House Sitting in Calumet Farms, Milwaukee

Find a loving dog sitter to watch your dog overnight in your home.

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
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Sitter Profile Image: Lily S.
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Sitter Profile Image: Lily S.
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1. Lily S.

Star Sitter
All-Day in Home Care For Critters
Milwaukee, WI, 53212
8.9 mi. away
House Sitting, Drop-In Visits
from
$75
per night
5.0 out of 5 stars
24 reviews
9 repeat clients
Profile image

This was our first time using a dog sitting service and we couldn’t have been more lucky to have Lily watch our dogs. She met with us multiple times to meet our pups and walk through our routine. During our trip she sent plenty of updates and pictures to keep us up to date. We couldn’t have asked for a better sitter for our pups and will definitely book Lily in the future!

Availability updated 2 days ago
Sitter Profile Image: Jeanee S.
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Sitter Profile Image: Jeanee S.
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2. Jeanee S.

Star Sitter
Pets just get me!
Menomonee Falls, WI, 53051
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$63
per night
5.0 out of 5 stars
16 reviews
7 repeat clients
Profile image

Jeanee was the most incredible dog sitter we have ever had. Lilly got to go on many adventures and walks. Once Lilly got to know Jeanne, she asked if Lilly could with on errands, Lilly loves car rides. I suggested if she wanted to take her home to introduce Lilly to her furbaby - she could give it a shot. Keeping in mind that Lilly is food & person possessive and can be aggressive with older dogs, but Jeanee knew exactly how to handle her. It worked out so well that Lilly stayed at her home the remaining 6 days! Her dog really enjoyed having another dog around. She took Lilly's bed, food, treats and favorite stuffie to her house, so Lilly felt right at home. It really helped Lilly, she wasn't constantly watching for us, missing us and she ate so well. We had constant communication and updates. Anytime I sent a message she responded very quickly. This was the most confident and secure we have ever felt on our vacation. It made for a very relaxing and fun vacation. Knowing we now have an incredible sitter for Lilly, we are looking to book future vacations. 100% recommend!! Your furbaby will be in incredible hands!!

Availability updated 6 days ago
Sitter Profile Image: Samantha L.
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Sitter Profile Image: Samantha L.
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3. Samantha L.

caring for animals is my calling !
Ridgeview, Milwaukee, WI, 53538
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5.0 out of 5 stars
3 reviews
1 repeat client
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Everything worked out great. Highly recommended if need a over night in-house sitter. Will definitely use again when needed. Thank You!!!

Availability updated yesterday
Sitter Profile Image: Jamila M.
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Sitter Profile Image: Jamila M.
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4. Jamila M.

Rover 101
Neighbor providing additional love
Washington Heights, milwaukee, WI, 53208
7.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
65 reviews
22 repeat clients
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Jeremy was delight for dog and house sitting, he truly loves being with dogs and it shows. I would highly recommend him for your pet care needs!

Availability updated yesterday
Sitter Profile Image: Katie M.
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Sitter Profile Image: Katie M.
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5. Katie M.

Happy Pets, Self-Insured Care!
Milwaukee, WI, 53225
2.9 mi. away
Boarding, House Sitting, Drop-In Visits
from
$30
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
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From the moment Katie came for the Meet and Greet I knew she was awesome! I have 3 rescue dogs and a psycho cat, and they all took to her immediately. Just finished up our first sit with Katie and it went great. I want to tell you it was horrible so I can keep her to myself, but that would be a lie! She will love your babies like her own - my super anxious boy whined at the window when she left. She is LEGIT!!

Availability updated 2 days ago
Sitter Profile Image: Katelyn A.
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Sitter Profile Image: Katelyn A.
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6. Katelyn A.

Eat. Play. Love.
Bayside, WI, 53217
6.1 mi. away
House Sitting, Dog Walking
from
$65
per night
5.0 out of 5 stars
11 reviews
8 repeat clients
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Katelyn is fantastic! She's incredibly responsive and caring. She came to meet the dogs beforehand, so we could chat which was awesome. One of our dogs in incredibly anxious and wary of strangers, and Katelyn's calm demeanor won her over! We already booked Katelyn for the near future.

Availability updated 3 months ago
Sitter Profile Image: Sean N.
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Sitter Profile Image: Sean N.
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7. Sean N.

Husband, father and dog lover.
Kops Park, Milwaukee, WI, 53222
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5.0 out of 5 stars
12 reviews
6 repeat clients
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Sean was our first time using rover since we moved across the country and he was AMAZING. We recently got a rescue Great Dane who is not the easiest when trusting others & with Sean’s patience and expertise my dog got comfortable with me rather quickly! He sent pictures through out the night & even a video. Looking forward to use Sean’s service again.

Availability updated today
Sitter Profile Image: Jeff G.
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Sitter Profile Image: Jeff G.
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8. Jeff G.

Care for dogs like they're children
Glendale, WI, 53209
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$68
per night
5.0 out of 5 stars
41 reviews
11 repeat clients
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Jeff stayed with our 6 year old springer spaniel for a week. He did a great job. He communicated via text frequently with updates, pics, and short videos. Jeff responded quickly and was easy to communicate with. My wife and I both liked him. Most importantly, when we got home it was clear that our pup just loved him.

Availability updated 9 days ago
Sitter Profile Image: Mackenzie M.
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Sitter Profile Image: Mackenzie M.
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9. Mackenzie M.

Best Friends with your Best Friends
Menomonee Falls, WI, 53051
5.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5.0 out of 5 stars
10 reviews
1 repeat client
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Mackenzie did a great job with Lambeau over the weekend. We were lucky enough to get her to stay at our house so we didn’t have to board our dog again. She played with Lamb, fed him and gave him all the cuddles. 5 stars, will book again, thank you!

Availability updated 33 days ago
Sitter Profile Image: Jeanne S.
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Sitter Profile Image: Jeanne S.
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10. Jeanne S.

Attentive and dependable caregiver
Milwaukee, WI, 53222
5.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5.0 out of 5 stars
5 reviews
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Jeanne was the perfect sitter for our dog Lucy. She sent updates, gave plenty of walks and cuddles while also watering our plants and leaving our house spotless! We will definitely rebook with her in the future!

Availability updated 6 days ago
Sitter Profile Image: Beth P.
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Sitter Profile Image: Beth P.
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11. Beth P.

Summer/weekend house sitting
Milwaukee, WI, 53210
6.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5.0 out of 5 stars
8 reviews
2 repeat clients
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Beth is a Godsend! She stayed at our home for five days and took exceptional care of our many animals: our dog, cats, rabbits, Guinea pig and fish. We came back to a tidy house and relaxed animals. She took our dog on two mile walks and sent photos and updates regularly. We couldn’t have asked for a better sitter. She is kind and considerate. We highly recommend Beth!

Availability updated 54 days ago
Sitter Profile Image: Emmalee M.
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Sitter Profile Image: Emmalee M.
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12. Emmalee M.

Current Professional Dog Handler!
Germantown, WI, 53022
5.9 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5.0 out of 5 stars
5 reviews
Profile image

Emmalee was an amazing sitter, and I would recommend her to everyone and anyone. She kept us updated with numerous photos and videos, was clear about her schedule, and took amazing care of our little boy. She was so considerate of all his needs and treated him like she was her own. Not to mention, she left our place better than we left it. Your fur baby will be in the best hands when with Emmalee. Five stars all around.

Availability updated 2 days ago
Sitter Profile Image: Alison S.
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Sitter Profile Image: Alison S.
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13. Alison S.

Here for you, and them
Glendale, WI, 53209
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
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Alison stayed at our house to watch our almost 2 year old dog for a long weekend. We really appreciated her communication and responsiveness! She left our house in great shape, and we came home to a well taken care of pup. We will certainly reach out to her next time we need someone to watch Callie.

Availability updated 10 days ago
Sitter Profile Image: Mollie G.
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Sitter Profile Image: Mollie G.
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14. Mollie G.

Dog lover
Milwaukee, WI, 53209
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$28
per night
1 review

Mollie is a true dog lover and dogs LOVE her back. Her interest in and care for a dogs well being is immediately evident and our dog immediately felt that and was comfortable with her when she can be skittish with new people. She taught our dog so many incredible skills such as how to close the door! Mollie is reliable, dependable, responsible and professional. Our dog is difficult to walk with strong hearding instincts and some reactivity towards other dogs and Mollie remains calm and doesn't get rattled walking her which in turn helps our high energy Australian Shepard stay more relaxed. She is comfortable giving our dog medication for her anxiety and she's very good at suggesting resources. Mollie keeps up with dog training techniques and offers helpful suggestions to keep our dog's busy mind engaged. She's a wealth of information about dog behavior and psychology and your fur baby will be in excellent hands under her care. I highly recommend Mollie!

Availability updated 9 days ago
Sitter Profile Image: Jessica s.
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Sitter Profile Image: Jessica s.
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15. Jessica s.

Provide care and comfort!
Whispering Hills, Milwaukee, WI, 53223
2.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$32
per night
5.0 out of 5 stars
15 reviews
2 repeat clients

Jessica is an outstanding dog sitter! She has been gracious enough to watch my dog Cowboy several times. :) She is very professional and courteous. Would highly recommend Jessica for any petsitting needs!

Availability updated 23 days ago
Sitter Profile Image: Dawn U.
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Sitter Profile Image: Dawn U.
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16. Dawn U.

Laid back furbaby care.
Menomonee Falls, WI, 53051
3.3 mi. away
House Sitting, Drop-In Visits
from
$50
per night
5.0 out of 5 stars
1 review

About: I am currently accepting clients who want in-home or drop-in care. No cats please. I have been a dog owner for over 25 years, as well as growing up with dogs in my home. I love to follow their lead with their activity needs - whether it be a rowdy romp in the back yard, a energetic walk (weather permitting) or a relaxing day of being a couch potato. We currently have 2 rescue furbabies who gets along with other dogs and like to interact with our fur guests. Will only be caring for one furbaby family at a timne. No other pets in the home, no children and no smoking. We have a fenced in back yard and are not far from several dog parks, if that is an approved activity by the dog owner. I have a very flexible part-time schedule, so I can usually work around your schedule and care needs. For in home care I will come and go throughout the day with frequent check ins per your preference, as well as meals and overnight care. I am currently offering drop-in care for potty breaks and/or meals plus play time, and in your home days and overnight pet care. No cats in the home please.

Availability updated 48 days ago
Sitter Profile Image: Olivia W.
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Sitter Profile Image: Olivia W.
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17. Olivia W.

Passionate Pet Enthusiast
Heritage Heights, Milwaukee, WI, 53224
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$29
per night
5.0 out of 5 stars
2 reviews

We cannot give enough praise to Olivia for watching our three dogs over winter break in 2023. We have one rescue, Rex, who was abused before he became part of our family and he is very protective of us and aggressive towards strangers. With her experience and interest in dogs, Olivia knew exactly how to interact with Rex and it only took an hour or so before they were good buddies! I'm sure our mouths dropped in amazement, because that really had never happened before. Throughout or trip, Olivia kept us well informed and sent us pictures of the pups happily hanging out with her. Olivia is always welcome back at our home and I thinks the dogs already adopted her anyway! Olivia is a lovely person who is great with dogs. She is easily 11 out of 10 stars!

Availability updated 31 days ago
Sitter Profile Image: Jaclyn O.
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Sitter Profile Image: Jaclyn O.
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18. Jaclyn O.

The Friendly, Neighborhood Pet Lady
Park Knoll, Milwaukee, WI, 53225
2.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per night
5.0 out of 5 stars
80 reviews
34 repeat clients
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Jax was phenomenal! Our pup can be a handful at times and she handled him so well. She took the time to not only take him out but to play with him and get him tired out. Not to mention our pup absolutely loves her. I will be booking with her again!

Availability updated 82 days ago
Sitter Profile Image: Jenn L.
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Sitter Profile Image: Jenn L.
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19. Jenn L.

I like big mutts, and I cannot lie.
Mill Valley, Milwaukee, WI, 53224
1.9 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$63
per night
5.0 out of 5 stars
7 reviews
2 repeat clients
Profile image

Jenn was so great with my very spoiled Great Pyrenees at her home Christmas weekend. She was so good at communicating and sending pictures the weekend she was with him. I felt she genuinely cared so much about Koda and us too. I will definitely be contacting her again on our next travels. Thanks again Jenn!

Availability updated 18 days ago
Sitter Profile Image: Amari I.
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Sitter Profile Image: Amari I.
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20. Amari I.

Quality Care Your Pet Deserves!
Silver Swan, Milwaukee, WI, 53225
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
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I needed a dog sitter last minute and contacted Amari about taking care of my 70 lb Belgian Malinois rescue. I do not know how many times my dog has been re-homed so I was very anxious about leaving her with a stranger. When I got home after being away for 3 days my dog was happy as a clam and all of the signs of emotional distress she showed after previous trips -- not eating, not defecating, etc. -- were absent. Amari did a wonderful job! I will definitely employ her in the future.

Availability updated 3 months ago

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