House Sitting in Silver Spring, Milwaukee

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

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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1. Lily S.

Compassion, Experience, Flexibility
Milwaukee, WI, 53212
6.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
4 reviews
4 repeat clients
from
$50
per night

This was Lily’s first time house sitting Kai and she exceeded my expectations. She clearly developed a great connection with Kai, did a really nice job keeping me connected/informed, and overall left the house looking like it did when I left. I so much enjoyed her texts, pictures and video clips. Thank you Lily!

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Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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2. Jessica Z.

Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
7.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
93 reviews
32 repeat clients
from
$59
per night

Our family had recently experienced a loss of our other pet. It was a tough time for travel but Jessica supported our other pet while we were away. She kept us informed and made the world of difference being away during such a difficult time.

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Sitter Profile Image: Jeanee S.
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Sitter Profile Image: Jeanee S.
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3. Jeanee S.

Pets just get me!
Menomonee Falls, WI, 53051
7.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$40
per night

Jeanee is amazing! She took the best care of our pets, provided frequent updates, and was honestly a joy to communicate with! She will most definitely be my first choice for future pet sitting needs.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jenn S.
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Sitter Profile Image: Jenn S.
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4. Jenn S.

Dog lover 🐶 & cat mom 🐈🐈‍⬛🐈
West Allis, WI, 53227
8.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
40 reviews
10 repeat clients
from
$60
per night

We were very pleased on how well Jenn took care of our fur baby Zoey. Jenn sent us pictures and updates daily. We will definitely book Jenn again for future dog sitting.

Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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5. Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
7.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
77 reviews
22 repeat clients
from
$30
per night

Rachel was great with our two crazy dogs and her ability to watch them in our home was priceless. Our beagle has anxiety and does best in her own environment. Rachel kept us informed with texts and pictures and really provided peace of mind that our pups were in good hands.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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6. Jackie C.

Looking forward to meet your pet!
Brewer's Hill, Milwaukee, WI, 53212
6.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
67 reviews
22 repeat clients
from
$65
per night

I am a first time user of Rover.com and was nervous about leaving my dogs with someone the dogs and I didn't know. The meet and greet with Jackie helped put my mind at ease. Jackie did an amazing job taking care of my 2 dogs at my house for a little over 2 weeks. One the dogs does not trust people. It did not take him long to warm up to her, which says that she has good, calm energy. It was great that the dogs could be at home and she would come to them. I think this made the dogs less anxious. She sent us great pictures and promptly responded to texts. I would highly recommend Jackie and I would definitely use her again.

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Sitter Profile Image: Katie K.
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Sitter Profile Image: Katie K.
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7. Katie K.

Friend to felines & all animals
Menomonee Falls, WI, 53051
4.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$50
per night

Katie was amazing! She played fetch with our dogs, snuggled with our new kitten, and took very good care of our home while we were gone. I would highly recommend Katie for your pet care!

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Sitter Profile Image: Ali M.
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Sitter Profile Image: Ali M.
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8. Ali M.

I love dogs, cats, and herptiles !
Milwaukee, WI, 53211
6.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
36 reviews
17 repeat clients
from
$65
per night

My dog and cat seemed to really like Ali. She sent lots of pictures and kept me updated. I really appreciate that she was able to help me out in a pinch with a last-minute holiday booking!

Sitter Profile Image: Daniela & Michael P.
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Sitter Profile Image: Daniela & Michael P.
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9. Daniela & Michael P.

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
5.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
282 reviews
160 repeat clients
from
$65
per night

Daniela is just so amazing. My little meatball is a lot at times and she handled it all with grace. She continually communicated with me which just eased my anxiety and allowed me to enjoy my vacation because I knew my dog was being cared for so well. Also appreciate all the informed consent prior and taking time to meet him.

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Sitter Profile Image: Danica V.
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Sitter Profile Image: Danica V.
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10. Danica V.

PAWsitively reliable med student!
Wauwatosa, WI, 53226
5.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
19 reviews
7 repeat clients
from
$46
per night

Danica is consistent and professional throught the Rover experience. I've been burned before with previous dog sitters that have been inconsistent and unresponsive, but Danica is always punctual and quick to respond to any concerns/needs. I trust her to be with my pups when they are most stressed and take care of them when I'm away. That peace of mind is priceless and I love having Danica over to watch my pups.

Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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11. Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
4.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
30 reviews
8 repeat clients
from
$70
per night

Cindy was absolutely amazing! She gave plenty of updates of on fur baby photos included which made it so much better. She was super flexible on start and end time to make sure that our lucky was taken care of no matter what . Lucky came home so happy I just know he had a blast hanging with Cindy. Any time we need some one to watch lucky we will be asking Cindy first before any one else

Sitter Profile Image: Katelyn A.
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Sitter Profile Image: Katelyn A.
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12. Katelyn A.

Eat. Play. Love.
Bayside, WI, 53217
5.9 mi. away
House Sitting, Dog Walking
5.0 out of 5 stars
11 reviews
9 repeat clients
from
$65
per night

Kate was excellent!! Will definitely use her again. One of my dogs has high anxiety and they did great together. I can't say enough good things about her.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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13. Erica L.

Rover 101
Pro. Dog Handler with WFH job!
Park West, Milwaukee, WI, 53206
4.4 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
83 reviews
29 repeat clients
from
$75
per night

Erica is very professional and clearly has a passion for dogs and their happiness. Erica dog sat for our 13 week old puppy who was not fully potty trained and also hadn't had all his shots so wasn't "allowed" outside. She was very responsive to our new puppy-parent demands and requests, sent us daily updates through photos and videos and clearly had everything under control -- she had the initiative to continue what we'd already trained our pup as well as promote positive behaviors around walking on the leash and barking. We appreciated Erica's apparent experience with dealing with puppies and her friendly and relaxed demeanor. Our puppy loved her upon their first meeting! Thank you Erica :)

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sam P.
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Sitter Profile Image: Sam P.
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14. Sam P.

Rover 101
Loving, Responsive, Knowledgeable.
Hawthorne Glen, Milwaukee, WI, 53208
5.2 mi. away
Boarding, House Sitting, Drop-In Visits
5.0 out of 5 stars
120 reviews
58 repeat clients
from
$80
per night

Sam far surpassed our expectations! Noodles is a “handful” to say the least! He’s not quite a year and a half and still acts like a puppy in all ways. He’s also very hesitant around other dogs, which comes off as aggressive. Her first of many pictures sent to us was Noodles “calmly” sitting right in the middle of three others dogs during a pack walk! He came out of this weekend with new friends, human and four-leggers! We’ve already booked Sam for another weekend of “Noodle sitting” as well as dog walking and training! Couldn’t be happier for us and Noodles~ The McBride’s

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Lance C.
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Sitter Profile Image: Lance C.
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15. Lance C.

Coffee loving dog walker!
Enderis Park, Milwaukee, WI, 53210
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night

I had an amazing experience with Lance as my dog sitter! He was incredibly attentive to my furry friend's needs and went above and beyond to ensure their comfort and happiness while I was away. Lance provided regular updates and even sent adorable photos of my pup enjoying their time together. I felt completely at ease knowing that my dog was in such capable and caring hands. I highly recommend Lance to anyone in need of a reliable and compassionate dog sitter.

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Sitter Profile Image: Giovanni M.
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Sitter Profile Image: Giovanni M.
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16. Giovanni M.

Rover 101
Your Pup's Home Away from Home
Milwaukee, WI, 53222
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
7 reviews
from
$40
per night

I am so thankful for Giovanni! I was new to the Rover App and honestly didn’t expect to find someone who would be willing to take care of two nine week old energetic puppies that were not even potty trained. Giovanni agreed to puppy sit in my home for three days! He was extremely patient, gentle, and kind with Cedar and Ivy. From day one I was confident that Gio would care for the puppies the same way I do. He was communicative with me regarding his arrival time and during the day he provided me with an update on the puppies. It was a pleasure getting to know him. My only regret is that I didn’t get a picture of Gio with the puppies! Next time, Gio! 😊

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Marilia D.
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Sitter Profile Image: Marilia D.
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17. Marilia D.

I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
7 repeat clients
from
$65
per night

Marilia did a great job staying with our pup and walking , feeding, playing and just being there for him. She spent 3 nights and fleas very responsive and respectful of our home . Was thankful she was available, Will hire again .

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Ariela M.
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Sitter Profile Image: Ariela M.
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18. Ariela M.

Experienced Veterinary Technician
Grantosa, Milwaukee, WI, 53222
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
4 repeat clients
from
$55
per night

Ariela is great! She is super kind and knowledgeable about animals! I felt extremely safe and good about leaving my puppy in her care! I highly recommended her!

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Sitter Profile Image: Jeff G.
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Sitter Profile Image: Jeff G.
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19. Jeff G.

Care for dogs like they're children
Glendale, WI, 53209
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
38 reviews
10 repeat clients
from
$68
per night

We are so grateful to have met Jeff! He treated our dogs like his own, was so easy to coordinate with, and very respectful and accommodating. Jeff stayed with our dogs in our home for about 10 hours. He gave frequent updates with pictures and brought us so much peace of mind that our dogs were in such caring hands.

Sitter Profile Image: Amari I.
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Sitter Profile Image: Amari I.
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20. Amari I.

Quality Care Your Pet Deserves!
Silver Swan, Milwaukee, WI, 53225
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
2 repeat clients
from
$55
per night

I needed a dog sitter last minute and contacted Amari about taking care of my 70 lb Belgian Malinois rescue. I do not know how many times my dog has been re-homed so I was very anxious about leaving her with a stranger. When I got home after being away for 3 days my dog was happy as a clam and all of the signs of emotional distress she showed after previous trips -- not eating, not defecating, etc. -- were absent. Amari did a wonderful job! I will definitely employ her in the future.

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Dog owners in Silver Spring, Milwaukee, WI love booking house sitting with sitters on Rover.com. Over 1089 pet owners have reviewed house sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking house 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 house sitting with Rover? Check out our average house sitting rates to get an idea before reaching out and starting a conversation with a house sitter near you in Silver Spring.

As dog lovers, we understand how difficult it can be to leave your dog when you have to head out of town. Luckily, you can find the perfect Silver Spring house sitter in seconds on Rover.com. If you're looking for trusted dog sitters while you're away, whether it's for one night or a whole month, you can find a house sitter in Silver Spring, Milwaukee, WI who meets your and your dog'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 dog, 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 dog lovers pet sitters and dog walkers.

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