Pet Setting & Drop Ins in Wilson 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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1. Sherry

Homemaker/Fenced yard

Lyons Park, Milwaukee, WI, 53220

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

"Sherry was absolutely wonderful!! She did drop in visits at my home while I was gone for the weekend. She kept me updated with lots of photos and videos. She... (more)"

Confirmed availability
This weekend
2. Tiffany

Caring Petsitter on the southside!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

"Tiffany was quick to respond to my messages, took detailed notes during our meet & greet, and was very friendly. I came home from vacation to two healthy, ha... (more)"

Confirmed availability
Christmas and New Year
3. Natalie

Social and Active, Loves Outdoors!

Cudahy, WI, 53110

House Sitting, Drop-In Visits, Dog Walking

"First time having a dog walker and Natalie was great. I would recommend her to anyone. (more)"

Confirmed availability
Christmas and New Year
4. Miranda

All Dogs go to heaven

Bay View, Milwaukee, WI, 53207

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

"I am so lucky to have contacted Miranda. She has gone above and beyond for my puppy. She spends more than enough time with her, is helping me get her trained... (more)"

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5. Lindsey

Fur mama and dedicated dog lover

Cudahy, WI, 53110

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 send... (more)"

6. Jen

Near parks and lake trail.

Fernwood, Milwaukee, WI, 53207

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

"Jen is a very special girl. She loves all animals from frogs to orangutans. But her special love is dogs. She had her own mixed terrier for over 16 years and... (more)"

Confirmed availability
Christmas and New Year
7. Amanda

Home full time, love to play

Greenfield, WI, 53221

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

"Amanda went above and beyond caring for our two Dobermans while we were out if town. Our female is a senior and requires meds in the morning and evening an... (more)"

8. Vanessa

Lots of TLC

Burnham Park, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"Vanessa did a great job with my old dog. She was patient with him since he moves slow and he took a liking to her calm demeanor immediately. Her check-ins we... (more)"

Confirmed availability
Christmas and New Year
9. Kaitlyn

All Breed-Loving, Optimist Sitter

Historic Mitchell Street, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

"Kaitlyn did an amazing job with our dogs. Both of our dogs have special needs and she handled them with care and contacted us along the way! We felt like our... (more)"

Confirmed availability
Christmas and New Year
10. Maria

Duplex with a fenced yard.

Burnham Park, Milwaukee, WI, 53215

Dog Boarding, Drop-In Visits, Dog Walking

"As a long time friend of Maria, I can confidently vouch for her empathy and compassion towards dogs, cats, and every animal in between. A kind soul, Maria c... (more)"

11. Kathleen

Big heart for all animals

Greenfield, WI, 53219

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

"Kathleen was great with my dog (and 2 cats) including giving daily meds to the dog, and making sure my super skittish, formerly feral, cat got food, even tho... (more)"

12. Anna

Home full time and live near Park

Mitchell West, Milwaukee, WI, 53221

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

"I was traveling and very nervous about leaving my dog with a new caregiver for the day. Anna was so caring with Kona, and he was very content with his visit.... (more)"

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13. Janel

Pawsitively just like home!

Jackson Park, Milwaukee, WI, 53219

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

"Janel is awesome. She's rad with our dogs and she's a very much a dog person. The pups immediately took to her. Communication was very good and she was on ti... (more)"

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14. Erendira

Outdoorsy dog loving student!

Bay View, Milwaukee, WI, 53207

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

"Eren was amazing. I literally had my original sitter cancel last second due to a family emergency, then Eren stepped up into an unknown situation and knocked... (more)"

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15. Maddy

Your Furry Friend in Great Hands

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Maddy was great!! I was able to rest assured my cat was in good hands during my time away. Maddy was responsible, attentive to my cats needs, and provided th... (more)"

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16. Heather

Puppy breath, snuggles & love!

Saint Francis, WI, 53235

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

"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)"

Confirmed availability
Christmas and New Year
17. Hannah

Great backyard for outside time!

Bay View, Milwaukee, WI, 53207

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

"Great person who took the time to meet our dog before working with him. She consistently informed us on how he was doing and sent pictures. (more)"

Confirmed availability
Christmas and New Year
18. Courtney & Timothy

Fenced in yard made for playing!

Greenfield, WI, 53221

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

"Courtney is a responsible, friendly young lady who will take awesome care of your pet!! She has had pets all of her life and has experience caring for other... (more)"

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19. Alexa

Devoted, Fun-Loving, Outdoorsy

St. Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

"I have known Alexa for years and I have found her to be very creative, loving, and incredibly caring to others. Not only does she display these qualities, bu... (more)"

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20. Alysha

Warm Home with a Fenced Yard

Bay View, Milwaukee, WI, 53207

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

"Alysha was great! She was always very professional and offered to meet us and our cat Ghost prior to our trip. We were impressed with her care and enjoyed t... (more)"

Dog owners in Wilson 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 Wilson Park.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect Wilson Park pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a pet sitter in Wilson Park, Milwaukee who meets your and your pet's needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet, including background checks, sitter testimonials, community reviews. We also offer educational opportunities and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet sitters and dog walkers.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a dog sitter. 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 Wilson 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: