Dog Walking in Dineen Park, Milwaukee

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Top rated Dineen Park dog walkers

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Sitter Profile Image: Kathy S.
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Kathy S.
Star Sitter
from
$16
per walk
5 out of 5.0 stars
155 reviews
44 repeat clients
40 years of experience
Wauwatosa, WI, 53213

My little Mario 🐾 gets excited when I tell him Kathy is coming to walk him. She took him for a car ride and to the park for an extra fun time. I got a full report on how my little guy is doing and I’m so happy Kathy takes such good care while I’m away.

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Paula L.
Sitter Profile Image: Kat K.
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Kat K.
from
$16
per walk
5 out of 5.0 stars
4 reviews
1 repeat client
10 years of experience
Milwaukee, WI, 53208

All of us love having Kat walk our dog. She is usually hesitant to go with someone she doesn’t know, but took to Kat immediately and loves going for a walk with her. I would absolutely recommend Kat!

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Margaret M.
Sitter Profile Image: Caitlin K.
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Caitlin K.
Star Sitter
from
$15
per walk
5 out of 5.0 stars
18 reviews
8 repeat clients
20 years of experience
Milwaukee, WI, 53213

Caitlin was super friendly and respectful. She followed all my instructions and took awesome care of my dog Remi. We will definitely work with her again!

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Sabrina
Sitter Profile Image: Madelyn B.
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Madelyn B.
from
$20
per walk
5 out of 5.0 stars
4 reviews
10 years of experience
Wauwatosa, WI, 53213

Took great care of my babies!!

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Anthony A.
Sitter Profile Image: Taylor K.
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Taylor K.
from
$17
per walk
5 out of 5.0 stars
9 reviews
3 repeat clients
15 years of experience
Milwaukee, WI, 53222

Taylor was very responsive and great to work with. She answered messages quickly and clearly. My dogs are not the easiest to walk and she handled them with care.

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Felicia K.
Sitter Profile Image: McKenna D.
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McKenna D.
from
$18
per walk
5 out of 5.0 stars
10 reviews
2 repeat clients
2 years of experience
Wauwatosa, WI, 53213

McKenna was great with Randall! Would definitely recommend her!

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Abby
Sitter Profile Image: Esterah B.
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Esterah B.
from
$16
per walk
5 out of 5.0 stars
5 reviews
1 repeat client
4 years of experience
wauwatosa, WI, 53213

Honestly best walker on this app. She’s so sweet, more than a walker she actually cares about your puppy! Loved the pictures and updates!! And as a person, she is super sweet and kind:) Bella loves Esterah. Don’t doubt in hiring her.

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Ana A.
Sitter Profile Image: Michelle Y.
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Michelle Y.
Star Sitter
from
$18
per walk
5 out of 5.0 stars
69 reviews
20 repeat clients
15 years of experience
Cooper Park, Milwaukee, WI, 53222

Michelle was a lifesaver for a last minute booking. Great correspondence, timely arrival and excellent skills with my dog. Will definitely book again. Thank you!

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Kenneth K.
Sitter Profile Image: Curtis K.
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Curtis K.
from
$16
per walk
10 years of experience
Wauwatosa, WI, 53213

About: Dogs are my kind of people, loyal, silly, soulful, and always ready for a good walk or cuddle. I bring genuine enthusiasm to every visit, whether it’s tossing a tennis ball for the fifth time or patiently encouraging a shy pup to come out of their shell. Because I truly love dogs, I pay close attention to their routines, moods, and energy levels. Whether it’s a rambunctious retriever or a slow-strolling senior, I adapt my care to what makes them happiest and healthiest. Your dog isn’t just a client they become part of my daily joy. Pet care blends seamlessly into my daily rhythm, acting as gentle checkpoints that anchor my routine. Feeding, cleaning, and playtime create consistency, while weekly tasks like grooming or toy rotation keep things fresh. These moments build a quiet connection between me and my pet and often serve as welcome pauses in a busy day. For happy, healthy pets at home, stick to consistent routines, clean litter boxes and feeding schedules for cats, daily walks and playtime for dogs. Offer cozy spaces, rotate toys, and check their health regularly. A bit of structure and love goes a long way for any furry friend.

Sitter Profile Image: Charlotte M.
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Charlotte M.
from
$21
per walk
5 out of 5.0 stars
77 reviews
8 repeat clients
12 years of experience
Milwaukee, WI, 53210

Charlotte was awesome. The dogs were a bit over excited at first but she did a great job of calming them down. Would recommend.

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J F.
Sitter Profile Image: Sharla B.
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Sharla B.
from
$20
per walk
5 out of 5.0 stars
6 reviews
1 repeat client
23 years of experience
Wauwatosa, WI, 53213

About: I grew up on a farm with all kinds of animals and with dogs my whole life! Friends always ask me to watch their dogs because they know how much I love to! I have done a variety of services on Rover over the past few years. I will soon graduate from PA school and will have many months before I start my job. I’m looking to fill that time with fun activities and also trying to make a little bit of money! I will have lots of time to give your dog(s) some love! I’m currently a physician associate student so my schedule varies. I graduate in a few short weeks and will then have a wide open schedule! I live in a large house with my older sister. We live in a quiet neighborhood and have a small unfenced backyard! Caring for dogs at their respective houses is preferable.

Sitter Profile Image: Krystal D.
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Krystal D.
Star Sitter
from
$20
per walk
5 out of 5.0 stars
30 reviews
6 repeat clients
26 years of experience
Milwaukee, WI, 53210

Krystal is greatl! Sent lots of photos for an afternoon walk while we were at work.

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Rebecca H.
Sitter Profile Image: Brooke L.
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Brooke L.
from
$25
per walk
5 out of 5.0 stars
5 reviews
1 repeat client
15 years of experience
Cooper Park, Milwaukee, WI, 53222

About: I have experience pet-sitting and walking dogs and caring for cats of all ages. I am comfortable with post-op care and administering medications. I will care for your pets as if they are my own! I am available most mornings (before 6 am), evenings (6-9 pm), Fridays, and weekends! I am interested in taking dogs for walks and drop-in visits for dogs and cats. The care and safety of your pets and home are extremely important to me, as a cat mom to four kitties. I am happy to adhere to your preferences and requests for your pet’s comfort and safety.

Sitter Profile Image: Monsserath C.
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Monsserath C.
from
$12
per walk
5 out of 4.7 stars
15 reviews
4 repeat clients
2 years of experience
Enderis Park, Milwaukee, WI, 53210

Monsserath does great with my shy and anxious dog. She is very patient and understanding and has so much love to give my pup. She is super reliable and I can tell looks forward to seeing my pup every week! I am so lucky to have connected with her and look forward to working with her again in the future.

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Samantha G.
Sitter Profile Image: Jess M.
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Jess M.
from
$15
per walk
17 years of experience
Lenox Heights, Milwaukee, WI, 53210

About: I've had dogs at home since I was 6 years old. I have provided in-home, short term care, and dog walking services for fur babies of all sizes for the last 10 years! I will love & treat your dogs like my own to help ease your mind while you're away. I am a night shift nurse with a variable schedule, so I am very flexible for walks and visits. If you need late night walks, I'm your girl. If you need walks in the middle of your 9-5 day, I can take care of it for you! My dog is my entire world. She is allowed on the couch, sleeps in my bed, and goes for her own walks as often as possible. I will care for and love your pet like they're my own, regardless of the service you need!

Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$30
per walk
5 out of 5.0 stars
49 reviews
19 repeat clients
5 years of experience
Dineen Park, Milwaukee, WI, 53216

I have been using these 2 for a couple of weeks with both Wag and now Rover. They have been great to my girl. They are helping her get the energy out in a safe way and even working on her focus in public. Much appreciated ?

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Amy G.
Sitter Profile Image: Catherine C.
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Catherine C.
from
$16
per walk
13 years of experience
Nash Park, Milwaukee, WI, 53222

About: I've been surrounded by animals my entire life. I grew up with multiple cats in the house as well as a large dog. When I was 10 my mom and I began to foster cats for the Wisconsin Humane Society. We have cared for nearly 200 cats and kittens, which ranged from bottle babies to feral cats to disabled and sick cats. I have also been dog walking since I was around 12. I have experience administering a variety of medications to animals, including oral, topical, and diabetic medication. I've helped to take care of my family's senior pets as they age. I also have experience with more exotic pet care, namely turtles and frogs! I have just finished my undergrad and am currently working part-time. My days are largely free to care for animals and am fully flexible depending on your schedule! Safety is the most important part of caring for an animal. Creating feelings of proper safety allows for trust to be built and a good relationship between animal and person. I have years of experience in creating trust with the most feral cats and know how to listen to animal body language and needs.

Sitter Profile Image: Crystal H.
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Crystal H.
from
$20
per walk
5 out of 5.0 stars
54 reviews
13 repeat clients
15 years of experience
Enderis Park, Milwaukee, WI, 53210

About: Hello, and thank you for looking at my profile! As a dog owner myself I completely understand how hard it is to know where to turn for dog sitting. You have come to the right spot. I will make sure that while you’re out of town the only thing you need to worry about, is what drink to order. I have had cats since I was about 7 years old. I learned from a young age to be responsible for feeding them, cleaning the litter box and giving them all the love they required. I’ve also had dogs including a pup with special needs so I’ve had plenty of experience administering medicine and shots if your pup needs some extra care. I love giving dog walks, playing fetch and snuggling with them. I love and care for all animals and will treat your fur baby as my own. I’m very excited to meet your pup and make sure they are loved as if they were at home. I am currently a full time student taking classes on line so I am home nearly all day. I also live with my husband and one middle aged American bulldog named Zoe. This allows me to have a very flexible schedule. I have a medium sized fenced back yard. I live in a neighborhood next to a great walking path and three schools that have parks for playtime and sidewalks for safety. We have a room where pups can play and mess around without hurting them selves and they are welcome to the entire house unless you prefer they not be. There are no kids or cats and lots of fun toys and balls to chew on and couches to lay on.

Sitter Profile Image: April C.
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April C.
from
$20
per walk
20 years of experience
Enderis Park, Milwaukee, WI, 53210

About: As someone who’s naturally calm, observant, and patient, I connect easily with pets who need gentle energy—whether they’re playful pups, anxious rescues, or sweet senior companions. I’m a homebody at heart, so your pet will always have consistent attention, a peaceful environment, and plenty of snuggles. I’m especially comfortable with older dogs who need slower walks or extra care, and I have experience reading subtle body language cues to keep pets happy and safe. I treat every animal like my own, and I’m here for the quiet moments, quirky habits, and unconditional love that come with pet care. I have open availability so pet care is the best part of my day! I’m home often, love quiet routines, and prefer paws over people anyway. I provide care in your pet’s home where they feel most safe. I follow routines, give calm attention, cuddles, and keep their space clean and cozy.

Sitter Profile Image: Cassie & Ben O.
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Cassie & Ben O.
from
$25
per walk
5 out of 5.0 stars
27 reviews
11 repeat clients
9 years of experience
Enderis Park, Milwaukee, WI, 53210

Cassie was excellent to work with, quick to respond, and followed all instructions for our pup. There was even a large storm that came through and she still followed through with walking Stark albeit the bad weather. We highly recommend Cassie to anyone in the area and look forward to working with her in the future!

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Jacob W.
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Sitter Profile Image: Kathy S.
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Sitter Profile Image: Kathy S.
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Kathy S.
Rover 101
Star Sitter

Patient walker and caregiver.
Wauwatosa, WI, 53213
1.3 mi. away
Drop-In Visits, Dog Walking
from
$16
per walk
5 out of 5.0 stars
155 reviews
44 repeat clients
Profile image

My little Mario 🐾 gets excited when I tell him Kathy is coming to walk him. She took him for a car ride and to the park for an extra fun time. I got a full report on how my little guy is doing and I’m so happy Kathy takes such good care while I’m away.

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kat K.
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Sitter Profile Image: Kat K.
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Kat K.

Ready to care for your fur babies!
Milwaukee, WI, 53208
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$16
per walk
5 out of 5.0 stars
4 reviews
1 repeat client
Profile image

All of us love having Kat walk our dog. She is usually hesitant to go with someone she doesn’t know, but took to Kat immediately and loves going for a walk with her. I would absolutely recommend Kat!

Availability updated 4 days ago
Sitter Profile Image: Caitlin K.
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Sitter Profile Image: Caitlin K.
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Caitlin K.
Star Sitter

Dogs are life
Milwaukee, WI, 53213
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$15
per walk
5 out of 5.0 stars
18 reviews
8 repeat clients
Profile image

Caitlin was super friendly and respectful. She followed all my instructions and took awesome care of my dog Remi. We will definitely work with her again!

Availability updated 7 days ago
Sitter Profile Image: Madelyn B.
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Sitter Profile Image: Madelyn B.
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Madelyn B.

Hi! I'm Maddie!
Wauwatosa, WI, 53213
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
4 reviews
Profile image

Took great care of my babies!!

Availability updated 5 days ago
Sitter Profile Image: Taylor K.
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Sitter Profile Image: Taylor K.
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Taylor K.

Walk, visit, stay, pawty 🐾
Milwaukee, WI, 53222
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per walk
5 out of 5.0 stars
9 reviews
3 repeat clients
Profile image

Taylor was very responsive and great to work with. She answered messages quickly and clearly. My dogs are not the easiest to walk and she handled them with care.

Availability updated 8 days ago
Sitter Profile Image: McKenna D.
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Sitter Profile Image: McKenna D.
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McKenna D.

Paws in good hands:)
Wauwatosa, WI, 53213
1.5 mi. away
Drop-In Visits, Dog Walking
from
$18
per walk
5 out of 5.0 stars
10 reviews
2 repeat clients
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McKenna was great with Randall! Would definitely recommend her!

Availability updated today
Sitter Profile Image: Esterah B.
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Sitter Profile Image: Esterah B.
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Esterah B.

Your Pet's New Best Buddy!
wauwatosa, WI, 53213
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$16
per walk
5 out of 5.0 stars
5 reviews
1 repeat client
Profile image

Honestly best walker on this app. She’s so sweet, more than a walker she actually cares about your puppy! Loved the pictures and updates!! And as a person, she is super sweet and kind:) Bella loves Esterah. Don’t doubt in hiring her.

Availability updated 4 months ago
Sitter Profile Image: Michelle Y.
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Sitter Profile Image: Michelle Y.
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Michelle Y.
Star Sitter

Trusted & Insured Dog Mom 🐾❤
Cooper Park, Milwaukee, WI, 53222
1.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$18
per walk
5 out of 5.0 stars
69 reviews
20 repeat clients
Profile image

Michelle was a lifesaver for a last minute booking. Great correspondence, timely arrival and excellent skills with my dog. Will definitely book again. Thank you!

Availability updated today
Sitter Profile Image: Curtis K.
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Sitter Profile Image: Curtis K.
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Curtis K.

Dog - Approved, Cat - Certified
Wauwatosa, WI, 53213
1.6 mi. away
Drop-In Visits, Dog Walking
from
$16
per walk
1 review

Curt is one of those rare people who animals just get, and the feeling is mutual. He’s calm, kind, and genuinely attentive, which makes pets instantly feel at ease around him. I’ve seen him go the extra mile to make sure every tail is wagging and every whisker feels safe..Whether it’s long walks, belly rubs, or just respectful quiet company, Curt treats every pet like family.

Availability updated 3 days ago
Sitter Profile Image: Charlotte M.
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Sitter Profile Image: Charlotte M.
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Charlotte M.

happy pets, happy life
Milwaukee, WI, 53210
1.0 mi. away
Drop-In Visits, Dog Walking
from
$21
per walk
5 out of 5.0 stars
77 reviews
8 repeat clients
Profile image

Charlotte was awesome. The dogs were a bit over excited at first but she did a great job of calming them down. Would recommend.

Availability updated 40 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Sharla B.
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Sitter Profile Image: Sharla B.
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Sharla B.

I can’t wait to meet your dog(s)!!!
Wauwatosa, WI, 53213
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
6 reviews
1 repeat client

Sharla was a great person to work with! She took amazing care of our old yellow lab and communicated with us at all times throughout our vacation. We’ve worked with her a few times now and it’s been great each time - would highly recommend!

Availability updated 24 days ago
Sitter Profile Image: Krystal D.
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Sitter Profile Image: Krystal D.
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Krystal D.
Star Sitter

Pawsitively Reliable Dog Sitter!
Milwaukee, WI, 53210
0.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per walk
5 out of 5.0 stars
30 reviews
6 repeat clients
Profile image

Krystal is greatl! Sent lots of photos for an afternoon walk while we were at work.

Availability updated yesterday
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Brooke L.
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Sitter Profile Image: Brooke L.
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Brooke L.

Cat mom
Cooper Park, Milwaukee, WI, 53222
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
5 reviews
1 repeat client

Brooke is wonderful. You can tell she genuinely loves animals. It can be nerve wracking to have someone watch your pet, but I would not hesitate to have Brooke back! She did an overnight with our dog while we were away and it was so comforting knowing our dog was safe and didn’t have to change up his routine. She took him on multiple walks, played with him outside, made sure his medications were given at night, and we loved getting pup-dates (pictures). Prior to watching our dog, she asked great questions to make sure she had the information she needed to ensure success! If you are looking for someone responsible, kind, honest, and helpful, I recommend Brooke.

Availability updated 9 days ago
Sitter Profile Image: Monsserath C.
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Sitter Profile Image: Monsserath C.
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Monsserath C.

star of love
Enderis Park, Milwaukee, WI, 53210
0.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$12
per walk
5 out of 4.7 stars
15 reviews
4 repeat clients
Profile image

Monsserath does great with my shy and anxious dog. She is very patient and understanding and has so much love to give my pup. She is super reliable and I can tell looks forward to seeing my pup every week! I am so lucky to have connected with her and look forward to working with her again in the future.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Jess M.
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Sitter Profile Image: Jess M.
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Jess M.

