House Sitting in Highwood Estates, 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
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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
6.0 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

Blythe was great! She took care of our girls while we were away for a quick weekend trip and when we arrived home they were very happy and content and the house was clean and neat. There’s no doubt we’ll be booking with her again!

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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
7.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
93 reviews
32 repeat clients
from
$59
per night

Jessica Z stayed in my house with my 14 y/o blind Boston Terrier. She was wonderful. I received daily updates and photos, she clearly took excellent care of my pup. She left my place spotless and I would highly recommend her. She is excellent and I will definitely use her again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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3. 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
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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4. Rachel H.

** 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 goes above and beyond every time she house sits for us. I hate leaving my pets, but I feel so much better knowing she’s there. She keeps us updated every day, and we always come home to a very happy dog and cat!

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

Dog lover 🐶 & cat mom 🐈🐈‍⬛🐈
West Allis, WI, 53227
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
40 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: Patricia N.
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Sitter Profile Image: Patricia N.
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6. Patricia N.

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

We loved having Pat watch our 2 fur boys. She sent pics and texts and we felt so comfortable knowing that Dill and Rocky were in great hands!!

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Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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7. 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
43 repeat clients
from
$37
per night

I was overjoyed to see Erica bright and early at 7:30 am. I really needed to rely on someone to show up and take care of my fur babies that morning and she delivered. Very dependable and easy-going attitude helped me to realize I must have her dog sit again! Thank you, Erica.

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Sitter Profile Image: Danica V.
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Sitter Profile Image: Danica V.
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8. Danica V.

PAWsitively reliable med student!
Wauwatosa, WI, 53226
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
19 reviews
7 repeat clients
from
$46
per night

Danica is consistent and professional throught the Rover experience. I've been burned before with previous dog sitters that have been inconsistent and unresponsive, but Danica is always punctual and quick to respond to any concerns/needs. I trust her to be with my pups when they are most stressed and take care of them when I'm away. That peace of mind is priceless and I love having Danica over to watch my pups.

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Sitter Profile Image: Julie M.
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Sitter Profile Image: Julie M.
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9. Julie M.

Rover 101
Pet and homes are safe with me!
Wauwatosa, WI, 53226
4.9 mi. away
House Sitting
5.0 out of 5 stars
27 reviews
14 repeat clients
from
$60
per night

Lola, my 6yr old frenchie had the best weekend getaway at Julie’s! I received pictures and videos during her visit. I booked with Julie before in 2018 when Lola was just a puppy and couldn’t have been happier with my experience. I was so excited to see Julie back on rover to re-book again! Lola and Lilly (her Lab) were reunited and had the best time together- full of plenty of play time. I highly recommend Julie and will absolutely be contacting her for future visits for little Lola!!

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

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
11 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!

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Sitter Profile Image: Lauren Z.
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Sitter Profile Image: Lauren Z.
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11. 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
$55
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.

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Sitter Profile Image: Amanda S.
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Sitter Profile Image: Amanda S.
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12. Amanda S.

I’ll love them like my own!
West Allis, WI, 53219
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
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.

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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13. Katherine B.

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!!

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Sitter Profile Image: Lauren B.
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Sitter Profile Image: Lauren B.
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14. Lauren B.

I fetch amazing results.
Greendale, WI, 53129
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
4.5 out of 5 stars
2 reviews
1 repeat client
from
$28
per night

About: Throughout my life, I’ve grown up with cats & dogs and have learned to care for all their needs. I love making pets happy! I am interested in taking care of dogs & cats. I am open every morning from 7am - 11am. Afternoons from 2pm - 4pm & again in the evening 6pm - 8pm. I will make it a priority that your pet is cared for while you are away. I enjoy taking them on walks, giving them play time and extra love! Each morning, I take my dog out for a walk or play time for about 20 min. This gives him a chance to go potty. I take my dog out every 3-4 hours. I always make sure my pet has food and water throughout the day. Depending on the weather, and if I have to be gone for 3-4 hours, my dog gets to go to the dog park for more exercise later that afternoon. I will always make sure your pet has fresh water, good exercise, and enough potty time too. Making sure your pet is taken care of & feels loved while you’re away will be my priority!

Sitter Profile Image: Stephen & Wipawee D.
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Sitter Profile Image: Stephen & Wipawee D.
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15. 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
45 reviews
17 repeat clients
from
$75
per night

Stephen and Amelie provided exemplary care for our dogs, Cameron and Colby. Their kindness, coupled with their commitment to regular exercise and clear communication, put us completely at ease. They frequently updated us with photos and videos, and their prompt responses to our questions were much appreciated. In addition to taking great care of our dogs, they kept our house in perfect condition. We wholeheartedly recommend Stephen and Amelie to anyone needing reliable and loving pet sitters. We can't thank them enough for their top-notch service!

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
1.0 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.

Sitter Profile Image: Ruth W.
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Sitter Profile Image: Ruth W.
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17. Ruth W.

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

Ruth loves dogs. She has been around dogs her entire life. She has been a 2 dog owner for over 15 years. She also really enjoys walking.

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Sitter Profile Image: Holly H.
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Sitter Profile Image: Holly H.
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18. Holly H.

Animal lover since 1994!
West Allis, WI, 53219
1.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
1 repeat client
from
$60
per night

This was our first time working with Holly, and she was fantastic! I'm so thankful we met her, and she was willing to work with us. She is an excellent communiator, connected easily with our pups, and helped us feel confident that our dogs were in good hands while we were away. She stayed at our house and we felt at ease with her in our home. We would definitely like to work with Holly again in the future and I'd confidently recommend her to our friends and family. Thank you Holly!!

Sitter Profile Image: Amanda B.
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Sitter Profile Image: Amanda B.
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19. 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
105 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.

Sitter Profile Image: Amanda J.
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Sitter Profile Image: Amanda J.
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20. Amanda J.

True love exists because animals do
Highwood Estates, Milwaukee, WI, 53219
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$30
per night

Thank you for taking such great care of my 2 crazy girls! 😉🥰

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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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