House Sitting in Highwood Estates, Milwaukee

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Top rated Highwood Estates house sitters

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Sitter Profile Image: Addoris D.
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Addoris D.
from
$50
per night
5 out of 5.0 stars
11 reviews
1 repeat client
5 years of experience
Lower East Side, Milwaukee, WI, 53202

Did a great job managing our house full of animals while we were away for two weeks. We came home to happy healthy animals, and I could tell they'd been well-cared for!

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Nikki C.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$31
per night
5 out of 5.0 stars
24 reviews
12 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha was amazing!! She sent lots of updates on our dog and spent really good time with her the whole 5 day trip. She was in such good hands and we would DEFINITELY use her again! Thank you!!

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Elissa G.
Sitter Profile Image: Ashley W.
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Ashley W.
from
$45
per night
5 out of 5.0 stars
15 reviews
6 repeat clients
10 years of experience
Washington Heights, Milwaukee, WI, 53208

As usual, a smooth transaction/stay! We absolutely love Ashley. She is very flexible, punctual and most importantly - clean (we only do home stays). Our pup is always happy to see Ashley and enjoys her company very much.

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Kristina S.
Sitter Profile Image: Mallory Q.
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Mallory Q.
Star Sitter
from
$45
per night
5 out of 5.0 stars
13 reviews
3 repeat clients
30 years of experience
West Allis, WI, 53719

Mallory is so nice! She ensured that Kermit was comfortable despite fireworks and a thunderstorm in the same weekend. She sent us updates twice a day to reassure us that he was doing okay.

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Miranda D.
Sitter Profile Image: Blythe R.
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Blythe R.
Star Sitter
from
$75
per night
5 out of 5.0 stars
182 reviews
66 repeat clients
7 years of experience
Bay View, Milwaukee, WI, 53207

Blythe was great! She took care of our girls while we were away for a quick weekend trip and when we arrived home they were very happy and content and the house was clean and neat. There’s no doubt we’ll be booking with her again!

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Kimberly M.
Sitter Profile Image: Rachel H.
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Rachel H.
from
$30
per night
5 out of 5.0 stars
92 reviews
23 repeat clients
11 years of experience
West Allis, WI, 53214

Rachel was great with our pup and cats, as always! While away we can feel confident the house and pets are being cared for and they all get lots of snuggles!

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Todd S.
Sitter Profile Image: Emily M.
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Emily M.
from
$45
per night
5 out of 5.0 stars
6 reviews
1 repeat client
30 years of experience
Milwaukee, WI, 53213

Did amazing

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Justin F.
Sitter Profile Image: Emily S.
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Emily S.
Star Sitter
from
$40
per night
5 out of 4.9 stars
35 reviews
20 repeat clients
6 years of experience
West Allis, WI, 53227

Emily did a great job with our older dog. She communicated any concerns she had with him. The house was left in pristine condition. We were thankful to have her staying with Louie.

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Cheryl D.
Sitter Profile Image: Sydnee E.
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Sydnee E.
from
$50
per night
10 years of experience
Milwaukee, WI, 53204

About: I’ve had at least 1 pet my entire life, so I’m no stranger to caring for pets in my home. Beginning in middle school and until now, I’ve been entrusted by family, friends, and coworkers to take care of their pets while they’re away. I have experience with house visits, walking or dog park trips, and overnight care. While I don’t have direct experience with pets who require medical attention, I’d be happy to learn with you. I do have experience with senior pet care. Overall, I guarantee I’ll take care of your pet like my own! I recently graduated from PA school and am job searching currently, so I have plenty of time to play with your pets! I’m available for daytime care or overnight care daily. When looking after your pet, I will always take care of them like my own. I’m happy to play with them in the yard, take them on walks or to the park, lounge with them on the couch on a rainy day, or crate them if needed. I can stick to strict meal or medication times and will ensure they have potty breaks with appropriate clean up.

Sitter Profile Image: Alexander A.
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Alexander A.
from
$30
per night
5 out of 5.0 stars
6 reviews
2 repeat clients
12 years of experience
West Milwaukee, WI, 53214

Alex was a great person to have watch our dog. He made sure she was walked, fed and protected when she was scared that we were not here. He is a kind and respectable man. He even made sure that any dishes he used were ran thru the dishwasher before he left. We will definitely look to have him sit for us again when we are out of town again.

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Jack V.
Sitter Profile Image: Sarah J.
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Sarah J.
Star Sitter
from
$50
per night
5 out of 5.0 stars
323 reviews
70 repeat clients
5 years of experience
West allis, WI, 53219

Sarah was amazing!!sent updates and pictures during her stay. Came back to a clean house and happy pets! We will definitely be having her watch our girls again :)

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Justine R.
Sitter Profile Image: Zoey Y.
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Zoey Y.
from
$28
per night
5 out of 5.0 stars
4 reviews
5 years of experience
Milwaukee, WI, 53213

Zoey was amazing with my dogs and had incredible communication. This is the first time I have left my babies alone with someone and she couldn’t have made me feel more comfortable about it. Highly Recommended and I will, without hesitation, book her again!

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Antonino D.
Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$62
per night
5 out of 5.0 stars
76 reviews
20 repeat clients
40 years of experience
West Allis, WI, 53227

Jen has been so responsive and communicated with us during the process of hiring a pet sitter from Rover for the first time. More importantly she did a phenomenal job caring for our pets. We will definitely request her again!!

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Diane C.
Sitter Profile Image: Samantha B.
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Samantha B.
from
$60
per night
5 out of 4.9 stars
12 reviews
4 repeat clients
13 years of experience
Milwaukee, WI, 53215

Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.

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Alyssa T.
Sitter Profile Image: Makenzie M.
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Makenzie M.
from
$25
per night
6 years of experience
West Allis, WI, 53220

About: I have taken care of dogs and puppies since the beginning of high school. Friends and family have always asked me back to care for their animals while they are away. I have done basic training with puppies, have taken care of senior dogs, and am able to give medication if needed. I am currently in college and on summer break. I have always very open schedule at the moment and am willing to care for animals almost any day of the week at any time. I will only care for animals in the clients' home and I will assure to follow everything that the client leaves me regarding their pet and their home.

Sitter Profile Image: Liz B.
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Liz B.
Star Sitter
from
$50
per night
5 out of 4.9 stars
37 reviews
13 repeat clients
7 years of experience
West Allis, WI, 53214

Liz was wonderful! Excellent communication. This was my first time using Rover and she made for an amazing first experience. I will definitely use her services again.

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Stacy J.
Sitter Profile Image: Jordanne H.
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Jordanne H.
from
$75
per night
5 out of 4.9 stars
18 reviews
6 repeat clients
5 years of experience
West Allis, WI, 53214

We were happy to re-connect with Jordanne for dog sitting this summer. She is prompt, attentive and responsible, and so we are very comfortable with her caring for our senior dog Connor. We have already booked her for another visit!

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Curtis G.
Sitter Profile Image: Stephanie C.
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Stephanie C.
from
$28
per night
20 years of experience
Jackson Park, Milwaukee, WI, 53215

About: I've been around animals my whole life and currently share my home with three cats and one dog - it's a full house! I have hands-on experience caring for senior dogs, including my own 13-year-old who needs daily medication. I also grew up with huskies, so I'm no stranger to high-energy breeds and the active care they require. On the flip side, I'm just comfortable with laid-back pus - my pug keeps things goofy and fun. Whether it's administering meds, going for long walks, or just providing companionship, I bring patience, energy, and love to every pet I care for. I work full-time remotely, which gives me the flexibility to offer morning and afternoon drop-ins and walks during the week. On weekends, I'm fully available for all listed services and can accommodate a wider range of times. My home has a partially fenced yard and system of tall gates inside to safely separate cats and dogs when needed, so every pet can feel secure and relaxed. I'm happy to kennel your pup if that's part of their routine or needed for comfort. Your pet's safety and peace of mind are always my top priority.

Sitter Profile Image: Katherine B.
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Katherine B.
from
$70
per night
5 out of 5.0 stars
24 reviews
10 repeat clients
15 years of experience
West Allis, WI, 53219

I could not say enough great things about katie! As a new dog mom to a puppy, she was so patient and so attentive to my boy. Katie sent tons of pictures, videos and kept me updated routinely on anything that had changed. She was a respectful house guest and provided excellent care to my dog while I was working very long hours for three consecutive days. My mama heart was at ease knowing I had such an excellent person taking the best care of my dog!!

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Abbey V.
Sitter Profile Image: Jessica R.
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Jessica R.
from
$45
per night
5 out of 5.0 stars
13 reviews
16 years of experience
Woodland Court, Milwaukee, WI, 53220

Jessica was great with our lab! Also sent pictures and spent quality time with her! Would definitely book with her again.

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Amelia G.
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Sitter Profile Image: Addoris D.
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Sitter Profile Image: Addoris D.
Verified Enhanced Background Check

Addoris D.

Queer Friendly & Energetic Sitter
Lower East Side, Milwaukee, WI, 53202
7.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
11 reviews
1 repeat client
Profile image

Did a great job managing our house full of animals while we were away for two weeks. We came home to happy healthy animals, and I could tell they'd been well-cared for!

Availability updated 5 days ago
Sitter Profile Image: Keisha P.
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Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter

Your Furbabies will Love Me
Clarke Square, Milwaukee, WI, 53204
4.2 mi. away
House Sitting, Drop-In Visits
from
$31
per night
5 out of 5.0 stars
24 reviews
12 repeat clients
Profile image

Keisha was amazing!! She sent lots of updates on our dog and spent really good time with her the whole 5 day trip. She was in such good hands and we would DEFINITELY use her again! Thank you!!

Availability updated today
Sitter Profile Image: Ashley W.
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Sitter Profile Image: Ashley W.
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Ashley W.

Active person loves active dogs
Washington Heights, Milwaukee, WI, 53208
5.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
15 reviews
6 repeat clients
Profile image

As usual, a smooth transaction/stay! We absolutely love Ashley. She is very flexible, punctual and most importantly - clean (we only do home stays). Our pup is always happy to see Ashley and enjoys her company very much.

Availability updated today
Sitter Profile Image: Mallory Q.
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Sitter Profile Image: Mallory Q.
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Mallory Q.
Star Sitter

Dedicated Animal Friend!
West Allis, WI, 53719
1.4 mi. away
House Sitting, Drop-In Visits
from
$45
per night
5 out of 5.0 stars
13 reviews
3 repeat clients
Profile image

Mallory is so nice! She ensured that Kermit was comfortable despite fireworks and a thunderstorm in the same weekend. She sent us updates twice a day to reassure us that he was doing okay.

Availability updated today
Sitter Profile Image: Blythe R.
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Sitter Profile Image: Blythe R.
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Blythe R.
Star Sitter

Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
6.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
182 reviews
66 repeat clients
Profile image

Blythe was great! She took care of our girls while we were away for a quick weekend trip and when we arrived home they were very happy and content and the house was clean and neat. There’s no doubt we’ll be booking with her again!

Availability updated 3 days ago
Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
92 reviews
23 repeat clients
Profile image

Rachel was great with our pup and cats, as always! While away we can feel confident the house and pets are being cared for and they all get lots of snuggles!

Availability updated 11 days ago
Sitter Profile Image: Emily M.
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Sitter Profile Image: Emily M.
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Emily M.

Raised on urban farm, pet sitter
Milwaukee, WI, 53213
3.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
6 reviews
1 repeat client
Profile image

Did amazing

Availability updated today
Sitter Profile Image: Emily S.
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Sitter Profile Image: Emily S.
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Emily S.
Star Sitter

Enjoy making pets happy and loved
West Allis, WI, 53227
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 4.9 stars
35 reviews
20 repeat clients
Profile image

Emily did a great job with our older dog. She communicated any concerns she had with him. The house was left in pristine condition. We were thankful to have her staying with Louie.

Availability updated today
Sitter Profile Image: Sydnee E.
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Sitter Profile Image: Sydnee E.
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Sydnee E.

Your pet’s next best friend!
Milwaukee, WI, 53204
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
4 reviews

Sydnee is a wonderful dog walker. She took care of my Australian Shepherd for the last 1 year. She is trustworthy and treated Tucker like her own! Recommend her to anyone needing someone to look after their pets!

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Alexander A.
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Sitter Profile Image: Alexander A.
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Alexander A.

Dog’s Best friend
West Milwaukee, WI, 53214
3.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$30
per night
5 out of 5.0 stars
6 reviews
2 repeat clients
Profile image

Alex was a great person to have watch our dog. He made sure she was walked, fed and protected when she was scared that we were not here. He is a kind and respectable man. He even made sure that any dishes he used were ran thru the dishwasher before he left. We will definitely look to have him sit for us again when we are out of town again.

Availability updated 13 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Sarah J.
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Sitter Profile Image: Sarah J.
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Sarah J.
Star Sitter

I’m awkward with humans.
West allis, WI, 53219
0.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 5.0 stars
323 reviews
70 repeat clients
Profile image

Sarah was amazing!!sent updates and pictures during her stay. Came back to a clean house and happy pets! We will definitely be having her watch our girls again :)

Availability updated today
Sitter Profile Image: Zoey Y.
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Sitter Profile Image: Zoey Y.
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Zoey Y.

Recent college grad who loves pets!
Milwaukee, WI, 53213
4.4 mi. away
House Sitting
from
$28
per night
5 out of 5.0 stars
4 reviews
Profile image

Zoey was amazing with my dogs and had incredible communication. This is the first time I have left my babies alone with someone and she couldn’t have made me feel more comfortable about it. Highly Recommended and I will, without hesitation, book her again!

Availability updated 2 days ago
Sitter Profile Image: Jenn S.
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Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter

Dedicated & Reliable 🐕🐈🦜🐟
West Allis, WI, 53227
1.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$62
per night
5 out of 5.0 stars
76 reviews
20 repeat clients
Profile image

Jen has been so responsive and communicated with us during the process of hiring a pet sitter from Rover for the first time. More importantly she did a phenomenal job caring for our pets. We will definitely request her again!!

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Samantha B.
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Sitter Profile Image: Samantha B.
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Samantha B.

Animal lover for both dogs or cats
Milwaukee, WI, 53215
2.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 4.9 stars
12 reviews
4 repeat clients
Profile image

Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.

Availability updated 8 days ago
Sitter Profile Image: Makenzie M.
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Sitter Profile Image: Makenzie M.
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Makenzie M.

I deeply care about all animals.
West Allis, WI, 53220
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per night
1 review

I’ve known Kenzie for a while now, and saying she’s good with pets would be an understatement. She cares so deeply for her own cat and dog, Poppy and Ash, and she cares for others’ pets just the same which was shown to me as I watched her care for her college suite mate’s cat like it was her own! She is gentle and can read cues from cats and dogs very well. Kenzie would be an amazing caretaker for your pet!!

Availability updated 8 days ago
Sitter Profile Image: Liz B.
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Sitter Profile Image: Liz B.
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Liz B.
Rover 101
Star Sitter

Senior pet lover and expert!
West Allis, WI, 53214
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.9 stars
37 reviews
13 repeat clients
Profile image

Liz was wonderful! Excellent communication. This was my first time using Rover and she made for an amazing first experience. I will definitely use her services again.

Availability updated yesterday
Sitter Profile Image: Jordanne H.
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Sitter Profile Image: Jordanne H.
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Jordanne H.

I’m a teacher with all summer off!!
West Allis, WI, 53214
2.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$75
per night
5 out of 4.9 stars
18 reviews
6 repeat clients
Profile image

We were happy to re-connect with Jordanne for dog sitting this summer. She is prompt, attentive and responsible, and so we are very comfortable with her caring for our senior dog Connor. We have already booked her for another visit!

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

Stephanie C.

Love the Fur Babies
Jackson Park, Milwaukee, WI, 53215
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
2 reviews

Stephanie is a top-tier dog whisperer—equal parts dependable caregiver and canine concierge. Whether she welcomed our pups into her home or came to ours, she showed up with love, energy, and a camera roll full of happy tails. She played, she pampered, and she always made sure the outdoor business got handled (dignity intact). Our dogs practically packed their own bags when it was time to visit her—and didn’t even give us a second glance. If Rover had a 10-star rating system, she’d break it.

Availability updated 3 days ago
Sitter Profile Image: Katherine B.
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Sitter Profile Image: Katherine B.
Verified Enhanced Background Check

Katherine B.

Dogs are happiness 😊
West Allis, WI, 53219
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$70
per night
5 out of 5.0 stars
24 reviews
10 repeat clients
Profile image

I could not say enough great things about katie! As a new dog mom to a puppy, she was so patient and so attentive to my boy. Katie sent tons of pictures, videos and kept me updated routinely on anything that had changed. She was a respectful house guest and provided excellent care to my dog while I was working very long hours for three consecutive days. My mama heart was at ease knowing I had such an excellent person taking the best care of my dog!!

Availability updated 5 days ago
Sitter Profile Image: Jessica R.
Verified Enhanced Background Check
Sitter Profile Image: Jessica R.
Verified Enhanced Background Check

Jessica R.

A dogs best friend🩷
Woodland Court, Milwaukee, WI, 53220
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
13 reviews
Profile image

Jessica was great with our lab! Also sent pictures and spent quality time with her! Would definitely book with her again.

Availability updated 8 days ago

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