House Sitting in Jackson Park, 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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Blythe R.
1.
Every animal makes me smile!Bay View, Milwaukee, WI, 53207
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Blythe was absolutely amazing from start to finish! I am always worried leaving my dogs as they are my baby's! I get the highest of anxieties having to leave th… (more)

from
$35
per night
Travis H.
2.
Love & Exercise for your dog or catMartin Drive, Milwaukee, WI, 53208
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Travis did a great job. He communicated well throughout the entire process and was easy to work with. He provided photos and updates throughout the 3 days he … (more)

from
$40
per night
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Rachel H.
3.
** Mission: meet ALL the dogs **Lower East Side, Milwaukee, WI, 53211
House Sitting, Drop-In Visits, Dog Walking

Rachel went above and beyond house sitting my two pets for the week. When my dog had some unexpected stomach issues, she took great care of him and provided upd… (more)

from
$27
per night
Teri B.
4.
Animal lover, friendly, will spoil!St. Francis, WI, 53235
House Sitting, Drop-In Visits, Dog Walking

Teri was wonderful! She checked in everyday and sent us pictures. The animals were happy and well cared for when we got home and the house was very clean. Defin… (more)

from
$30
per night
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Renee R.
5.
Happy to take orders from your pet!Oak Creek, WI, 53154
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

My dogs were so well loved and cared for while we were out of town. Renee did a great job, and my dogs were so happy in all the pictures she sent. I don't think… (more)

from
$35
per night
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6.
Meg 
Verified Background Check
I love to walk and play with dogsAvenues West, Milwaukee, WI, 53233
House Sitting, Drop-In Visits, Dog Walking

Meg has frequently taken care of my two dogs and one cat. She is responsible and loving while caring for my pets. Meg has proven to be dependable, timely and … (more)

from
$35
per night
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7.
Experienced, reliable, retired!!!!!Historic Third Ward, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Laurie is truly the best dog walker/home sitter we have ever had for our Bearded Collie Buzz. He is always so excited to see Laurie for his walks. We just rec… (more)

from
$50
per night
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8.
Ready to give all the belly rubs!Greenfield, WI, 53228
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

I have known Alyssa since she was in first grade. From the time I have known her, she has been a true animal lover. She has volunteered at dog rescues and has t… (more)

from
$35
per night
9.
Neighbor providing additional loveJuneau Town, milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

I cannot recommend Jeremy enough. He is easy to work with, thoughtful and considerate, and has a wonderful way with dogs. We were concerned that our red heeler … (more)

from
$33
per night
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10.
Love is a Four Legged Word <3Greenfield, WI, 53221
House Sitting, Drop-In Visits, Dog Walking

Once again, Valeria has been beyond accommodating. We booked her for a weekend while we got away, but when flight after flight got cancelled, extending our time… (more)

from
$45
per night
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11.
Never met a dog I didn't likeWest Allis, WI, 53214
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care

About: I've had dogs of all sorts and sizes my entire life. From training to going for walks to simply hanging on the couch, I always enjoy furry company. … (more)

from
$30
per night
Confirmed availability: Memorial day
12.
True compassion for all animalsWauwatosa, WI, 53213
House Sitting, Drop-In Visits, Dog Walking

My dog loves Gina more than my dog loves me.....Gina is simply wonderful with the care of my 5 year old Golden. (more)

from
$40
per night
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13.
Purrrrrrfect and Roof Roof!!!West Allis, WI, 53214
House Sitting, Drop-In Visits, Dog Walking

Our dogs loved their time with Lori! She spent time with them, took them on walks, and even got them some toys they love. Lori was great at communicating with u… (more)

from
$45
per night
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14.
I <3 furry friends & miss my fam’sLower East Side, Milwaukee, WI, 53202
Dog Boarding, House Sitting

Talor was amazing!!! Super responsive, personable, and made sure to send photo updates each day we were away. She was very attentive to our dog and made sure he… (more)

from
$30
per night
Confirmed availability: Memorial day
15.
All Dogs go to heavenBay View, Milwaukee, WI, 53207
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Miranda did a great job taking care of our dog and cat for the weekend! Communication was always consistent and the photos she took are definitely frame-worthy! (more)

from
$30
per night
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16.
WHO let the 🐕 🐩 🐕 dogs out ???!?Bay View, Milwaukee, WI, 53207
House Sitting, Drop-In Visits, Dog Walking

Becca would be the perfect dog caregiver for you! She is a reliable, friendly and compassionate person. She has a dog who she loves dearly! Becca has spent many… (more)

from
$45
per night
Calendar Recently Updated
17.
Professional Sitter, Fenced YardMorgandale, Milwaukee, WI, 53215
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sara is great. She takes wonderful care of my pets as if they were her own. She is gentle with my blind, almost 16 year old dog and patient with my nervous and … (more)

from
$125
per night
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Welcome dog owners!Bay View, Milwaukee, WI, 53207
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Christina is wonderful and our interactions have been excellent right from the start. Our meet and greet went smooth, she followed all our instructions and was … (more)

from
$35
per night
Confirmed availability: Memorial day
19.
Compassionate Animal Lover!Greenfield, WI, 53220
House Sitting, Drop-In Visits, Dog Walking

She is a very energetic person with extensive knowledge on most pets and animals. She is super sensitive to your pets needs. We hired her for a month while me a… (more)

from
$50
per night
Confirmed availability: Memorial day
20.
Dog mom who loves all animals!Greenfield, WI, 53220
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Janice has both walked and watched my dog for a long time now and all I have to say is, she’s awsome with Luca my dog. She is very patient with him as he can b… (more)

from
$55
per night

Rover also offers House Sitting in:

When it comes to house sitting, dog owners in Jackson Park, Milwaukee, WI love Rover.com. Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of house sitting in Jackson Park 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.com is the simple, savvy way to find and book Jackson Park house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Jackson Park, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Jackson Park house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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 Jackson Park, 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: