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.

1. Molly

Here to make your doggo's day!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Molly is a great pet sitter! I have three dogs, small, medium and large and she has watched them for multiple days on numerous occasions. I never worry when... (more)"

2. 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)"

3. Mary & Joe

Large fenced in yard, lots of room

St. francis, WI, 53235

Dog Boarding, Drop-In Visits, Dog Walking

2 repeat clients

"I work 2nd shift and Mary comes over to let my dog out while I am away. She is trustworthy and my dog is always very happy to see her. (more)"

4. April

Worry Free Pet Sitter & Birthing He

Polonia, Milwaukee, WI, 53215

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

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)"

Available this weekend
5. 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)"

6. Sonja

Experienced, Reliable, Trustworthy

Bay View, Milwaukee, WI, 53207

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

"I had Sonja watch my sweet little papillon, Jolene, while I was on vacation. I was very grateful to have Jolene in her care because I never had to worry abou... (more)"

7. 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)"

8. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

39 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)"

9. 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)

10. Kirstie

I have had animals all my life!

New Coeln, Milwaukee, WI, 53207

Drop-In Visits, Dog Walking

13 repeat clients

About: My name is Kirstie, I grew up with pets (cats and dogs), I currently have a 1 year and 7months old dog and a 3 month old puppy of my own; I have ex... (more)

11. Jasna

Take a Paws

College Heights, Milwaukee, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

3 repeat clients

"Jasna was awesome with my Puppies, she even went above and beyond what she had to do and took care of some mess puppies made home before she got there. (more)"

12. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

7 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)"

13. Gail

Safe, secure and lots of TLC!

Town Of Lake, Milwaukee, WI, 53207

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

8 repeat clients

"Gail was great with entertaining Oscar and smart enough to bring treats. Oscar doesn't always take to women right away but he seemed to enjoy Gail's company. (more)"

14. Breanna

Dog Loving Grad Student

Greenfield, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I have observed Breanna's dog caregiving skills for over ten years. I have seen her care for our own pets, including four different breeds of dogs, as well a... (more)"

15. Brea

Fetch, walks, and snuggles :)

Greenfield, WI, 53221

Drop-In Visits, Dog Walking

3 repeat clients

About: Hi my name is Brea! I have grown up with dogs my whole life and love to be around them whenever I can. Growing up I had a black lab setter mix and ... (more)

16. Celia

I'll tire your dog out!

Bay View, Milwaukee, WI, 53207

Drop-In Visits, Dog Walking

"Able to accommodate my crazy work schedule to meet the dog and kept me informed through the day. (more)"

17. 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)"

18. Zhanae

The best care for your best friend!

Greenfield, WI, 53221

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

4 repeat clients

About: (Please call my Rover phone number to discuss services) It has always been a dream of mine to become a pet sitter. I have 10+ years of pet sitting,... (more)

19. 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)"

20. 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)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

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: