Dog Boarding in Highwood Estates, Milwaukee

Find a loving dog sitter to watch your dog overnight at your sitter's home.

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Kathy & Brad K.
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Sitter Profile Image: Kathy & Brad K.
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1.

Kathy & Brad K.

Your Dog's Home Away from Home
Greendale, WI, 53129
Boarding, Doggy Day Care
5.0
31 reviews
14 repeat clients
from
$40
per night

Kathy and Brad are the best! Kept in great communication while we were gone; we could tell Benjamin settled right in. We are so happy to have a new home away from home!

Sitter Profile Image: Karen & Toy
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Sitter Profile Image: Karen & Toy
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2.

Karen & Toy

Rover 101
Ready to play and cuddle
Alverno, Greenfield, WI, 53220
Boarding
5.0
77 reviews
39 repeat clients
from
$35
per night

They provided great last minute care for Jax. Karen and Toy sent great photos and their children kept our dog busy and entertain. My dog was comfortable when he first when there. We did not do the meet and greet since I didn’t have time. But I will definitely book with them again.

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Sitter Profile Image: Sarah J.
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Sitter Profile Image: Sarah J.
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3.

Sarah J.

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

Sarah and her family is so amazing. They took care of my pet with least notice and shown so much love towards my pet. I would definitely recommend her to any customers.

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Sitter Profile Image: Daniel & Holly L.
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Sitter Profile Image: Daniel & Holly L.
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4.

Daniel & Holly L.

Rover 101
Warm, loving, home like suroundings
West Allis, WI, 53219
Boarding, Doggy Day Care
5.0
366 reviews
157 repeat clients
from
$35
per night

Dan and Holly took awesome care of Frodo while I was out of town for a business trip. Frodo is a rescue and has had a lot of trouble with separation anxiety, but Dan handled him excellently. Frodo was soon playing all day with another puppy they were taking care of and sleeping on their bed with them at night. I got lots of picture updates so I could see Frodo was doing well. I was pretty nervous about leaving Frodo for an extended period of time, but Dan made it worry-free. Dan and Holly are true dog lovers - would recommend!

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Brooke K.
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Sitter Profile Image: Brooke K.
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5.

Brooke K.

Loving your precious babies
West Allis, WI, 53227
Boarding, Doggy Day Care, Dog Walking
5.0
15 reviews
8 repeat clients
from
$38
per night

Brooke was so wonderful to coordinate with and gave my puppy a wonderful home for a couple days! You can tell she absolutely loves doing this and my puppy had a blast with hers. Thanks Brooke!

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Sitter Profile Image: Jayme F.
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Sitter Profile Image: Jayme F.
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6.

Jayme F.

Dog lover and Groomer
New Berlin, WI, 53151
Boarding, Drop-In Visits, Doggy Day Care
5.0
23 reviews
8 repeat clients
from
$40
per night

Nala had the best time, Jayme treated her like family. She got a bath and a quick trim and nail file before coming home too. She was exhausted when she got home. We will be using Jayme again!

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Sitter Profile Image: Mandi B.
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Sitter Profile Image: Mandi B.
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7.

Mandi B.

Dog house that is people friendly!
West allis, WI, 53214
Boarding
5.0
17 reviews
6 repeat clients
from
$45
per night

Mandi was a great first experience for me with Rover. Super responsive, easy to plan with, and takes awesome care of dogs. Sent pictures and updates daily and gave Rizzo lots of extra treats and special dinners. Would rebook with Mandi in a heartbeat!

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Sitter Profile Image: Angela & Justin M.
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Sitter Profile Image: Angela & Justin M.
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8.

Angela & Justin M.

We're a family of dog lovers!
Wauwatosa, WI, 53226
Boarding, Dog Walking
5.0
23 reviews
7 repeat clients
from
$30
per night

Angela and Justin are wonderful! They kept me updated with photos and did so much with Ace just in the two days they had him. Highly recommend them to watch your fur baby!

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Sitter Profile Image: Blythe R.
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Sitter Profile Image: Blythe R.
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9.

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
$45
per night

My husband and I could not be more excited to have found Blythe as a sitter for our two needy pups! Not only was she flexible with us regarding our pick-up and drop off times, but she was SO understanding with our dogs’ specific needs. We have a very energetic & lovable pit bull named Roxy and a very ANXIOUS Vizsla-mix named Romeo. Blythe went above and beyond to keep Romeo calm while we were away, all while fulfilling Roxy’s needs for attention with daily brushing, cuddles and exercise. She kept us updated with photos and gave this worried puppy mom so much comfort to step away and enjoy our one year wedding anniversary weekend getaway! Thanks again Blythe! I know Roxy and Romeo are already looking forward to their next stay with you ???

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Sitter Profile Image: Marilynn M.
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Sitter Profile Image: Marilynn M.
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10.

Marilynn M.

You KNOW Marilynn Mee LOVES Pets!
White Manor, Milwaukee, WI, 53219
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
34 reviews
18 repeat clients
from
$30
per night

Maizey loves staying at Marilyn’s! She always has such a fun time and I know she’s in great hands. We are repeat customers and would recommend her to anyone!

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Sitter Profile Image: Carina K.
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Sitter Profile Image: Carina K.
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11.

Carina K.

