Pet Sitting & Drop Ins in Holler Park, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

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

Search Results

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Kailey S.
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Sitter Profile Image: Kailey S.
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1.

Kailey S.

Committed to making your pet happy
Oak creek, WI, 53154
Drop-In Visits, Dog Walking
5.0
48 reviews
9 repeat clients
from
$18
per visit

Kailey was awesome! She kept me up to date on my cat with pics and care given.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Sarah J.
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Sitter Profile Image: Sarah J.
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2.

Sarah J.

I’m awkward with humans.
West allis, WI, 53219
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
61 reviews
25 repeat clients
from
$13
per visit

Sarah, was fantastic. Our dog was very well taken care of. Sarah took care of Odie as if he was her own dog, she played with and sent picture of the interactions between them.. she went way past our expectations. We will be calling on her again.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Lisa W.
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Sitter Profile Image: Lisa W.
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3.

Lisa W.

Here to be kind to your pets!
Bay View, MILWAUKEE, WI, 53207
House Sitting, Drop-In Visits, Dog Walking
5.0
18 reviews
6 repeat clients
from
$12
per visit

Lisa did great with drop ins to check on our pup, take out him potty, and hang out for a bit. She followed instructions & made an effort to get comfortable with our pup beforehand. We will definitely book again for future needs!

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Sitter Profile Image: Michele M.
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Sitter Profile Image: Michele M.
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4.

Michele M.

15+ yr pet owner & dog foster
Milwaukee, WI, 53221
Drop-In Visits, Dog Walking
5.0
21 reviews
10 repeat clients
from
$20
per visit

Michele was awesome and very accommodating! She was able to help out with my kitties at the last minute and even stopped by beforehand for a meet and greet. Thank you!!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Joshua J.
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Sitter Profile Image: Joshua J.
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5.

Joshua J.

All breeds & behaviors ❤️ All-Ages❤
South Milwaukee, WI, 53172
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
38 reviews
18 repeat clients
from
$18
per visit

Can't say enough good things about Joshua! I run a cleaning business full time and I have been sitting with Joshua for a year now. He is a life saver, he takes great care of my cat Sabrina, and my dog Aurora, they always get excited when I arrive to his home. He always welcomes them with a smile on his face and open arms. Thank you Joshua, see you tomorrow!

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Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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6.

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
85 reviews
32 repeat clients
from
$15
per visit

Leandrea did a superb job with my kitty Sunny! I was anxious about leaving him due to him just having surgery a couple of days prior, but I was immediately put at ease with her quality of care! I would recommend her to anyone looking for care for their pet! I will definitely be booking for all my pet needs in the future! Thank you for being so wonderful!

Sitter Profile Image: Stephanie R.
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Sitter Profile Image: Stephanie R.
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7.

Stephanie R.

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

Stephanie did such a great job watching my boys! She sent tons of pictures and updates that make being away from your pet easier. My pups were well taken care of while I was away ?

Sitter Profile Image: Mary C.
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Sitter Profile Image: Mary C.
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8.

Mary C.

Will care for pet your like my own!
GREENFIELD, WI, 53220
Drop-In Visits, Dog Walking
5.0
39 reviews
13 repeat clients
from
$15
per visit

Mary is a great communicator - she let me know when she was at my house and sent pics during her visit. Overall, she was a caring, attentive friend to my furries! I would absolutely partner with Mary again. 😊

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Berenice B.
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Sitter Profile Image: Berenice B.
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9.

Berenice B.

Rover 101
I walk to keep their tails waggin’
Bay View, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
17 reviews
10 repeat clients
from
$20
per visit

Berenice takes an interactive approach with our dog. She loves playing with and taking the dog around the neighborhood. We loved having her take him for the weekend.

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Sitter Profile Image: Jennifer F.
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Sitter Profile Image: Jennifer F.
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10.

Jennifer F.

Lots of Love & Care from Jenn
Jackson Park, Milwaukee, WI, 53215
Drop-In Visits, Dog Walking
5.0
2 reviews
2 repeat clients
from
$15
per visit

Jennifer is super organized and very patient. She walked and talked with Charlotte. All good stuff.

Sitter Profile Image: Julia R.
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Sitter Profile Image: Julia R.
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11.

Julia R.

I have experience for dogs
Cudahy, WI, 53110
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
3 reviews
2 repeat clients
from
$14
per visit

Julia has been SUCH a huge help to me with my dog Payton. She’s very responsive, reliable, kind, sends the cutest pics while I’m away at work and takes amazing care of P. I would recommend her for any service you may need :)

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Sitter Profile Image: Hillary S.
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Sitter Profile Image: Hillary S.
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12.

Hillary S.

Rover 101
Experienced and loving pet sitter!
Town Of Lake, Milwaukee, WI, 53207
House Sitting, Drop-In Visits, Dog Walking
5.0
50 reviews
18 repeat clients
from
$23
per visit

Hillary did an amazing job with my dogs!!! She was super helpful, and very accommodating to my weird schedule! My dogs are older, and she took such great care of them! My one dog is even on a special diet, and she made sure the feedings were right. Took them on a little walk, and even sent me pictures. Very trustworthy and compassionate!!!!! Plan on continuing to utilize her while in the area, and highly recommend her to everyone!:)

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Sitter Profile Image: Katerina H.
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Sitter Profile Image: Katerina H.
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13.

Katerina H.

RN looking to care for non humans
Milwaukee, WI, 53215
Drop-In Visits, Dog Walking
5.0
16 reviews
5 repeat clients
from
$20
per visit

Very friendly, responsible, and reliable!

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Sitter Profile Image: Katie D.
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Sitter Profile Image: Katie D.
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14.

Katie D.

I can't wait to meet your fur baby!
Cudahy, WI, 53110
House Sitting, Drop-In Visits, Dog Walking
5 reviews
1 repeat client
from
$18
per visit

Katie was great with Chatty who is a 6 month old Jack Russell/Dalmatian mix. Chatty is a very active dog who is difficult to control on the leash but Katie was up to the task and handled her well. I highly recommend Katie as she is very caring and dependable.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Connie A.
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Sitter Profile Image: Connie A.
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15.

Connie A.

I will treat your's like my own
Cudahy, WI, 53110
House Sitting, Drop-In Visits, Dog Walking
5.0
8 reviews
5 repeat clients
from
$15
per visit

Super awesome with our dog. He seemed so happy when I went home to take him out later!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Markita H.
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Sitter Profile Image: Markita H.
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16.

Markita H.

Friendly/Compassionate/Responsible
Saint Francis, WI, 53235
House Sitting, Drop-In Visits, Dog Walking
5.0
59 reviews
4 repeat clients
from
$18
per visit

Markita was excellent-gave lots of great care and attention to my cats and great communication. I appreciate that she makes sure to know your exact communication and update preferences since many owners may differ on the level of detail and specificity of updates on the visits. I definitely will be a repeat customer!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Hannah O.
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Sitter Profile Image: Hannah O.
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17.

Hannah O.

Rover 101
I will treat your dogs like my own!
Cudahy, WI, 53110
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
371 reviews
181 repeat clients
from
$25
per visit

Hannah was recommended to me from a friend, and she was great with Lucy! My dog is shy with new people and not always willing to go outside to potty but she was able to coax Lucy out. Hannah wrote detailed care cards on how her visits went and sent great pictures. Will definitely book again when needed in the future!

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Sitter Profile Image: Anjalee G.
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Sitter Profile Image: Anjalee G.
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18.

Anjalee G.

ur pets next best friend 🩵
Tippecanoe, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
3 reviews
from
$18
per visit

Hello! Love Anjalee, she was always so great around my fur babies, they would always love when she was around. She would take them to the park, she even got one of them kinda trained! He can sit, roll over, and play dead! 😂 Super awesome 👍🏽

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Elaine P.
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Sitter Profile Image: Elaine P.
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19.

Elaine P.

Experienced & loving pet owner!
Milwaukee, WI, 53207
Drop-In Visits, Dog Walking
5.0
15 reviews
6 repeat clients
from
$17
per visit

As always, very dependable and my girls love her! Kaia and Pepper were well taken care of and I looked forward to reading the check in notes and seeing their pictures. I can appreciate the thoughtfulness and care Elaine provides. I will continue to use Elaine whenever she is available. 😊

Sitter Profile Image: Taylor H.
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Sitter Profile Image: Taylor H.
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20.

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
1 repeat client
from
$20
per visit

About: I’ve taken care of every different kind of dog. I owned a ranch and people would drop dogs off and leave them. From puppies all the way up to seniors. My dog of 13 years passed away from old age in 2021. Not ready to have my own but I’d love to be around others dogs. I’m off work every Wednesday, Thursday, Saturday, and Sunday. I will be home all day on each of those days. I can spend as much time with your dog as you/they want. There is a dog park near my house that I can take your dog to. Also many places to walk them. I can play with them as much as they want.

Search Map

When it comes to pet care and pet sitting, pet owners in Holler Park, Milwaukee, WI trust their pets with sitters on Rover.com. Over 1,089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5. Pet sitting doesn't have to be expensive. In fact, it's probably a lot more affordable than you think. You'll quickly find that there's a pet sitter on Rover for just about every price range and lifestyle. Wondering how much you might expect to pay for a pet sitter and pet care on Rover? Check out our average pet sitting rates to get an idea before you begin a conversation with a sitter who seems like a great match.

Rover.com is the simple, savvy way to find and book Holler Park, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 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, so you're sure to find the perfect pet sitter in Holler Park, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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:

Drop-In Visits