Pet Sitting & Drop Ins in Highwood Estates, 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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To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Sitter Profile Image: Karsyn R.
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Sitter Profile Image: Karsyn R.
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1. Karsyn R.

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

Karsyn is great! She put up with our mischievous cats, sent lots of pictures and was super responsive! Definitely have her watch your fur babies :)

Sitter Profile Image: Ashley Y.
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Sitter Profile Image: Ashley Y.
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2. Ashley Y.

Star Sitter
English Bulldog/Catahoula Mom
West Allis, WI, 53214
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
4 repeat clients
from
$18
per visit
Profile image

Ashley was flexible, thorough and when I came home my critters were just as relaxed and comfy as can be! She is a great pet sitter, anyone would be lucky to have her!

Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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3. 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
108 reviews
37 repeat clients
from
$15
per visit
Profile image

Great communication always on time if there were any questions she asked. Very friendly and very good with the dog. Would highly recommend her for taking care of your dogs. Always sent pictures and an update on what was going on.

Sitter Profile Image: Lexi K.
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Sitter Profile Image: Lexi K.
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4. Lexi K.

Star Sitter
Lover of all animals big and small
Cannon Park, Milwaukee, WI, 53214
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
44 reviews
12 repeat clients
from
$16
per visit
Profile image

Lexi & Aaron did drop-in visits for Louis, our attention needy :) cat. They were dependable and I'm sure if cats could talk, Louis would say 'they were great!' He was a happy guy when we got home & his litter box was so clean. Knowing someone was dropping in to hang out with him (& give him his wet nummy food) made our vacation more enjoyable.

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
2.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
40 reviews
10 repeat clients
from
$20
per visit
Profile image

Katie was awesome and our Luna loved her! Luna tends to be shy at first with new people but she warmed right up after a day and loved all the attention and playtime she was getting. Katie was thorough with her updates & sent great photos as well, I highly recommend and will be rebooking!

Sitter Profile Image: Danielle S.
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Sitter Profile Image: Danielle S.
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6. Danielle S.

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

Danielle watched our two small dogs in our home recently and she was fantastic. I received updates on how they were doing and eating as well as a few photos. Danielle is very caring and made us feel so much better about going on vacation and leaving our pups at home.

Sitter Profile Image: Sarah J.
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Sitter Profile Image: Sarah J.
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7. Sarah J.

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

Sarah, was fantastic. Our dog was very well taken care of. Sarah took care of Odie as if he was her own dog, she played with and sent picture of the interactions between them.. she went way past our expectations. We will be calling on her again.

Sitter Profile Image: Michele M.
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Sitter Profile Image: Michele M.
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8. Michele M.

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

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 :)

Sitter Profile Image: Hillery F.
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Sitter Profile Image: Hillery F.
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9. Hillery F.

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

Hillery is fantastic! I cannot stay how much I appreciate her services. She has helped put our minds at ease while we are are away knowing that someone so dedicated to the well being of furry family members is there to make sure they are cared for. We are so thankful and blessed to have found Hillery.

Sitter Profile Image: April & Brad R.
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Sitter Profile Image: April & Brad R.
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10. April & Brad R.

Star Sitter
Opening home after losing pet
West Allis, WI, 53214
3.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
23 reviews
9 repeat clients
from
$20
per visit

April is a great person to take care of your dog! She has a love and passion for animals. I know that I can trust her with my pets because she is reliable and has experience taking care of them. Any dog would be lucky to have her as their watcher!!

Sitter Profile Image: Megan C.
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Sitter Profile Image: Megan C.
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11. Megan C.

Tell your dog I said Hey! ❤
west allis, WI, 53214
2.3 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
6 repeat clients
from
$15
per visit
Profile image

Megan has been nothing but fantastic with our dogs for drop-ins. They can be a little rambunctious and crazy but they always seem to enjoy her company....and trust me that's hard to find with our dogs. We will be using Megan for a very long time! Thanks Megan for always being so wonderful to our crazy loving dogs ❤️ 🐕

Sitter Profile Image: Amanda B.
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Sitter Profile Image: Amanda B.
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12. Amanda B.

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

Our first experience with a pet sitter was flawless. Amanda understood our concerns about leaving our cats to her care and went above and beyond to put us at ease. We will be requesting her services in the near future.

Sitter Profile Image: Allie S.
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Sitter Profile Image: Allie S.
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13. Allie S.

Teacher with a fenced-in yard here!
West Allis, WI, 53219
1.0 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
Profile image

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: Erica L.
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Sitter Profile Image: Erica L.
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14. Erica L.

I'll love them like my own
West Allis, WI, 53227
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
82 reviews
44 repeat clients
from
$15
per visit
Profile image

Erica has been great with our little puppy, Hazy Rey! She has been very flexible with our last minute requests which we appreciate a ton! Thank you Erica!!

Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
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15. Katherine B.

Star Sitter
Dogs are happiness 😊
West Allis, WI, 53219
1.2 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
Profile image

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.

Sitter Profile Image: Jessica E.
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Sitter Profile Image: Jessica E.
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16. Jessica E.

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

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

Sitter Profile Image: Jenn S.
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Sitter Profile Image: Jenn S.
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17. Jenn S.

Star Sitter
Animal lover and cat mom of 3 🐈
West Allis, WI, 53227
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
42 reviews
10 repeat clients
from
$23
per visit
Profile image

Jenn was great! Came before hand to meet my dog and to get to know the usual routine. She sent pictures and updates and had great communication!

Sitter Profile Image: Kevin H.
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Sitter Profile Image: Kevin H.
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18. Kevin H.

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

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!

Sitter Profile Image: Hannah W.
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Sitter Profile Image: Hannah W.
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19. Hannah W.

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

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.

Sitter Profile Image: Angie B.
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Sitter Profile Image: Angie B.
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20. Angie B.

Rover 101
Loving Family to Care for your Dog
West Allis, WI, 53219
0.4 mi. away
Boarding, Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
7 repeat clients
from
$20
per visit
Profile image

Angie was wonderful with communication and photos. I would highly recommend and would use again. Thank you!

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Rover also offers Pet Sitting & Drop Ins in these neighborhoods:

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

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Highwood Estates pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Highwood Estates, Milwaukee, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Highwood Estates pet sitters and avoid the kennel.

Drop-In Visits