Pet Setting & Drop Ins in Jackson Park, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

1. Lori

Experienced dog & cat sitter

Story Hill, Milwaukee, WI, 53208

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

29 repeat clients

"I needed a pet sitter quickly. I just moved to the area and haven't had the time nor needed a sitter but something came up last minute and I was in need of o... (more)"

2. Alison

Fun & Adventurous Dental Student

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Alison is so sweet with my pit/lab mix. She is kind and caring when walking him. I love that she is very accountable and always dependable. She hasn't missed... (more)"

3. Cassie

Full time animal lover!

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"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)"

4. 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)"

5. Wendy

Book nerd who loves dogs!

West Allis, WI, 53219

House Sitting, Drop-In Visits, Dog Walking

About: I've had dogs all my life until just a few months ago. I'm a full-time graduate student working on my dissertation in English Literature. My 17 yea... (more)

6. Katherine

Reliable, devoted, diciplined.

Bay View, Milwaukee, WI, 53207

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

"Katherine kept an eye on both of our pets while we were away. She was prompt with scheduling a meet and greet and remained in good contact with us (texts and... (more)"

7. 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)"

8. 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)"

9. 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)"

10. Marisaa

Care for your pet as it were my own

Muskego Way, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

About: Hello my name is Marissa, I am an extreme dog lover. I have had experience with dogs as small as a mix chihuahua to a Doberman pincher. I absolute... (more)

11. Andrea

Cavalier mom who loves animals

West Allis, WI, 53219

Dog Boarding, Drop-In Visits, Doggy Day Care

About: I have two Cavalier King Charles Spaniels and a cat, all little ladies. I also foster dogs and cats through local rescues. My dogs get along with a... (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)"

13. Nicole

Dog-lover with time to spare!

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Nicole was wonderful to work with and made the process of booking a pet sitter very easy. She took the time to keep us posted on how things were going at hom... (more)"

14. Amy

Furry family members are the best!

West Allis, WI, 53214

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

"Amy has been a dog lover for as long as I can remember and it is apparent whenever she is around them. She has a professional and loving approach when it com... (more)"

15. Natalie

dogs are my happiness

Walker's Point, Milwuakee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

"I personally do not know anyone who is better equipped to take care of someones pet. Natalie is more than qualified she is a certified trainer, teaches class... (more)"

Available this weekend
16. 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)

17. 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)

18. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

24 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)"

19. Sam

We'll love your furbaby like ours

Martin Drive, Milwaukee, WI, 53208

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

About: Experienced dog owner of 3. We are local business owners who work from home, so we are available to be there for your furbaby, while they play with... (more)

20. Kaicey

Proud Dog Momma!

West Allis, WI, 53219

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

2 repeat clients

"Kaicey is a great dog sitter! She easily handled our elderly dog's many special needs. (more)"

Experience exceptional service and a personalized match

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

Learn About Premier

Dog owners in Jackson Park, Milwaukee, WI love booking pet sitting with sitters on Rover.com. Over 1,089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking pet sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book pet sitting with Rover? Check out our average pet sitting rates to get an idea before reaching out and starting a conversation with a pet sitter near you in Jackson Park.

Rover.com is the simple, savvy way to find and book Jackson Park, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more than 65,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Jackson Park, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

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 Jackson 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: