House Sitting in Holler Park, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Blythe R.
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Sitter Profile Image: Blythe R.
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1. Blythe R.

Star Sitter
Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
2.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
143 reviews
64 repeat clients
from
$55
per night

We can’t say enough good things here. We had a really bad boarding experience and needed to do something different. We were a little hesitant with having someone in our home but Blythe was awesome. We have a large dog who is pretty needy and a little old man. She took pics, gave us updates and did everything we asked and our home looked the exact way we left it. Would highly recommend!

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Sitter Profile Image: Markita H.
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Sitter Profile Image: Markita H.
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2. Markita H.

Star Sitter
Friendly/Compassionate/Responsible
Saint Francis, WI, 53235
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
70 reviews
6 repeat clients
from
$57
per night

Markita is an excellent dog sitter. She is my go to gal for staying the weekend at my house. She communicates well and gives adorable updates. Her love for animals is obvious!

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Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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3. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
7.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
98 reviews
33 repeat clients
from
$59
per night

Our family had recently experienced a loss of our other pet. It was a tough time for travel but Jessica supported our other pet while we were away. She kept us informed and made the world of difference being away during such a difficult time.

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Sitter Profile Image: Jenn S.
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Sitter Profile Image: Jenn S.
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4. Jenn S.

Star Sitter
Animal lover and cat mom of 3 🐈
West Allis, WI, 53227
6.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
41 reviews
10 repeat clients
from
$60
per night

Jenn is amazing!! I have 2 cats and an anxious dog. She treated them all with so much love and cared for them while I was out of town.Updates and pictures every day!!

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Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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5. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
7.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$50
per night

This was Lily’s first time house sitting Kai and she exceeded my expectations. She clearly developed a great connection with Kai, did a really nice job keeping me connected/informed, and overall left the house looking like it did when I left. I so much enjoyed her texts, pictures and video clips. Thank you Lily!

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Sitter Profile Image: Alexy & Dylan G.
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Sitter Profile Image: Alexy & Dylan G.
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6. Alexy & Dylan G.

Star Sitter
Animals are my passion and joy!
Bay View, Milwaukee, WI, 53207
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$28
per night

Alexy watched my puppy and cat for a few days and gave him constant attention and activity while keeping me updated with frequent pictures. My puppy is very energetic and still going through training and Alexy was accomdating and understanding. Returned home to the house in great shape. I would definitely have Alexy watch my pets again.

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Sitter Profile Image: Patricia N.
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Sitter Profile Image: Patricia N.
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7. Patricia N.

Star Sitter
Love them all!
Franklin, WI, 53132
6.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
51 reviews
14 repeat clients
from
$30
per night

Patricia was wonderful! This was our first time using Rover, and it could not have been a better experience. Patricia went above and beyond, sending regular updates on our pups, the bird and the house! And when we returned, she had even washed the linens! Highly recommend Patricia!

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
5.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
77 reviews
22 repeat clients
from
$30
per night

Rachel was great with our two crazy dogs and her ability to watch them in our home was priceless. Our beagle has anxiety and does best in her own environment. Rachel kept us informed with texts and pictures and really provided peace of mind that our pups were in good hands.

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Sitter Profile Image: Elba M.
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Sitter Profile Image: Elba M.
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9. Elba M.

Rover 101
Star Sitter
Wiggle waggle and roll!
Cudahy, WI, 53110
2.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
129 reviews
51 repeat clients
from
$45
per night

Elba was amazing. She took great care of our boys, and kept us in the loop of everything they were doing. A ton of pictures were taken, and I think our boys are excited to be watched by her again. Thank you!

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Sitter Profile Image: Bret H.
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Sitter Profile Image: Bret H.
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10. Bret H.

Star Sitter
Work from home and reliable
Bay View, Milwaukee, WI, 53207
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$55
per night

Our usual dog sitter was unable to stay at our house so I decided to check Rover. It's a leap of faith to have someone who you don't know staying in your house with your dogs, so I spent a lot of time searching Rover and Bret ended up being our #1 choice. I am thrilled that we chose Bret - he was fantastic! He was great with communication, sent photos, and took impeccable care of our house and dogs. I highly recommend Bret!

Sitter Profile Image: Liz N.
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Sitter Profile Image: Liz N.
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11. Liz N.

Fun, energetic animal lover!
Fernwood, Milwaukee, WI, 53207
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
3 repeat clients
from
$40
per night

Liz was great with my two pups. I was a little nervous about leaving them. I had just adopted a senior pup about 10 months prior and my other pup is pretty attached to me. This was my first time leaving them for such a long time. They were happy and well taken care of. I got pictures and updates through out my trip. It definitely made my trip easier knowing Liz was there loving on them!

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Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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12. Leandrea R.

Rover 101
Star Sitter
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
4.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
106 reviews
37 repeat clients
from
$60
per night

Leandrea is wonderful! She took great care of our dog while we were out of town and sent lots of pictures and updates to put our mind at ease. Our dog LOVED playing with her pup too, which was a nice bonus! We will definitely be booking Leandrea again in the future.

