House Sitting in Washington Heights, 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: Lily S.
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Sitter Profile Image: Lily S.
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1. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
3.1 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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2. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
4.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
97 reviews
33 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.

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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3. Katherine B.

Star Sitter
Dogs are happiness 😊
West Allis, WI, 53219
3.9 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: 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
4.4 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 stayed at our house for a weekend away. One of our dogs recently went blind and we felt in-home care was our only option. Jenn didn't seem concerned about managing our blind dog, senior greyhound, and cat. I appreciated that she came out twice to the house to meet us and talk through our routine. I was also impressed that she read up a bit on greyhounds since Leo was the first greyhound she watched. She was great about communicating her schedule and sending us pictures. We would definitely try to schedule with Jenn again.

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

Star Sitter
** Mission: meet ALL the dogs **
West Allis, WI, 53214
3.0 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!

Sitter Profile Image: Danica V.
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Sitter Profile Image: Danica V.
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6. Danica V.

Star Sitter
PAWsitively reliable med student!
Wauwatosa, WI, 53226
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
20 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.

Sitter Profile Image: Daniela & Michael P.
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Sitter Profile Image: Daniela & Michael P.
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7. Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
282 reviews
160 repeat clients
from
$65
per night

Daniela did a wonderful job watching Chewie. When we were feeling anxious, she was so quick to respond with a photo of our happy pup. Highly recommend.

Sitter Profile Image: Brooke L.
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Sitter Profile Image: Brooke L.
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8. Brooke L.

Cat mom
Milwaukee, WI, 53222
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
1 repeat client
from
$50
per night

Brooke did such a great jobs letting my dogs out. They love her and so do I! I had such peace of mind knowing they were in good hands and she still sent me updates. Great communication skills and you can tell how much she loves and cares for your pets. 10/10 would recommend!!

Sitter Profile Image: Lexi K.
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Sitter Profile Image: Lexi K.
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9. Lexi K.

Star Sitter
Lover of all animals big and small
Cannon Park, Milwaukee, WI, 53214
2.9 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: Sam P.
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Sitter Profile Image: Sam P.
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10. Sam P.

Rover 101
Loving, Responsive, Knowledgeable.
Hawthorne Glen, Milwaukee, WI, 53208
0.6 mi. away
Boarding, House Sitting, Drop-In Visits
5.0 out of 5 stars
120 reviews
58 repeat clients
from
$80
per night

This was our first experience with a pet sitter for our senior dog. Our old girl is a bit shy with strangers and I’m not sure she knew what was going on when Sam first got there since we’ve always had friends or family stay with her but Sam was patient and exactly who she needed for her first pet sitting experience. It wasn’t long before they were settled and our pup was completely relaxed and enjoying their time together. The experience was better than I could have imagined and we will definitely be using her again now that they are good friends.

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

Rover 101
Pro. Dog Handler with WFH job!
Park West, Milwaukee, WI, 53206
2.4 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
84 reviews
29 repeat clients
from
$75
per night

Erica was thorough in her communication, notes, and care of our dog, Sheba. I appreciated all the messages and clarifications on the details. It certainly gave us peace of mind having Erica care for Sheba for the first time! She provided many wonderful pictures and video, as well as clear reports as to how the visit was going. We are very happy and grateful for the service Erica provided. We would hire her again and also recommend her.

Sitter Profile Image: Lance C.
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Sitter Profile Image: Lance C.
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12. Lance C.

Coffee loving dog walker!
Enderis Park, Milwaukee, WI, 53210
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$38
per night

Lance has watched my dog Lupe a number of times. My dog loves him! He gets a lot of love, walks, and hang out time. He's very responsible, asks all the right questions and provides updates to make sure my wife and I are never concerned. I highly recommend Lance if you want peace of mind while you're away.

Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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13. Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
0.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
31 reviews
8 repeat clients
from
$70
per night

We had a great experience with Cindy. She took care of our furbabies like they were her own. Excellent communication, got daily pictures and updates. I did not have to worry at all will 100% rebook with Cindy.

Sitter Profile Image: Samantha A.
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Sitter Profile Image: Samantha A.
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14. Samantha A.

falls in love with any & all dogs
Washington Heights, Milwaukee, WI, 53208
0.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$40
per night

I've known Samantha for nearly 10 years and have seen her work with numerous animals! She is very loving, attentive, and has genuine compassion for animals and their human companions! She has watched my sweet (yet strong-willed... dare I say stubborn) german shepherd, Dante, and he loves spending time with her. I'd highly recommend trusting Sam with your beloved pets as she is reliable, caring, and fun! Dante can't wait to see her again soon!

Sitter Profile Image: Gabriella I.
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Sitter Profile Image: Gabriella I.
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15. Gabriella I.

Part-time RN, full-time pet lover!
Wauwatosa, WI, 53213
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
1 repeat client
from
$60
per night

Gabriella was absolutely awesome! We had one phone call initially to get things going, then that was it! She improvised when she needed too to take proper care of my gal and that was impressive! Also I had to book her last second, so it was awesome how I could get set up with her at such short notice! HIGHLY RECOMMEND this gal 👊😉🍻

Sitter Profile Image: Jeremy M.
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Sitter Profile Image: Jeremy M.
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16. Jeremy M.

Rover 101
Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
0.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
51 reviews
21 repeat clients
from
$55
per night

We have high energy dogs. Jeremy came over ahead of time for a meet and greet so they could get to know him. That was important because one of our dogs will nip if he doesn’t know you. He needs that introduction. They both took to him and snuggled in for Jeremy’s stay.

Sitter Profile Image: Molly O.
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Sitter Profile Image: Molly O.
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17. Molly O.

All the walks and all the cuddles
Wick Field, Milwaukee, WI, 53208
0.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
27 reviews
13 repeat clients
from
$65
per night

Molly did a great job watching our three bulldogs for a long weekend. She sent lots of pics and responded quickly any time I sent a question or note. Two of our girls have had some weird behaviors around meal time right before we left and she rolled with it with ease (and everyone ate all meals under her care). Definitely would hire her again!

Sitter Profile Image: Maggie S.
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Sitter Profile Image: Maggie S.
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18. Maggie S.

I'll Treat Your Dog Like My Own
Milwaukee, WI, 53213
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$50
per night

Maggie is the best! She is a true dog lover and she is our automatic go-to whenever we need a dog sitter. She has always given our pup the best care from the puppy days into his senior years. We trust her to stay at our house, and he has also done extended stays at her place. Can’t say enough great things about her!

Sitter Profile Image: Jordan J.
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Sitter Profile Image: Jordan J.
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19. Jordan J.

Patient animal lover
Wauwatosa, WI, 53223
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$60
per night

Jordan has been an animal lover all her life and would give your pet so much love while you are away. Jordan has been caring for cats and dogs her whole life and she is currently caring for an elderly cat of her own that has a complex regiment including: giving fluids, liquid oral medication and pills and powder. She would do anything for this cat, and knows how much pets weigh in our hearts. She is someone you can trust and know she would communicate any small detail while caring for your fur baby! You bet I would book with her!

Sitter Profile Image: Casandra E.
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Sitter Profile Image: Casandra E.
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20. Casandra E.

Dog mom dog lover
Milwaukee, WI, 53208
0.9 mi. away
House Sitting
5.0 out of 5 stars
5 reviews
from
$33
per night

Cassandra was great! She spent a lot of time with our animals and sent me updates frequently. She went above and beyond to make sure the dogs got a walk in everyday. She left the house exceptionally clean. I felt very at ease knowing she was caring for our pets. I would definitely reach out to her and hire her again. Thanks Cassandra!

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When it comes to house sitting, dog owners in Washington Heights, 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 Washington Heights 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.

Never beg a friend to watch your dog again. With Rover, you can find your the perfect Washington Heights house sitter in seconds. When you book house sitting on Rover, your dog will enjoy a loving, relaxing stay in their own home. If you're looking for care for pets other than dogs, you can find a pet sitter who offers care for cats, caged pets, and even horses. No matter what, you'll know that your pet is getting loving care. By removing common pet care obstacles, Rover ensures dogs nationwide are happy and well-cared for even when their human is away, and empowers dog lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a dog, Rover makes it easy for you to reach trusted house sitters in Washington Heights, Milwaukee who can provide the care your dog needs, when they need it.

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