House Sitting In Uptown 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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Jessica Z.
Loving sitter, enthusiastic walkerRiverwest, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Jessica was terrific! My 2 cats who really don’t like to be left alone,(ie: hold a grudge and snub me) behaved as if I had not left them! Not much more to say! (more)

from
$40
per night
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Malissa N.
Specialized in House/Dog SittingUpper East Side, Milwaukee, WI, 53211
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Malissa was absolutely wonderful! She watched our pups Wednesday - Saturday overnight and took great care of them! You could tell they were super comfortable wi… (more)

from
$65
per night
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Dominique L.
Flexible and willing to travel!Murray Hill, Milwaukee, WI, 53212
House Sitting, Drop-In Visits, Dog Walking

Dominique is simply wonderful. She cared for my menagerie of pets - dogs, cat, and chickens - for a 3-day weekend. This was my first time leaving the entire cre… (more)

from
$37
per night
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Marina M.
4.
You deserve a worry free getaway!Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

If you are looking for a stress-free getaway knowing that your pet is in great hands, I truly cannot recommend Marina enough! Marina stayed 3 nights with our do… (more)

from
$65
per night
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Briana M.
5.
Active, responsible, kind pet loverWauwatosa, WI, 53213
House Sitting, Drop-In Visits, Dog Walking

Bri took excellent care of our puppy! She made sure he was keeping with his regular schedule as well as adding to his daily activities! He was in great spirits … (more)

from
$50
per night
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6.
Ready for a puur-fect getaway? 🦮🐱Riverwest, Milwaukee, WI, 53212
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Sarah was a perfect fit for us and our dogs! She was super energetic and affectionate towards our pups. She sent lots of pictures and videos of our doggies and … (more)

from
$32
per night
Confirmed availability: 4th of July
7.
Can't Wait to Meet Your Fur Baby!Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking

Ameera has watched after our bernese mountain dog twice now: once for a walk and once for an overnight stay. She is reliable and good at communication. Defin… (more)

from
$70
per night
8.
** Mission: meet ALL the dogs **Milwaukee, WI, 53214
House Sitting, Drop-In Visits, Dog Walking

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… (more)

from
$27
per night
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9.
I <3 furry friends & miss my fam’sLower East Side, Milwaukee, WI, 53202
Dog Boarding, House Sitting

Talor was a great sitter! She asked a bunch of questions when booking to make sure she understood my pet and how to best care for him. She checked in often and … (more)

from
$95
per night
Confirmed availability: 4th of July
10.
The right sitter FUR you ♥️Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits

Shabana stayed in our home with our 2 large dogs for 6 nights while we were on vacation and she did amazing! She gave us updates and pictures every day. One of … (more)

from
$50
per night
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11.
Hardworking, passionate, and lovingWauwatosa, WI, 53226
House Sitting, Drop-In Visits, Dog Walking
3 years of experience

About: I’ve worked in multiple boarding facilities since 2020. I became a surgical vet assistant in 2021 and I’m in school to become a certified veterinary … (more)

from
$60
per night
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12.
"Wag More, Bark Less"Martin Drive, Milwaukee, WI, 53208
House Sitting, Drop-In Visits, Dog Walking

Margit was thorough. She loves our dogs (we have a senior and a puppy so we run the gamut of needs) and attended to all their needs perfectly. She took tremendo… (more)

from
$35
per night
13.
Former teacher needs pet loveWauwatosa, WI, 53213
House Sitting, Drop-In Visits, Dog Walking

Mary's service is amazing, truly like trusted family. So detailed, conscientious, trustworthy, communicative, and so knowledgeable and loving with our dog. We a… (more)

from
$40
per night
14.
Love Them Like My OwnBluemound Heights, Milwaukee, WI, 53213
House Sitting, Drop-In Visits, Dog Walking

This was my first time leaving my babes for an extended period of time with a dog sitter and I am thoroughly impressed with Laura! She was very nice and patient… (more)

from
$50
per night
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15.
Love & Exercise for your dog or catMartin Drive, Milwaukee, WI, 53208
House Sitting, Drop-In Visits, Dog Walking

Travis was great with our pets. Our three dogs and two cats were well cared for. The dogs were surprisingly chill when we got home not crazy, barking pups like … (more)

from
$50
per night
Calendar Recently Updated
16.
Love all animals like they are mineKops Park, Milwaukee, WI, 53222
Dog Boarding, House Sitting, Doggy Day Care
15 years of experience

About: I have had pets my whole life. I pet sit for my friends often. I love all pets and will treat them as if they are mine. I work from home, so I will … (more)

from
$28
per night
Calendar Recently Updated
17.
Pet loving medical studentWashington Heights, Milwaukee, WI, 53208
House Sitting, Drop-In Visits, Dog Walking

Heidi was a great sitter. Easy to communicate with and Duke liked her! We will use her again (more)

from
$50
per night
Calendar Recently Updated
18.
Loving Pet SitterEnderis Park, Milwaukee, WI, 53210
House Sitting, Drop-In Visits, Dog Walking
10 years of experience

About: Hello all! I'm a 22 year-old college student currently studying to get my undergraduate degree with plans to go to graduate school in the future. I'v… (more)

from
$30
per night
19.
Experienced Flexible ResponsibleWauwatosa, WI, 53213
House Sitting, Drop-In Visits, Dog Walking

Shelby watched my two cats recently, she was great she pictures to me of my kitties and her communication skills are super helpful! She is extremely responsible… (more)

from
$40
per night
Confirmed availability: 4th of July
20.
Where your pups are loved and comfyUptown, Milwaukee, WI, 53210
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Growing up with dogs made me have a passion to care for them… they are truly my babies! I go the extra mile to ensure they are well taken care of. D… (more)

from
$40
per night

When it comes to house sitting, dog owners in Uptown, 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 Uptown 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 Uptown 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 Uptown, 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 Uptown 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 dog sitter. 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 Uptown, 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: