updated yesterday
Sitter Profile Image: Carole & Shannon C.
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Sitter Profile Image: Carole & Shannon C.
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4. Carole & Shannon C.

Star Sitter
east side dog-whisperers
Murray Hill, Milwaukee, WI, 53211
4.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5.0 out of 5 stars
76 reviews
25 repeat clients
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Very responsive and attentive. I booked them last minute for an evening visit and they responded right away! They gave lots of picture/text updates and I felt like my pup was in great hands.

Availability updated yesterday
Sitter Profile Image: Rachel W.
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Sitter Profile Image: Rachel W.
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5. Rachel W.

Experienced dog walker & lover!
Martin Drive, Milwaukee, WI, 53208
2.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$13
per visit
5.0 out of 5 stars
21 reviews
10 repeat clients
Profile image

Timely, cared for my two large dogs well, and sent great photos! Even dried them off after playing in the rain with them, will be booking again!

Availability updated 23 days ago
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
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$22
per visit
5.0 out of 5 stars
44 reviews
13 repeat clients
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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.

Availability updated today
Sitter Profile Image: Emily V.
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Sitter Profile Image: Emily V.
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7. Emily V.

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

Emily is always so great with our two pups! She took time to take them outside to potty and played with them inside! We are so thankful to have someone to come check on them during the day when we are both gone!

Availability updated 13 days ago
Sitter Profile Image: Michelle Y.
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Sitter Profile Image: Michelle Y.
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8. Michelle Y.

#1 Dog Mom ❤️🐾
Cooper Park, Milwaukee, WI, 53222
3.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$17
per visit
5.0 out of 5 stars
4 reviews

Michelle one of the most caring and attentive dog lovers I know! She has loved (and spoiled) her own dogs since the day she rescued them 13 years ago. I would trust her with my dogs and provide her access to my home for any length of time. She has that kind of personality that even the most timid dogs fall in love with and warm up to immediately. Whether you need someone to walk your dog periodically or keep an eye on the pup while you are gone on vacation, Michelle is an excellent choice! I can't recommend her enough.

Availability updated today
Sitter Profile Image: Jamila M.
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Sitter Profile Image: Jamila M.
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9. Jamila M.

Rover 101
Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
64 reviews
22 repeat clients
Profile image

Jeremy was an amazing cat sitter! Both my cats were immediately comfortable and really grew to like Jeremy’s daily visits and play time. Super responsive and always sending lots of pics for me to check in on- it’s was such a relief to have them in Jeremy’s care. Highly recommend!!!

Availability updated 2 days ago
Sitter Profile Image: Sydney P.
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Sitter Profile Image: Sydney P.
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10. Sydney P.

Happy Dog Happy Syd
Wauwatosa, WI, 53213
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
3 reviews

I have never met anyone who loves dogs as much as Syd! She is a great care taker and extremely responsible. She has loved dogs since she was a little kid. She grew up with a German Shepherd and LOTS of goldendoodles. And now she has her dream dog, a blue heeler named Luella. Lu gets along with every dog she meets, and after one day staying with Syd, your dog will feel right at home. They will get lots of love, exercise and snuggles.

Availability updated 2 days ago
Sitter Profile Image: Austin M.
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Sitter Profile Image: Austin M.
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11. Austin M.

WFH dog lover w/ flexible schedule
Wick Field, Milwaukee, WI, 53208
2.8 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5.0 out of 5 stars
5 reviews
3 repeat clients
Profile image

Austin is very professional, personable, timely and great with our dogs! We highly recommend him for the care of your animals and will be inviting him back soon. Thank you again Austin!!

Availability updated 59 days ago
Sitter Profile Image: Kristin R.
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Sitter Profile Image: Kristin R.
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12. Kristin R.

Animal lover
Enderis Park, Milwaukee, WI, 53210
2.4 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
40 reviews
15 repeat clients
Profile image

Kristin has been a great dog sitter for our older dog. She spends plenty of time with our dog when our family is away. Harper is always happy to see us but it’s clear she’s received attention when we’re away!

Availability updated 4 days ago
Sitter Profile Image: Anna L.
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Sitter Profile Image: Anna L.
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13. Anna L.

