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. Svea

Dog mom w/extra time & love to give

Bay View, Milwaukee , WI, 53207

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Our pups love having Svea drop in to let them out! (more)"

2. Matt

Ready to hang with your dogs!

St. Francis, WI, 53235

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

"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)"

3. Heather

Puppy breath, snuggles & love!

Saint Francis, WI, 53235

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

4 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. Terry

Paws On the Move

Southpoint, Milwaukee, WI, 53221

House Sitting, Drop-In Visits, Dog Walking

9 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)"

5. 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)"

6. Loni

Doggie vacation!

Woodland Court, Milwaukee, WI, 53220

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

2 repeat clients

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

7. 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

"Jen watched my dog, Bailey, last summer when I went on a two month trip. She was great with Bailey and really flexible about my return date. Bailey is a s... (more)"

8. 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)"

9. 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)"

10. Margaret

Stand-in best friend

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Margaret is one of those animal lovers. You know the ones. I fully trust her with my very spoiled pets. My dogs love her. She gives the best scratches. I can... (more)"

11. Dale

Dogs will be treated like family.

Cudahy, WI, 53110

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

"Dale and Diane are dog lovers. Some years ago, while visiting Hawaii, they found a wounded and abandoned dog. They brought him to the vet and then brought hi... (more)"

12. Laci

A dog lover and animal enthusist

Red Oak Heights, Milwaukee, WI, 53220

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

About: I grew up around dogs. My first dog was a greyhound rescue. As he got older his joint went bad so I have plenty of experience caring for large olde... (more)

13. 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)"

14. Laura

Dog loving, caring

Bay View, Milwaukee, WI, 53207

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

1 repeat client

About: I have experience pet sitting and dog walking for a couple people over the years. I am looking to care for dogs for my own benefit and yours. I a... (more)

15. Nancy

An affectionate animal lover!

Jackson Park, Milwaukee, WI, 53219

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

About: I am a very hands-on pet owner/ pet caretaker with an open communication style who is looking mainly for weekend opportunities as I work and go to ... (more)

16. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

25 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)"

Available this weekend
17. Lauren

Your dog won't be "ruffing" it

Bay View, Milwaukee, WI, 53207

Dog Boarding, House Sitting, Drop-In Visits

9 repeat clients

About: Watching countless hours of dogs on youtube? Guilty. Spending all of a party hanging with the host’s dog? Guilty. Staring at a dog walking ... (more)

18. 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 11 month old dog of my own; I have experience with taking care of puppie... (more)

19. Justine

energetic dog lover ❤

St Francis , WI, 53235

Dog Boarding, Drop-In Visits, Dog Walking

About: Hi, I'm Justine! I am a successful 23 year old with a love for life and adventure. I grew up with a dog my entire life, I'd love to have my own but... (more)

20. Kendra

Walks/Home Visits, South Milwaukee

South Milwaukee, WI, 53172

House Sitting, Drop-In Visits, Dog Walking

About: NOTE: I will be unavailable until further notice due to travel. (Not sure how to temporarily deactivate account). I have always loved animals, ... (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: