House Sitting in Maitland Park, Milwaukee

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?

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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.

Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
3.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
141 reviews
63 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: Jessica Z.
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Sitter Profile Image: Jessica Z.
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2. Jessica Z.

Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
7.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
93 reviews
32 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: Markita H.
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Sitter Profile Image: Markita H.
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3. Markita H.

Friendly/Compassionate/Responsible
Saint Francis, WI, 53235
3.5 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 the best! She took care of my dog the same way I would (probably even better) and left my house spotless. She is a great communicator and made me completely comfortable.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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4. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
8.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 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!

Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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5. Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
6.1 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 wonderful! She kept us updated the whole time and our boy was so happy! She took him to the dog park every day and made sure she had a great time while we were gone. We’ll use her every time we can if she’s free!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jenn S.
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Sitter Profile Image: Jenn S.
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6. Jenn S.

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

Jenn was absolutely PHENOMENAL with our furbabies, and we have a lot! She sent regular updates and we felt so comfortable knowing that she was okay with both cats and dogs. We would absolutely hire her again.

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Sitter Profile Image: Elba M.
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Sitter Profile Image: Elba M.
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7. Elba M.

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

Elba was the best sitter for my pups while I was out of town! Daily updates and photos kept my worries at bay. She provided lots of playtime and multiple walks for my reactive dogs. I will absolutely have her house sit for me every time I need a sitter!

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Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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8. Erica L.

I'll love them like my own
West Allis, WI, 53227
7.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
82 reviews
43 repeat clients
from
$37
per night

Erica was great to work with and she was great with our dogs and cat. It was so nice to not have to worry about them while we were gone, especially with an anxious dog that doesn’t handle change well.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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9. Jackie C.

Looking forward to meet your pet!
Brewer's Hill, Milwaukee, WI, 53212
8.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
67 reviews
21 repeat clients
from
$65
per night

Jackie is incredible! Great communication, she is punctual, sent so many pictures, and best part was my pup was so happy. I definitely recommend! Thanks again Jackie!!

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Sitter Profile Image: Patricia N.
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Sitter Profile Image: Patricia N.
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10. Patricia N.

Love them all!
Franklin, WI, 53132
5.8 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 very attuned to ensuring a smooth stay, and that she had all the necessary instructions to ensure our sweet pets were well-looked after while we were away. We really appreciated her help and kindness with our dogs!

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Sitter Profile Image: Bret H.
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Sitter Profile Image: Bret H.
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11. Bret H.

Work from home and reliable
Bay View, Milwaukee, WI, 53207
4.2 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: Alexy & Dylan G.
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Sitter Profile Image: Alexy & Dylan G.
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12. Alexy & Dylan G.

Animals are my passion and joy!
Milwaukee, WI, 53207
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
12 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: Kelli H.
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Sitter Profile Image: Kelli H.
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13. Kelli H.

Dog and exercise lover!
Bay View, Milwaukee, WI, 53207
4.4 mi. away
Boarding, House Sitting
5.0 out of 5 stars
14 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.

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Sitter Profile Image: Samantha R.
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Sitter Profile Image: Samantha R.
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14. Samantha R.

Rover 101
It’s like a dog hotel but better ;)
Cudahy, WI, 53110
4.0 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

One of the things that I will miss about moving from San Diego is being able to have Samantha watch Savannah for me. She would send pictures and text messages to keep me updated on how things were going. I whole heartedly recommend her!!!

Sitter Profile Image: Ruth W.
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Sitter Profile Image: Ruth W.
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15. Ruth W.

Caring. Depenable. Trustworthy.
Greenfield, WI, 53220
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night

Ruth has been taking care of pets for as long as I’ve known her. Ruth has owned a cat, A bunny, two turtles, a total of four dogs, and a green-checked Conard from the past 18 years. She loves her dogs especially because of the relationship they have created over the past 5 years and the dogs love her.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jessica R.
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Sitter Profile Image: Jessica R.
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16. Jessica R.

All dogs are good babies
Woodland Court, Milwaukee, WI, 53220
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
from
$30
per night

Jessica was great with our lab! Also sent pictures and spent quality time with her! Would definitely book with her again.

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Sitter Profile Image: Stephanie R.
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Sitter Profile Image: Stephanie R.
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17. 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
60 reviews
19 repeat clients
from
$50
per night

Stephanie took amazing care of our dogs! Definitely 5/5 stars!! She was loving, kind, and prompt and we would definitely use her services again in the future!

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Sitter Profile Image: Rita B.
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Sitter Profile Image: Rita B.
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18. Rita B.

Rover 101
Pets Thrive, Owners Relax!
Oak Creek, WI, 53154
2.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
49 reviews
30 repeat clients
from
$85
per night

Rita was great … kept me updated and sent lots of pictures and walked them. I wasn’t worried about them at all. I will definitely book with her again.

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Sitter Profile Image: Carolina G.
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Sitter Profile Image: Carolina G.
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19. Carolina G.

I enjoy pets company!
Cudahy, WI, 53110
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 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: 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
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
11 repeat clients
from
$50
per night

Felicity was wonderful while we were away. She took great care of the animals and the house and she sent lots of pictures which I always appreciate! It's so nice to come home to relaxed animals who are just happy to see us and not stressed that we left!

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Rover also offers House Sitting in these neighborhoods:

Rover also offers other services in Maitland Park:

When it comes to pet care and house sitting, pet owners in Maitland Park, Milwaukee, WI trust their pets with sitters on Rover.com. Over 1089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5. House sitting doesn't have to be expensive. In fact, it's probably a lot more affordable than you think. You'll quickly find that there's a house sitter on Rover for just about every price range and lifestyle. Wondering how much you might expect to pay for a house sitter and pet care on Rover? Check out our average house sitting rates to get an idea before you begin a conversation with a sitter who seems like a great match.

Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog and your home, turn to Rover for your Maitland Park, Milwaukee house sitting needs. On Rover, it's easy to find a loving dog sitter in Maitland Park, Milwaukee, WI who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Maitland Park house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover: it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Maitland Park, Milwaukee, WI for your dog: people who'll treat him like family.

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