House Sitting in Roosevelt Grove, Milwaukee

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

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Isabella C.
Open and flexible dog attendeeKilbourn Town, 53233, WI, 53233
Dog Boarding, Doggy Day Care, Dog Walking

Isabella was amazing! She help us out with taking care of our little pup Bigos on last minute request. She was very flexible and easy to communicate and Bigos w… (more)

from
$35
per night
Confirmed availability: Memorial Day
Cindy T.
2.
TOTAL DOG LOVER :)Wauwatosa, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Our one year old German Shepherd had a wonderful weekend with Cindy and her family. We loved getting pics and updates about his stay. I would recommend Cindy … (more)

from
$35
per night
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Mae V.
3.
Mae 
Verified Background Check
Welcome to Our Pawsome Family!Washington Park, Milwaukee, WI, 53208
Dog Boarding, Drop-In Visits, Dog Walking

I recommend Mae. She makes sure my puppy is good hands. She keeps me updated/ sends me pictures and videos of my Biscotti from time to time. I will definitely … (more)

from
$55
per night
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Megan P.
4.
I love pets! Pets are family :)Avenues West, Milwaukee, WI, 53233
Dog Boarding, Drop-In Visits, Dog Walking

Megan has been a dog lover since she was a toddler. She grew up with a dog from birth and later helped raise a puppy starting at 10 years old. Over the years … (more)

from
$35
per night
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Deann R.
5.
Multiple walks and cuddles!Washington Heights, Milwaukee, WI, 53208
Dog Boarding, Doggy Day Care

Deann was great! She sent us updates and pictures of walks and playing. I know that Waski had a great time with the other dogs too. Thanks a bunch! (more)

from
$35
per night
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6.
Every animal makes me smile!Bay View, Milwaukee, WI, 53207
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Blythe watched my dog for the first time this past week, which is the longest I’ve been away from him! I was nervous to leave him with a new-to-us dog sitter fo… (more)

from
$35
per night
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7.
I am a avid pet lover.West Allis, WI, 53214
Dog Boarding

She is fantastic. I had a good feeling about her when I made my choice. And if I were to need Willowsitting services again. Dawn will be my first choice! (more)

from
$40
per night
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8.
Where your pups are loved and comfyUptown, Milwaukee, WI, 53210
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Laila had a great time and I can tell she was well cared for, Ariel was fun, sweet, and respectful thru out. Thanks Again (more)

from
$60
per night
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9.
Dog lover work from homeWest Allis, WI, 53214
Dog Boarding, Doggy Day Care

Jill took wonderful care of our pup in the week that he stayed with her. I was nervous about being separated from Macchi for the first time since we adopted him… (more)

from
$45
per night
Confirmed availability: Memorial Day
10.
I’m a dog lover! ?Lincoln Creek, Milwaukee, WI, 53216
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Kadijah was great! Would definitely feel comfortable having her board my dog again and would recommend her to any friends or family that needed a dog boarded. … (more)

from
$60
per night
We’ll meet your dog's needs!Grasslyn Manor, Milwaukee, WI, 53216
Dog Boarding, Drop-In Visits, Dog Walking

Elizabeth and her family are awesome. She took excellent care of Lovey and kept me updated with daily pictures and messages. I would rebook without hesistatio… (more)

from
$32
per night
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12.
Accommodating, responsible, lovingKops Park, MILWAUKEE, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Sara was such a great choice for my dog. It was very late notice but she really came through and took great care of Bubba. She updated me multiple times during … (more)

from
$34
per night
13.
Kim 
Verified Enhanced Background Check
Fenced yard and lots of love!Timmerman West, MILWAUKEE, WI, 53225
Dog Boarding

Kim and Joe watched our pups at the last minute and were so wonderful! Our dogs have quite a bit of specific instructions and needs and they were so accommodati… (more)

from
$27
per night
Confirmed availability: Memorial Day
14.
Lover of all pets!Mount Mary, Milwaukee, WI, 53222
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

She seemed very nice & caring towards my dog. Let him play in the yard & etc. Sent pictures just about everyday. Responds to your messages in a timely manner. (more)

from
$45
per night
Confirmed availability: Memorial Day
your pets are my priority.West Allis, WI, 53227
Dog Boarding, Drop-In Visits, Doggy Day Care

Leandrea was amazing with my only 2 month old puppy! She has an older pup who played really well with him and she was amazing at keeping me updated on how he wa… (more)

from
$40
per night
16.
Love to walk and cuddle.Whitefish Bay, WI, 53217
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Rhonda took very good care of Pickles. She sent lots of pictures. Took her on lots walks, and gave her a lot of attention. Very satisfied with the care Pickles … (more)

from
$30
per night
Calendar Recently Updated
17.
Warm, loving, home like suroundingsWest Allis, WI, 53219
Dog Boarding, Doggy Day Care

My Ronaldo had a great time with Dan and Holly! Dan was really good about giving me updates on how he is doing. I will be rebooking them again. (more)

from
$35
per night
Confirmed availability: Memorial Day
18.
Wee looove the fur babies ♥️Kops Park, Milwaukee, WI, 53222
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Yisel took amazing care of my dog! She provided many updates and was super detailed! Would highly recommend! (more)

from
$40
per night
Confirmed availability: Memorial Day
19.
Home 24/7 NO KennelingLincoln Village, Milwaukee, WI, 53215
Dog Boarding, Doggy Day Care

Awwwww, words can not describe how amazing I feel relative to the service Carina provided for my baby boy! We had to leave one another for approximately 5 days … (more)

from
$45
per night
Calendar Recently Updated
Ready to play and cuddleAlverno, Milwaukee, WI, 53220
Dog Boarding

They were so flexible and accommodating to my indecisive times for drop off and pickup. I truly appreciated the flexibility and my dog had a blast. She was so… (more)

from
$28
per night

Dog owners in Roosevelt Grove, Milwaukee, WI turn to house sitters on Rover.com for their house sitting needs. Over 1,089 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.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Roosevelt Grove, Milwaukee donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Milwaukee.

We're proud to support over 200 organizations across the nation, including: