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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed Holiday Availability
1. Loni

Doggie vacation!

Woodland Court, Milwaukee, WI, 53220

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

1 repeat client

"Sweet! Loves dogs. Will book again in the future... (more)"

2. Matt

Ready to hang with your dogs!

St. Francis, WI, 53235

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

"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)"

3. Heather

Puppy breath, snuggles & love!

Saint Francis, WI, 53235

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

3 repeat clients

"Heather was great with our dog! She is a crazy puppy and took to her very quickly. I loved the Rover Report cards she sent each day. (more)"

4. Tiffany

Pet sitter in the southside area!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"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)"

5. Jennifer

Love and Play while You're Away

Bay View, Milwaukee, WI, 53207

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

"Jenn is great with animals and very reliable. I will definitely call her again to take care of our dog Sam. Great to have someone right here in Bay View. (more)"

Confirmed Holiday Availability
6. Jessica

Animal Lover to the fullest!

Town Of Lake, Milwaukee , WI, 53207

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Our separation-anxiety-ridden, scared-of-strangers, doesn't-eat-when-she's-alone dog LOVED Jessica! I truly appreciated getting text updates while we were aw... (more)"

Confirmed Holiday Availability
7. Katherine

Reliable, devoted, diciplined.

Bay View, Milwaukee, WI, 53207

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

"In my mind, Katherine and dogs are inseparable. Over the ten plus years we have known each other, her love and care for dogs has always shined though. I woul... (more)"

Confirmed Holiday Availability
8. Isaiah

A Good Time Training and Playing

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Isaiah understood my unique instructions and provided detailed feedback during time spent with my puppy. He took great pictures and set my mind at ease. I wo... (more)"

Confirmed Holiday Availability
9. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

8 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)"

Confirmed Holiday Availability
10. Amanda

Young Dog Enthusiast

Alverno, Milwaukee, WI, 53221

House Sitting, Drop-In Visits

2 repeat clients

About: -I have owned a dog for 5 years -I have dog sat for multiple families for over 10 years -I am comfortable with and have experience with dogs of a... (more)

Confirmed Holiday Availability
11. Chrissy

Bay View area sitter.

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

5 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)"

12. Baylie

I am a compassionate animal lover.

Wedgewood, Milwaukee, WI, 53220

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Baylie is a fantastic dog sitter! She is very patient, attentive and nice. Super professional also. She watched my Maltese and Maltichon for 2 nights this pa... (more)"

Confirmed New Years Availability
13. Lauren

Your dog won't be "ruffing" it

Bay View, Milwaukee, WI, 53207

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

8 repeat clients

"Super great and flexible with our ever changing schedule! Loved the updates while we were away. (more)"

14. Julia

Kind pup lover

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: Ive personally had a dog for 9 years, his name is Oscar and hes a super human loving shi zhu. I walk oscar 3 times a day, since he doesnt use our y... (more)

15. Svea

Dog mom w/extra time & love to give

Bay View, Milwaukee , WI, 53207

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

"Svea stayed at my house for a week-end while we were away. I have two mini-dachsunds who get stressed when we are away. Svea sent me a video of the dogs pla... (more)"

16. Aleisha

Nothin but Smooches for your Pooch!

Bay View, Milwaukee, WI, 53207

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

1 repeat client

"I asked Aleisha, last minute, to watch my Corgi 'Rose' so that I could attend a family get together. She had no issues with the short notice and I was able t... (more)"

17. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

18 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)"

18. Amanda

Pet lover and enthusiast.

Oak Creek, WI, 53154

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Thank you for being available very last minute when I couldn't make it home. (more)"

19. Kendra

Walks/Home Visits, South Milwaukee

South Milwaukee, WI, 53172

House Sitting, Drop-In Visits, Dog Walking

About: I have always loved animals, especially dogs, and throughout my life I have seeked out jobs that allow me to work with animals. I walked dogs and d... (more)

20. Katie

Fit and active animal lover

Morgandale, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"Katie has done exceptional work with dogs in the past. Her recent volunteer work with her local dog shelter has shown that. She loves and cares for each and ... (more)"

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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: