House Sitting in Woodland Court, Milwaukee

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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Karen & Toy
Ready to play and cuddleAlverno, Milwaukee, WI, 53220
Dog Boarding

They were so flexible and accommodating to my indecisive times for drop off and pickup. I truly appreciated the flexibility and my dog had a blast. She was so… (more)

from
$28
per night
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Jill F.
2.
Dog lover work from homeWest Allis, WI, 53214
Dog Boarding, Doggy Day Care

Jill took wonderful care of our pup in the week that he stayed with her. I was nervous about being separated from Macchi for the first time since we adopted him… (more)

from
$45
per night
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Daniel L.
3.
Warm, loving, home like suroundingsWest Allis, WI, 53219
Dog Boarding, Doggy Day Care

My Ronaldo had a great time with Dan and Holly! Dan was really good about giving me updates on how he is doing. I will be rebooking them again. (more)

from
$35
per night
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Scott H.
4.
Dog lover and frequent sitterFairview, Milwaukee, WI, 53219
Dog Boarding, Doggy Day Care, Dog Walking

Scott did a great job watching over our chocolate lab Maverick. Maverick is an older dog and Scott was very attentive to some of our dogs different needs due t… (more)

from
$55
per night
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Ismael C.
5.
Dog loving familyWest Allis, WI, 53214
Dog Boarding, Doggy Day Care

Ismael was great! Very friendly and communicative. We loved the photos and videos. Very homey place for our dog while we were away. Will definitely use them ag… (more)

from
$48
per night
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Basically an all inclusive pet stayWest allis, WI, 53227
Dog Boarding

Patrisha is an amazing dog sitter! She loves dogs and puts their welfare first! I wish she could sit for my dogs every time! I know they are well cared for w… (more)

from
$50
per night
Confirmed availability: Memorial Day
your pets are my priority.West Allis, WI, 53227
Dog Boarding, Drop-In Visits, Doggy Day Care

Leandrea was amazing with my only 2 month old puppy! She has an older pup who played really well with him and she was amazing at keeping me updated on how he wa… (more)

from
$40
per night
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8.
I have a big fenced in yard and luvGreenfield, WI, 53228
Dog Boarding

Mary took great care of Luna, and sent lots of photos and videos which we really appreciated. So comforting to have a reliable person when we go out of town aga… (more)

from
$25
per night
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Can't wait to meet your puppy dawg!West Allis, WI, 53227
Dog Boarding, Doggy Day Care, Dog Walking

Oh my goodness, where to start with these wonderful humans?! From the start, MJ and James went above and beyond to be accommodating, kind, understanding, and ov… (more)

from
$40
per night
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10.
Loving and caring dog momWest Milwaukee, WI, 53214
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Mary took great care of our dog and took photos to boot, keeping us informed as to his stay. We will definitely be having Mary watch our dog again. (more)

from
$42
per night
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11.
Pampered poochOak Creek, WI, 53154
Dog Boarding

Debbie did a great job with both of my dogs. She figured out their personalities and individual needs within a few days an established a routine that worked for… (more)

from
$50
per night
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12.
My love fur pets is unconditional !West Allis, WI, 53227
Dog Boarding

Joanna has a big heart with animals she is always kind and thoughtful when she takes care of all animals she makes sure to walk my dog and always makes sure the… (more)

from
$50
per night
Confirmed availability: Memorial Day
13.
Your dog's home away from homeGreendale, WI, 53129
Dog Boarding, Doggy Day Care

I have known Kathy for about 10 years. She is a kind & loving person. I have witnessed firsthand how much care & attention she puts forth towards caring for her… (more)

from
$30
per night
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14.
WAH Dog Lover - Nice suburban setupGreenfield, WI, 53219
Dog Boarding, Dog Walking

Tyler is excellent with dogs. He has a ton of experience taking care of them including puppies and he genuinely loves animals. He is my go-to dog walker/sitte… (more)

from
$40
per night
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15.
Home All Day!Tippecanoe, Milwaukee, WI, 53207
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

The morning of our 1-night trip, I woke up to a text from my normal dog sitter, canceling. I didn't want to postpone the whole thing so I started looking for so… (more)

from
$40
per night
Calendar Recently Updated
16.
I am a avid pet lover.West Allis, WI, 53214
Dog Boarding

She is fantastic. I had a good feeling about her when I made my choice. And if I were to need Willowsitting services again. Dawn will be my first choice! (more)

from
$40
per night
17.
Love, cuddles, huge fenced in yard!Franklin, WI, 53132
Dog Boarding, Drop-In Visits, Doggy Day Care

Janel is excellent!! She loved on my dog just as if he were her own. I received multiple updates/pics everyday and never had to question whether or not my dog w… (more)

from
$35
per night
Confirmed availability: Memorial Day
18.
Home 24/7 NO KennelingLincoln Village, Milwaukee, WI, 53215
Dog Boarding, Doggy Day Care

Awwwww, words can not describe how amazing I feel relative to the service Carina provided for my baby boy! We had to leave one another for approximately 5 days … (more)

from
$45
per night
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19.
Let me love your baby like my own!Milwaukee, WI, 53221
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

April has taken care of my dog many times! As a fellow dog lover, she is the most reliable and responsible person that I trust as a dog caregiver! I have known … (more)

from
$50
per night
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20.
Experience foster and dog sitter!Hales Corners, WI, 53130
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Eric is Awesome!! My dog Teddy stayed with him for a long weekend while I was out of town. Teddy came home happier than when I dropped him off! Eric sent me lot… (more)

from
$42
per night

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: