House Sitting in Roosevelt Grove, 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: Jessica Z.
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Sitter Profile Image: Jessica Z.
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1. Jessica Z.

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

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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2. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
2.8 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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3. Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
5.2 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: Jackie C.
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Sitter Profile Image: Jackie C.
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4. Jackie C.

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

I am a first time user of Rover.com and was nervous about leaving my dogs with someone the dogs and I didn't know. The meet and greet with Jackie helped put my mind at ease. Jackie did an amazing job taking care of my 2 dogs at my house for a little over 2 weeks. One the dogs does not trust people. It did not take him long to warm up to her, which says that she has good, calm energy. It was great that the dogs could be at home and she would come to them. I think this made the dogs less anxious. She sent us great pictures and promptly responded to texts. I would highly recommend Jackie and I would definitely use her again.

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Sitter Profile Image: Ali M.
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Sitter Profile Image: Ali M.
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5. Ali M.

I love dogs, cats, and herptiles !
Milwaukee, WI, 53211
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
36 reviews
17 repeat clients
from
$65
per night

Ali gave me such peace of mind when she watched my cat for the weekend. I’ve never used any pet sitting or boarding services prior to meeting Ali, so I really didn’t know what to expect. She was very professional, friendly, and helpful with the entire process. She sent me photo updates of my cat when she stopped in and she took such good care of everything I asked her to do. I will definitely be using her again.

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Sitter Profile Image: Payton R.
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Sitter Profile Image: Payton R.
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6. Payton R.

making tails wag one walk at a time
Milwaukee, WI, 53211
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
1 repeat client
from
$40
per night

She was the best! Very flexible, great At communication and great with our pup. Highly recommend!

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Sitter Profile Image: Danica V.
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Sitter Profile Image: Danica V.
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7. Danica V.

PAWsitively reliable med student!
Wauwatosa, WI, 53226
3.9 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.

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

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
2.4 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 is wonderful and such a doting dogsitter. Our great dane loves it when she comes and is always sad when she leaves! She's attentive to his special diet and is highly communicative. Cannot recommend her enough!

Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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9. Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 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.

Confirmed availability: Memorial Day Weekend
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
2.8 mi. away
Boarding, House Sitting, Drop-In Visits
5.0 out of 5 stars
120 reviews
58 repeat clients
from
$80
per night

Sam far surpassed our expectations! Noodles is a “handful” to say the least! He’s not quite a year and a half and still acts like a puppy in all ways. He’s also very hesitant around other dogs, which comes off as aggressive. Her first of many pictures sent to us was Noodles “calmly” sitting right in the middle of three others dogs during a pack walk! He came out of this weekend with new friends, human and four-leggers! We’ve already booked Sam for another weekend of “Noodle sitting” as well as dog walking and training! Couldn’t be happier for us and Noodles~ The McBride’s

Sitter Profile Image: Beth P.
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Sitter Profile Image: Beth P.
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11. Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53212
3.0 mi. away
House Sitting
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$60
per night

Beth is a Godsend! She stayed at our home for five days and took exceptional care of our many animals: our dog, cats, rabbits, Guinea pig and fish. We came back to a tidy house and relaxed animals. She took our dog on two mile walks and sent photos and updates regularly. We couldn’t have asked for a better sitter. She is kind and considerate. We highly recommend Beth!

Sitter Profile Image: Samantha A.
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Sitter Profile Image: Samantha A.
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12. Samantha A.

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

Samantha is a dog lover! She has been around dogs her whole life. She was responsible for crate and house training for one of our labs. She is organized and conscientious and will work hard to be sure your dog thrives in her care.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lance C.
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Sitter Profile Image: Lance C.
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13. Lance C.

Coffee loving dog walker!
Enderis Park, Milwaukee, WI, 53210
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night

Lance does great with my two lab mix (5yr/1yr). Attention-to-detail, communication, and lovable are his key qualities! You can trust him with your fur babies!

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Sitter Profile Image: Riley N.
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Sitter Profile Image: Riley N.
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14. Riley N.

Animal lover since birth! PETS=FAM
Milwaukee, WI, 53212
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$60
per night

Our boys are crabby old men and pretty high maintenance. Riley won them over though! She was so patient and they eventually started warming up to her. Will definitely rebook!

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Sitter Profile Image: Andi D.
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Sitter Profile Image: Andi D.
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15. Andi D.

I love animals!
Midtown, Milwaukee, WI, 53205
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
from
$40
per night

Andi is great! She took great care of my two dogs and kept in communication throughout her stay. She also kept my place near and tidy, which is appreciated so much. No one likes to come home to a mess after a few days away!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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16. Erica L.

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

Our pup loves Erica and had a blast the week we were away. Erica's very responsible and so loving with him. She took great care of our apt too! Can't say enough great things about her! :)

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Sitter Profile Image: Giovanni M.
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Sitter Profile Image: Giovanni M.
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17. Giovanni M.

Rover 101
Your Pup's Home Away from Home
Milwaukee, WI, 53222
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
from
$40
per night

I am so thankful for Giovanni! I was new to the Rover App and honestly didn’t expect to find someone who would be willing to take care of two nine week old energetic puppies that were not even potty trained. Giovanni agreed to puppy sit in my home for three days! He was extremely patient, gentle, and kind with Cedar and Ivy. From day one I was confident that Gio would care for the puppies the same way I do. He was communicative with me regarding his arrival time and during the day he provided me with an update on the puppies. It was a pleasure getting to know him. My only regret is that I didn’t get a picture of Gio with the puppies! Next time, Gio! 😊

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Marilia D.
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Sitter Profile Image: Marilia D.
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18. Marilia D.

I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
7 repeat clients
from
$65
per night

My kitties had a great time with their new friend Marilia. When Marilia came back to the house, even my shy Chico cat came to see her. So I guess the cats say it all. When they come to the door to greet the pet sitter, that is all I need to say. They love her.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Marie H.
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Sitter Profile Image: Marie H.
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19. Marie H.

Your Pets New Favorite Sitter :)
Martin Drive, Milwaukee, WI, 53208
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$45
per night

We recently adopted a dog and this was our first time using Rover. Marie always communicated quick and kept us updated the whole time she was with our pets. She entertained our pets and took good care of our new dog during the potty training phase. She stayed overnight and we felt like our home was respected. Would recommend Marie!

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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
2.4 mi. away
House Sitting
5.0 out of 5 stars
5 reviews
from
$33
per night

Casey was WONDERFUL dogsitting and housesitting when I was traveling. She took such great care to follow the instructions I left, and she checked in with me frequently with pictures and messages that made me feel way more secure leaving my pup. My house was very clean when I came home, and she even left some amazing little poloroids! I'll absolutely be booking her again!

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Dog owners in Roosevelt Grove, 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.

Never beg a friend to watch your dog again. With Rover, you can find your the perfect Roosevelt Grove 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 Roosevelt Grove, Milwaukee who can provide the care your dog needs, when they need it.

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