House Sitting in Fair Park, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Holly

Plenty of exercise and play time

West Allis, WI, 53227

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

"Holly did a great job. Kept me updated. And sent pictures. She is awesome with animals!! (more)"

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2. Colleen

Walks, Runs, and Belly Rubs.

Avenues West, Milwaukee, WI, 53233

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

"Colleen was wonderful! She handled my reactive pitty on leash with no problems and put up with my stubborn shiba. She left my house spotless. The only sign s... (more)"

3. Hannah

Flexible student and dog lover!

Kilbourn Town, Milwaukee, WI, 53233

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

"great sitter. will use again (more)"

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4. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

Dog Boarding, House Sitting, Drop-In Visits

"Thank you to Sandy for being an excellent pet sitter to our Furry Herd. She not only took excellent care of our pets, she won over the heart of our Daschund... (more)"

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5. Briana

Active, responsible, kind pet lover

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Briana was great! Great communication, and lots of pics that updated us on how our pup was doing. She left the place clean and tidy! We will definitely use h... (more)"

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6. Peggy

I'm a stay at home dog mom!

Fairview, Milwaukee, WI, 53219

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

"Peggy watched three of my four dogs for a few hours while we had a trainer over to help us with our fourth. It was so worth having our dogs cared for so we ... (more)"

7. Amanda

Happy Paws make for Happy Owners!

Johnson's Woods, Milwaukee, WI, 53214

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

"Amanda took great care of our home, garden, and watered our flowers during the dry season. Most importantly she cared for our baby doggie, Gracie Girl. She s... (more)"

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8. Hannah

Happy Hannah is here to help!

Washington Heights, Milwaukee, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

"Hannah did a great job sitting Bailey for the day. They went on a few walks and played and he even got a nice nap in. Bailey was very happy when I picked hi... (more)"

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9. Jacey

I'd love to take your dog for a run

Wauwatosa, WI, 53226

House Sitting, Drop-In Visits, Dog Walking

"Jacey was great! My cavapoo, who sometimes can be anxious, warmed right up to her! Jacey was responsive with communication before and during the stay. I woul... (more)"

10. Natasha

Experienced & fun dog (&cat)-lover!

Milwaukee, WI, 53214

House Sitting, Drop-In Visits, Dog Walking

"Natasha was amazing with our two dogs! She was very responsive to all the texts that we exchanged and was very accommodating when it came to meeting with th... (more)"

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11. Anna

Dog Lover & Dental Student!

Story Hill, Milwaukee, WI, 53208

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

"Anna was great at watching Apollo, my Great Pyrenees, who isn’t always a fan of new people. He took to her right away! Anna also was a lifesaver and helped m... (more)"

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12. Tim

Retired Police Lieutenant

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Tim was an excellent dog sitter! Our dog is a little shy to say the least. Tim sat on the floor to play with our dog the first day they met-they have been ... (more)"

13. Lori

Experienced dog & cat sitter

Miller Valley, MILWAUKEE, WI, 53208

House Sitting, Drop-In Visits, Dog Walking

"Lori was super! Hit it off with my guy right away at the pre-meet. Sent me lots of photos and updates so I could keep tabs on my dude. Took great care of hi... (more)"

14. Vanessa

Lots of TLC

Burnham Park, Milwaukee, WI, 53215

House Sitting, Drop-In Visits, Dog Walking

"Vanessa was very accommodating of short notice request. She took great care of Lambeau and communicated with me via texts during the stay. She was eager to... (more)"

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15. Chris

Pawsitvely the best!

Story Hill, Milwaukee, WI, 53208

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

"Chris is fast to respond, punctual, and extremely passionate about all dogs. He gives my dog great attention and fun, energetic playtime while I am away - he... (more)"

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16. Elizabeth

If possible, dog-lover since birth!

Bluemound Heights, Milwaukee, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"I've known Elizabeth for over 10 years now and she's always been an amazing pet auntie to my fur-babes. It started with my two cats and, for the last 6 year... (more)"

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17. James

Retired Teacher in Tosa

wauwatosa, WI, 53213

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

"Jim has been watching my two dogs for a few years. He does a great job. Bill and Hillary always come back home very happy and I can tell they are well take... (more)"

18. Kristy

I'm their home away from home ❤

West Allis, WI, 53214

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

"I, and my family, have known Kristy for over 25 years. I have observed her taking care of her dogs over those years. You can tell by the way her dogs respond... (more)"

19. Daniela

Extra attentive to your fur baby

Wauwatosa, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Working in the medical field unfortunately means that I can't be there for my dogs all the time. However, Daniela is always the first person I think of to wa... (more)"

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20. Bridget

Adore dogs and make my own schedule

Bluemound Heights, Milwaukee, WI, 53213

House Sitting, Drop-In Visits, Dog Walking

"Bridget was wonderful with Bela! She kept us updated daily and took great care of our home and our little Bela while we were away. She responded quickly to... (more)"

In Fair Park, Milwaukee, WI, dog lovers trust Rover.com for their house sitting needs. Over 1,089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking house sitting in Fair Park can be incredibly affordable, no matter what price range you're looking for. Curious about what it might cost to book house sitting in Milwaukee on Rover? Check out our average house sitting rates to get an idea before reaching out and beginning a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Fair Park house sitting. It's easy to find the perfect house sitter: many sitters on Rover have a long history of dog sitting, and 95% of reviewed stays have received a perfect five-star rating. When you book house sitting in Fair Park, Milwaukee, WI on Rover, your dog will enjoy a loving staycation, right in your home. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Every dog sitter on Rover has the option to complete a free background check. Stays are booked on Rover every minute of every day, and more than 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. 95% of reviewed stays have received a perfect five-star rating. When you book with one of our trusted Fair Park house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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 Fair 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: