House Sitting in Highwood Estates, 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
6.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
142 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!

Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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2. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
7.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 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: 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
7.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
98 reviews
33 repeat clients
from
$59
per night

Jessica was amazing! She communicated with us every day and sent us pictures/videos of the dogs, which my daughters really enjoyed. She took extra special care of our geriatric dog, making and feeding him human food, per our request. We will definitely be hiring Jessica again! Thank you for taking care of our fur babies! Brandy

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
1.4 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 a amazing! She is the most kind and compassionate woman. This is the very first time we have ever left our two rescue dogs, so I wasn’t sure what to expect with our two pups and how they would react to anyone other than family watching them. she watched them for two stretches of time periods, one stretch of time was for a few hours while we were at a rehearsal dinner and with a second stretch of time it was for over 12 hours at our daughters wedding. The first stretch of time they barked continuously, and poor Jenn soldiered through like a champ, unscathed. I was afraid she wouldn’t show up the next day, but there she was bright and early the next day, ready to meet the challenge! Within 10 minutes, she texted me with a photo that our two beautiful pups were fast asleep and quiet. She had a wonderful day. It just took a while for them to get used to being with someone other than their owners. She was wonderful, kept us up-to-date throughout our time away. With photos and brief updates. Highly recommend, if I could leave more than five stars, I would!⭐️

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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5. Katherine B.

Star Sitter
Dogs are happiness 😊
West Allis, WI, 53219
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
9 repeat clients
from
$50
per night

I could not say enough great things about katie! As a new dog mom to a puppy, she was so patient and so attentive to my boy. Katie sent tons of pictures, videos and kept me updated routinely on anything that had changed. She was a respectful house guest and provided excellent care to my dog while I was working very long hours for three consecutive days. My mama heart was at ease knowing I had such an excellent person taking the best care of my dog!!

Sitter Profile Image: Patricia N.
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Sitter Profile Image: Patricia N.
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6. Patricia N.

Star Sitter
Love them all!
Franklin, WI, 53132
4.2 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 does a great job with our crazy cat! Would highly recommend if you need someone who provides special care for your pet. We don’t worry if Patricia is there.

Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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7. Rachel H.

Star Sitter
** Mission: meet ALL the dogs **
West Allis, WI, 53214
2.2 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 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 :)

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

Star Sitter
Animals are my passion and joy!
Bay View, Milwaukee, WI, 53207
5.3 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.

Sitter Profile Image: Bianca R.
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Sitter Profile Image: Bianca R.
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9. Bianca R.

Loving Dog Mom
New Berlin, WI, 53151
4.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
7 repeat clients
from
$40
per night

This was our first time with Bianca and she was amazing. We have 3 dogs, 2 of them are kind of anxious around strangers but she has a confidence about her and she handled them just fine. We got pics and videos everyday along with updates throughout the day. We had booked her for 3 day weekend and because of plane delays we couldn’t make it home until 2 days later and Bianca was so flexible and accommodating that we could relax knowing that she was there with our pups.

Sitter Profile Image: Lexi K.
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Sitter Profile Image: Lexi K.
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10. Lexi K.

Star Sitter
Lover of all animals big and small
Cannon Park, Milwaukee, WI, 53214
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
42 reviews
12 repeat clients
from
$35
per night

Lexi was delightful, and took great care of our babies. She was clearly an animal lover, and displayed a curiosity and interest in our pets (a dog and three cats). I am happy to have found her!

Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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11. Erica L.

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

Erica gave me the comfort of using this for the first time and gave me all the help and questions I had! My babies seemed so happy the entire time and are truly blessed to have had her just down the same block as us! She was great and will definitely use her again for any of our needs! Our 3 cats and baby tortoise were in the best hands with her!

Sitter Profile Image: Hillery F.
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Sitter Profile Image: Hillery F.
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12. Hillery F.

Happy to help!
West Allis, WI, 53214
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
84 reviews
35 repeat clients
from
$80
per night

Hillery was wonderful with our two high energy terrier mixes and our two cats. She was super patient with them and took excellent care of them while we were away. She was accommodating and very friendly (not to mention very knowledgeable about all things dogs and cats!!) We didn't have to worry one bit with her in charge of our babies. ? The daily updates were wonderful and overall experience was amazing.

Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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13. Leandrea R.

Rover 101
Star Sitter
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
4.3 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 exceeded our expectations! She stayed at our house with our two dogs and cat while we were out of the country for our destination wedding. She communicated with us everyday by sending updates and pictures of all the pets. Our dogs loved her and Crista!!! We will definitely rehire!

Sitter Profile Image: Ruth W.
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Sitter Profile Image: Ruth W.
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14. Ruth W.

Caring. Depenable. Trustworthy.
Greenfield, WI, 53220
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5 reviews
from
$50
per night

Ruth is my daughter. She has been around dogs her whole life. She loves them and knows how to care for them. Your dog will be cared for as if it was her own.

Sitter Profile Image: Lauren Z.
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Sitter Profile Image: Lauren Z.
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15. Lauren Z.

No dog too big or small
West Allis, WI, 53227
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
from
$50
per night

Lauren is a sweetheart! She was very communicative and sent photo updates throughout the day. My dog absolutely loved her! Will def book with her again.

Sitter Profile Image: Hannah W.
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Sitter Profile Image: Hannah W.
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16. Hannah W.

Full-time cuddler, part-time runner
Alcott Park, Milwaukee, WI, 53228
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
17 repeat clients
from
$22
per night

Hannah did an excellent job with our Furry Herd! Taking care of four dogs is no picnic, but she handled it like the pro she is. She even made it sound like fun! :) We think it is, but not everyone agrees with us, so we were happy Hannah did. She stayed in contact, let us know about a minor problem one of the dogs had, and kept us informed and happy. Thanks, Hannah!

Sitter Profile Image: Amanda S.
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Sitter Profile Image: Amanda S.
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17. Amanda S.

I’ll love them like my own!
West Allis, WI, 53219
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$28
per night

Amanda is so great the neighbors come over and ask us who our dog walker is. She's very conscientious of things we do with our dogs and they love her so much. Vey responsible and has great availability. We recommend her to all our friends and their friends.

Sitter Profile Image: Allie S.
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Sitter Profile Image: Allie S.
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18. Allie S.

Teacher with a fenced-in yard here!
West Allis, WI, 53219
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$28
per night

Allie has grown up with dogs around her family her entire life. When I met Allie, her Australian Shepherd/cattle dog mix went everywhere she went and held greater attention to her commands than other family members. She is a thorough pet lover and volunteers to watch friends' dogs without a second thought when they need a sitter for vacation (her friend's husky is her favorite). Allie is comfortable around just about any breed. The family holiday get-togethers include the 8 various breeds of dogs running around the holiday tree and dinner table. She's confident to step in and break up the party when those 8 get too rowdy and gracefully separate the troublemaker and make sure it gets lots of attention solo while the rest mingle. She takes as much care of any dog as she would any of her students, showing patience, assurance, and lots of love.

Sitter Profile Image: Stephen & Wipawee D.
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Sitter Profile Image: Stephen & Wipawee D.
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19. Stephen & Wipawee D.

Pawfessional w/ Love & Care <3
West Allis, WI, 53227
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
46 reviews
17 repeat clients
from
$75
per night

Stephen and Wipawee watched my dog and my sister’s dog at my house while we went away on a family vacation. The dogs were well cared for, had plenty of attention and were taken great care of! Couldn’t have asked for better sitters.

Sitter Profile Image: Amanda B.
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Sitter Profile Image: Amanda B.
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20. Amanda B.

Have loved animals since birth.
Greenfield, WI, 53220
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
109 reviews
36 repeat clients
from
$28
per night

Amanda was great! She sent me photos of my pup, and I felt secure knowing she was taking good care of her. We will definitely book with Amanda again.

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When it comes to house sitting, dog owners in Highwood Estates, Milwaukee, WI love Rover.com. Over 1089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of house sitting in Highwood Estates may surprise you - in a good way. That's because there's a house sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for house sitting on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

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 Highwood Estates, Milwaukee house sitting needs. On Rover, it's easy to find a loving dog sitter in Highwood Estates, 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 Highwood Estates 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 Highwood Estates, Milwaukee, WI for your dog: people who'll treat him like family.

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