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Sitter Profile Image: Breanna R.
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Sitter Profile Image: Breanna R.
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13. Breanna R.

Let’s get them 4 legged animals out
Oak Creek, WI, 53154
4.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
8 reviews
from
$40
per night

Breanna is one of the most responsible people I’ve ever met. She is always timely and attentive to all things. I definitely trust and would recommend her!!!!

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Sitter Profile Image: Stephanie R.
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Sitter Profile Image: Stephanie R.
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14. Stephanie R.

I love all animals
South Milwaukee, WI, 53172
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
64 reviews
19 repeat clients
from
$50
per night

Stephanie has watched our two dogs at our home numerous times and is absolutely amazing with them every single visit. She sends pictures and videos and takes our German Shepherd on hikes and trips to the park. She gives multiple updates throughout the day and truly loves our pups. Highly recommend!!

Sitter Profile Image: Kelli H.
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Sitter Profile Image: Kelli H.
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15. Kelli H.

Dog and exercise lover!
Bay View, Milwaukee, WI, 53207
3.4 mi. away
Boarding, House Sitting
5.0 out of 5 stars
16 reviews
3 repeat clients
from
$45
per night

Kelli was awesome house sitting for us. She was an awesome house guest and got along great with our dog. He was in high spirits while we were away. We appreciated all the photos Kelli sent and she was very responsive to our messages. 10 stars.

Sitter Profile Image: Anya B.
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Sitter Profile Image: Anya B.
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16. Anya B.

Rover 101
Experienced with flexible schedule!
Milwaukee, WI, 53221
2.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
12 reviews
5 repeat clients
from
$50
per night

Anya is great with my boys. I was comfortable leaving her in our home. Trusted her with administring meds. She made us feel enough trust that at I didn't feel the need to be consistently ask for updates. She is awesome 👍🐕🐕🐕🐕

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Sitter Profile Image: Carolina G.
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Sitter Profile Image: Carolina G.
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17. Carolina G.

I enjoy pets company!
Cudahy, WI, 53110
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$40
per night

I had Carolina do some dog sitting in my home while I was out of town and I could not be happier. She took great care of my senior dog, Joey. He had plenty of exercise and walks, was well loved, she kept him great company and treated him like he was her own. Joey has some medical issues and requires medications throughout the day and she was very diligent about following his schedule. She gave constant updates, pictures and videos, which was much appreciated. Carolina was extremely respectful of my home, and pretty sure my place looked better than when I left. The next time I need someone to look after my old guy, I hope Carolina is available, I highly recommend her.

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Sitter Profile Image: Megan S.
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Sitter Profile Image: Megan S.
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18. Megan S.

Teacher iso pet cuddles and walks!
Bay View, Milwaukee, WI, 53207
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
15 years of experience
from
$47
per night

About: Proud dog and cat owner with a knack for puppet whispering. Recently, my cat of over 10 years passed away and am in need of some puppy snuggles. Let me love your dog!? Haha! In all seriousness, I had a German Sheppard before I moved to Milwaukee. Raised him as a puppy until he passed on. My family also had two labs when I was growing up and a Doberman now. I have the most experience with larger breeds but am not apposed to watching smaller breeds either. I am open to kittens, puppy’s and cats too. I am available for over night stays, early am walks and day time play. Weekend are pretty free for drop ins or overnight stays as well. Any questions, just ask! Thank you, Megan I work from home during the day and like to get out on walks. I will always be home to watch over your pooch and cat care needs. I am a caregiver and naturally very nurturing. I would treat your pet as my own. I am the go to sitter for my friend group, including 4 golden doodles and one husky!

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Sitter Profile Image: Samantha R.
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Sitter Profile Image: Samantha R.
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19. Samantha R.

Rover 101
It’s like a dog hotel but better ;)
Cudahy, WI, 53110
3.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
103 reviews
41 repeat clients
from
$60
per night

I absolutely adore Samantha! I went on vacation for 6 days and felt at ease knowing she was here with all my babies taking good care of them. I received pictures and messages daily letting me know how things were going. She also wasn't afraid to ask me questions which was amazing! I came home to happy animals. If you want a stress free vacation, book with Samantha! Thanks again for everything :)

Sitter Profile Image: Felicity W.
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Sitter Profile Image: Felicity W.
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20. Felicity W.

Animals are my full time passion 🤍
St Francis, WI, 53235
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
25 reviews
12 repeat clients
from
$50
per night

Felicity was great! My pup loved her and was well taken care of while we were away. She has watched her twice now and we would definitely book again! She stayed at our home and the house was in great shape when we got home.

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Dog owners in Holler Park, Milwaukee, WI turn to house sitters on Rover.com for their house sitting needs. Over 1089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5. House sitting can be affordable, no matter where you live or what your price range may be. Curious about how much house sitting costs in Milwaukee with Rover.com? Check out our average house sitting rates near you to get an idea before getting a conversation started with a house sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

Rover.com is the simple, savvy way to find and book Holler Park house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Holler Park, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Holler Park house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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