Pet Setting & Drop Ins in Maitland Park, Milwaukee

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

Confirmed Holiday Availability
1. Simone

Let's Walk, Let's Run, Let's Hike!

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Simone is great! Very accommodating and pleasant to work with. We received updates and pictures throughout the week. Our fur babies seem very happy and we... (more)"

2. Kathleen

Big heart for all animals

Greenfield, WI, 53219

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

40 repeat clients

"This was our first time using this service with Katie, and we more than satisfied with her. Our dogs love her and she has great energy. We will definitely be... (more)"

3. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

9 repeat clients

"We had absolutely the BEST experience with Valeria. She made us feel very comfortable in understanding our fur-babies needs and taking care of them while we ... (more)"

Confirmed New Years Availability
4. Lindsey

Fur mama and dedicated dog lover

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Lindsey is pet crazy. She has a love for pets, especially dogs, that goes above and beyond. There is no dog that she does not want to keep as her own. She ... (more)"

5. Cassie

Full time animal lover!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"The instant we met Cassie, I knew it was a great fit. Her review of her drop-in visit was great. I can tell she really paid attention to my goofy shy dog whi... (more)"

6. Sonja

Experienced, Reliable, Trustworthy

Bay View, Milwaukee, WI, 53207

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Sonja was great! She always kept me updated when she went to check in! (more)"

Confirmed Holiday Availability
7. Erendira

Outdoorsy dog loving student!

Bay View, Milwaukee, WI, 53207

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Erendira is beyond awesome. She has watched my husky Tesla about 5 times now. She is a very friendly, caring, affectionate, and attentive dog sitter. I'll de... (more)"

8. April

Worry Free Pet Sitter & Whelper

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits

3 repeat clients

"Very good sitter. She was able to approach cats and interact with them quickly. I have and will recommend her to other pet lovers. (more)"

Confirmed Holiday Availability
9. Mason

Your pup will run and play all day

Saint Francis, WI, 53235

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

About: Hi, my name is Mason and I am an active dog lover. I have a Border Collie pup named Moose. So he will be with us if you're ok with a little sociali... (more)

10. Nathalia

Loving, Reliable & Energetic sitter

Gra-Ram, Milwaukee, WI, 53221

Drop-In Visits, Dog Walking

"Nathalia is just wonderful. She was so attentive and sweet with my two old boys. She gets 5 stars from me! (more)"

11. Elena

Your peace of mind is my paw-ority!

Fernwood, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Very happy with Elena. She goes above and beyond the call of duty! (more)"

Confirmed Holiday Availability
12. Kelly

Animal Lover - Responsible&Flexible

Bay View, Milwaukee, WI, 53207

Drop-In Visits, Dog Walking

2 repeat clients

"Kelly is trustworthy, kind, and professional! Since it was our first time using Rover we were worried about finding the perfect person to look after our dog ... (more)"

13. Matt

Ready to hang with your dogs!

St. Francis, WI, 53235

Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

1 repeat client

"Hi there! Matt and Jackie are wonderfully kind people. They have been involved in animal rescue groups and even adopted their former dog, Freddy, through a r... (more)"

14. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"Terry is the best, we immediately saw her love for animals, and Badger was comfortable with her right away. She was here when she said she was going to be h... (more)"

15. Erika

I'll run or walk with your dog

Bay View, Milwaukee, WI, 53207

Drop-In Visits, Dog Walking

"Erika took great care of the girls while we were out of town for the day. Both dogs were exercised and happy when we got home. Thanks!! (more)"

16. Collin

I love walks as much as your dog!

Bay View, Milwaukee, WI, 53207

Drop-In Visits, Dog Walking

"It's so valuable to have someone you trust to look after your pet - and Collin is definitely that person! He is responsible, kind, caring, and great with dog... (more)"

Available this weekend
17. Theresa

Home full time, LOVE all dogs!!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Theresa took great care of our pugs! Highly recommended. (more)"

18. Chrissy

Bay View area sitter.

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Chrissy was great! She helped me out last minute and gave me an update once she left! I will definitely consider Chrissy in the future! (more)"

19. Kara

I love dogs and the outdoors!

Cudahy, WI, 53110

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

About: As a fellow animal lover and pet owner, I understand how important it is to know that your babies are in good hands while you are busy and away. I ... (more)

20. Rebecca

Daily walks to park!

Holler Park, Milwaukee, WI, 53221

Dog Boarding, Drop-In Visits, Dog Walking

"Becky is a responsible and caring person. She is great with animals and they enjoy being with her as well! We have 2 dogs and a cat, Becky is always there if... (more)"

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 1,089 owners have reviewed sitters in Maitland Park, Milwaukee, WI, giving them an average rating of 5.0/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Maitland Park pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Maitland Park, Milwaukee, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Maitland Park pet sitters and avoid the kennel.

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 Maitland 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: