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
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Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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1. Lily S.

All-Day in Home Care For Critters
Milwaukee, WI, 53212
6.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
4 repeat clients
from
$60
per night
Profile image

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!

Sitter Profile Image: Heather C.
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Sitter Profile Image: Heather C.
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2. Heather C.

Star Sitter
Caring & loving Pet owner ❤️
Sussex, WI, 53089
9.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
30 reviews
7 repeat clients
from
$50
per night
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Heather did a great job of sending us photos and letting us know of activities she was doing with our pet while we were gone. Communication beforehand was great as well!

Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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3. Jessica Z.

Star Sitter
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
98 reviews
33 repeat clients
from
$59
per night
Profile image

Jessica was amazing! She communicated with us every day and sent us pictures/videos of the dogs, which my daughters really enjoyed. She took extra special care of our geriatric dog, making and feeding him human food, per our request. We will definitely be hiring Jessica again! Thank you for taking care of our fur babies! Brandy

Sitter Profile Image: Jenn S.
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Sitter Profile Image: Jenn S.
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4. Jenn S.

Star Sitter
Animal lover and cat mom of 3 🐈
West Allis, WI, 53227
8.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
43 reviews
12 repeat clients
from
$60
per night
Profile image

Jenn stayed at our house for a weekend away. One of our dogs recently went blind and we felt in-home care was our only option. Jenn didn't seem concerned about managing our blind dog, senior greyhound, and cat. I appreciated that she came out twice to the house to meet us and talk through our routine. I was also impressed that she read up a bit on greyhounds since Leo was the first greyhound she watched. She was great about communicating her schedule and sending us pictures. We would definitely try to schedule with Jenn again.

Sitter Profile Image: Jeanee S.
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Sitter Profile Image: Jeanee S.
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5. Jeanee S.

Star Sitter
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
12 reviews
5 repeat clients
from
$50
per night
Profile image

Jeanne is AMAZING. We got home to happy dog, clean house, an awesome day by day journal, and near daily check ins (that we kept requesting and appreciating). Jeanne is an awesome communicator, kept our house in immaculate condition, and all was well during our vacation. We will 100% use her again and knowing we have a great sitter for Winnie makes me even more inclined to book a future vacation. 100% recommend.

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
70 reviews
22 repeat clients
from
$65
per night
Profile image

Jackie is incredible! Great communication, she is punctual, sent so many pictures, and best part was my pup was so happy. I definitely recommend! Thanks again Jackie!!

Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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7. Rachel H.

Star Sitter
** 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
80 reviews
22 repeat clients
from
$30
per night
Profile image

Rachel goes above and beyond every time she house sits for us. I hate leaving my pets, but I feel so much better knowing she’s there. She keeps us updated every day, and we always come home to a very happy dog and cat!

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
18 repeat clients
from
$65
per night
Profile image

Ali gave me such peace of mind when she watched my cat for the weekend. I’ve never used any pet sitting or boarding services prior to meeting Ali, so I really didn’t know what to expect. She was very professional, friendly, and helpful with the entire process. She sent me photo updates of my cat when she stopped in and she took such good care of everything I asked her to do. I will definitely be using her again.

Sitter Profile Image: Beth P.
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Sitter Profile Image: Beth P.
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9. Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53212
6.0 mi. away
House Sitting
5.0 out of 5 stars
7 reviews
2 repeat clients
from
$60
per night
Profile image

Beth is a Godsend! She stayed at our home for five days and took exceptional care of our many animals: our dog, cats, rabbits, Guinea pig and fish. We came back to a tidy house and relaxed animals. She took our dog on two mile walks and sent photos and updates regularly. We couldn’t have asked for a better sitter. She is kind and considerate. We highly recommend Beth!

Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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10. 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
32 reviews
8 repeat clients
from
$62
per night
Profile image

Cindy never fails to please! I was able to leave my dog Daisy with her while we attended a wedding. Cindy sent lots of pictures, and it was clear that Daisy was getting along well with her little pups! Daisy is an older dog, and easily becomes stressed and anxious. At home, she becomes distressed if she awakes and I am not in the room. When I went to pick her up at Cindy's, she looked as though she was feeling totally safe and secure right where she was! It warms my heart to see her so content.

Sitter Profile Image: Lance C.
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Sitter Profile Image: Lance C.
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11. Lance C.

Coffee loving dog walker!
Enderis Park, Milwaukee, WI, 53210
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
3 reviews
from
$38
per night

Lance has watched my dog Lupe a number of times. My dog loves him! He gets a lot of love, walks, and hang out time. He's very responsible, asks all the right questions and provides updates to make sure my wife and I are never concerned. I highly recommend Lance if you want peace of mind while you're away.

Sitter Profile Image: Marilia D.
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Sitter Profile Image: Marilia D.
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12. Marilia D.

Star Sitter
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
8 repeat clients
from
$70
per night
Profile image

Marilia is fantastic! We felt very comfortable leaving our two dogs overnight in our home with Marilia even after meeting her for the first time. Our girls were happy and healthy when we returned, and we feel even better about having Marilia take care of Rae and Frankie sometime in the future! Thanks Marilia!!!

Sitter Profile Image: Jeremy M.
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Sitter Profile Image: Jeremy M.
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13. Jeremy M.

Rover 101
Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
52 reviews
21 repeat clients
from
$55
per night
Profile image

Jeremy was amazing. He was prompt, insanely responsive, and went above and beyond when we forgot to leave our son’s soccer stuff out for pick up. He even ran to purchase new shin guards when he couldn’t find them for us. This man is truly amazing and we appreciate him watching our three puppies. Our shepherd is usually super depressed when we are away and he looks so happy in all the pictures we received.

Sitter Profile Image: Jeff G.
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Sitter Profile Image: Jeff G.
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14. 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
Profile image

Jeff was very caring and loving towards both our dogs. The house was left, super tidy and clean! Tons of pictures and updates… I highly recommend Jeff as a pet sitter. He was so thorough about getting the house ready for our arrival, he even removed the PostIt notes I left him, off my kitchen cabinets doors LOL. Thank you Jeff!

Sitter Profile Image: Katie K.
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Sitter Profile Image: Katie K.
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15. 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
6 reviews
4 repeat clients
from
$50
per night
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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!

Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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16. 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
84 reviews
29 repeat clients
from
$75
per night
Profile image

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 :)

Sitter Profile Image: Ariela M.
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Sitter Profile Image: Ariela M.
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17. 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
Profile image

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!

Sitter Profile Image: Tegra R.
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Sitter Profile Image: Tegra R.
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18. Tegra R.

Star Sitter
The right Mama to care 4 your baby
Milwaukee, WI, 53223
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
19 reviews
9 repeat clients
from
$28
per night
Profile image

Tegra made me feel comfortable with leaving my senior pup. She provided photos and communicated with me when the many times I reached out to check in on Tedi. I came home to a happy pup!

Sitter Profile Image: Olivia W.
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Sitter Profile Image: Olivia W.
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19. Olivia W.

Passionate Pet Enthusiast
Heritage Heights, Milwaukee, WI, 53224
2.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$29
per night

We cannot give enough praise to Olivia for watching our three dogs over winter break in 2023. We have one rescue, Rex, who was abused before he became part of our family and he is very protective of us and aggressive towards strangers. With her experience and interest in dogs, Olivia knew exactly how to interact with Rex and it only took an hour or so before they were good buddies! I'm sure our mouths dropped in amazement, because that really had never happened before. Throughout or trip, Olivia kept us well informed and sent us pictures of the pups happily hanging out with her. Olivia is always welcome back at our home and I thinks the dogs already adopted her anyway! Olivia is a lovely person who is great with dogs. She is easily 11 out of 10 stars!

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
Profile image

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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