House Sitting in Woodland Court, Milwaukee

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Blythe R.
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Sitter Profile Image: Blythe R.
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1.

Blythe R.

Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
133 reviews
60 repeat clients
from
$55
per night

Blythe was awesome with my Aussie! My dog even wanted to sleep in bed with her, which is reserved only for people she really likes :) thank you so much!!

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Sitter Profile Image: Jessica Z.
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Sitter Profile Image: Jessica Z.
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2.

Jessica Z.

Loving sitter, enthusiastic walker
Lower East Side, Milwaukee, WI, 53202
House Sitting, Drop-In Visits, Dog Walking
5.0
78 reviews
25 repeat clients
from
$55
per night

Jessica Z stayed in my house with my 14 y/o blind Boston Terrier. She was wonderful. I received daily updates and photos, she clearly took excellent care of my pup. She left my place spotless and I would highly recommend her. She is excellent and I will definitely use her again.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Abigail B.
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Sitter Profile Image: Abigail B.
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3.

Abigail B.

Your pets are in good paws with me
Muskego, WI, 53150
House Sitting, Drop-In Visits, Dog Walking
5.0
18 reviews
3 repeat clients
from
$35
per night

I trust Leila with Abigail completely. She immediately informed me when Leila was having some stomach pain, and was generous in sharing her veterinary knowledge with us, going as far as to write down food recommendations and tips for identifying illness. She was diligent in watching her and provided me constant updates until she was sure Leila was okay. She is simply wonderful to work with, extremely trustworthy, reliable, and professional. We are very grateful to her!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Jenn S.
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Sitter Profile Image: Jenn S.
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4.

Jenn S.

Animal lover & cat mom of 3 ❤️
West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking
5.0
29 reviews
9 repeat clients
from
$60
per night

Jenn is a amazing! She is the most kind and compassionate woman. This is the very first time we have ever left our two rescue dogs, so I wasn’t sure what to expect with our two pups and how they would react to anyone other than family watching them. she watched them for two stretches of time periods, one stretch of time was for a few hours while we were at a rehearsal dinner and with a second stretch of time it was for over 12 hours at our daughters wedding. The first stretch of time they barked continuously, and poor Jenn soldiered through like a champ, unscathed. I was afraid she wouldn’t show up the next day, but there she was bright and early the next day, ready to meet the challenge! Within 10 minutes, she texted me with a photo that our two beautiful pups were fast asleep and quiet. She had a wonderful day. It just took a while for them to get used to being with someone other than their owners. She was wonderful, kept us up-to-date throughout our time away. With photos and brief updates. Highly recommend, if I could leave more than five stars, I would!⭐️

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Sitter Profile Image: Heidi F.
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Sitter Profile Image: Heidi F.
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5.

Heidi F.

Sit Stay Dog Care
Wauwatosa, WI, 53226
House Sitting, Dog Walking
5.0
4 reviews
from
$50
per night

House sat for me while I was away and watched my dog Hadley. Checked in frequently and communicated with me with any questions she had. Was a great guest and would have her watch my dog again.

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Sitter Profile Image: Erica L.
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Sitter Profile Image: Erica L.
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6.

Erica L.

I'll love them like my own
West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking
5.0
76 reviews
37 repeat clients
from
$37
per night

This was our first time having someone stay in our home and it was such a great experience! Erica was wonderful with Bear and Bean and sent photos and updates each day. We got to be with our pups until we left and immediately when we arrived home. Also, no packing food and toys, no drop-off and pickup, no worrying about our house being empty. Highly recommend!

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Sitter Profile Image: Leandrea R.
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Sitter Profile Image: Leandrea R.
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7.

Leandrea R.

Rover 101
your pets are my priority.
Muskego Way, Milwaukee, WI, 53204
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
84 reviews
32 repeat clients
from
$60
per night

Leandrea is wonderful! She took great care of our dog while we were out of town and sent lots of pictures and updates to put our mind at ease. Our dog LOVED playing with her pup too, which was a nice bonus! We will definitely be booking Leandrea again in the future.

Sitter Profile Image: Rachel H.
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Sitter Profile Image: Rachel H.
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8.

Rachel H.

** Mission: meet ALL the dogs **
West Allis, WI, 53214
House Sitting, Drop-In Visits, Dog Walking
5.0
72 reviews
22 repeat clients
from
$27
per night

Rachel was wonderful! She kept us updated the whole time and our boy was so happy! She took him to the dog park every day and made sure she had a great time while we were gone. We’ll use her every time we can if she’s free!

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Sitter Profile Image: Cindy H.
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Sitter Profile Image: Cindy H.
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9.

Cindy H.

Reincarnated Dog Here!
wauwatosa, WI, 53213
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
17 reviews
2 repeat clients
from
$55
per night

Cindy did a fantastic job taking care of my furbabies. Great communication and lots of pictures. No doubt Prema went on more walks than she does when I'm home with her and even an exciting day out on a hike and visiting her mom so there were definitely smiles all around. Thank you so much Cindy for helping to qualm my nerves while I was away and sending extra pictures!

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Sitter Profile Image: Felicity W.
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Sitter Profile Image: Felicity W.
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10.

Felicity W.

Animals are my full time passion 🤍
St Francis, WI, 53235
House Sitting, Drop-In Visits, Dog Walking
5.0
21 reviews
10 repeat clients
from
$50
per night

Felicity was wonderful while we were away. She took great care of the animals and the house and she sent lots of pictures which I always appreciate! It's so nice to come home to relaxed animals who are just happy to see us and not stressed that we left!

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Sitter Profile Image: Molly O.
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Sitter Profile Image: Molly O.
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11.

Molly O.

All the walks and all the cuddles
Wick Field, Milwaukee, WI, 53208
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
22 reviews
9 repeat clients
from
$55
per night

Wonderful! Molly was great again! Took care of Pearl like she was her own, and had great communication. I always feel comfortable leaving Pearl with Molly

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Sitter Profile Image: Jess W.
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Sitter Profile Image: Jess W.
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12.

Jess W.

Human Available for All Pet Needs
West Allis, WI, 53214
House Sitting, Drop-In Visits, Dog Walking
5.0
5 reviews
from
$50
per night

Jess was a life saver! We had a last minute cancellation from our other sitter and Jess was up for it without even meeting us in person. She has a natural gift to bond and earn trust with fur babies. We are so glad we found each other. Our cat was stuck to her the entire time and she spent almost everyday and night with our baby. Couldn’t have asked for anything more. She engaged in play whenever he asked for it and followed through with our cat diet religiously. She sent us pics everyday to reassure us. We would definitely have her again and recommend her to anyone looking for an experienced animal lover to take care of their fur baby

Sitter Profile Image: Stephen & Wipawee D.
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Sitter Profile Image: Stephen & Wipawee D.
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13.

Stephen & Wipawee D.

Pawfessional w/ Love & Care <3
West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking
5.0
40 reviews
17 repeat clients
from
$65
per night

Stephen and Wipawee were the absolute best. Super communicative, tons of pictures, and most importantly took great care of our boys. It was clear that the dogs were their top priority while they were here. We would welcome them back without hesitation.

Sitter Profile Image: Katelynn K.
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Sitter Profile Image: Katelynn K.
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14.

Katelynn K.

I’ve always had a passion for dogs!
Hales Corners, WI, 53130
House Sitting, Drop-In Visits, Dog Walking
5.0
9 reviews
from
$55
per night

Katelynn was very communicative and I felt safe entrusting her with Leila. She sent some great photos of Leila and was accommodating to her needs! We highly recommend her and would book with her again!

Sitter Profile Image: Samantha B.
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Sitter Profile Image: Samantha B.
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15.

Samantha B.

Animal lover for both dogs or cats
White Manor, Milwaukee, WI, 53219
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
12 reviews
3 repeat clients
from
$45
per night

Ive had Sam over twice now to watch my fur baby. My dog loves her and I never worry about her while Im gone. Shes trustworthy and communicates well while im gone. I will definitely use her again

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Sitter Profile Image: Sarah J.
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Sitter Profile Image: Sarah J.
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16.

Sarah J.

I’m awkward with humans.
West allis, WI, 53219
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
52 reviews
24 repeat clients
from
$25
per night

Sarah was awesome with my puppies and they both seems to love her. She gave them medications and hugged then as they need too. Thank u for your attention and for being patient with their needs, Sarah! I recommend Sarah for every pets and pet parents.

Sitter Profile Image: Amanda B.
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Sitter Profile Image: Amanda B.
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17.

Amanda B.

Have loved animals since birth.
Greenfield, WI, 53220
House Sitting, Drop-In Visits, Dog Walking
5.0
84 reviews
28 repeat clients
from
$28
per night

Amanda was awesome! She stayed at our house for almost a week and took amazing care of our little man Oliver. She sent updates every day with pictures and took very good care of our house. We will be using her again.

Sitter Profile Image: Patricia N.
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Sitter Profile Image: Patricia N.
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18.

Patricia N.

Love them all!
Franklin, WI, 53132
House Sitting, Drop-In Visits, Dog Walking
5.0
40 reviews
10 repeat clients
from
$30
per night

I am so glad we found Pat to take care of our girls! They just love to see her every time she steps in the door. I have only praise for Patricia with all her kindness she gives my 2 best friends, Heart and Livee. Thank you!!

Sitter Profile Image: Carissa N.
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Sitter Profile Image: Carissa N.
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19.

Carissa N.

Your Pets Second Mom❤️
Hales Corners, WI, 53130
House Sitting, Drop-In Visits
5.0
17 reviews
9 repeat clients
from
$55
per night

Carissa was an amazing sitter while we were out for vacation. She really spoiled our dogs and kept them very happy while we were away. One of our dogs has diabetes and we are always hesitant to have anyone outside the family watch him. He needed blood checking, insulin shots and a very strict schedule for feeding and she did everything as needed with no issue! She stayed at our house and left it cleaner than when she arrived! Carissa also texted us updates every day and evening letting us know Mojos blood sugar levels and how many units of insulin she gave him. We will definitely use her services again for any of our pet sitting needs! Thank you for the peace of mind while we cruised and got a much needed vacation!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Rochelle V.
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Sitter Profile Image: Rochelle V.
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20.

Rochelle V.

Teacher by day; paw friend at night
Jackson Park, Milwaukee, WI, 53215
House Sitting, Drop-In Visits, Dog Walking
20 years of experience
from
$28
per night

About: We had dogs when I was growing up, and I have passed my love of animals onto our daughters. We have had pets in our own home for over 20 years, raising some since they were puppies or adopting them for a rescue. I'm currently working full time as a teacher which means I am available after work and have a lot of open availability on the weekends. I have a fenced in yard and a crate available. I love to go for long walks so both my pets and myself can exercise.

Search Map

Pet parents in Woodland Court, Milwaukee, WI love dog sitters on Rover.com. 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. 95% of reviewed stays have received a perfect 5-star rating, and 92% of pet parents live within a short drive of a dog sitter on Rover. That means Rover is the perfect place to go when you're search for loving, safe care for your best friend. Wondering how much you can expect to pay for a day on Rover? Check out our average house sitting rates to get an idea before you start a conversation with a sitter.

Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog and your home, turn to Rover for your Woodland Court, Milwaukee house sitting needs. On Rover, it's easy to find a loving dog sitter in Woodland Court, Milwaukee, WI who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Woodland Court house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover: it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Woodland Court, Milwaukee, WI for your dog: people who'll treat him like family.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Woodland Court, Milwaukee donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Milwaukee.

We're proud to support over 200 organizations across the nation, including:

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