House Sitting in Cold Spring Park, Milwaukee

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Top rated Cold Spring Park house sitters

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Sitter Profile Image: Ashley W.
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Ashley W.
from
$45
per night
5 out of 5.0 stars
14 reviews
5 repeat clients
10 years of experience
Washington Heights, Milwaukee, WI, 53208

Ashley was GREAT! I had a last minute trip pop up this weekend and she immediately responded to help me out. She even dropped what she was doing to come meet her that night! She was super responsive while I was away, and Brooklyn is worn out tonight- which I know is because she had so much fun! Thanks again, Ashley!

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Graham B.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$31
per night
5 out of 5.0 stars
15 reviews
9 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

We were very happy with the communication and attention to detail while watching bella. Not only did she take great care of our dog but also our house 🧡 we would definitely recommend her and use her in the future

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Amy G.
Sitter Profile Image: Megan D.
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Megan D.
Star Sitter
from
$63
per night
5 out of 5.0 stars
30 reviews
10 repeat clients
11 years of experience
Milwaukee, WI, 53204

Megan was so great! We got lots of pics and videos and our pups were happy and chill when we got back, even after it being too cold to go outside much. Will definitely call again - thanks!

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Carley M.
Sitter Profile Image: Melissa H.
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Melissa H.
Star Sitter
from
$60
per night
5 out of 5.0 stars
29 reviews
8 repeat clients
40 years of experience
Milwaukee, WI, 53211

Melissa is truly the best dog sitter! I am so grateful for her love and passion for dogs and always keeping me in the loop and sending adorable photos and videos!!

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payton t.
Sitter Profile Image: Devany M.
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Devany M.
from
$65
per night
5 out of 5.0 stars
34 reviews
11 repeat clients
15 years of experience
Milwaukee, WI, 53205

We were so thankful to have Devany as our sitter for our trip. One of our dogs went blind a few weeks before our trip requiring him to take a lot of medications and to be guided around the house now too. This was our first time using a house sitter and I was nervous about leaving him. Devany was so sweet and took such good care of him. She sent me a lot of updates which really made me feel comforted. I highly recommend her and we will be booking with her again!

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Katelin C.
Sitter Profile Image: Joanne & Becky J.
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Joanne & Becky J.
Star Sitter
from
$45
per night
5 out of 5.0 stars
9 reviews
2 repeat clients
20 years of experience
Milwaukee, WI, 53203

Joann and Becky stayed with our dog and cat for almost a week a d they were terrific! They sent lots of updates and pics, and I could see my pets were comfortable, happy and well cared for. I will book with them again in the future. Highly recommend!

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Sarah O.
Sitter Profile Image: Carole & Shannon C.
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Carole & Shannon C.
Star Sitter
from
$75
per night
5 out of 5.0 stars
123 reviews
33 repeat clients
23 years of experience
Murray Hill, Milwaukee, WI, 53211

Carole and Max are amazing. The last time she sat for me, I had two dogs. Sadly, I had to put one of them down and Carole and Max left me a framed photo on my beloved Sequoia. Their thoughtfulness meant the world to me and I know my dog Miley was well cared for.

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Robin F.
Sitter Profile Image: Rachel H.
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Rachel H.
Star Sitter
from
$30
per night
5 out of 5.0 stars
90 reviews
23 repeat clients
11 years of experience
West Allis, WI, 53214

Rachel is amazing! One of our dogs is hesitant with new people, and Rachel deals well with her noise and makes her feel comfortable quickly every time. Our dogs love spending time with Rachel and we love getting regular photos of all the fun they're having :)

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Bekka G.
Sitter Profile Image: Berenice B.
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Berenice B.
Star Sitter
from
$75
per night
5 out of 4.9 stars
167 reviews
77 repeat clients
15 years of experience
Bay View, Milwaukee, WI, 53207

Berenice was an excellent sitter. My first time working with her was for an extended period of time and I came home to a clean house and happy, healthy dogs. My two pitties are not trained well on a leash and she did well walking them despite that. She left me at ease while on my trip with daily communication and pictures. We already have our next stay booked with her! Thank you Berenice! 💕

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Amy N.
Sitter Profile Image: Adrienne N.
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Adrienne N.
Star Sitter
from
$50
per night
5 out of 5.0 stars
45 reviews
7 repeat clients
14 years of experience
Lower East Side, Milwaukee, WI, 53214

Adrienne was absolutely amazing. I have never had someone dog sit in my home before as I was never comfortable with it, but Adrienne I could tell was a trustworthy person from the start. I have one extremely hyper puppy and a senior who barely leaves her bed, and she did an amazing job watching both. She went above and beyond what I could of asked of her, and we will most definitely use her in the future.

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Lexi M.
Sitter Profile Image: Addoris D.
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Addoris D.
from
$32
per night
5 out of 5.0 stars
7 reviews
1 repeat client
5 years of experience
Lower East Side, Milwaukee, WI, 53202

Our animals were well taken care of and got lots of love! The communication was great and will definitely book again.

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Parchim F.
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Jessica Z.
Star Sitter
from
$64
per night
5 out of 5.0 stars
159 reviews
49 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Jessica was great! Our emotionally needy animals soaked up her attention and loved on her right back. Super great communication throughout the stay, and lots of great photos. Thanks again, Jessica!

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Nicole D.
Sitter Profile Image: Lanaya O.
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Lanaya O.
from
$60
per night
5 out of 5.0 stars
8 reviews
4 repeat clients
15 years of experience
Yankee Hill, Milwaukee, WI, 53202

Lanaya was great. She could handle our Great Dane with no problems for a whole day, even sending us pictures through the day without us asking for them which was really nice of her. First time using rover for us but it won’t be the last. Thanks Lanaya! We will see you soon.

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Leonardo P.
Sitter Profile Image: Maiah D.
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Maiah D.
from
$75
per night
5 out of 5.0 stars
9 reviews
2 repeat clients
16 years of experience
Juneau Town, Milwaukee, WI, 53963

About: I have grown up with our family dog in the home that I had responsibilities to take care of, as well as various dogs from my neighborhood. I love to go on walks, so bringing a pet with me is a bonus! I’m currently working 2 part-time jobs, one in the morning and one in the evening. Therefore, I can fit pet care in around lunchtime, plus before and after work. I have a work schedule that I can be flexible with! I will fully abide by whatever pet care requirements you have (a set walk schedule, using a pet leash, carrying safety equipment, etc.). Please let me know what you are comfortable with and we can work together to ensure your pet is in good hands.

Sitter Profile Image: William L.
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William L.
from
$48
per night
18 years of experience
Merrill Park, Milwaukee, WI, 53208

About: ## INTRODUCTION Howdy there, thanks for choosing my Rover! I go by Billy! First things first — My highest priority is the safety and well-being of any dog in my care. Outside of that, I'm also big on making sure they have a blast, are loved, and feel secure in my home. I am energetic and warm, yet firm. I've owned and raised 4 dogs over the course of 18 years, from puppydom to old age, and have cared for many more. I am adept at handling dogs large and small - physically and training-wise. ## SCHEDULE I am fortunate to have a highly flexible schedule. Your dog will always be safe by my side. I’m quite fond of dogs, so it’s a joy for me to spend my time in this way. ## APPROACH TO CARE I want to understand the needs and expected behaviors of any pet in my care, given your specific guidance and instructions. I am highly communicative and err on the side of caution, as your doggo’s safety and well-being are absolutely the highest priority for me. I have a highly flexible schedule since I'm in the middle of a job search, so I'll have all the time in the world to hang, play with, and co-work with your pup! I have the entire upper floor of my house available for your dog to lounge and roam in, equipped with multiple dog beds and lots of toys. There's also a fenced yard in the back whose concretedness is optimal for ball bouncing and catching, keep away, chasing, and more!

Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$75
per night
5 out of 5.0 stars
107 reviews
35 repeat clients
10 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Jackie stayed in our house with our dog for the weekend and she was great. Our husky Zero is our baby and a bit particular sometimes but she took it all in stride. She sent pictures throughout the weekend and reached out when she had questions. We also tried to make the house nice and neat for her time here and when she left we were wondering if she actually touched anything it was still so clean! We highly recommend Jackie and plan on booking her in the future when we're away for any extended amount of time.

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Brandon C.
Sitter Profile Image: Kat K.
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Kat K.
from
$28
per night
5 out of 5.0 stars
3 reviews
1 repeat client
10 years of experience
Milwaukee, WI, 53208

About: Hi! I’m Kat. I have experience looking after animals of all kinds - dogs (big and small), cats, guinea pigs, hamsters, rats, turtles, you name it. I have three cats at home who get lovingly spoiled every day, and I have experience dog walking, dog-sitting (included overnight stays), and cat-sitting for neighbors, friends, and family. I have a genuine love for all types of animals, and I put their well-being, care, and enrichment above all else. I work from home as a jewelry maker, so my schedule during the week is flexible as can be. I can easily make time for morning, midday, and evening visits. I am detail-oriented and will follow any given care instructions to the letter. My goal is to treat your pet just like you would, with the same love and attention you give them every day.

Sitter Profile Image: Jamila M.
Verified Background Check
Jamila M.
Star Sitter
from
$57
per night
5 out of 4.9 stars
80 reviews
24 repeat clients
27 years of experience
Washington Heights, milwaukee, WI, 53208

Jeremy was extremely professional! You can tell he truly loves animals and spends time getting to know them so that everything goes smoothly. I had just gotten a new dog, and by the time I had gotten back he had taught them all how to go on a walk at the same time! I love that he sends pictures during his stay, so you can check in. I highly recommend him!

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Megan I.
Sitter Profile Image: Eleyna E.
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Eleyna E.
from
$30
per night
5 out of 5.0 stars
5 reviews
2 years of experience
Story Hill, Milwaukee, WI, 53213

About: I’ve trained my own dogs since childhood, and I’ve also helped friends teach their dogs basic commands like sit, stay, lay down, and touch. I’m patient, consistent, and genuinely enjoy helping pets feel safe, happy, and well-behaved. Whether it’s a playful puppy or a senior dog who needs a gentler pace, I adjust my care to meet their needs. I am a student, so my schedule is incredibly flexible. I’m happy to help with your pets whenever you need— weekdays, weekends, mornings, and evenings. I would love to help however I can for your pet, using leashes, crates, toys, etc in your pet’s home for what makes them comfortable

Sitter Profile Image: Nikki G.
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Nikki G.
from
$64
per night
5 out of 5.0 stars
9 reviews
7 years of experience
Milwaukee, WI, 53208

Nikki did an excellent job caring for our puppy, Moose, and Kitty, our 10yo cat! She stayed in our home, which was great for our pets, because in the past we’ve utilized drop-in sitters, and they did not drop-in as often as they should have. But with Nikki there, they had plenty of attention since she was staying at our house and working from our house. She went above and beyond in making sure that our house was clean when we arrived home. She sent pictures and updates and even watered our vegetable plants while we were away. If you need an in-home pet sitter that will lessen the stress on your pets (and you) while you are away from home, consider Nikki!

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Emily S.
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Sitter Profile Image: Ashley W.
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Sitter Profile Image: Ashley W.
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1. Ashley W.

Active person loves active dogs
Washington Heights, Milwaukee, WI, 53208
1.4 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
14 reviews
5 repeat clients
Profile image

Ashley was GREAT! I had a last minute trip pop up this weekend and she immediately responded to help me out. She even dropped what she was doing to come meet her that night! She was super responsive while I was away, and Brooklyn is worn out tonight- which I know is because she had so much fun! Thanks again, Ashley!

Availability updated 60 days ago
Sitter Profile Image: Keisha P.
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Sitter Profile Image: Keisha P.
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2. Keisha P.

Star Sitter
Your Furbabies will Love Me
Clarke Square, Milwaukee, WI, 53204
1.8 mi. away
House Sitting, Drop-In Visits
from
$31
per night
5 out of 5.0 stars
15 reviews
9 repeat clients
Profile image

We were very happy with the communication and attention to detail while watching bella. Not only did she take great care of our dog but also our house 🧡 we would definitely recommend her and use her in the future

Availability updated yesterday
Sitter Profile Image: Megan D.
Verified Enhanced Background Check
Sitter Profile Image: Megan D.
Verified Enhanced Background Check

3. Megan D.

Star Sitter
Please pick me!
Milwaukee, WI, 53204
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$63
per night
5 out of 5.0 stars
30 reviews
10 repeat clients
Profile image

Megan was so great! We got lots of pics and videos and our pups were happy and chill when we got back, even after it being too cold to go outside much. Will definitely call again - thanks!

Availability updated 6 days ago
Sitter Profile Image: Melissa H.
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Sitter Profile Image: Melissa H.
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4. Melissa H.

Star Sitter
Their Favorite Pawsome Auntie 🐾
Milwaukee, WI, 53211
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
29 reviews
8 repeat clients
Profile image

Melissa is truly the best dog sitter! I am so grateful for her love and passion for dogs and always keeping me in the loop and sending adorable photos and videos!!

Availability updated 3 days ago
Sitter Profile Image: Devany M.
Verified Enhanced Background Check
Sitter Profile Image: Devany M.
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5. Devany M.

Can’t wait to meet your pet!
Milwaukee, WI, 53205
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
34 reviews
11 repeat clients
Profile image

We were so thankful to have Devany as our sitter for our trip. One of our dogs went blind a few weeks before our trip requiring him to take a lot of medications and to be guided around the house now too. This was our first time using a house sitter and I was nervous about leaving him. Devany was so sweet and took such good care of him. She sent me a lot of updates which really made me feel comforted. I highly recommend her and we will be booking with her again!

Availability updated 6 days ago
Sitter Profile Image: Joanne & Becky J.
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Sitter Profile Image: Joanne & Becky J.
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6. Joanne & Becky J.

Star Sitter
Wannabe Fur Moms - For Our Fur Fund
Milwaukee, WI, 53203
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
9 reviews
2 repeat clients
Profile image

Joann and Becky stayed with our dog and cat for almost a week a d they were terrific! They sent lots of updates and pics, and I could see my pets were comfortable, happy and well cared for. I will book with them again in the future. Highly recommend!

Availability updated 14 days ago
Sitter Profile Image: Carole & Shannon C.
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Sitter Profile Image: Carole & Shannon C.
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7. Carole & Shannon C.

Star Sitter
east side dog-whisperers
Murray Hill, Milwaukee, WI, 53211
3.8 mi. away
House Sitting, Drop-In Visits
from
$75
per night
5 out of 5.0 stars
123 reviews
33 repeat clients
Profile image

Carole and Max are amazing. The last time she sat for me, I had two dogs. Sadly, I had to put one of them down and Carole and Max left me a framed photo on my beloved Sequoia. Their thoughtfulness meant the world to me and I know my dog Miley was well cared for.

Availability updated yesterday
Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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8. Rachel H.

Star Sitter
** Mission: meet ALL the dogs **
West Allis, WI, 53214
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
90 reviews
23 repeat clients
Profile image

Rachel is amazing! One of our dogs is hesitant with new people, and Rachel deals well with her noise and makes her feel comfortable quickly every time. Our dogs love spending time with Rachel and we love getting regular photos of all the fun they're having :)

Availability updated 12 days ago
Sitter Profile Image: Berenice B.
Verified Enhanced Background Check
Sitter Profile Image: Berenice B.
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9. Berenice B.

Rover 101
Star Sitter
I walk to keep their tails waggin’
Bay View, Milwaukee, WI, 53207
3.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per night
5 out of 4.9 stars
167 reviews
77 repeat clients
Profile image

Berenice was an excellent sitter. My first time working with her was for an extended period of time and I came home to a clean house and happy, healthy dogs. My two pitties are not trained well on a leash and she did well walking them despite that. She left me at ease while on my trip with daily communication and pictures. We already have our next stay booked with her! Thank you Berenice! 💕

Availability updated yesterday
Sitter Profile Image: Adrienne N.
Verified Enhanced Background Check
Sitter Profile Image: Adrienne N.
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10. Adrienne N.

Star Sitter
WFH, med experience, and pet lover!
Lower East Side, Milwaukee, WI, 53214
2.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 5.0 stars
45 reviews
7 repeat clients
Profile image

Adrienne was absolutely amazing. I have never had someone dog sit in my home before as I was never comfortable with it, but Adrienne I could tell was a trustworthy person from the start. I have one extremely hyper puppy and a senior who barely leaves her bed, and she did an amazing job watching both. She went above and beyond what I could of asked of her, and we will most definitely use her in the future.

Availability updated 2 days ago
Sitter Profile Image: Addoris D.
Verified Enhanced Background Check
Sitter Profile Image: Addoris D.
Verified Enhanced Background Check

11. Addoris D.

Queer Friendly & Energetic Sitter
Lower East Side, Milwaukee, WI, 53202
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$32
per night
5 out of 5.0 stars
7 reviews
1 repeat client
Profile image

Our animals were well taken care of and got lots of love! The communication was great and will definitely book again.

Availability updated 11 days ago
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check

12. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$64
per night
5 out of 5.0 stars
159 reviews
49 repeat clients
Profile image

Jessica was great! Our emotionally needy animals soaked up her attention and loved on her right back. Super great communication throughout the stay, and lots of great photos. Thanks again, Jessica!

Availability updated today
Sitter Profile Image: Lanaya O.
Verified Enhanced Background Check
Sitter Profile Image: Lanaya O.
Verified Enhanced Background Check

13. Lanaya O.

Animal lover here to help out
Yankee Hill, Milwaukee, WI, 53202
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
8 reviews
4 repeat clients
Profile image

Lanaya was great. She could handle our Great Dane with no problems for a whole day, even sending us pictures through the day without us asking for them which was really nice of her. First time using rover for us but it won’t be the last. Thanks Lanaya! We will see you soon.

Availability updated 10 days ago
Sitter Profile Image: Maiah D.
Verified Enhanced Background Check
Sitter Profile Image: Maiah D.
Verified Enhanced Background Check

14. Maiah D.

Let me be your pet’s 2nd bestie!
Juneau Town, Milwaukee, WI, 53963
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
9 reviews
2 repeat clients

Maiah is one of the most dependable and loving pet caregivers I’ve ever met. She treats every animal with kindness, patience, and genuine affection. Whether it’s daily walks, playtime, or just providing comfort, she goes above and beyond to make sure pets feel safe and happy. I’ve seen how attentive she is to each pet’s unique needs, and I would wholeheartedly recommend her to anyone looking for trustworthy, compassionate care.

Availability updated today
Sitter Profile Image: William L.
Verified Enhanced Background Check
Sitter Profile Image: William L.
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15. William L.

U.S. Secretary of Dogs
Merrill Park, Milwaukee, WI, 53208
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$48
per night
9 reviews

Billy watched my dog for me in nyc on and off for months. She loved him! He’s accountable, and fun. Can’t go wrong! Thanks billy

Availability updated 2 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Jackie C.
Verified Enhanced Background Check
Sitter Profile Image: Jackie C.
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16. Jackie C.

Star Sitter
Looking forward to meet your pet!
Brewer's Hill, Milwaukee, WI, 53212
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
107 reviews
35 repeat clients
Profile image

Jackie stayed in our house with our dog for the weekend and she was great. Our husky Zero is our baby and a bit particular sometimes but she took it all in stride. She sent pictures throughout the weekend and reached out when she had questions. We also tried to make the house nice and neat for her time here and when she left we were wondering if she actually touched anything it was still so clean! We highly recommend Jackie and plan on booking her in the future when we're away for any extended amount of time.

Availability updated today
Sitter Profile Image: Kat K.
Verified Enhanced Background Check
Sitter Profile Image: Kat K.
Verified Enhanced Background Check

17. Kat K.

Ready to care for your fur babies!
Milwaukee, WI, 53208
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
5 out of 5.0 stars
3 reviews
1 repeat client

Kat is a phenomenal care giver and all around amazing human. They have cared for our cats, dogs, and guinea pigs for several years and are extremely attentive, communicative, and kind. My family has complete trust in Kat and will continue to use them to care for our pet family members forevermore.

Availability updated 17 days ago
Sitter Profile Image: Jamila M.
Verified Background Check
Sitter Profile Image: Jamila M.
Verified Background Check

18. Jamila M.

Rover 101
Star Sitter
Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$57
per night
5 out of 4.9 stars
80 reviews
24 repeat clients
Profile image

Jeremy was extremely professional! You can tell he truly loves animals and spends time getting to know them so that everything goes smoothly. I had just gotten a new dog, and by the time I had gotten back he had taught them all how to go on a walk at the same time! I love that he sends pictures during his stay, so you can check in. I highly recommend him!

Availability updated 10 days ago
Sitter Profile Image: Eleyna E.
Verified Enhanced Background Check
Sitter Profile Image: Eleyna E.
Verified Enhanced Background Check

19. Eleyna E.

Your Pet’s New Best Friend
Story Hill, Milwaukee, WI, 53213
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
5 reviews

I have trusted Eleyna to take care of my dog, Violet, on multiple occasions and she has never let me down. Violet is fairly young, and Eleyna is very patient and understanding with her. She has even helped with training a bit! Violet loves to see Eleyna!

Availability updated today
Sitter Profile Image: Nikki G.
Verified Enhanced Background Check
Sitter Profile Image: Nikki G.
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20. Nikki G.

Teacher/Traveler/Trusted Pet Sitter
Milwaukee, WI, 53208
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$64
per night
5 out of 5.0 stars
9 reviews
Profile image

Nikki did an excellent job caring for our puppy, Moose, and Kitty, our 10yo cat! She stayed in our home, which was great for our pets, because in the past we’ve utilized drop-in sitters, and they did not drop-in as often as they should have. But with Nikki there, they had plenty of attention since she was staying at our house and working from our house. She went above and beyond in making sure that our house was clean when we arrived home. She sent pictures and updates and even watered our vegetable plants while we were away. If you need an in-home pet sitter that will lessen the stress on your pets (and you) while you are away from home, consider Nikki!

Availability updated 3 days ago

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  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

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  3. 3. Book & Pay

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The median cost per night for house sitting in Cold Spring Park is $40

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