Big or small we love them all🥰
Lincoln Village, Milwaukee, WI, 53215
Boarding, Doggy Day Care
5.0
56 reviews
18 repeat clients
from
$45
per night

Carina did a great job taking care of our Sadie, she was flexible with our schedule and stayed in communication with us during the stay. She and her girls are great dog sitters, thanks!

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Sitter Profile Image: Cindy T.
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Sitter Profile Image: Cindy T.
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12.

Cindy T.

TOTAL DOG LOVER :)
Wauwatosa, WI, 53222
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
547 reviews
336 repeat clients
from
$40
per night

Cindy has taken care of my 3 month old puppy Sully for the 3rd time now. I’m a travel nurse so was hesitant using rover and having a complete stranger watch him but she is always sure to send me updates and pictures. He loves going back and is worn out every single time I get him back. I would definitely recommend Cindy to any travel nurse out there looking for someone reliable and friendly to take care of your fur baby.

Confirmed availability: Christmas and New Year's
Sitter Profile Image: Allie C.
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Sitter Profile Image: Allie C.
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13.

Allie C.

I love all animals ❤️
Jackson Park, Milwaukee, WI, 53215
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
2 reviews
from
$45
per night

Allie was the best this was our family first time trying a dog sitter for Bruno she really treated Bruno like her very own she keep us updated on everything.we really like that thanks Allie for taking care of our Bruno

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Sitter Profile Image: Shannon A.
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Sitter Profile Image: Shannon A.
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14.

Shannon A.

Work from home dog lover.
West Allis, WI, 53214
Boarding, Doggy Day Care
5.0
75 reviews
35 repeat clients
from
$38
per night

Shannon does a great job with our dog! She updates us while we are gone with pictures. Our dog loves going here and comes home exhausted. I would highly recommend!

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Sitter Profile Image: Jackie L.
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Sitter Profile Image: Jackie L.
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15.

Jackie L.

Care for yours like they're mine
Greendale, WI, 53129
Boarding, Drop-In Visits, Dog Walking
5.0
10 reviews
1 repeat client
from
$45
per night

Layla must have taken full advantage of Jackie’s family being able to keep up with her energy level, coming home very tired. Jackie was very attentive to the information we left about Layla and was focusing on making our pet comfortable in their home. Jackie also shared photos and a video to show us how quickly our pup was getting comfortable interacting with her and her family.

Sitter Profile Image: Adrienne & Jacob B.
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Sitter Profile Image: Adrienne & Jacob B.
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16.

Adrienne & Jacob B.

Animal lover and behaviorist
New Berlin, WI, 53151
Boarding, Drop-In Visits, Doggy Day Care
5.0
11 reviews
4 repeat clients
from
$40
per night

Adrianne and Jacob always do a tremendous job with my pups! They are always attentive, loving and have so many tricks up their sleeves to make sure they’re exhausted mentally and physically. They are truly their home away from home!

Sitter Profile Image: April & Brad R.
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Sitter Profile Image: April & Brad R.
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17.

April & Brad R.

Opening home after losing pet
West Allis, WI, 53214
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
19 reviews
8 repeat clients
from
$50
per night

April and Brad were excellent dog sitters - besides daily photos, they even sent us a video! Upon learning that we were staying at a hotel near his work, Brad also delivered Shayna to us, saving us a trip to their house. I would definitely recommend them highly and will use them again.

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Sitter Profile Image: Lane & Alexis G.
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Sitter Profile Image: Lane & Alexis G.
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18.

Lane & Alexis G.

Loving Pet Sitter, Works from Home!
New Berlin, WI, 53151
Boarding, Doggy Day Care
5.0
10 reviews
3 repeat clients
from
$38
per night

Lane would be an ideal pet caregiver. He is very responsible person who truly loves animals. As he had a golden retriever, and he cared for 'Boone' like his baby, with lots of love, lots of walks and lots of fun! He has a great yard that any dog would enjoy, it is huge with lots of trees. He and his wife Alexis are very reliable and conscientious, and very well educated about Pets.

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Sitter Profile Image: Kelle B.
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Sitter Profile Image: Kelle B.
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19.

Kelle B.

Trustworthy, dependable, caring
Honey Creek Parkway, Milwaukee, WI, 53214
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0
41 reviews
6 repeat clients
from
$50
per night

Lexie had an awesome stay with Kelle while I was on vacation! Lexie was smiling in every picture Kelle sent and happy and rested when I picked her up. We’ll definitely rebook with Kelle☺️

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Sitter Profile Image: Kim L.
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Sitter Profile Image: Kim L.
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20.

Kim L.

Caring and experience dog lover
Wauwatosa, WI, 53213
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
11 reviews
2 repeat clients
from
$35
per night

Kim and family were very accommodating, great care, happy dog, excellent property and great home for watching my dog. She provided pictures and many updates. I would highly recommend her to anyone! :)

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When it comes to dog boarding, dog owners in Highwood Estates, Milwaukee, WI love Rover.com. Over 1,089 owners have reviewed sitters in Milwaukee, giving them an average rating of 5.0/5. The cost of dog boarding in Highwood Estates may surprise you - in a good way. That's because there's a dog sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for dog boarding on Rover? Check out our average dog boarding rates to get an idea before you start a conversation with a sitter.

Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Highwood Estates dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Highwood Estates, Milwaukee, WI, 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. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

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 Highwood Estates, 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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