House Sitting In Uptown 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
3.0 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
4.1 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.

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

Dog lover 🐶 & cat mom 🐈🐈‍⬛🐈
West Allis, WI, 53227
5.1 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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4. Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
3.6 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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5. Jackie C.

Looking forward to meet your pet!
Brewer's Hill, Milwaukee, WI, 53212
3.4 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.

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

Rover 101
Paws Down, the Best in Town!
Milwaukee, WI, 53205
2.5 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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7. Danica V.

PAWsitively reliable med student!
Wauwatosa, WI, 53226
2.4 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.

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Sitter Profile Image: Lexi K.
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Sitter Profile Image: Lexi K.
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8. Lexi K.

Lover of all animals big and small
Cannon Park, Milwaukee, WI, 53214
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
42 reviews
11 repeat clients
from
$35
per night

Lexi is wonderful with our elderly pup Daisy. Daisy becomes stressed when we are not home, but with Lexi there, she was calm as a cucumber when we returned from an evening out! It was clear she felt safe and cared for by Lexi.

Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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9. Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
0.8 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

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

Rover 101
Pro. Dog Handler with WFH job!
Park West, Milwaukee, WI, 53206
2.0 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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11. Sam P.

Rover 101
Loving, Responsive, Knowledgeable.
Hawthorne Glen, Milwaukee, WI, 53208
1.2 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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12. Lance C.

Coffee loving dog walker!
Enderis Park, Milwaukee, WI, 53210
1.2 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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13. Giovanni M.

Rover 101
Your Pup's Home Away from Home
Milwaukee, WI, 53222
1.6 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: Travis H.
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Sitter Profile Image: Travis H.
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14. Travis H.

Rover 101
Love & Exercise for your dog or cat
Martin Drive, Milwaukee, WI, 53208
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
188 reviews
77 repeat clients
from
$62
per night

We met Travis for a meet and greet ahead of time and he was always very attentive, friendly, communicative, and willing to listen. He took great care of our pup for a week and kept our apartment just how it was when we left. We're looking forward to working with him again in the future!

Sitter Profile Image: Samantha A.
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Sitter Profile Image: Samantha A.
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15. Samantha A.

falls in love with any & all dogs
Washington Heights, Milwaukee, WI, 53208
0.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$40
per night

Samantha is a dog lover! She has been around dogs her whole life. She was responsible for crate and house training for one of our labs. She is organized and conscientious and will work hard to be sure your dog thrives in her care.

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Sitter Profile Image: Andi D.
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Sitter Profile Image: Andi D.
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16. Andi D.

I love animals!
Midtown, Milwaukee, WI, 53205
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
from
$40
per night

Andi is great! She took great care of my two dogs and kept in communication throughout her stay. She also kept my place near and tidy, which is appreciated so much. No one likes to come home to a mess after a few days away!

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Sitter Profile Image: Casandra E.
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Sitter Profile Image: Casandra E.
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17. Casandra E.

Dog mom dog lover
Milwaukee, WI, 53208
1.2 mi. away
House Sitting
5.0 out of 5 stars
5 reviews
from
$33
per night

Cassandra was great! She spent a lot of time with our animals and sent me updates frequently. She went above and beyond to make sure the dogs got a walk in everyday. She left the house exceptionally clean. I felt very at ease knowing she was caring for our pets. I would definitely reach out to her and hire her again. Thanks Cassandra!

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Marie H.
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Sitter Profile Image: Marie H.
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18. Marie H.

Your Pets New Favorite Sitter :)
Martin Drive, Milwaukee, WI, 53208
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
3 repeat clients
from
$45
per night

We recently adopted a dog and this was our first time using Rover. Marie always communicated quick and kept us updated the whole time she was with our pets. She entertained our pets and took good care of our new dog during the potty training phase. She stayed overnight and we felt like our home was respected. Would recommend Marie!

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Sitter Profile Image: Molly O.
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Sitter Profile Image: Molly O.
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19. Molly O.

All the walks and all the cuddles
Wick Field, Milwaukee, WI, 53208
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
26 reviews
13 repeat clients
from
$65
per night

Molly absolutely crushed it- I can’t say enough good things. Our dogs have huge personalities, some bizarre behaviors, and special needs (and so does our weird old rental house) and she handled all of it with aplomb. Our resident canine klutz tore his paw pad the night before we left, and even though we totally sprung this development on Molly at the last minute, pro that she is, she jumped in and changed his dressings, kept the area clean, AND kept the dog calm to prevent further injury. He was basically fully healed upon our return. Thanks, Molly! We will be back if you’ll have us- with fewer surprises next time, we hope!

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Sitter Profile Image: Jordan J.
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Sitter Profile Image: Jordan J.
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20. Jordan J.

Patient animal lover
Wauwatosa, WI, 53223
1.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$60
per night

Jordan has been an animal lover all her life and would give your pet so much love while you are away. Jordan has been caring for cats and dogs her whole life and she is currently caring for an elderly cat of her own that has a complex regiment including: giving fluids, liquid oral medication and pills and powder. She would do anything for this cat, and knows how much pets weigh in our hearts. She is someone you can trust and know she would communicate any small detail while caring for your fur baby! You bet I would book with her!

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When it comes to house sitting, dog owners in Uptown, Milwaukee, WI love Rover.com. Over 1089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of house sitting in Uptown may surprise you - in a good way. That's because there's a house sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for house sitting on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover.com is the simple, savvy way to find and book Uptown 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 Uptown, 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 Uptown house sitters on Rover, your dog gets the loving care they deserve, and you get peace of mind.

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