Local & committed to your pup!
Lenox Heights, Milwaukee, WI, 53210
0.8 mi. away
Drop-In Visits, Dog Walking
from
$15
per walk
2 reviews

Jess loves all animals especially dogs and we see that every time she takes care of our 2 dogs. She is always on time when we have needed her to walk or stay with our dogs. We never have to worry because she is very responsible and respectful and she communicates very well.

Availability updated 28 days ago
Sitter Profile Image: Stephen & Wipawee D.
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Sitter Profile Image: Stephen & Wipawee D.
Verified Enhanced Background Check

Stephen & Wipawee D.

Pawfessional w/ Love & Care <3
Dineen Park, Milwaukee, WI, 53216
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per walk
5 out of 5.0 stars
49 reviews
19 repeat clients
Profile image

I have been using these 2 for a couple of weeks with both Wag and now Rover. They have been great to my girl. They are helping her get the energy out in a safe way and even working on her focus in public. Much appreciated ?

Availability updated 9 days ago
Sitter Profile Image: Catherine C.
Verified Enhanced Background Check
Sitter Profile Image: Catherine C.
Verified Enhanced Background Check

Catherine C.

Lifelong Animal Caretaker
Nash Park, Milwaukee, WI, 53222
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$16
per walk
1 review

Catherine has had a great affinity for cats since she was born. She has been fostering them and nursing them back to health for years. She’s always who I go to when I have questions about cats wild or domestic. She understands their body language and how they feel better than almost anyone. Just take her cat Eclipse for example! Saved from the outdoors and only known a safe, happy life since! N.C.

Availability updated 7 days ago
Sitter Profile Image: Crystal H.
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Sitter Profile Image: Crystal H.
Verified Enhanced Background Check

Crystal H.

Our animals are family members too!
Enderis Park, Milwaukee, WI, 53210
0.9 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per walk
5 out of 5.0 stars
54 reviews
13 repeat clients

I’ve known Crystal for 11 years and she has always been a responsible pet owner and would be a great pet sitter. Crystal has had both cats and dogs during the time I’ve known here as well as a turtle! She loved them all. When she lived in Panama she started a meet up group of dog owners so her puppies would have a group of dogs to play with that would meet almost daily. They would even have pet birthday parties! One of Crystals dogs was a stray that she took in and it turned out he had some health issues. Crystal didn’t shy away or surrender the dog, instead she rose to the challenge. She made sure that dog had everything it needed to live as long and as loved as it possibly could. I know she would give him medicine on a daily basis and even administered IV fluids. Crystal is a an animal lover! She makes bandanas for all the neighborhood dogs and sets up play dates for her current dog to play and run around with other dogs. She walks her dog almost religiously, every day, sometimes twice a day. She even started an Instagram for her dog. Her and her husband built an amazing dog house for their dogs with a doggy door, windows and even a deck! She is as loving, caring and responsible of a person as you will find and would make an excellent pet sitter. I’d definitely let her take care of my pets and would recommend her to anyone looking for a trustworthy caring pet sitter.

Availability updated 39 days ago
Sitter Profile Image: April C.
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Sitter Profile Image: April C.
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April C.

Calm, Cozy & Pet-Approved.
Enderis Park, Milwaukee, WI, 53210
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
1 review

I’m thrilled to recommend my friend April for anyone looking for a trustworthy, attentive, and loving pet sitter on Rover. She has a natural way with animals—patient, gentle, and genuinely caring. Whether it’s dogs, cats, or more unique pets, April treats each one like family. What really sets her apart is her attention to detail. She follows care instructions to the letter and always goes the extra mile to make sure pets are comfortable and happy. On top of that, her communication is top-notch—you’ll always know how your pet is doing with regular updates and photos that show just how much they’re being cared for. If you want peace of mind while you’re away, April is the one to trust. Your pets will be in excellent hands.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Cassie & Ben O.
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Sitter Profile Image: Cassie & Ben O.
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Cassie & Ben O.
Rover 101

Animal Loving Full Time Pet Sitter
Enderis Park, Milwaukee, WI, 53210
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
27 reviews
11 repeat clients
Profile image

Cassie was excellent to work with, quick to respond, and followed all instructions for our pup. There was even a large storm that came through and she still followed through with walking Stark albeit the bad weather. We highly recommend Cassie to anyone in the area and look forward to working with her in the future!

Availability updated yesterday

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