Pet Sitting & Drop Ins in Havenwoods, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Havenwoods pet sitters

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Sitter Profile Image: Nari S.
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Nari S.
from
$15
per visit
24 years of experience
Hampton Heights, Milwaukee, WI, 53218

About: Hi! I’m a full-time teacher and lifelong dog caregiver — I’ve been raising and training dogs since I could walk. I currently care for my two Border Collie mixes, Lilo and Winter, both of whom I fully self-trained with love, consistency, and a deep understanding of canine behavior. Over the years, I’ve rescued, rehomed, and rehabilitated dogs of all temperaments — from anxious pups to high-energy breeds. I bring calm, confident leadership, lots of patience, and a playful energy that dogs love. Whether it’s structured walks, reinforcing good habits, or just making sure your pup feels loved and secure, I’ve got you covered. Your dog will be in the hands of someone who treats every animal like her own — with heart, respect, and skill. I work full time currently as a dance teacher. During summer I prefer to spend my time with babies of the fur kind and am available the vast majority of times. When caring for pets in their own home, I focus on creating a calm, safe, and consistent environment that mirrors their normal routine as closely as possible. I follow all care instructions carefully — from feeding schedules to preferred walking routes to playtime and cuddles — and I make sure each animal feels loved and secure while their people are away. I bring a nurturing, attentive presence that animals naturally respond to, especially those who may be anxious or high-energy. I’m also experienced in reinforcing positive behaviors and setting gentle boundaries when needed, thanks to years of self-training my own dogs and working with rescues. While I currently don’t host pets in my own home, I treat every visit or overnight stay as an opportunity to provide companionship, safety, and structure — with plenty of affection and photo updates to keep you in the loop!

Sitter Profile Image: Becky R.
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Becky R.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
138 reviews
31 repeat clients
15 years of experience
Glendale, WI, 53209

This was our first time hiring a Rover caregiver for our two cats. Becky R. is so awesome! We were thoroughly pleased and impressed with her attentive care for our two cats. She sent lots of photos and gave us wonderful details about her visits with our cats, which gave us peace of mind while vacationing. Our cats warmed up to Becki right away, and they and Becki were wonderfully affectionate toward each other. Made us so happy! We are already booking Becky for our next getaway.😃

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Christina T.
Sitter Profile Image: Charles B.
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Charles B.
Star Sitter
from
$14
per visit
5 out of 5.0 stars
20 reviews
2 repeat clients
17 years of experience
Fox Point, WI, 53217

Very personable and reliable.

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Jon H.
Sitter Profile Image: Genesis A.
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Genesis A.
from
$23
per visit
5 out of 5.0 stars
6 reviews
2 repeat clients
10 years of experience
Old North Milwaukee, Milwaukee, WI, 53209

Great communication, very easy to work with!

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Andrea L.
Sitter Profile Image: Dieana D.
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Dieana D.
from
$14
per visit
30 years of experience
Silver Spring, Milwaukee, WI, 53218

About: Hello Rover World. I am a nurse hoping to help you with your fur baby on my off days. I have always had a dog in my home growing up and currently I have one fur baby of my own. I work three days per week, that leaves me plenty of playtime and cuddles with your pet. I am available day and evening hours. We can further discuss your individual pet needs. I am available for playtime and walks near your home. If your dog has special needs, I would love to hear more about their unique traits. I understand the frustration of finding a trustworthy caregiver. I am ready to give your fur baby love as if they were my very own.

Sitter Profile Image: Tierney V.
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Tierney V.
from
$14
per visit
25 years of experience
River Hills, WI, 53217

About: Growing up, my mom fostered 15 dogs along with our 2 resident Golden Retrievers. This sparked my passion for animals and I now have a rescue dog of my own, Maddie, a 6 y/o black lab. I also volunteer at MADACC and enjoy walking the dogs there. I’m comfortable with all sizes of dogs but have the most experience with large breeds. I’d love the opportunity to meet your dog(s)! I’m currently in between jobs, so my schedule is very flexible! I’m willing to work with you to align on a time/date that works well. For dog walking, I am comfortable utilizing any type of collar/harness and leash combination. At home, I walk my dog twice a day regardless of weather - I’ll be there rain or shine!

Sitter Profile Image: Kim S.
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Kim S.
Star Sitter
from
$28
per visit
5 out of 5.0 stars
114 reviews
26 repeat clients
30 years of experience
Glendale, WI, 53217

Kim has great communication and attention to detail. She clearly cares for animals dearly so I felt very comfortable having her check in on my cats. She gave nice updates and pictures.

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Casey O.
Sitter Profile Image: Marilia D.
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Marilia D.
Star Sitter
from
$22
per visit
5 out of 5.0 stars
60 reviews
15 repeat clients
15 years of experience
Estabrook Park, Milwaukee, WI, 53217

Marilia has looked after my kitty several times now, and she always does a great job. I appreciate that she patiently tries hard to make friends with her, even though those overtures are typically rebuffed by the aloof kitty!

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Julie B.
Sitter Profile Image: Alyssa S.
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Alyssa S.
from
$14
per visit
5 out of 5.0 stars
6 reviews
2 repeat clients
4 years of experience
Glendale, WI, 53217

Alyssa was great! Did exactly what I asked her to do during her drop-in visits with my cat. I definitely recommend her!

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Mary S.
Sitter Profile Image: Cindy T.
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Cindy T.
Star Sitter
from
$22
per visit
5 out of 4.9 stars
587 reviews
357 repeat clients
30 years of experience
Wauwatosa, WI, 53222

Cindy took great care of our dog and sent great pictures of him playing. I feel confident that she loved and cared for him just as we would have. We will be using her again!

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Rebekah B.
Sitter Profile Image: Ella V.
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Ella V.
from
$13
per visit
5 out of 5.0 stars
3 reviews
1 repeat client
5 years of experience
Milwaukee, WI, 53209

About: Since working at a humane society for two years I’ve gained invaluable knowledge of all animals and how they work! I’m able to administer medicine and not only see your pet through a loving caregiver lens but an attentive understanding lens as well. I have 2, 75 minute classes Monday-Thursday and am able to care for the animal at all other times. I wake up early and usually go to bed around midnight so I am able to be attentive. I have a fenced in dog park in my building available 24/7 and go on daily walks anyway. The animal would be able to sleep in my room/bed with food and water readily available.

Sitter Profile Image: Melainie T.
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Melainie T.
from
$20
per visit
5 out of 5.0 stars
43 reviews
15 repeat clients
25 years of experience
Enderis Park, Milwaukee, WI, 53210

I felt very comfortable with Lainie caring for Trixie while I'm at work from day one. She's so great with her! She sends adorable pictures of Trixie and receiving them are the best part of my work day!

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Stephanie L.
Sitter Profile Image: Jeff G.
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Jeff G.
Star Sitter
from
$25
per visit
5 out of 4.9 stars
50 reviews
13 repeat clients
15 years of experience
Glendale, WI, 53209

Jeff is very conscientious and even has studied the commands we use with our year old puppy. He anticipates issues and asks about them ahead of time. Jeff stays in touch during his visits, making me feel very confident that my pup is in good hands.

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Katie S.
Sitter Profile Image: Krystal D.
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Krystal D.
from
$16
per visit
5 out of 5.0 stars
23 reviews
5 repeat clients
26 years of experience
Milwaukee, WI, 53210

Excellent communicator and did a great job with making sure Bo had everything he needed.

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Luke B.
Sitter Profile Image: Adrianna H.
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Adrianna H.
from
$15
per visit
5 out of 4.9 stars
9 reviews
1 repeat client
15 years of experience
Milwaukee, WI, 53209

So caring... Thanks Adri!

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Luana S.
Sitter Profile Image: Alyssa B.
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Alyssa B.
from
$20
per visit
5 out of 5.0 stars
7 reviews
3 repeat clients
10 years of experience
Whitefish Bay, WI, 53217

About: I have been passionate about animals, big and small, my entire life! I have volunteered at humane societies, fostered animals in need, cared for the pets of family members and friends, interned at AZA-accredited zoos, and worked at wildlife sanctuaries. Currently I am a full-time licensed wildlife rehabilitator caring for injured and orphaned Wisconsin wildlife with the goal of releasing them back into the wild, but I have previously worked with a variety of domestic animals both in my personal and in my professional life. I am well versed in animal behavior, body language, and positive reinforcement. I promise to treat (and spoil) your pets like they are my own! At the moment I have 3 sweet cats, a high-energy dog, a mischievous chinchilla, and a gentleman of a ball python! Please do not hesitate to reach out and get to know me more! I currently work 4 days of the week at my full time job so I am only available select days. I am eager to spend time with your pets, however, so if my schedule shows I am unavailable, please reach out anyway as I try to be as flexible as possible! It is extremely important to me to use Fear Free tactics when interacting with any animal. Gaining the trust of you and your pet are my top priority!

Sitter Profile Image: Charlotte M.
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Charlotte M.
from
$17
per visit
5 out of 5.0 stars
67 reviews
8 repeat clients
12 years of experience
Milwaukee, WI, 53210

About: I’ve never NOT had an animal in my life, and Rover is a great way to be around pets even more! Life with pets is the best way to live ☺️ I work from home remotely full-time with a very flexible schedule, and love to fill my break time with a drive or a walk. Perfect for taking care of someone’s pet! In a client’s home, I’ll take care of their pets with any space they have available (indoor play, outdoor fenced play, etc) or walk the dog outside as needed!

Sitter Profile Image: Sheree P.
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Sheree P.
from
$14
per visit
5 out of 5.0 stars
1 review
20 years of experience
Menomonee River Hills East, Milwaukee, WI, 53223

About: Ive have dog since i was about 7 i cared for them since i was 20 they always kept me happy and they always loved on me so hard I work from home and ha e alot of free time so figured this job would be a great fit for me and I get to be around different dogs I have 4 dogs they are groomed once a week they been out their cages more than they be in them. Sometimes I make steak for them just cause they live on me so much and they are walked about 4 times a day . We also love going to the doggie park to have some free time

Sitter Profile Image: Suzi A.
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Suzi A.
from
$22
per visit
5 out of 5.0 stars
48 reviews
9 repeat clients
25 years of experience
Fox Point, WI, 53217

Suzi was excellent with our puppy. She communicated well during the day and he was in great hands. Will use again when I need someone to pop by.

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Erik B.
Sitter Profile Image: Tegra R.
Verified Enhanced Background Check
Tegra R.
Star Sitter
from
$40
per visit
5 out of 5.0 stars
40 reviews
12 repeat clients
30 years of experience
Milwaukee, WI, 53223

Tegra is super sweet and I immediately felt comfortable into our home and trusting her with our little rascal Kitty cat. Assuming she accepts I'll happily use her services again!

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Heather B.
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Sitter Profile Image: Nari S.
Verified Enhanced Background Check
Sitter Profile Image: Nari S.
Verified Enhanced Background Check

1. Nari S.

Lifelong pet rescuer & teacher
Hampton Heights, Milwaukee, WI, 53218
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
4 reviews

Nari is an incredibly responsible and loving pet caregiver. She’s cared for her rescue cat for over 8 years and her gentle collie/pit mix for 9 years with deep compassion and consistency. She’s also frequently pet sits for my sweet lab/collie mix that is 7 years old and I have had since a pup. Nari treats every animal like family. Nari is patient, attentive, and truly understands rescue pets and their unique needs. I wholeheartedly recommend her to anyone seeking reliable, heartfelt care for their furry loved ones. 🐾

Availability updated 11 days ago
Sitter Profile Image: Becky R.
Verified Background Check
Sitter Profile Image: Becky R.
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2. Becky R.

Rover 101
Star Sitter
Northshore Dog Walker!
Glendale, WI, 53209
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
138 reviews
31 repeat clients
Profile image

This was our first time hiring a Rover caregiver for our two cats. Becky R. is so awesome! We were thoroughly pleased and impressed with her attentive care for our two cats. She sent lots of photos and gave us wonderful details about her visits with our cats, which gave us peace of mind while vacationing. Our cats warmed up to Becki right away, and they and Becki were wonderfully affectionate toward each other. Made us so happy! We are already booking Becky for our next getaway.😃

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Charles B.
Verified Enhanced Background Check
Sitter Profile Image: Charles B.
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3. Charles B.

Star Sitter
Pet lover ready 2 watch your bestie
Fox Point, WI, 53217
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$14
per visit
5 out of 5.0 stars
20 reviews
2 repeat clients
Profile image

Very personable and reliable.

Availability updated yesterday
Sitter Profile Image: Genesis A.
Verified Enhanced Background Check
Sitter Profile Image: Genesis A.
Verified Enhanced Background Check

4. Genesis A.

Exercise, relax time and hugs! :)
Old North Milwaukee, Milwaukee, WI, 53209
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$23
per visit
5 out of 5.0 stars
6 reviews
2 repeat clients
Profile image

Great communication, very easy to work with!

Availability updated 19 days ago
Sitter Profile Image: Dieana D.
Verified Enhanced Background Check
Sitter Profile Image: Dieana D.
Verified Enhanced Background Check

5. Dieana D.

Help is on the way!
Silver Spring, Milwaukee, WI, 53218
1.4 mi. away
Drop-In Visits, Dog Walking
from
$14
per visit
1 review

Dieana is the greatest! She has such a natural love for dogs. Her warm and calm spirit naturally attracts fur babies of all kinds. My 2 dogs love when she's around. She really treats your dog, like her own. I'm excited to have someone I TRUST to care for my dogs. I highly recommend booking with Dieana. Your dogs will love you for it! 🐶

Availability updated 22 days ago
Sitter Profile Image: Tierney V.
Verified Enhanced Background Check
Sitter Profile Image: Tierney V.
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6. Tierney V.

Lifelong animal lover!
River Hills, WI, 53217
2.9 mi. away
Drop-In Visits, Dog Walking
from
$14
per visit
3 reviews

I highly recommend Tierney as a caretaker for anyone’s dog. With a wide range of experiences from being a dog mom, volunteering at madacc, and growing up fostering dogs, you can feel assured she will treat your loved ones as her own.

Availability updated 2 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Kim S.
Verified Enhanced Background Check
Sitter Profile Image: Kim S.
Verified Enhanced Background Check

7. Kim S.

Star Sitter
Never lived a day without a pet
Glendale, WI, 53217
3.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$28
per visit
5 out of 5.0 stars
114 reviews
26 repeat clients
Profile image

Kim has great communication and attention to detail. She clearly cares for animals dearly so I felt very comfortable having her check in on my cats. She gave nice updates and pictures.

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Marilia D.
Verified Enhanced Background Check
Sitter Profile Image: Marilia D.
Verified Enhanced Background Check

8. Marilia D.

Star Sitter
I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
3.4 mi. away
House Sitting, Drop-In Visits
from
$22
per visit
5 out of 5.0 stars
60 reviews
15 repeat clients
Profile image

Marilia has looked after my kitty several times now, and she always does a great job. I appreciate that she patiently tries hard to make friends with her, even though those overtures are typically rebuffed by the aloof kitty!

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Alyssa S.
Verified Enhanced Background Check
Sitter Profile Image: Alyssa S.
Verified Enhanced Background Check

9. Alyssa S.

Looking to make new furry friends!
Glendale, WI, 53217
3.3 mi. away
Drop-In Visits, Dog Walking
from
$14
per visit
5 out of 5.0 stars
6 reviews
2 repeat clients
Profile image

Alyssa was great! Did exactly what I asked her to do during her drop-in visits with my cat. I definitely recommend her!

Availability updated 22 days ago
Sitter Profile Image: Cindy T.
Verified Background Check
Sitter Profile Image: Cindy T.
Verified Background Check

10. Cindy T.

Star Sitter
TOTAL DOG LOVER :)
Wauwatosa, WI, 53222
3.7 mi. away
Boarding, Drop-In Visits
from
$22
per visit
5 out of 4.9 stars
587 reviews
357 repeat clients
Profile image

Cindy took great care of our dog and sent great pictures of him playing. I feel confident that she loved and cared for him just as we would have. We will be using her again!

Availability updated 10 days ago
Sitter Profile Image: Ella V.
Verified Enhanced Background Check
Sitter Profile Image: Ella V.
Verified Enhanced Background Check

11. Ella V.

Loving Animal Girls ❤️
Milwaukee, WI, 53209
2.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$13
per visit
5 out of 5.0 stars
3 reviews
1 repeat client

Ella has been an animal lover forever! I think it is awesome that on top of this she has volunteered and worked at animal shelters growing up. Her cat “Cheeto” is her best friend and she will do anything and everything to make any animal feel loved!

Availability updated 3 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Melainie T.
Verified Background Check
Sitter Profile Image: Melainie T.
Verified Background Check

12. Melainie T.

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

I felt very comfortable with Lainie caring for Trixie while I'm at work from day one. She's so great with her! She sends adorable pictures of Trixie and receiving them are the best part of my work day!

Availability updated 14 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Jeff G.
Verified Enhanced Background Check
Sitter Profile Image: Jeff G.
Verified Enhanced Background Check

13. Jeff G.

Star Sitter
Care for dogs like they're children
Glendale, WI, 53209
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 4.9 stars
50 reviews
13 repeat clients
Profile image

Jeff is very conscientious and even has studied the commands we use with our year old puppy. He anticipates issues and asks about them ahead of time. Jeff stays in touch during his visits, making me feel very confident that my pup is in good hands.

Availability updated yesterday
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Krystal D.
Verified Enhanced Background Check
Sitter Profile Image: Krystal D.
Verified Enhanced Background Check

14. Krystal D.

Pawsitively Reliable Dog Sitter!
Milwaukee, WI, 53210
4.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$16
per visit
5 out of 5.0 stars
23 reviews
5 repeat clients
Profile image

Excellent communicator and did a great job with making sure Bo had everything he needed.

Availability updated 8 days ago
Sitter Profile Image: Adrianna H.
Verified Background Check
Sitter Profile Image: Adrianna H.
Verified Background Check

15. Adrianna H.

Dogs are life.
Milwaukee, WI, 53209
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 4.9 stars
9 reviews
1 repeat client
Profile image

So caring... Thanks Adri!

Availability updated 10 days ago
Sitter Profile Image: Alyssa B.
Verified Enhanced Background Check
Sitter Profile Image: Alyssa B.
Verified Enhanced Background Check

16. Alyssa B.

Compassionate Pet Sitter
Whitefish Bay, WI, 53217
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
7 reviews
3 repeat clients

About: I have been passionate about animals, big and small, my entire life! I have volunteered at humane societies, fostered animals in need, cared for the pets of family members and friends, interned at AZA-accredited zoos, and worked at wildlife sanctuaries. Currently I am a full-time licensed wildlife rehabilitator caring for injured and orphaned Wisconsin wildlife with the goal of releasing them back into the wild, but I have previously worked with a variety of domestic animals both in my personal and in my professional life. I am well versed in animal behavior, body language, and positive reinforcement. I promise to treat (and spoil) your pets like they are my own! At the moment I have 3 sweet cats, a high-energy dog, a mischievous chinchilla, and a gentleman of a ball python! Please do not hesitate to reach out and get to know me more! I currently work 4 days of the week at my full time job so I am only available select days. I am eager to spend time with your pets, however, so if my schedule shows I am unavailable, please reach out anyway as I try to be as flexible as possible! It is extremely important to me to use Fear Free tactics when interacting with any animal. Gaining the trust of you and your pet are my top priority!

Availability updated 5 days ago
Sitter Profile Image: Charlotte M.
Verified Enhanced Background Check
Sitter Profile Image: Charlotte M.
Verified Enhanced Background Check

17. Charlotte M.

happy pets, happy life
Milwaukee, WI, 53210
3.5 mi. away
Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
67 reviews
8 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 30 days ago
Sitter Profile Image: Sheree P.
Verified Enhanced Background Check
Sitter Profile Image: Sheree P.
Verified Enhanced Background Check

18. Sheree P.

I love dogs they make me happy
Menomonee River Hills East, Milwaukee, WI, 53223
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$14
per visit
5 out of 5.0 stars
1 review

About: Ive have dog since i was about 7 i cared for them since i was 20 they always kept me happy and they always loved on me so hard I work from home and ha e alot of free time so figured this job would be a great fit for me and I get to be around different dogs I have 4 dogs they are groomed once a week they been out their cages more than they be in them. Sometimes I make steak for them just cause they live on me so much and they are walked about 4 times a day . We also love going to the doggie park to have some free time

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Suzi A.
Verified Enhanced Background Check
Sitter Profile Image: Suzi A.
Verified Enhanced Background Check

19. Suzi A.

Caring, safe & dependable pet care!
Fox Point, WI, 53217
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$22
per visit
5 out of 5.0 stars
48 reviews
9 repeat clients
Profile image

Suzi was excellent with our puppy. She communicated well during the day and he was in great hands. Will use again when I need someone to pop by.

Availability updated 3 days ago
Sitter Profile Image: Tegra R.
Verified Enhanced Background Check
Sitter Profile Image: Tegra R.
Verified Enhanced Background Check

20. Tegra R.

Star Sitter
The right Mama to care 4 your baby
Milwaukee, WI, 53223
2.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per visit
5 out of 5.0 stars
40 reviews
12 repeat clients
Profile image

Tegra is super sweet and I immediately felt comfortable into our home and trusting her with our little rascal Kitty cat. Assuming she accepts I'll happily use her services again!

Availability updated 55 days ago

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