Pet Sitting & Drop Ins in Maitland Park, 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

Sitter Profile Image: Alyssa Z.
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Sitter Profile Image: Alyssa Z.
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1. Alyssa Z.

Star Sitter
I specialize in senior dog care.
Franklin, WI, 53132
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$14
per visit
5.0 out of 5 stars
24 reviews
7 repeat clients
Profile image

Alyssa stepped in on short notice and made sure my cat was comfortable and well cared for. She was attentive, communicative, and took extra steps to ensure my cat had plenty of attention.

Availability updated today
Sitter Profile Image: Rebecca S.
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Sitter Profile Image: Rebecca S.
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2. Rebecca S.

Star Sitter
Trainer w/ lrg fenced in yard
Town Of Lake, Milwaukee, WI, 53207
2.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5.0 out of 5 stars
65 reviews
20 repeat clients
Profile image

Shows immense amounts of care, always communicative and my dog always enjoys Rebecca’s visits!

Availability updated today
Sitter Profile Image: Devon W.
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Sitter Profile Image: Devon W.
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3. Devon W.

Rover 101
Star Sitter
Lover of all creatures!
Fernwood, Milwaukee, WI, 53207
4.1 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit
5.0 out of 5 stars
79 reviews
33 repeat clients
Profile image

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.

Availability updated 14 days ago
Sitter Profile Image: Hannah Z.
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Sitter Profile Image: Hannah Z.
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4. Hannah Z.

Star Sitter
Tell your pet I said hi
St. Francis, WI, 53235
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$10
per visit
5.0 out of 5 stars
7 reviews
2 repeat clients
Profile image

Hannah was and continues to be great with my puppy Ivy!! She has been instrumental in getting Ivy adjusted to her new life with us and getting her on a schedule when we’re at work. We plan on continuing to use Hannah for as long as she’ll let us! Thanks Hannah!! 😊

Availability updated today
Sitter Profile Image: Alexy G.
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Sitter Profile Image: Alexy G.
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5. Alexy G.

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

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. 💜

Availability updated 13 days ago
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
1.8 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
27 reviews
10 repeat clients
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Michelle is a saint! Every time we leave our biggest girl gets sick and Michelle is a trooper and makes sure she is taken care of and cleans up the messes. 🤢 Both our girls love her and would always check her availability first when in need.

Availability updated 8 days ago
Sitter Profile Image: Courtney B.
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Sitter Profile Image: Courtney B.
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7. Courtney B.

Now serving snuggles and walks!
Saint Francis, WI, 53235
3.3 mi. away
Drop-In Visits, Dog Walking
from
$16
per visit
5.0 out of 5 stars
11 reviews
1 repeat client
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Courtney did a wonderful job with my very people selective senior dog. She was wonderful at the meet and greet, and I had zero concerns about her interacting with Miley. I will definitely have Courtney walk Miley again!

Availability updated 3 days ago
Sitter Profile Image: Hailey S.
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Sitter Profile Image: Hailey S.
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8. Hailey S.

Wagging tails, Happy hearts❤️
Milwaukee, WI, 53221
3.1 mi. away
Drop-In Visits, Dog Walking
from
$14
per visit
5.0 out of 5 stars
3 reviews
1 repeat client
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Hailey spent time with my cat while I was out of town. She was so sweet - sending numerous photos & detailed report cards. It was so comforting knowing Hailey was taking care of my fur baby. Will definitely book with her again.

Availability updated 24 days ago
Sitter Profile Image: Julia R.
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Sitter Profile Image: Julia R.
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9. Julia R.

I have experience for dogs
Cudahy, WI, 53110
2.9 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$23
per visit
5.0 out of 5 stars
20 reviews
6 repeat clients
Profile image

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 :)

Availability updated 2 days ago
Sitter Profile Image: Markita H.
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Sitter Profile Image: Markita H.
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10. Markita H.

Star Sitter
Friendly/Compassionate/Responsible
Saint Francis, WI, 53235
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per visit
5.0 out of 5 stars
86 reviews
7 repeat clients
Profile image

Markita was excellent-gave lots of great care and attention to my cats and great communication. I appreciate that she makes sure to know your exact communication and update preferences since many owners may differ on the level of detail and specificity of updates on the visits. I definitely will be a repeat customer!

Availability updated 14 days ago
Sitter Profile Image: Felicity W.
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Sitter Profile Image: Felicity W.
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11. Felicity W.

Animals are my full time passion 🤍
St Francis, WI, 53235
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
31 reviews
12 repeat clients
Profile image

Felicity is always so professional and quick to respond! I made an appointment 20 min before the requested time and she made her self available immediately. Lexi always looks forward to her visits!!

Availability updated 4 days ago
Sitter Profile Image: Taylor K.
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Sitter Profile Image: Taylor K.
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12. Taylor K.

A Dog's best friend!
Greenfield, WI, 53221
2.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5.0 out of 5 stars
39 reviews
7 repeat clients
Profile image

Taylor went above and beyond taking care of our dog. We wanted her to stop by in the late afternoon. She had a wedding to attend, so she stopped by early, then came late to make sure our dog was good.

Availability updated 5 days ago
Sitter Profile Image: Leilani M.
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Sitter Profile Image: Leilani M.
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13. Leilani M.

Star Sitter
will trade love and care for pets<3
Goldman Park, Milwaukee, WI, 53221
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$15
per visit
5.0 out of 5 stars
4 reviews
2 repeat clients
Profile image

Leilani truly was the best sitter for my baby girl Nahla. She updated me daily with pictures. My pup had so much fun with her. I can’t recommend her enough! My experience was 10/10!!

Availability updated today
Sitter Profile Image: Eimar H.
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Sitter Profile Image: Eimar H.
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14. Eimar H.

Dog walking done right 😎
Milwaukee, WI, 53221
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
1 review

I have known Eimar for several years now and he has always been a very responsible and reliable caretaker of animals. Eimar has helped me to train my dog and learn to have more patience when it comes to obedience and my husky. I would 10/10 feel comfortable and confident leaving any of my pets in Eimars care.

Availability updated 4 days ago
Sitter Profile Image: Kelsey S.
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Sitter Profile Image: Kelsey S.
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15. Kelsey S.

Star Sitter
Dogs over People
Mitchell West, Milwaukee, WI, 53221
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per visit
5.0 out of 5 stars
15 reviews
4 repeat clients
Profile image

Kelsey was fantastic with my nervous pup. She gave him the space he needed, but got him to eat dinner, and he even relaxed on the couch while I was gone, which is rare for him. She kept me updated all night and was very communicative. I'm looking forward to using Kelsey's services in the future!

Availability updated 4 days ago
Sitter Profile Image: Jessica B.
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Sitter Profile Image: Jessica B.
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16. Jessica B.

New to this but familiar with dogs
Milwaukee, WI, 53221
1.3 mi. away
Drop-In Visits, Dog Walking
from
$14
per visit
5 years of experience

About: I have had dogs of my own, but do not currently have one. I'm more than happy to walk your dog, feed them, and/or play with them to keep them happy and comfy when you're away. I work fully remote and can fit pet care into my day pretty easily. I'll let you know if your request doesn't work due to work meetings, etc. I have house sat and pet sat for people across the state. I will stick to your instructions and plans, minimizing disruption for your pets. I'm more than happy to share affection and play!

Availability updated 14 days ago
Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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17. Rachel H.

Reliable, communicative, flexible
Mitchell West, Milwaukee, WI, 53221
0.9 mi. away
Drop-In Visits, Dog Walking
from
$16
per visit
5.0 out of 5 stars
2 reviews

Rachel is the only person outside of my family that I trust to care for my two dogs. My dogs are complicated, needing to be separated and treated specifically. Rachel doesn't bat an eye and does what needs to be done. I'm super thankful for her and would 1000% recommend her to others.

Availability updated 15 days ago
Sitter Profile Image: Vanessa D.
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Sitter Profile Image: Vanessa D.
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18. Vanessa D.

Exercise and Enrichment Specialist
Milwaukee, WI, 53221
0.5 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 reviews

Vanessa has 2 dogs of her own and they are both incredibly reliable and well behaved. Down to the last detail the dogs don’t beg or even sit in the same room as food, they will wait until a command is called to eat treats, and they overall are just really well trained. I firmly believe Vanessa would be an amazing pick for dog walking or training as she has proven that she can do it with ease.

Availability updated 10 days ago
Sitter Profile Image: Meggan G.
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Sitter Profile Image: Meggan G.
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19. Meggan G.

Animals are family
Milwaukee, WI, 53221
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5.0 out of 5 stars
6 reviews
2 repeat clients

Meggan is fantastic with pets of all kinds. She is very caring and really takes great care of our dog. She loves animals I think she is a perfect person

Availability updated 54 days ago
Sitter Profile Image: Jasmine B.
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Sitter Profile Image: Jasmine B.
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20. Jasmine B.

Fun energetic dog lover!
Goldman Park, Milwaukee, WI, 53211
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$14
per visit
4.5 out of 5 stars
7 reviews
1 repeat client

Super friendly and energetic, took my dog to parks and gave them a lot of exercise. Great communication before, during and after visit. Texts updates and cute photos throughout visit.

Availability updated 51 days ago

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