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

Availability updated 3 months ago
Sitter Profile Image: Fiona G.
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Sitter Profile Image: Fiona G.
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14. Fiona G.

Patient & trustworthy animal lover
Uptown, Milwaukee, WI, 53210
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5.0 out of 5 stars
17 reviews
5 repeat clients

Fiona has always been an avid dog lover for as long as I have known her.(15years) She is patient and understands that each dog has its own set of needs and personality but I know and have seen her gets along with them all, she even has her own rescue pit bull that takes a lot of work and patients, I’ve never seen anyone be more fit for taking care of and giving love to dogs of any kind.

Availability updated 7 days ago
Sitter Profile Image: Charlotte M.
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Sitter Profile Image: Charlotte M.
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15. Charlotte M.

Pets > people :)
Milwaukee, WI, 53210
1.1 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5.0 out of 5 stars
36 reviews
6 repeat clients

Charlotte is an important part of my pets life. Whether she is spending time on a long walk or just playing with them in the yard, they thoroughly enjoy every minute they spend with her. Charlotte is the first person I call when I am unable to spend quality time with my pets.

Availability updated yesterday
Sitter Profile Image: Melainie T.
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Sitter Profile Image: Melainie T.
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16. Melainie T.

Care for all Animals
Enderis Park, Milwaukee, WI, 53210
1.9 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
43 reviews
15 repeat clients
Profile image

Melainie is great with Trixie! She comes to let her out while I'm at work and I love getting the updates and photos during their visits 🥰 Trixie can be shy with new people and she's taken to Melainie so, so well!

Availability updated today
Sitter Profile Image: Payton R.
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Sitter Profile Image: Payton R.
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17. Payton R.

Star Sitter
making tails wag one walk at a time
Milwaukee, WI, 53206
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
13 reviews
2 repeat clients

Finding caregivers for your pet - especially a new puppy - can be stressful and worrisome but we were very happy with Payton! She was timely and instantly bonded with "Poppie" providing us a carefree evening out! I would (and will) contact her again in the future to care for our loved one. Terri

Availability updated today
Sitter Profile Image: Beth P.
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Sitter Profile Image: Beth P.
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18. Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53210
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
8 reviews
2 repeat clients

Beth is amazing!! She is gentle, kind, and loving person. Not only does Beth take care our kitties and water our plants but she also makes sure to give snuggles and play with them while we are away. Beth keeps us informed and sends us pictures of our fur balls which is always reassuring. We have used Beth over multiple summers and will continue to do so because of the Trust and Love she offers to take care of our kitties and our house! Thank You Beth for taking care of our girls! We are so grateful to have a wonderful person who we trust!!!

Availability updated 47 days ago
Sitter Profile Image: Jackson E.
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Sitter Profile Image: Jackson E.
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19. Jackson E.

Pet lover
Milwaukee, WI, 53210
1.6 mi. away
Drop-In Visits, Dog Walking
from
$10
per visit
5.0 out of 5 stars
12 reviews
1 repeat client
Profile image

Jackson took incredible care of my cat while I was out of town over Labor Day Weekend. Not only was he attentive to my cat’s needs, but he also provided regular updates that gave me peace of mind during my trip. Jackson was very respectful of my home, leaving everything exactly as I had left it. It’s clear that he genuinely cares about the pets he looks after. I highly recommend Jackson to anyone in need of a reliable, caring, and professional pet sitter. I will definitely be booking him again in the future!

Availability updated 33 days ago
Sitter Profile Image: Keana H.
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Sitter Profile Image: Keana H.
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20. Keana H.

Experienced & loving animal sitter!
Milwaukee, WI, 53216
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$12
per visit
4.5 out of 5 stars
5 reviews
Profile image

Keana was very nice and easy to talk to. She took notes to make sure she understood the care for my cats. However, she did only stay for 7 minutes during the 30 minute visit. I had her scheduled for 2 drop ins. The 2nd one she messaged me early in the morning with an emergency and that she wouldn’t be able to feed my cats their breakfast. I 100% understand that emergencies come up but I was 4 hours away and had to scramble to try and get my cats their breakfast. Luckily, my friend had a spare key and happened to be in the area. As I mentioned earlier, Keana had a great personality but I don’t feel that I could rely on her in the future.

Availability updated 6 days ago

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