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.

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$10
$150
1. Sami

Will treat your dog like family!

Franklin, WI, 53132

Drop-In Visits, Dog Walking

No Reviews Yet

About: I have been around animals my whole life. I own two small dogs (Chihuahua mixes) and have experience with larger breeds, such as Labradors and Germ... (more)

from
$13
per visit
2. Sara

Animal loving 20-something

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

No Reviews Yet

About: I am an energetic, fun-loving, twenty-something in search for some extra travel cash! I I have had dogs my whole life and I absolutely love all kin... (more)

from
$13
per visit
3. Kai

Very love, much doggo, so fun ?

South Milwaukee, WI, 53172

House Sitting, Drop-In Visits, Dog Walking

No Reviews Yet

About: I love every doggo I meet! I have been taking care of dogs since I started watching my grandmas when I was a child. I'm all about the right care of... (more)

from
$10
per visit
4. Leah

Home full-time, fenced in yard

West allis, WI, 53219

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

3 reviews

"Awesome job with Lady!! Took her on multiple walks a day and made her feel right at home as if we never left. multiple updates a day from her that included p... (more)"

from
$13
per visit
5. Simone

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

Saint Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

1 review

"Simone is a caring and attentive friend both to me and to all of the animals she works with. She has a variety of experience with owning, taking care of, and... (more)"

from
$12
per visit
6. Alisia

I like dogs better than most people

South Milwaukee, WI, 53172

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

1 review

"SHE IS THE DOG LOVER OF TODAYS GENERATION.VERY WARM HEARTED INDIVIDUAL. .WHO I SEE PLAYING..LOVING N WALKING HER DOGS..N OTHERS AS WELL AS SHE WALKS HER OWN.... (more)"

from
$13
per visit
7. April

Worry Free Pet Sitter

Polonia, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

5 reviews

"April is a caring person. She loves animals(all) animals. I think she is an excellent candidate for this position. Reliable and trustworthy. If you give her ... (more)"

from
$15
per visit
8. Laura

"Love dogs and their companionship"

Castle Manor, Milwaukee, WI, 53221

House Sitting, Drop-In Visits

2 reviews

"Laura watched my two big dogs, husky and lab while we were away on vacation on multiple occasions. Our dogs are our babies and we do not trust them with just... (more)"

from
$13
per visit
9. Cassie

Full time animal lover!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients
3 reviews

"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)"

from
$17
per visit
10. Mary & Joe

Large fenced in yard, lots of room

St. francis, WI, 53235

Dog Boarding, Drop-In Visits, Dog Walking

4 reviews

"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)"

from
$15
per visit
11. Tiffany

Pet sitter in the southside area!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients
13 reviews

"We had a meet and greet with Tiffany before and we're so impressed by how attentive she was to our dog & her daily routine. We then booked her for 3 visits ... (more)"

from
$10
per visit
12. Jordan

?Every animal is a loved animal!?

Cudahy, WI, 53110

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

1 review

"She is funny and kind. Knowledgeable and understanding would make a great dog sitter knowing she owns her own and takes great care of her pup I highly recomm... (more)"

from
$13
per visit
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
7 reviews

"Matt and Jackie are wonderful dog owners. They adopted a foster dog that needed some extra love and attention. They gave Freddy the exact home he needed with... (more)"

from
$13
per visit
14. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

11 repeat clients
23 reviews

"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)"

from
$15
per visit
15. Kirstie

I have had animals all my life!

New Coeln, Milwaukee, WI, 53207

Drop-In Visits, Dog Walking

13 repeat clients
14 reviews

About: My name is Kirstie, I grew up with pets(cats and dogs), I currently have a 11 month old dog of my own; I have experience with taking care of puppie... (more)

from
$12
per visit
16. Valeria

Love is a Four Legged Word <3

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

4 repeat clients
7 reviews

"Valeria and her husband took such amazing care of our siberian husky while we were on vacation for a week. we normally leave or dog with a family member so w... (more)"

from
$15
per visit
17. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

34 repeat clients
62 reviews

"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)"

from
$15
per visit
18. Lindsay

Born and raised dog lover for life.

Bay View, Milwaukee, WI, 53207

Dog Boarding, Drop-In Visits, Dog Walking

No Reviews Yet

About: I've volunteered with multiple dog shelters, helped organized an adoption event and have owned dogs all my life. I'm an aspiring dog trainer lookin... (more)

from
$13
per visit
19. Chrissy

Bay View area sitter.

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients
11 reviews

"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)"

from
$15
per visit
20. Zhanae

The best care for your best friend!

Greenfield , WI, 53221

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

2 repeat clients
4 reviews

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)

from
$12
per visit

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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:

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