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Add your dates and pets to get accurate pricing. Prices are estimates per day. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

Sitter Profile Image: Lillian T.
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Sitter Profile Image: Lillian T.
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1. Lillian T.
Star Sitter

Experienced and playful dog lover!
Polonia, Milwaukee, WI, 53215
1.3 mi. away
from
$27
per day
5.0 out of 5.0 stars
18 reviews
5 repeat clients
Profile image

Lillian was the sweetest! My baby boy Kross had the best time with her. She cared for him very well, kept him entertained with enriching activities, and sent lots of updates during the day with pictures and videos. 10/10 no notes! Will definitely be booking again in the future

Availability updated 5 days ago
Sitter Profile Image: Joe S.
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Sitter Profile Image: Joe S.
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2. Joe S.
Star Sitter

Loving, stay at home, Dog parents
Tippecanoe, Milwaukee, WI, 53207
0.9 mi. away
from
$40
per day
5.0 out of 5.0 stars
124 reviews
52 repeat clients
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Markie and Logan came home smiling and tired, which is really all I ask. they had a blast playing with all of the other dogs, and Logan didn't want to come inside from Joe's back yard!

Availability updated yesterday
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Miranda O.
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Sitter Profile Image: Miranda O.
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3. Miranda O.
Star Sitter

All Dogs go to heaven
Bay View, Milwaukee, WI, 53207
1.3 mi. away
from
$35
per day
4.9 out of 5.0 stars
175 reviews
85 repeat clients
Profile image

Miranda has been great to work with. She is flexible and really good with my puppy. In the pictures she sent my puppy looks happy as can be. I’m really happy we found her!

Availability updated yesterday
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Katrina M.
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Sitter Profile Image: Katrina M.
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4. Katrina M.

Home Full Time- Always Available!
Town Of Lake, Milwaukee, WI, 53207
0.6 mi. away
from
$35
per day
5.0 out of 5.0 stars
423 reviews
205 repeat clients
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We were looking for a dog boarder for an upcoming vacation nd decided to do a test run with Katrina. Our experience was fantastic! Katrina was easy to coordinate with. Is great with communication and updates during the visit. Our dog has separation anxiety, so she was more of a challenge but Katrina had her relaxed and napping in a couple hours. Looks like we have definitely found our go to for boarding!

Availability updated over 1 year ago
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Katrina E.
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Sitter Profile Image: Katrina E.
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5. Katrina E.
Star Sitter

Work from home, dog lover.
Saint Francis, WI, 53235
2.0 mi. away
from
$25
per day
5.0 out of 5.0 stars
35 reviews
5 repeat clients
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Lotte gets along great with Katrina’s dogs and Katrina is wonderful with her and communicates regularly to let us know how who she is doing. We’re thankful to find someone who can watch her regularly.

Availability updated 2 days ago
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Katie B.
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Sitter Profile Image: Katie B.
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6. Katie B.

Dogs! Cats! Chickens! Oh My!
Bay View, Milwaukee, WI, 53207
1.1 mi. away
from
$40
per day
5.0 out of 5.0 stars
8 reviews
2 repeat clients
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Logan loves spending time with Katie! He was so excited to see her, and she always does a great job keeping him entertained and tiring him out!

Availability updated 23 days ago
Sitter Profile Image: Kait S.
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Sitter Profile Image: Kait S.
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7. Kait S.

professional dog mama
Morgandale, Milwaukee, WI, 53215
0.7 mi. away
from
$40
per day
5.0 out of 5.0 stars
52 reviews
18 repeat clients
Profile image

Thank you Kait for taking care of Joker. She was updating me all day which is great. Kait’s dog, Zelda, is a wonderful host. We will keep Kait as a regular pet sitter when possible.

Availability updated 7 days ago
Sitter Profile Image: Wendy N.
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Sitter Profile Image: Wendy N.
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8. Wendy N.
Rover 101
Star Sitter

Home all day! Near the airport!
Bay View, Milwaukee, WI, 53207
0.6 mi. away
from
$48
per day
5.0 out of 5.0 stars
85 reviews
23 repeat clients
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Wendy is the absolute best! Professional, always gives so much love to my Dexter and all her other doggie pals that come over. She gives plenty updates and pictures to assure you that your fur baby is having the time of his his/her life! She’s the best and so friendly and loving. Safety is a big concern of mine. As I’m an over protective dog mom. Quality 10/10 safety 10/10 communication 10/10 and flexibility with scheduling 10/10.

Availability updated today
Sitter Profile Image: Elba M.
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Sitter Profile Image: Elba M.
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9. Elba M.
Rover 101

Wiggle waggle and roll!
Cudahy, WI, 53110
3.8 mi. away
from
$38
per day
5.0 out of 5.0 stars
173 reviews
64 repeat clients
Profile image

Elba was amazing with my little 9 mo. old anxious dog. It was her first time in doggy daycare and Elba was up for the challenge. She had very useful observations and connected well with my little girl, making her feel much more comfortable. We had a great experience!

Availability updated 9 days ago
Sitter Profile Image: Daniel & Holly L.
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Sitter Profile Image: Daniel & Holly L.
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10. Daniel & Holly L.
Rover 101
Star Sitter

Warm, loving, home like suroundings
West Allis, WI, 53219
4.0 mi. away
from
$34
per day
4.9 out of 5.0 stars
475 reviews
195 repeat clients
Profile image

Daniel and Holly definitely love dogs and are personable and friendly every time we go there. They sent us numerous text messages, including pictures, telling us how things were going. Bug is a very active dog and really benefits from a couple walks each day. I’m not sure if that happened.

Availability updated yesterday
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Amy K.
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Sitter Profile Image: Amy K.
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11. Amy K.
Star Sitter

Honored w/the Opportunity to Help
Cudahy, WI, 53110
4.0 mi. away
from
$40
per day
5.0 out of 5.0 stars
105 reviews
36 repeat clients
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Amy was fantastic! She was kind enough to pick up my last minute request and definitely showed Elliot lots of love during his time with her. Great communication and would definitely book with Amy again!

Availability updated 6 days ago
Sitter Profile Image: Iuscely F.
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Sitter Profile Image: Iuscely F.
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12. Iuscely F.

Pet Lover Ready To Love Yours
Historic Mitchell Street, Milwaukee, WI, 53204
2.4 mi. away
from
$38
per day
5.0 out of 5.0 stars
12 reviews
Profile image

Luscely was available last minute and didn't make me jump through hoops to dogsit. She was communicative, fair, and my dog was happy. I will absolutely use her again!

Availability updated 14 days ago
Sitter Profile Image: Berenice B.
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Sitter Profile Image: Berenice B.
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13. Berenice B.
Rover 101

I walk to keep their tails waggin’
Bay View, Milwaukee, WI, 53207
1.6 mi. away
from
$75
per day
4.9 out of 5.0 stars
229 reviews
95 repeat clients
Profile image

Bernice is great! I’d recommend her to anyone. My dogs love going there. She provides great communication and has been flexible when things come up.

Availability updated yesterday
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Kristine K.
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Sitter Profile Image: Kristine K.
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14. Kristine K.
Star Sitter

Experienced dog & cat mom
Merrill Park, Milwaukee, WI, 53208
4.5 mi. away
from
$35
per day
5.0 out of 5.0 stars
79 reviews
24 repeat clients
Profile image

My dog Simba loves going to Kristine’s house for boarding and daycare! It makes me feel at ease that he is having fun, getting exercise, and not anxious there despite his high separation anxiety. Kristine sends pictures and loves all dogs like her own. Simba even knows which house is hers and sprints from the car to her front door! Would highly recommend!!!!

Availability updated 19 days ago
Sitter Profile Image: Tyler P.
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Sitter Profile Image: Tyler P.
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15. Tyler P.

They call me the Dog Runner
Greenfield, WI, 53219
3.0 mi. away
from
$27
per day
5.0 out of 5.0 stars
19 reviews
4 repeat clients

Tyler cared for my cat while I spent 5 days on vacation. He took excellent care of her - shes particularly shy, quiet, and untrusting. Tyler not only did exactly what I asked, he took time to help my cat feel more comfortable as she is not used to me being away. I work from home so my absence is particularly hard for her. He took the time to gain her trust and she noticeably warmed up to him in the video he sent. He definitely helped ease my worries about her being alone. I will be asking again for future pet sitting needs!

Availability updated 8 days ago
Sitter Profile Image: Crystal R.
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Sitter Profile Image: Crystal R.
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16. Crystal R.

WFH fenced in yard. Come over! :)
Bay View, Milwaukee, WI, 53207
1.4 mi. away
from
$40
per day
4.9 out of 5.0 stars
36 reviews
12 repeat clients
Profile image

My dog is afraid of cats and they still accepted him in and were very patient with him! Wonderful people and an all around wonderful experience ❤️

Availability updated 5 months ago
Sitter Profile Image: Alexandrea S.
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Sitter Profile Image: Alexandrea S.
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17. Alexandrea S.

Let’s raise the woof and have fun!
Bay View, Milwaukee, WI, 53207
2.0 mi. away
from
$15
per day
5.0 out of 5.0 stars
20 reviews
7 repeat clients
Profile image

Alexandrea took great care of my 12 week old puppy Driggs. 😊 She sent me lots of photos of Driggs and kept me updated on how he was doing. She also watched him back to back last minute and I appreciated her willingness to do so! I will definitely be using her again and totally recommend her!

Availability updated 4 months ago
Sitter Profile Image: Krystle S.
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Sitter Profile Image: Krystle S.
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18. Krystle S.

Lovable and caring person.
Honey Creek Manor, Milwaukee, WI, 53220
3.1 mi. away
from
$50
per day
4.3 out of 5.0 stars
11 reviews
4 repeat clients

About: I love any type of dog, any type of dog is welcome in my home for caring, people I know describe me as a nice loving person . I work from home on my own time, I am self employed, dog sitting will fit in my schedule routine just perfectly right to welcome any dog. Anything the owner does for the care of there dog fits right in with me, communication on how you would like for me to take care of your dog is the key, I would love for your dog to feel right at home .

Availability updated 2 days ago
Confirmed availability for Christmas and New Year's
Sitter Profile Image: Kathy & Brad K.
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Sitter Profile Image: Kathy & Brad K.
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19. Kathy & Brad K.
Star Sitter

Your Dog's Home Away from Home
Greendale, WI, 53129
5.6 mi. away
from
$35
per day
5.0 out of 5.0 stars
57 reviews
22 repeat clients
Profile image

Kathy did an amazing job caring for my pup! She was dependable and Latte had loads of fun her doggy playdate Missy. I would have no hesitation leaving my puppy with Kathy again!

Availability updated 18 days ago
Sitter Profile Image: Jacob B.
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Sitter Profile Image: Jacob B.
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20. Jacob B.

AKC CGC Professssional Dog Trainer
Oak Creek, WI, 53154
4.4 mi. away
from
$35
per day
5.0 out of 5.0 stars
5 reviews
Profile image

Jacob was so good with my girl! he sent multiple picture and video updates as well as written updates to let me know how she was doing! would give a 10/10 if i could!

Availability updated 4 days ago

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