Pet Sitting & 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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
Confirmed availability: 4th of July
Miranda O.
All Dogs go to heavenBay View, Milwaukee, WI, 53207
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Miranda arranged her schedule to fit our request and was much appreciated as we had a new puppy in the house. A life saver for us and we can see she’s a true do… (more)

from
$18
per visit
Confirmed availability: 4th of July
Aly L.
2.
Aly 
Verified Enhanced Background Check
Warning! Pets are spoiled here!Southgate, Milwaukee, WI, 53215
Dog Boarding, Drop-In Visits, Dog Walking

Aly has been so great and caring with my dog for visits! He just loves her and is so excited when she visits! (more)

from
$13
per visit
Confirmed availability: 4th of July
Hannah O.
3.
I will treat your dogs like my own!Cudahy, WI, 53110
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Hannah did an amazing job taking care of our fur babies!! She checked in at the beginning and end of every visit. She sent at least 4 pictures with every visit.… (more)

from
$20
per visit
Confirmed availability: 4th of July
Hillery F.
Happy to help!Greendale, WI, 53129
House Sitting, Drop-In Visits, Dog Walking

Hillary was great with our girls! She was very punctual and professional. She gave us the confidence and peace of mind that we were looking for! Will use again! (more)

from
$14
per visit
Calendar Recently Updated
Allie T.
5.
Experienced and Flexible SitterBay View, Milwaukee, WI, 53207
House Sitting, Drop-In Visits, Dog Walking

About: Hi my name is Allie! I’ve had pets of all shapes and sizes for my whole life, cats, dogs, squirrels, lizards you name it! For over 15 years I’ve been… (more)

from
$15
per visit
Calendar Recently Updated
6.
Jen 
Verified Background Check
Dog and cat friend for life!Cudahy, WI, 53110
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

About: I have had a dog in my house since I was 10. I have a 1 year old dog who loves playing with other dogs. I have a large basement which is great for pu… (more)

from
$13
per visit
Confirmed availability: 4th of July
Dogs Make Me HappyBay View, Milwaukee, WI, 53207
Drop-In Visits, Dog Walking

Jessica was fantastic! She was very prompt and even spent extra time with my big dogs. She left a very detailed summary and uploaded a ton of photos. Thank you … (more)

from
$15
per visit
Calendar Recently Updated
8.
Dog loving NurseOak Creek, WI, 53154
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Holly treats her two dogs like they are her children. They are loved beyond comprehension and treated with the most care. Her dogs come first and she will exten… (more)

from
$20
per visit
9.
Every animal makes me smile!Bay View, Milwaukee, WI, 53207
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Blythe is amazing with my puppy, she is very quick to respond and she is more than flexible with my crazy nursing schedule. She sent many photos and updates and… (more)

from
$35
per visit
Calendar Recently Updated
10.
Young or Old, All Dogs are WelcomeTown Of Lake, Milwaukee, WI, 53207
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Erin is great! My wife and I got a lab puppy who can't wait until I go home for lunch to let her out. Erin has been fantastic with being able to help come by … (more)

from
$15
per visit
11.
Animal lover, friendly, will spoil!St. Francis, WI, 53235
House Sitting, Drop-In Visits, Dog Walking

Teri was wonderful with my boy! He looked so happy in the photos she sent and was so tuckered out from playtime that he didn't even wake up when I came home. I'… (more)

from
$20
per visit
Calendar Recently Updated
Will treat your animals like my ownCudahy, WI, 53110
House Sitting, Drop-In Visits, Dog Walking

Brooke is very caring, responsible, and comfortable with a wide variety of animals. She is amazing with pets and will treat them like her own. My pets seem at e… (more)

from
$16
per visit
Confirmed availability: 4th of July
13.
Fur mama and dedicated dog snugglerSt. Francis, WI, 53235
House Sitting, Drop-In Visits, Dog Walking

Lindsey has looked after Bella several times, Bella is always happy and well taken care of when I get home. Lindsey communication is great and is always sending… (more)

from
$15
per visit
Confirmed availability: 4th of July
14.
Experienced, Loving CareGreenfield, WI, 53220
Drop-In Visits, Dog Walking

About: Although I'm new to paid pet sitting, I have been taking care of dogs since I was 5. I truly love dogs and will care for your furry family members … (more)

from
$16
per visit
Calendar Recently Updated
15.
Fenced yard and couch space!!Cudahy, WI, 53110
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Dean is the bomb... he is a true dog lover and my go-to caretaker. Your pup is in good hands! If you love your pet, get in contact with this guy. (more)

from
$13
per visit
16.
Part-time vet Tech FT Pet loverMaitland Park, Milwaukee, WI, 53221
House Sitting, Drop-In Visits

Leeana was nothing short of amazing. I, myself, do wildlife & small animal rescue. This (I fully admit lol) means I can be more picky than most when it comes to… (more)

from
$16
per visit
Confirmed availability: 4th of July
17.
15+ yr pet owner & dog fosterMilwaukee, WI, 53221
Drop-In Visits, Dog Walking

Michele was FANTASTIC! I had so much confidence in her, she has extensive experience with dogs, cats and small animals that I knew my pets were in great hands! … (more)

from
$13
per visit
Confirmed availability: 4th of July
18.
Experienced Animal Care TakerTown Of Lake, Milwaukee, WI, 53207
House Sitting, Drop-In Visits, Dog Walking

Mikayla is INCREDIBLE. She cared for my very reactive pitbull regularly - he didn’t like dogs, cats, or strangers. When he met Mikayla he took to her right away… (more)

from
$15
per visit
Calendar Recently Updated
19.
You leave them, I’ll love them.Greenfield, WI, 53221
House Sitting, Drop-In Visits, Dog Walking

About: I’ve had a dog of my own for 10 years, I worked at Caesars Pets in Greendale that is no longer open, I volunteered at the Humane Society. I have expe… (more)

from
$15
per visit
20.
Happy to take orders from your pet!Oak Creek, WI, 53154
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Renee really relates with all animals, I've never met anyone so compassionate about protecting them. She worked at an animal rescue in a previous occupation and… (more)

from
$15
per visit

Rover also offers Pet Sitting & Drop Ins in:

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: