House Sitting in 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. Maddy

Your Furry Friend in Great Hands

Bay View, Milwaukee, WI, 53207

House Sitting, Drop-In Visits, Dog Walking

"Maddy was amazing!! She is so very sweet and professional. And my Addie girl loved her! She even left my house cleaner than what I left it! I would use Maddy... (more)"

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2. Paige

Play time is my favorite time!

Avenues West, MILWAUKEE, WI, 53233

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

"Paige was great with Rupert! Rupert loved spending his day with her. We will be booking Paige again! (more)"

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3. Abigail

LOVE long walks more than your pup.

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Abigail was terrific: I found my kittens happy, joyous, and bounding about, she nicely documented everything they were doing and sent me photos and entertai... (more)"

4. Alexa

Devoted, Fun-Loving, Outdoorsy

St. Francis, WI, 53235

House Sitting, Drop-In Visits, Dog Walking

"Alexa was great! She's very responsive to texts and also was willing to come "learn the ropes" before booking and meet our cat. We enjoyed meeting Alexa and... (more)"

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5. Samantha

Sam's Dog Days

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"Samantha was absolutely amazing and my puppy loved her! She took such good care of Murphy and sent over pictures and videos. will definitely be using Samanth... (more)"

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6. Tasha

Rehabilitative Dog Rescue Worker!

Glendale, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Tasha is amazing and so organized and professional! We got pics of our doggy the whole time we were gone! She left the house so clean and tidy and we felt ve... (more)"

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7. Sandy

Mature & Special Needs Dogs Welcome

Story Hill, Milwaukee, WI, 53208

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

"Sandy did a great job watching Terry and Bailey. She was professional with all communication, sent updates a couple times a day, and was overall pleasant to... (more)"

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8. Audra

Flexible schedule, love walks/runs

Downer Woods, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Audra is amazing. She stayed with our pup at our home longer than we asked her to and she was so caring and such a nice person! Couldn’t recommend her enough... (more)"

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9. Isaiah

Walks, Belly Rubs & Treats - Oh my!

Kilbourn Town, Milwaukee, WI, 53203

House Sitting, Drop-In Visits, Dog Walking

"I will definitely recommend Isaiah for house sitting! I had to find house sitter for my dog last minute and he was able to fit it in his schedule and stopped... (more)"

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10. Kaitlyn

All Breed-Loving, Optimist Sitter

Historic Mitchell Street, Milwaukee, WI, 53204

House Sitting, Drop-In Visits, Dog Walking

"She is a very hard worker and she loves animals. More than people it seems sometimes, she is very smart and caring. Loves to learn and is very ambitious. (more)"

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11. Kayla

Young dog-lover!

Bay View, Milwaukee, WI, 53207

Dog Boarding, House Sitting

"Kayla’s communication and flexibility was great. She took great care of our place and our two little terrors. We will be using her again if she’s available. (more)"

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12. Taylor

Dog lover with flexible schedule

Yankee Hill, Milwaukee, WI, 53202

House Sitting

"Taylor was great! She was very respectful of the house and gave me great updates about my dog and cat. I will be using her in the future and you should too! ... (more)"

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13. Colleen

Walks, Runs, and Belly Rubs.

Marquette, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Colleen was great! She was very responsive, easy to talk to, and sent regular updates. We felt very comfortable both leaving our dog and home in her hands. W... (more)"

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14. Emily

Caring & Active Dental Student

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Emily is so great! She was very easy to make arrangements with, was so enthusiastic about our dogs, and sent updates that made us feel at ease. We will defin... (more)"

Confirmed availability
Christmas and New Year
15. Devon

Dogs are better than people, mostly

Northpoint, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Devon is a kind, responsible, energetic and fun animal lover. Devon cared for my my cat and dog over the years- I've always been super happy and so have my ... (more)"

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16. Hannah

Happy to care for all ages/sizes

Lower East Side, Milwaukee, WI, 53202

House Sitting, Drop-In Visits, Dog Walking

"I have known Hannah for over 25 years! She is one the most responsible people I know! She has always loved my dogs (and of course her own) and shown them lov... (more)"

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17. Shakiela

Dogs comfort me & help me relax

Murray Hill, Milwaukee, WI, 53211

House Sitting, Drop-In Visits, Dog Walking

"Shakiela is the biggest dog lover I have ever met. Her compassion shows no bounds and she would be the perfect candidate for this. She treats all dogs and pe... (more)"

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18. Savannah

Dog lover for hire! (Holidays too!)

Brewer's Hill, Milwaukee, WI, 53212

House Sitting, Drop-In Visits, Dog Walking

"Savannah was great. She was a good communicator and responded to my inquiries right away. Gunner was well taken care of. I recommend her services. I know I w... (more)"

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19. Rachel

Dogs are woman's best friend!

Historic Third Ward, Milwaukee, WI, 53202

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

"Rachel was great! We were very nervous leaving our 14 week old puppy and she made us feel at ease. She followed our written schedule and took a ton of not... (more)"

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20. Alexis

Dogs are my passion!

Avenues West, Milwaukee, WI, 53233

House Sitting, Drop-In Visits, Dog Walking

"Alexis was so great with my dog and cat!! I was out of the country without service, and she did an amazing job taking care of them. I came home to super happ... (more)"


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