House Sitting in Holler Park, Milwaukee

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?

Search Results

Calendar Recently Updated
Sitter Profile Image: Blythe R.
Verified Background Check
Sitter Profile Image: Blythe R.
Verified Background Check
1.

Blythe R.

Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
115 reviews
58 repeat clients
from
$55
per night

Blythe was excellent! Gordon was very well taken care of. Blythe went the EXTRA MILE for my guy!! She really gave him extra TLC. He has some leg weaknesses and she was so good with him‼️She’s coming back for another 2 weeks and I know Gordon will be so happy to see her❗️I highly recommend her❤️‼️‼️‼️

Calendar Recently Updated
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
Sitter Profile Image: Jessica Z.
Verified Enhanced Background Check
2.

Jessica Z.

Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking
5.0
72 reviews
24 repeat clients
from
$55
per night

I had Jessica stay with my 9 year old hound for three weeks while we were abroad. Daily updates, wonderful communication, great pics of our furry family member, a tidy house upon our return and a happy doggo lead me to give her top marks. I feel very lucky to have found her as a dog sitter and believe you would too! Thanks Jessica!

Calendar Recently Updated
Sitter Profile Image: Jenn S.
Verified Enhanced Background Check
Sitter Profile Image: Jenn S.
Verified Enhanced Background Check
3.

Jenn S.

Animals❤️me-Available all holidays!
West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking
5.0
21 reviews
8 repeat clients
from
$60
per night

Jenn was absolutely PHENOMENAL with our furbabies, and we have a lot! She sent regular updates and we felt so comfortable knowing that she was okay with both cats and dogs. We would absolutely hire her again.

Calendar Recently Updated
Sitter Profile Image: Stephen & Wipawee D.
Verified Enhanced Background Check
Sitter Profile Image: Stephen & Wipawee D.
Verified Enhanced Background Check
4.

Stephen & Wipawee D.

Pawfessional w/ Love & Care <3
West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking
5.0
35 reviews
16 repeat clients
from
$65
per night

Stephen and Amelie provided exemplary care for our dogs, Cameron and Colby. Their kindness, coupled with their commitment to regular exercise and clear communication, put us completely at ease. They frequently updated us with photos and videos, and their prompt responses to our questions were much appreciated. In addition to taking great care of our dogs, they kept our house in perfect condition. We wholeheartedly recommend Stephen and Amelie to anyone needing reliable and loving pet sitters. We can't thank them enough for their top-notch service!

Sitter Profile Image: Katelynn K.
Verified Enhanced Background Check
Sitter Profile Image: Katelynn K.
Verified Enhanced Background Check
5.

Katelynn K.

I’ve always had a passion for dogs!
Hales Corners, WI, 53130
House Sitting, Drop-In Visits, Dog Walking
5.0
5 reviews
from
$40
per night

Katelynn was great with our puppy Hazy Rey! She sent multiple updates with pictures which was greatly appreciated! Hazy was definitely sad when she left..we could tell she missed her!!

Calendar Recently Updated
Sitter Profile Image: Felicity W.
Verified Enhanced Background Check
Sitter Profile Image: Felicity W.
Verified Enhanced Background Check
6.

Felicity W.

Animals are my full time passion 🤍
St Francis, WI, 53235
House Sitting, Drop-In Visits
5.0
19 reviews
7 repeat clients
from
$50
per night

We met Felicity the week we left for a family trip 6 hours north. She did a fantastic job of taking care of our animals (dog and two cats)! Felicity sent pictures and updates, walked the dog, let us know if he was eating, etc. and was overall very communicative. We appreciated her willingness to stay at our house within the same week we booked and we would definitely reach out again with a need for pet-sitting. Thank you Felicity!

Calendar Recently Updated
Sitter Profile Image: Patricia N.
Verified Enhanced Background Check
Sitter Profile Image: Patricia N.
Verified Enhanced Background Check
7.

Patricia N.

Love them all!
Franklin, WI, 53132
House Sitting, Drop-In Visits, Dog Walking
5.0
35 reviews
9 repeat clients
from
$30
per night

I am so glad we found Pat to take care of our girls! They just love to see her every time she steps in the door. I have only praise for Patricia with all her kindness she gives my 2 best friends, Heart and Livee. Thank you!!

Sitter Profile Image: Rachel H.
Verified Background Check
Sitter Profile Image: Rachel H.
Verified Background Check
8.

Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
House Sitting, Drop-In Visits, Dog Walking
5.0
69 reviews
21 repeat clients
from
$27
per night

Rachel was absolutely great! She stayed at my house and watched my dog who always does better at home in her own space. She sent photos throughout the weekend and my dog totally loved her. I would highly recommend her!!

Calendar Recently Updated
Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check
Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check
9.

Leandrea R.

Rover 101
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
80 reviews
30 repeat clients
from
$60
per night

Leandrea was absolutely amazing! We left for a week vacation and throughout the entire time Leandrea updated with text, photos and videos. Communication was so easy and Leandrea responded immediately!! I felt so relaxed leaving knowing my dogs were in amazing hands. We are definitely going to book Leandrea again!!! Could not recommend enough!!

Calendar Recently Updated
Sitter Profile Image: Katrina K.
Verified Enhanced Background Check
Sitter Profile Image: Katrina K.
Verified Enhanced Background Check
10.

Katrina K.

Animal Lover & Exercise Enthusiast
Fernwood, Milwaukee, WI, 53204
House Sitting, Drop-In Visits, Dog Walking
5.0
3 reviews
from
$50
per night

Simply the best.

Calendar Recently Updated
Sitter Profile Image: Miranda O.
Verified Background Check
Sitter Profile Image: Miranda O.
Verified Background Check
11.

Miranda O.

All Dogs go to heaven
Bay View, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
149 reviews
78 repeat clients
from
$70
per night

Miranda was incredible, she helped me out on such short notice, came by to meet my fur children and myself so I could feel 100% comfortable with her during her stay. She sent me photos and updates multiple times a day of all of their little quirks which was a perfect pick me up when I missed them all day. She is the sweetest animal lover and I’m pretty sure that my dogs didn’t even care about me when I returned home because they missed her head scratches (which my nail biting habit doesn’t allow). 15/10 would recommend to anyone looking for a trustworthy, caring, angel of a human to watch your fur babies. Thanks again Miranda!

Sitter Profile Image: Stephanie R.
Verified Enhanced Background Check
Sitter Profile Image: Stephanie R.
Verified Enhanced Background Check
12.

Stephanie R.

Lots of freetime=More time with dog
South Milwaukee, WI, 53172
House Sitting, Drop-In Visits, Dog Walking
5.0
32 reviews
13 repeat clients
from
$50
per night

Stephanie took amazing care of our dogs! Definitely 5/5 stars!! She was loving, kind, and prompt and we would definitely use her services again in the future!

Calendar Recently Updated
Sitter Profile Image: Samantha B.
Verified Background Check
Sitter Profile Image: Samantha B.
Verified Background Check
13.

Samantha B.

Animal lover for both dogs or cats
White Manor, Milwaukee, WI, 53219
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
11 reviews
3 repeat clients
from
$45
per night

Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.

Sitter Profile Image: Amanda B.
Verified Enhanced Background Check
Sitter Profile Image: Amanda B.
Verified Enhanced Background Check
14.

Amanda B.

Have loved animals since birth.
Greenfield, WI, 53220
House Sitting, Drop-In Visits, Dog Walking
5.0
80 reviews
26 repeat clients
from
$28
per night

Amanda took great care of our dog, and our home. She communicated every day, and was available when I checked in on the home and dog. She was amazing and I highly recommend her.

Sitter Profile Image: Markita H.
Verified Background Check
Sitter Profile Image: Markita H.
Verified Background Check
15.

Markita H.

Friendly/Compassionate/Responsible
Saint Francis, WI, 53235
House Sitting, Drop-In Visits, Dog Walking
5.0
57 reviews
4 repeat clients
from
$45
per night

Markita sent pictures and videos assuring me my babies were safe thank you so much!

Calendar Recently Updated
Sitter Profile Image: Stephanie  G.
Verified Background Check
Sitter Profile Image: Stephanie  G.
Verified Background Check
16.

Stephanie G.

Steph's Bay View Dog Support
Tippecanoe, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
48 reviews
19 repeat clients
from
$56
per night

Stephanie was amazing! She really came through for us in a pinch, and connected immediately with my elderly mini schnauzer. Seeing the daily photos of their interactions made me feel secure in the knowledge that all was well at home as we traveled. I would highly recommend Stephanie, and look forward to having her watch my pup again.

Calendar Recently Updated
Sitter Profile Image: Melissa M.
Verified Background Check
Sitter Profile Image: Melissa M.
Verified Background Check
17.

Melissa M.

Will spoil your animals rotten!!!!!
South Milwaukee, WI, 53172
House Sitting
5.0
36 reviews
16 repeat clients
from
$25
per night

As a repeat customer, I cannot recommend Melissa enough. Each time I entrust my dog and cats to her care, I am filled with peace of mind. Melissa's consistent dedication to providing top-notch care is truly remarkable. Her genuine love for dogs shines through in every interaction, and my fur babies are always happy and content when I return home. I appreciate her professionalism and reliability, as well as the regular updates and photos she provides, which make being away from my pet much easier. I am grateful to have found such a reliable and caring dog sitter in Melissa.

Sitter Profile Image: Margit B.
Verified Enhanced Background Check
Sitter Profile Image: Margit B.
Verified Enhanced Background Check
18.

Margit B.

"Wag More, Bark Less"
Milwaukee, WI, 53207
House Sitting, Drop-In Visits, Dog Walking
5.0
26 reviews
6 repeat clients
from
$40
per night

Margit was absolutely wonderful with my two big dogs. I was so impressed with her professionalism and she was great at communicating any questions and concerns. I will certainly be using her services again, thanks Margit!

Sitter Profile Image: Taylor H.
Verified Enhanced Background Check
Sitter Profile Image: Taylor H.
Verified Enhanced Background Check
19.

Taylor H.

Love being around all types of dogs
Town Of Lake, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
3 reviews
from
$27
per night

Taylor was great! He consistently sent updates and pictures of my pup while I was out of town. I never stressed with my dog in his hands.

Sitter Profile Image: Britnee S.
Verified Enhanced Background Check
Sitter Profile Image: Britnee S.
Verified Enhanced Background Check
20.

Britnee S.

Big dog, busy schedule? No problem!
Milwaukee, WI, 53207
House Sitting, Drop-In Visits, Dog Walking
1 review
from
$28
per night

Britnee has watched my two cats many times and is always very good and responsible. He has owned both dogs and cats as well as more unique pets already. I know he loves animals a lot and knows how to treat them and care for them correctly. He's trustworthy and will take good care of your pets.

Search Map

Dog owners in Holler Park, 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.

Rover.com is the simple, savvy way to find and book Holler 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 Holler 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 Holler 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 Holler 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:

House Sitting