Pet Sitting & Drop Ins in Red Oak Heights, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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1. Leandrea R.

Rover 101
Star Sitter
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
4.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
106 reviews
37 repeat clients
from
$15
per visit

Leandrea did a superb job with my kitty Sunny! I was anxious about leaving him due to him just having surgery a couple of days prior, but I was immediately put at ease with her quality of care! I would recommend her to anyone looking for care for their pet! I will definitely be booking for all my pet needs in the future! Thank you for being so wonderful!

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Sitter Profile Image: Karsyn R.
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Sitter Profile Image: Karsyn R.
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2. Karsyn R.

Rover 101
Star Sitter
Dog Buddy & Reliable Care
Milwaukee, WI, 53207
5.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
156 reviews
51 repeat clients
from
$18
per visit

Great communication and takes good care of our dog during drop-ins. Follows instructions for taking our dog out, and engages with our dog for fun playtime and training during the visit.

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Sitter Profile Image: Michele M.
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Sitter Profile Image: Michele M.
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3. Michele M.

Star Sitter
15+ yr pet owner & dog foster
Milwaukee, WI, 53221
2.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
22 reviews
10 repeat clients
from
$20
per visit

Michele is so kind and so helpful and Samson is always so happy to have had a visitor in the middle of my long days at work! Thanks Michele :)

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Sitter Profile Image: Alexy & Dylan G.
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Sitter Profile Image: Alexy & Dylan G.
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4. Alexy & Dylan G.

Star Sitter
Animals are my passion and joy!
Bay View, Milwaukee, WI, 53207
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
6 repeat clients
from
$15
per visit

Alexy & Dylan are sweet! they took great care of my girl’s needs while I was away & sent plenty of pictures. I will contact them for future needs. 💜

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Katie N.
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Sitter Profile Image: Katie N.
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5. Katie N.

Star Sitter
Here kitty kitty (and doggies too!)
Greendale, WI, 53129
1.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
39 reviews
10 repeat clients
from
$20
per visit

Katie is wonderful. She took great care of our shy kitty. Sat and played with her. She noted that she drank much water and put out another bowl for her. Pictures and updates put us at ease. Will definitely use Katie again.

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Sitter Profile Image: Hillery F.
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Sitter Profile Image: Hillery F.
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6. Hillery F.

Happy to help!
West Allis, WI, 53214
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
84 reviews
35 repeat clients
from
$19
per visit

Hillery was very reliable and helpful! She gave detailed descriptions of her visits. She was able to observe and identify something going on with our cat's health that we had not noticed, so we were able to follow up with the vet. We would definitely have Hillery pet sit again.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Deanna S.
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Sitter Profile Image: Deanna S.
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7. Deanna S.

I will provide unconditional love.
Greendale, WI, 53130
2.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
7 repeat clients
from
$18
per visit

Deanna did a great job taking care of our dog and cat while we were away for a weekend. She always provided updates and photos and my dog and cat absolutely adore her! Will hire her again when we are in need of her services.

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Sarah J.
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Sitter Profile Image: Sarah J.
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8. Sarah J.

I’m awkward with humans.
West allis, WI, 53219
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
117 reviews
39 repeat clients
from
$13
per visit

Sarah is awesome! I recently adopted a very high maintenance half Persian cat. I had to leave town to visit family for 4 days. I found Sarah on Rover based on reviews. She came to meet my cat and his routine. She came to the house daily when I was gone. She very willingly, happily, and efficiently followed a long list of to do things (meal times with specific types of foods, food puzzles, setup automatic feeders, play time, litter box maintenance, etc) I Sarah went above and beyond to make me feel better about leaving my cat behind home alone for the first time. She did a wonderful job at taking care of the cat and making him feel safe and loved 🥰 I highly recommend Sarah with your fur babies!

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Sitter Profile Image: Allie S.
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Sitter Profile Image: Allie S.
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9. Allie S.

Teacher with a fenced-in yard here!
West Allis, WI, 53219
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$18
per visit

Allie was fantastic! We booked her last minute and she was super accommodating to us. As nervous pup parents we were super unsure about leaving him, but she was so sweet, took extra good care of him, sent us tons of report cards and photos and made us feel as though he was in great hands! We will definitely book with her again in the future. He misses you already!

Sitter Profile Image: Danielle S.
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Sitter Profile Image: Danielle S.
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10. Danielle S.

Puppy-lover and kitty-cuddler.
West Allis, WI, 53227
3.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
58 reviews
13 repeat clients
from
$18
per visit

Danielle is amazing and really saved the day watching my 3 cats! I will definitely use her in the future and recommend her for your animals needs!

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Sitter Profile Image: Jessica E.
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Sitter Profile Image: Jessica E.
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11. Jessica E.

Loving Sitter With a Fenced In Yard
West Allis, WI, 53227
1.9 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$14
per visit

Jessica did an incredible job with my furry baby :) Thank you for everything!

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Sitter Profile Image: Christine H.
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Sitter Profile Image: Christine H.
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12. Christine H.

Experienced Dog Foster
Greenfield, WI, 53221
2.6 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
28 reviews
9 repeat clients
from
$20
per visit

Came on short notice and did a great job!

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Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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13. Katherine B.

Star Sitter
Dogs are happiness 😊
West Allis, WI, 53219
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
9 repeat clients
from
$25
per visit

I could tell our pup was very happy and comfortable with Katie. Katie was both friendly and professional. I was pleased with all of photos and regular updates we recieved. It was clear she gave our dog plenty of exercise as our dog was pooped. I will definitely be booking again.

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Sitter Profile Image: Jennifer F.
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Sitter Profile Image: Jennifer F.
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14. Jennifer F.

Lots of Love & Care from Jenn
Jackson Park, Milwaukee, WI, 53215
2.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
2 repeat clients
from
$15
per visit

Jennifer was amazing. My dogs were very well taken care of and she was patient with them and their accidents/separation anxiety. I really appreciated her help over the holidays and highly recommend.

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Sitter Profile Image: Kelly M.
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Sitter Profile Image: Kelly M.
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15. Kelly M.

Rover 101
Star Sitter
I love dogs and being outside!
Greenfield, WI, 53227
2.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
27 reviews
9 repeat clients
from
$20
per visit

It was a pleasure having Kelly watch after my puppy Stormi. I received many updates, pictures and videos during her time visiting Stormi. I will definitely be booking with her in the near future. Thank you Kelly!

Sitter Profile Image: Amanda B.
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Sitter Profile Image: Amanda B.
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16. Amanda B.

Have loved animals since birth.
Greenfield, WI, 53220
0.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
109 reviews
36 repeat clients
from
$14
per visit

Thanks to Amanda doing such a great job we were able to enjoy our time away even more. She is friendly, reliable and professional. We enjoyed getting her pictures and updates of our girls. Highly recommend and trust her to take good care of our pets.

Sitter Profile Image: Mary C.
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Sitter Profile Image: Mary C.
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17. Mary C.

Will care for pet your like my own!
GREENFIELD, WI, 53220
0.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
47 reviews
16 repeat clients
from
$15
per visit

Mary is a great communicator - she let me know when she was at my house and sent pics during her visit. Overall, she was a caring, attentive friend to my furries! I would absolutely partner with Mary again. 😊

Confirmed availability: Memorial Day Weekend
Sitter Profile Image: Hannah W.
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Sitter Profile Image: Hannah W.
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18. Hannah W.

Full-time cuddler, part-time runner
Alcott Park, Milwaukee, WI, 53228
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
17 repeat clients
from
$15
per visit

Hannah did a great job watching our cat Diego. This was her second time caring for him while we were out of town. I cannot tell you what a relief it was to have her watch him again. He’s an older cat and usually very shy. She was able to make him comfortable enough to come out of hiding and spend time with her. I received adorable photos and updates that put me at ease the entire time.

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Sitter Profile Image: Kevin H.
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Sitter Profile Image: Kevin H.
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19. Kevin H.

Star Sitter
Your best friend's new best friend
Fairview, Milwaukee, WI, 53219
1.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$19
per visit

Kevin did a great job walking my not-so-easy to walk dog. He took some photos of my dog and updated me on how their walk and play time went. I really appreciated Kevin's thoroughness about the walk! I have already booked Kevin again for my fluffy boy!

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Sitter Profile Image: Lacie G.
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Sitter Profile Image: Lacie G.
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20. Lacie G.

Nurse and Dog Mom! 💕
Greenfield, WI, 53228
1.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$14
per visit

Lacie is amazing! Our two dogs absolutely love her. She went above and beyond to make sure the dogs were taken care of and sent lots of updates to let me know everything was going wonderfully. Couldn’t recommend her more if you’re needing someone to check on your fur babies. Will definitely be using her again after having such a positive & very reassuring experience!!

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Dog owners in Red Oak Heights, Milwaukee, WI turn to pet sitters on Rover.com for their pet sitting needs. Over 1089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5. Pet sitting can be affordable, no matter where you live or what your price range may be. Curious about how much pet sitting costs in Milwaukee with Rover.com? Check out our average pet sitting rates near you to get an idea before getting a conversation started with a pet sitter on Rover. When you leave your dog with a sitter you've connected with on Rover, you can relax, knowing your dog will be treated like family.

Rover.com is the simple, savvy way to find and book Red Oak Heights, Milwaukee drop in pet sitting. It's easy to find the perfect pet sitter. Many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a free background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 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, so you're sure to find the perfect pet sitter in Red Oak Heights, Milwaukee . When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.

Drop-In Visits