Dog Boarding in Hillside, Milwaukee, WI

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Top rated Hillside dog boarders

1 / 1
Sitter Profile Image: Maria & Nayibe B.
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Maria & Nayibe B.
Star Sitter
from
$45
per night
5 out of 5.0 stars
197 reviews
63 repeat clients
20 years of experience
Brookfield, WI, 53005

They took great care of our dog and were very communicative. Love that they only watch little dogs, so we didn't have to worry about a larger dog being too rough. They're super sweet people

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Kaitlyn R.
Sitter Profile Image: Yolanda W.
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Yolanda W.
Star Sitter
from
$40
per night
5 out of 5.0 stars
150 reviews
60 repeat clients
35 years of experience
Brown Deer, WI, 53223

Yolanda and her family are precious! we received around the clock updates and pictures. My dog was immediately in love with them. They offered lots of play time, treats, and even a new toy. we felt very comfortable and confident in their care, and will def use them again!

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Tori C.
Sitter Profile Image: Michelle G.
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Michelle G.
Star Sitter
from
$48
per night
5 out of 5.0 stars
144 reviews
33 repeat clients
10 years of experience
Wauwatosa, WI, 53233

Michelle was absolutely wonderful! She sent me regular updates, was very attentive to my puppies needs and was overall very kind. I would definitely let her watch my pup again!

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Aaron R.
Sitter Profile Image: Kathy & Brad K.
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Kathy & Brad K.
from
$40
per night
5 out of 5.0 stars
53 reviews
20 repeat clients
30 years of experience
Greendale, WI, 53129

Kathy and Brad are the best! Kept in great communication while we were gone; we could tell Benjamin settled right in. We are so happy to have a new home away from home!

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Johnathan W.
Sitter Profile Image: Katharine & Michael S.
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Katharine & Michael S.
Star Sitter
from
$44
per night
5 out of 5.0 stars
19 reviews
5 repeat clients
35 years of experience
Wauwatosa, WI, 53213

Katharine and Michael were able to help me out in an emergencies situation and were so wonderful to work with. Gus was well cared for and came home happy and content. I will absolutely work with them again in the future.

Profile image
Lenore B.
Sitter Profile Image: Rebecca S.
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Rebecca S.
Star Sitter
from
$45
per night
5 out of 5.0 stars
133 reviews
45 repeat clients
30 years of experience
Town Of Lake, Milwaukee, WI, 53207

Rebecca & her family are the best with my pup! He gets to be on vacation when I’m on vacation. I love getting updates - he is hanging out with the other pups, playing outside, or snuggly & resting in every one!

Profile image
Taylor S.
Sitter Profile Image: Ashlee K.
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Ashlee K.
from
$35
per night
5 out of 5.0 stars
73 reviews
29 repeat clients
7 years of experience
Silver City, Milwaukee, WI, 53215

I needed last minute boarding and Ashley was eager to help. She was a great communicator and took great care of Duncan. I definitely recommend boarding with Ashley.

Profile image
Heather R.
Sitter Profile Image: Michelle Y.
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Michelle Y.
Star Sitter
from
$46
per night
5 out of 5.0 stars
72 reviews
21 repeat clients
15 years of experience
Cooper Park, Milwaukee, WI, 53222

Michelle was wonderful! She took care of our two younger dogs. Provided updates throughout the day and gave our boys plenty of love! Great communication, and plenty of excessive given. I would definitely ask Michelle to sit for us again! Thank you Michelle!

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Abigail B.
Sitter Profile Image: Daniel & Holly L.
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Daniel & Holly L.
Star Sitter
from
$36
per night
5 out of 4.9 stars
466 reviews
192 repeat clients
45 years of experience
West Allis, WI, 53219

Dan and Holly were just awesome! My Toby has a wonderful time vacationing with them and their bassetts. You can tell they are extremely passionate dog lovers and genuinely enjoy and love every dog that comes into their home. We will definitely be booking again!

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Torri M.
Sitter Profile Image: Rhonda G.
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Rhonda G.
Star Sitter
from
$30
per night
5 out of 5.0 stars
111 reviews
50 repeat clients
15 years of experience
Whitefish Bay, WI, 53217

Was very accommodating with a same day request! Thank you, Rhonda! It was very much appreciated, so I could spend some time with my family after recently arriving in town.

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Mj G.
Sitter Profile Image: Karen D.
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Karen D.
from
$45
per night
5 out of 4.9 stars
15 reviews
4 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

The best rover user we’ve had the pleasure of meeting. Plenty of walks, photos, and updates throughout. We will certainly be using Karen again.

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David G.
Sitter Profile Image: Lillian T.
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Lillian T.
Star Sitter
from
$35
per night
5 out of 5.0 stars
15 reviews
5 repeat clients
5 years of experience
Polonia, Milwaukee, WI, 53215

Lillian was wonderful and attentive to my dog. She sent videos and messages often to keep me updated on their adventures. Would love to book her again in the future!

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Jennifer A.
Sitter Profile Image: Megan & Richard S.
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Megan & Richard S.
Star Sitter
from
$55
per night
5 out of 5.0 stars
23 reviews
8 repeat clients
20 years of experience
Historic Third Ward, Milwaukee, WI, 53202

They did a great job with Cooper he loved them and he loved the way he had. Even though he is just a puppy when we locked him up he was pooped out from his walks and was calm and relaxed the rest of the night I would definitely have them watch Cooper again

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Danielle W.
Sitter Profile Image: Kim S.
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Kim S.
Star Sitter
from
$49
per night
5 out of 5.0 stars
126 reviews
30 repeat clients
30 years of experience
Glendale, WI, 53217

Kim did such a wonderful job caring for my pup, even when he was a bit hard to handle right away. She was communicative and transparent and worked hard to make sure that he was active, comfortable, and well-loved. I wouldn’t hesitate to recommend her services.

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A.J. D.
Sitter Profile Image: dawn s.
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dawn s.
Star Sitter
from
$40
per night
5 out of 4.9 stars
44 reviews
26 repeat clients
20 years of experience
West Allis, WI, 53214

This was my first time using Rover and I couldn’t be happier with Dawn and her husband! They were so welcoming at our Meet and Greet and made us feel very comfortable leaving Zeke overnight. She sent us updates and pictures of him having a blast in their back yard, so I could tell Zeke was having a great time. I highly recommend Dawn and will definitely be booking with her again in the future!

Profile image
jordyn w.
Sitter Profile Image: Sarah K.
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Sarah K.
from
$30
per night
5 out of 5.0 stars
9 reviews
1 repeat client
20 years of experience
Wauwatosa, WI, 53213

We couldn't be happier with Sarah! Her and her family were incredibly reliable, warm & welcoming, and went above and beyond to ensure Moose was comfortable and well-cared for. When our flight was changed last minute, Sarah was understanding and flexible. We appreciated the daily updates and so many amazing photos. It was so reassuring to see how happy Moose was during his stay. We highly recommend Sarah to anyone looking for a trustworthy and caring dog sitter! We will absolutely be rebooking for our next vacation.

Profile image
Rebecca Z.
Sitter Profile Image: Alberto V.
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Alberto V.
from
$33
per night
5 out of 5.0 stars
59 reviews
15 repeat clients
21 years of experience
Historic Mitchell Street, Milwaukee, WI, 53204

Alberto and Chance took good care of our dog while we were on vacation. Meet and greet: Had some scheduling issues but went well once scheduled. Listened to recommendations as our dog can be a difficult greeter, and it went excellently. Intake: Asked lots of good thoughtful questions, somethings I hadn't even thought about. Finn was left in good hands. Stay: Sent lots of pictures and complimented our dogs behavior, and reassured us he was doing well while we were away. Pick-up: I think there were some communication challenges that occurred due to unexpected circumstances so I cannot reasonably deduct a star for that. However if we had a firm pickup this may have created some challenges. I imagine this was a fluke but wanted to share incase it becomes a trending issue. Overall went well and will consider re-booking in the future if it works.

Profile image
Chantelle R.
Sitter Profile Image: Michael J K.
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Michael J K.
Star Sitter
from
$40
per night
5 out of 4.9 stars
176 reviews
96 repeat clients
30 years of experience
Grasslyn Manor, Milwaukee, WI, 53216

MJ is truly a dogowner's kind of sitter. Extremely well attuned to a dog's needs & feelings, whenever I drop off my Abby girl, I know she is staying with someone who actually cares and likes to be around dogs. I've had Abby stay with him several times and MJ is always extremely easy to work with, genuinely affectionate to my dog and responds to bookings ASAP. Plus his house is great for a dog to hang out and explore and he is right next to McLaren Park- which is any dogs dream! Very happy I came across MJ in my Rovering.

Profile image
Davis L.
Sitter Profile Image: Lisa W.
Verified Enhanced Background Check
Lisa W.
Star Sitter
from
$35
per night
5 out of 4.9 stars
184 reviews
56 repeat clients
30 years of experience
Bay View, MILWAUKEE, WI, 53207

Lisa took great care of my dog while I was away for about a week! She sent lots of cute and cozy pictures of him hanging out with her animals and was always easy to get in touch with. She also did a good job handling his food aggression and making adjustments to make things work for everyone. I’d definitely recommend her!

Profile image
Sylvia B.
Sitter Profile Image: Tekoya C.
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Tekoya C.
from
$28
per night
5 out of 5.0 stars
4 reviews
1 year of experience
Lower East Side, Milwaukee, WI, 53202

Tekoya did an excellent job watching our dog while we were on vacation. Communication was great and he was so easy to work with, I highly recommend Tekoya!

Profile image
Ashley E.
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Sitter Profile Image: Maria & Nayibe B.
Verified Enhanced Background Check
Sitter Profile Image: Maria & Nayibe B.
Verified Enhanced Background Check

Maria & Nayibe B.
Star Sitter

The Best Vacation for your Dogs!
Brookfield, WI, 53005
9.3 mi. away
Boarding, Doggy Day Care
from
$45
per night
5 out of 5.0 stars
197 reviews
63 repeat clients
Profile image

They took great care of our dog and were very communicative. Love that they only watch little dogs, so we didn't have to worry about a larger dog being too rough. They're super sweet people

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Yolanda W.
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Sitter Profile Image: Yolanda W.
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Yolanda W.
Star Sitter

I miss our pup & hope 2 spoil yours
Brown Deer, WI, 53223
8.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5 out of 5.0 stars
150 reviews
60 repeat clients
Profile image

Yolanda and her family are precious! we received around the clock updates and pictures. My dog was immediately in love with them. They offered lots of play time, treats, and even a new toy. we felt very comfortable and confident in their care, and will def use them again!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Michelle G.
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Sitter Profile Image: Michelle G.
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Michelle G.
Rover 101
Star Sitter

Welcome to my Home!
Wauwatosa, WI, 53233
4.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$48
per night
5 out of 5.0 stars
144 reviews
33 repeat clients
Profile image

Michelle was absolutely wonderful! She sent me regular updates, was very attentive to my puppies needs and was overall very kind. I would definitely let her watch my pup again!

Availability updated yesterday
Sitter Profile Image: Kathy & Brad K.
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Sitter Profile Image: Kathy & Brad K.
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Kathy & Brad K.

Your Dog's Home Away from Home
Greendale, WI, 53129
8.4 mi. away
Boarding, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
53 reviews
20 repeat clients
Profile image

Kathy and Brad are the best! Kept in great communication while we were gone; we could tell Benjamin settled right in. We are so happy to have a new home away from home!

Availability updated 3 days ago
Sitter Profile Image: Katharine & Michael S.
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Sitter Profile Image: Katharine & Michael S.
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Katharine & Michael S.
Star Sitter

We ❤️ Dogs! Both WFH, Walk Tons
Wauwatosa, WI, 53213
3.8 mi. away
Boarding, Doggy Day Care
from
$44
per night
5 out of 5.0 stars
19 reviews
5 repeat clients
Profile image

Katharine and Michael were able to help me out in an emergencies situation and were so wonderful to work with. Gus was well cared for and came home happy and content. I will absolutely work with them again in the future.

Availability updated today
Sitter Profile Image: Rebecca S.
Verified Enhanced Background Check
Sitter Profile Image: Rebecca S.
Verified Enhanced Background Check

Rebecca S.
Star Sitter

Trainer w/ lrg fenced in yard
Town Of Lake, Milwaukee, WI, 53207
5.9 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
133 reviews
45 repeat clients
Profile image

Rebecca & her family are the best with my pup! He gets to be on vacation when I’m on vacation. I love getting updates - he is hanging out with the other pups, playing outside, or snuggly & resting in every one!

Availability updated today
Sitter Profile Image: Ashlee K.
Verified Enhanced Background Check
Sitter Profile Image: Ashlee K.
Verified Enhanced Background Check

Ashlee K.

Pets are family 💕
Silver City, Milwaukee, WI, 53215
3.1 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$35
per night
5 out of 5.0 stars
73 reviews
29 repeat clients
Profile image

I needed last minute boarding and Ashley was eager to help. She was a great communicator and took great care of Duncan. I definitely recommend boarding with Ashley.

Availability updated 7 days ago
Sitter Profile Image: Michelle Y.
Verified Enhanced Background Check
Sitter Profile Image: Michelle Y.
Verified Enhanced Background Check

Michelle Y.
Star Sitter

Trusted & Insured Dog Mom 🐾❤
Cooper Park, Milwaukee, WI, 53222
5.0 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$46
per night
5 out of 5.0 stars
72 reviews
21 repeat clients
Profile image

Michelle was wonderful! She took care of our two younger dogs. Provided updates throughout the day and gave our boys plenty of love! Great communication, and plenty of excessive given. I would definitely ask Michelle to sit for us again! Thank you Michelle!

Availability updated today
Sitter Profile Image: Daniel & Holly L.
Verified Background Check
Sitter Profile Image: Daniel & Holly L.
Verified Background Check

Daniel & Holly L.
Rover 101
Star Sitter

Warm, loving, home like suroundings
West Allis, WI, 53219
4.8 mi. away
Boarding, Doggy Day Care
from
$36
per night
5 out of 4.9 stars
466 reviews
192 repeat clients
Profile image

Dan and Holly were just awesome! My Toby has a wonderful time vacationing with them and their bassetts. You can tell they are extremely passionate dog lovers and genuinely enjoy and love every dog that comes into their home. We will definitely be booking again!

Availability updated today
Sitter Profile Image: Rhonda G.
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Sitter Profile Image: Rhonda G.
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Rhonda G.
Star Sitter

Love to walk and cuddle.
Whitefish Bay, WI, 53217
4.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per night
5 out of 5.0 stars
111 reviews
50 repeat clients
Profile image

Was very accommodating with a same day request! Thank you, Rhonda! It was very much appreciated, so I could spend some time with my family after recently arriving in town.

Availability updated 3 days ago
Sitter Profile Image: Karen D.
Verified Enhanced Background Check
Sitter Profile Image: Karen D.
Verified Enhanced Background Check

Karen D.

Newly retired want to share my time
Lower East Side, Milwaukee, WI, 53202
1.5 mi. away
Boarding
from
$45
per night
5 out of 4.9 stars
15 reviews
4 repeat clients
Profile image

The best rover user we’ve had the pleasure of meeting. Plenty of walks, photos, and updates throughout. We will certainly be using Karen again.

Availability updated today
Sitter Profile Image: Lillian T.
Verified Background Check
Sitter Profile Image: Lillian T.
Verified Background Check

Lillian T.
Star Sitter

Experienced and playful dog lover!
Polonia, Milwaukee, WI, 53215
4.4 mi. away
Boarding, House Sitting, Doggy Day Care
from
$35
per night
5 out of 5.0 stars
15 reviews
5 repeat clients
Profile image

Lillian was wonderful and attentive to my dog. She sent videos and messages often to keep me updated on their adventures. Would love to book her again in the future!

Availability updated 14 days ago
Sitter Profile Image: Megan & Richard S.
Verified Enhanced Background Check
Sitter Profile Image: Megan & Richard S.
Verified Enhanced Background Check

Megan & Richard S.
Rover 101
Star Sitter

Stay at Home Dog Mom
Historic Third Ward, Milwaukee, WI, 53202
1.8 mi. away
Boarding, Drop-In Visits
from
$55
per night
5 out of 5.0 stars
23 reviews
8 repeat clients
Profile image

They did a great job with Cooper he loved them and he loved the way he had. Even though he is just a puppy when we locked him up he was pooped out from his walks and was calm and relaxed the rest of the night I would definitely have them watch Cooper again

Availability updated 13 days ago
Sitter Profile Image: Kim S.
Verified Enhanced Background Check
Sitter Profile Image: Kim S.
Verified Enhanced Background Check

Kim S.
Star Sitter

Never lived a day without a pet
Glendale, WI, 53217
3.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$49
per night
5 out of 5.0 stars
126 reviews
30 repeat clients
Profile image

Kim did such a wonderful job caring for my pup, even when he was a bit hard to handle right away. She was communicative and transparent and worked hard to make sure that he was active, comfortable, and well-loved. I wouldn’t hesitate to recommend her services.

Availability updated 2 days ago
Sitter Profile Image: dawn s.
Verified Background Check
Sitter Profile Image: dawn s.
Verified Background Check

dawn s.
Rover 101
Star Sitter

I am a avid pet lover.
West Allis, WI, 53214
3.8 mi. away
Boarding
from
$40
per night
5 out of 4.9 stars
44 reviews
26 repeat clients
Profile image

This was my first time using Rover and I couldn’t be happier with Dawn and her husband! They were so welcoming at our Meet and Greet and made us feel very comfortable leaving Zeke overnight. She sent us updates and pictures of him having a blast in their back yard, so I could tell Zeke was having a great time. I highly recommend Dawn and will definitely be booking with her again in the future!

Availability updated 17 days ago
Sitter Profile Image: Sarah K.
Verified Enhanced Background Check
Sitter Profile Image: Sarah K.
Verified Enhanced Background Check

Sarah K.

Dog lover with lots of experience!
Wauwatosa, WI, 53213
3.8 mi. away
Boarding
from
$30
per night
5 out of 5.0 stars
9 reviews
1 repeat client
Profile image

We couldn't be happier with Sarah! Her and her family were incredibly reliable, warm & welcoming, and went above and beyond to ensure Moose was comfortable and well-cared for. When our flight was changed last minute, Sarah was understanding and flexible. We appreciated the daily updates and so many amazing photos. It was so reassuring to see how happy Moose was during his stay. We highly recommend Sarah to anyone looking for a trustworthy and caring dog sitter! We will absolutely be rebooking for our next vacation.

Availability updated 22 days ago
Sitter Profile Image: Alberto V.
Verified Background Check
Sitter Profile Image: Alberto V.
Verified Background Check

Alberto V.
Rover 101

Welcome to our home! 🏡
Historic Mitchell Street, Milwaukee, WI, 53204
3.1 mi. away
Boarding
from
$33
per night
5 out of 5.0 stars
59 reviews
15 repeat clients
Profile image

Alberto and Chance took good care of our dog while we were on vacation. Meet and greet: Had some scheduling issues but went well once scheduled. Listened to recommendations as our dog can be a difficult greeter, and it went excellently. Intake: Asked lots of good thoughtful questions, somethings I hadn't even thought about. Finn was left in good hands. Stay: Sent lots of pictures and complimented our dogs behavior, and reassured us he was doing well while we were away. Pick-up: I think there were some communication challenges that occurred due to unexpected circumstances so I cannot reasonably deduct a star for that. However if we had a firm pickup this may have created some challenges. I imagine this was a fluke but wanted to share incase it becomes a trending issue. Overall went well and will consider re-booking in the future if it works.

Availability updated today
Sitter Profile Image: Michael J K.
Verified Background Check
Sitter Profile Image: Michael J K.
Verified Background Check

Michael J K.
Star Sitter

They'll be loved while you're gone!
Grasslyn Manor, Milwaukee, WI, 53216
3.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5 out of 4.9 stars
176 reviews
96 repeat clients
Profile image

MJ is truly a dogowner's kind of sitter. Extremely well attuned to a dog's needs & feelings, whenever I drop off my Abby girl, I know she is staying with someone who actually cares and likes to be around dogs. I've had Abby stay with him several times and MJ is always extremely easy to work with, genuinely affectionate to my dog and responds to bookings ASAP. Plus his house is great for a dog to hang out and explore and he is right next to McLaren Park- which is any dogs dream! Very happy I came across MJ in my Rovering.

Availability updated 10 days ago
Sitter Profile Image: Lisa W.
Verified Enhanced Background Check
Sitter Profile Image: Lisa W.
Verified Enhanced Background Check

Lisa W.
Star Sitter

Here to be kind to your pets!
Bay View, MILWAUKEE, WI, 53207
3.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5 out of 4.9 stars
184 reviews
56 repeat clients
Profile image

Lisa took great care of my dog while I was away for about a week! She sent lots of cute and cozy pictures of him hanging out with her animals and was always easy to get in touch with. She also did a good job handling his food aggression and making adjustments to make things work for everyone. I’d definitely recommend her!

Availability updated 4 days ago
Sitter Profile Image: Tekoya C.
Verified Enhanced Background Check
Sitter Profile Image: Tekoya C.
Verified Enhanced Background Check

Tekoya C.

Reliable and loving pet care!!
Lower East Side, Milwaukee, WI, 53202
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
5 out of 5.0 stars
4 reviews
Profile image

Tekoya did an excellent job watching our dog while we were on vacation. Communication was great and he was so easy to work with, I highly recommend Tekoya!

Availability updated 54 days ago

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