House Sitting in Havenwoods, Milwaukee

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Sitter Profile Image: Katie M.
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Sitter Profile Image: Katie M.
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1. Katie M.

Star Sitter
Happy Pets, Self-Insured Care!
Elm Grove, WI, 53122
7.9 mi. away
Boarding, House Sitting, Drop-In Visits
from
$50
per night
5 out of 5.0 stars
23 reviews
6 repeat clients
Profile image

Katie did a great job with our two dogs, one which is a senior and needs a lot of help! She sent us plenty of pics and even brought in our mail while we were away. She did an excellent job!

Availability updated 3 days ago
Sitter Profile Image: Emily S.
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Sitter Profile Image: Emily S.
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2. Emily S.

Enjoy making pets happy and loved
West Allis, WI, 53227
8.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 4.9 stars
21 reviews
17 repeat clients
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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 yesterday
Sitter Profile Image: Ashley W.
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Sitter Profile Image: Ashley W.
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3. Ashley W.

Active person loves active dogs
Washington Heights, Milwaukee, WI, 53208
4.7 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
13 reviews
5 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 6 days ago
Sitter Profile Image: Keisha P.
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Sitter Profile Image: Keisha P.
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4. Keisha P.

Star Sitter
Your Furbabies will Love Me
Clarke Square, Milwaukee, WI, 53204
7.4 mi. away
House Sitting, Drop-In Visits
from
$31
per night
5 out of 5.0 stars
11 reviews
7 repeat clients
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As always, Keisha did a wonderful job taking care of my fur babies while I was out of town! Came home to happy pets and a clean house after a long day of traveling.

Availability updated yesterday
Sitter Profile Image: Jasmine T.
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Sitter Profile Image: Jasmine T.
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5. Jasmine T.

Star Sitter
🐈‍⬛Caring for your furry family🐕
Timmerman West, Milwaukee, WI, 53225
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
7 reviews
3 repeat clients
Profile image

Jasmine watched our 3 month old puppy and was awesome! She provided plenty of updates (lots of pictures!), was able to let her out regularly, and kept her entertained all day while we were gone! Would definitely recommend her to anyone looking for a reliable puppy sitter!

Availability updated yesterday
Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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6. Lily S.

Star Sitter
Certified Sitter!
Milwaukee, WI, 53212
5.4 mi. away
House Sitting, Drop-In Visits
from
$75
per night
5 out of 5.0 stars
38 reviews
12 repeat clients
Profile image

As always, Lily goes above and beyond. Helped navigate an u expected, significant GI problem with one of the dogs that required a visit for emergency care and helping mitigate a significant clean-up job. Communicated fantastically throughout the saga

Availability updated 3 days ago
Sitter Profile Image: Melissa H.
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Sitter Profile Image: Melissa H.
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7. Melissa H.

Star Sitter
Their Favorite Pawsome Auntie 🐾
Milwaukee, WI, 53211
6.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
24 reviews
5 repeat clients
Profile image

Melissa is a great overnight dogsitter. She followed all the instructions for my dog and bullies have a lot of instructions. Ha! She provided updates everyday and you can tell she enjoys dogsitting. I came back to happy dog.

Availability updated 3 days ago
Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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8. Jessica Z.

Star Sitter
Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
6.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$64
per night
5 out of 5.0 stars
151 reviews
46 repeat clients
Profile image

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.

Availability updated today
Sitter Profile Image: Linnea G.
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Sitter Profile Image: Linnea G.
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9. Linnea G.

Rover 101
Home Full Time Dog Lover!
Lower East Side, Milwaukee, WI, 53202
6.3 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 4.9 stars
47 reviews
14 repeat clients
Profile image

Linnea was absolutely amazing! She went above and beyond to make sure my puppy was well taken care of (which included a vet visit). I could not recommend Linnea enough. She was super communicative and my puppy loved her. She also was a perfect house guest.

Availability updated today
Sitter Profile Image: Alyssa B.
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Sitter Profile Image: Alyssa B.
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10. Alyssa B.

Compassionate Pet Sitter
Whitefish Bay, WI, 53217
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
6 reviews
3 repeat clients
Profile image

I loved Alyssa's help taking care of my dog ​​Tango. She did everything I asked her to do. She was very responsible and my dog ​​Tango loved her. During my trip, she sent me photos of Tango's walks with her in the park. 100% recommended.

Availability updated 3 days ago
Sitter Profile Image: Liz P.
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Sitter Profile Image: Liz P.
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11. Liz P.

Star Sitter
Pet Lover who works from home!
Riverwest, Milwaukee, WI, 53212
5.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
116 reviews
38 repeat clients
Profile image

Liz watched our two dogs and cat for a week and she was so kind and communicative! We felt very comfortable leaving our pets in her hands, they were very well cared for! We will definitely be using her again in the future.

Availability updated yesterday
Sitter Profile Image: Kelsey H.
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Sitter Profile Image: Kelsey H.
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12. Kelsey H.

flexible schedule for walks/sitting
Mount Mary, Milwaukee, WI, 53222
4.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$39
per night
5 out of 5.0 stars
58 reviews
16 repeat clients
Profile image

Our dogs have never had a sitter in our home, but we wanted to give it a try, as they are always out of sorts if we pick them up from a kennel. Kelsey gave several pupdates with photos, and we got to come home to 2 very happy boys that probably didn’t even notice we were gone. Hope she’d be willing to sit for them once in awhile in the future.

Availability updated 3 days ago
Sitter Profile Image: Ava W.
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Sitter Profile Image: Ava W.
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13. Ava W.

Dog-lover happy to help you out!
Fox Point, WI, 53217
3.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
2 reviews

Ava is a great dog sitter! She took such good care of my pup while I was away. She is attentive, loving, and super responsible. I came home to a happy dog and regular updates throughout my trip made me feel totally at ease. Highly recommend Ava to anyone looking for peace of mind and a truly caring sitter!

Availability updated 4 days ago
Sitter Profile Image: Jamila M.
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Sitter Profile Image: Jamila M.
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14. Jamila M.

Rover 101
Star Sitter
Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
4.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$57
per night
5 out of 4.9 stars
80 reviews
24 repeat clients
Profile image

Jeremy was amazing. He was prompt, insanely responsive, and went above and beyond when we forgot to leave our son’s soccer stuff out for pick up. He even ran to purchase new shin guards when he couldn’t find them for us. This man is truly amazing and we appreciate him watching our three puppies. Our shepherd is usually super depressed when we are away and he looks so happy in all the pictures we received.

Availability updated 15 days ago
Sitter Profile Image: Charles B.
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Sitter Profile Image: Charles B.
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15. Charles B.

Pet lover ready 2 watch your bestie
Fox Point, WI, 53217
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
5 out of 5.0 stars
14 reviews
2 repeat clients
Profile image

Charles was amazing with our dog!! Our dog is massive and can be ornery at times but he took to Charley immediately. Charley came to our house several times a day while we were out of town so our dog could remain in the place where he is comfortable. Often, Charley would stay and work out of our house just so our dog wouldn’t be alone. It was very comforting knowing our dog was well cared for and loved while we were away. Thank you Charley!!

Availability updated 5 days ago
Sitter Profile Image: Marilia D.
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Sitter Profile Image: Marilia D.
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16. Marilia D.

Star Sitter
I've had 7 dogs at once. Trust me.
Estabrook Park, Milwaukee, WI, 53217
3.4 mi. away
House Sitting, Drop-In Visits
from
$70
per night
5 out of 5.0 stars
60 reviews
15 repeat clients
Profile image

My kitties had a great time with their new friend Marilia. When Marilia came back to the house, even my shy Chico cat came to see her. So I guess the cats say it all. When they come to the door to greet the pet sitter, that is all I need to say. They love her.

Availability updated today
Sitter Profile Image: Perseus M.
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Sitter Profile Image: Perseus M.
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17. Perseus M.

Rover 101
Caring & respectful animal lover
Milwaukee, WI, 53223
3.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
12 reviews

When I needed someone to care for my two dachshunds, two cats, and even my turtle while I was out of town for a work trip, Perseus stepped up without hesitation. I was initially nervous about leaving my pets, but knowing Perseus would be watching my babies put my mind at ease. He took the time to understand each animal’s unique needs—the dachshunds' love for belly rubs and short walks, the cats' different personalities and feeding schedules, and even how to properly care for my turtle’s tank. Not only was everything spotless when I returned, but my pets seemed calm and happy, which is the ultimate testament to how well they were cared for. Perseus has a natural connection with animals and goes above and beyond to ensure their comfort and safety. I wouldn’t hesitate to trust him again and would wholeheartedly recommend him to any pet parent looking for someone dependable, kind, knowledgeable, and attentive.

Availability updated today
Sitter Profile Image: Tegra R.
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Sitter Profile Image: Tegra R.
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18. Tegra R.

Star Sitter
The right Mama to care 4 your baby
Milwaukee, WI, 53223
2.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5 out of 5.0 stars
38 reviews
12 repeat clients
Profile image

Tegra made me feel comfortable with leaving my senior pup. She provided photos and communicated with me when the many times I reached out to check in on Tedi. I came home to a happy pup!

Availability updated 31 days ago
Sitter Profile Image: Jeff G.
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Sitter Profile Image: Jeff G.
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19. Jeff G.

Star Sitter
Care for dogs like they're children
Glendale, WI, 53209
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 4.9 stars
50 reviews
13 repeat clients
Profile image

Jeff was a wonderful sitter!! We will absolutely be asking him to dogsit again soon! He came to meet us a week ahead of time to learn about Winnie’s routine, confirmed the sitting the day before, and maintained great communication throughout her care. She has separation anxiety but she calmed down very quickly with Jeff and snuggled him all night. He ensured that timing was flexible and we felt so confident leaving our disabled pup with Jeff! Definitely recommend!

Availability updated 4 days ago
Sitter Profile Image: Genesis A.
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Sitter Profile Image: Genesis A.
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20. Genesis A.

Exercise, relax time and hugs! :)
Old North Milwaukee, Milwaukee, WI, 53209
1.7 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
6 reviews
2 repeat clients

Génesis es una amante a los animales y es muy apasionada a su trabajo, es muy cariñosa con las mascotas, y está estudiando veterinaria ya que es algo que le apasiona, es atenta y cuidadosa con los animales.

Availability updated 11 days ago

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  1. 1. Search

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  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

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  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

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