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Pet Sitting & 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.

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1. Hannah Verified Enhanced Background CheckRover 101

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)"

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2. Jenni Verified Enhanced Background Check

Professional Tummy Rubber & Cuddler

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

"Jenni was our first Rover, as we needed someone to watch our 10 year old pitbull mix while we got married. Jenni came over prior to watching Goon to introduce … (more)"

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3. Cassidy Verified Background Check

I can’t wait to be fur-iends!

Wauwatosa, WI, 53213

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

"Cassidy truly treats every dog with as much care and attention as she does her own. I have left my dog in Cassidy’s care several times, and my pup is as happy … (more)"

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4. Kristen Verified Enhanced Background Check

Let's adopt all the animals :)

Bay View, Milwaukee, WI, 53207

Drop-In Visits, Dog Walking

"Kristen took such great care of my cats! Communication with her was fantastic and she even sent many pictures. Will definitely ask her to take care of my cats … (more)"

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5. Blythe Verified Background Check

Every animal makes me smile!

Bay View, Milwaukee, WI, 53207

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

"Blythe is an awesome sitter! She was so patient with my anxious kitty and sent me daily images (mostly of her hiding) and reports to keep me up to date. I will… (more)"

6. Erin Verified Background Check

Young or Old, All Dogs are Welcome

Town Of Lake, Milwaukee, WI, 53207

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

"Our boys loved Erin! And wow, what a great job she did unraveling the fact that we left her locked out somehow, and we had to direct her to our hidden key (wh… (more)"

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7. Elaina Verified Background Check

College student missing dog time

Avenues West, Milwaukee, WI, 53233

Drop-In Visits, Dog Walking

"Kind, gentle, trustworthy and responsible— all wrapped into one animal-loving package: that’s Elaina! Elaina stayed in our house for 12 days with two dogs and … (more)"

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8. Ellisha Verified Enhanced Background Check

Experienced, Loving & Compassionate

Walker's Point, Milwaukee, WI, 53204

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

"I personally recommend Ellie as a trustworthy dog sitter. She watched our 7 year old dog when we went out of town for a vacation last year and she successfull… (more)"

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9. Stephanie Verified Background Check

Steph's Bay View Dog Spot

Tippecanoe, Milwaukee, WI, 53207

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

"Steph took care of our cat Banjo while we were out of town and did a wonderful job! Thank you so much! (more)"

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10. Megan Verified Enhanced Background Check

Mama Meg’s Doggy Daycare Services

West Allis, WI, 53219

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

"There are very few people I would leave my sweet darling four legged loves with and I have to say not a single regret choosing Megan, she is out of this world!… (more)"

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11. Miranda Verified Background Check

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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12. Lori Verified Background Check

Purrrrrrfect and Roof Roof!!!

West Allis, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

"Lori is an amazing animal lover. Since she was a little girl she had a close relationship with her pets. Every year for her birthday she selflessly asks for … (more)"

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13. Sara Verified Background CheckRover 101

Professional Sitter, Fenced Yard

Morgandale, Milwaukee, WI, 53215

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

"This was my first time using drop in service and it was great! I needed the service last minute, and Sara and Angelise were very flexible so everything worke… (more)"

14. Vanessa Verified Background Check

Love & Treats Galore

Layton Park, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Doggy Day Care, 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 were… (more)"

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15. Allyssa Verified Background Check

Passionate, caring dog lover!

Johnson's Woods, Milwaukee, WI, 53214

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

About: Hello! I grew up caring for dogs and cats at my family home and now am raising a dog of my own with the help of my roommate and best friend! I am an … (more)

16. Amanda Verified Background Check

I’ll love your babies as my own!

Greenfield, WI, 53221

Dog Boarding, House Sitting, Drop-In Visits

"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 and … (more)"

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17. Kristina Verified Background Check

Hikes with your pup!

West Allis, WI, 53219

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

About: I am a professional who loves dogs and wants to enjoy being around dogs more! I have two very social, friendly dogs that always love making more fri… (more)

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18. Kristy Verified Background Check

I'm their home away from home ❤

West Allis, WI, 53214

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

"We had Kristy come over for drop-in visits while we were on vacation a few weeks ago. She came each day around the same time and played with our kitty Harley.… (more)"

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19. Valeria Verified Background CheckRover 101

Love is a Four Legged Word <3

Greenfield, WI, 53221

House Sitting, Drop-In Visits

"We had absolutely the BEST experience with Valeria. She made us feel very comfortable in understanding our fur-babies needs and taking care of them while we we… (more)"

20. Joyce Verified Background Check

Lifelong doggie mom

Jackson Park, Milwaukee, WI, 53215

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

About: My home is set up for my dogs and cats. My last two dogs lived to ages 15 and 16. My living room has low windows they can look out. I have a wireless… (more)

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: