Dog Boarding in Highwood Estates, Milwaukee

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Sitter Profile Image: Kathy & Brad K.
Verified Enhanced Background Check
Sitter Profile Image: Kathy & Brad K.
Verified Enhanced Background Check

1. Kathy & Brad K.

Star Sitter
Your Dog's Home Away from Home
Greendale, WI, 53129
2.1 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
41 reviews
18 repeat clients
from
$40
per night

Kathy and Brad were fantastic! Definitely true animal lovers ! I was a bit nervous leaving my dog , but they sent multiple pictures. Definitely welcomed cooper in their home ! Next vacation we will be sending him back !

Sitter Profile Image: Brooke K.
Verified Enhanced Background Check
Sitter Profile Image: Brooke K.
Verified Enhanced Background Check

2. Brooke K.

Star Sitter
Loving your precious babies
West Allis, WI, 53227
1.6 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
54 reviews
23 repeat clients
from
$38
per night

Brooke was great! She sent many pictures and videos throughout the stay, and introduced her animals to my dog gradually to make sure they were all comfortable with each other. Extremely responsive and flexible. My dog came home healthy and happy!

Sitter Profile Image: Daniel & Holly L.
Verified Background Check
Sitter Profile Image: Daniel & Holly L.
Verified Background Check

3. Daniel & Holly L.

Rover 101
Warm, loving, home like suroundings
West Allis, WI, 53219
1.8 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
383 reviews
161 repeat clients
from
$36
per night

Daniel and Holly were wonderful with my bulldog Jasmine! They were super sweet and very thorough with their interview process to make sure they didn't miss anything. I'm definitely going to use them in the future. You should too!

Sitter Profile Image: Mindy W.
Verified Enhanced Background Check
Sitter Profile Image: Mindy W.
Verified Enhanced Background Check

4. Mindy W.

Rover 101
A paw-fect home away from home...
West View, Milwaukee, WI, 53227
1.1 mi. away
Boarding
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$43
per night

Mindy was fantastic with our fur baby, we felt extremely comfortable leaving Star with her and it was clear Star had a great time! Tons of cuddles, walks and playing + we were sent some great photos that put our mind at ease while traveling.

Sitter Profile Image: April & Brad R.
Verified Enhanced Background Check
Sitter Profile Image: April & Brad R.
Verified Enhanced Background Check

5. April & Brad R.

Star Sitter
Opening home after losing pet
West Allis, WI, 53214
3.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
9 repeat clients
from
$50
per night

April and Brad were very welcoming to Carson and gave him lots of TLC. When we stopped for the meet and greet, I immediately felt comfortable about leaving Carson in their care. April texted pictures of Carson while we were away and it was obvious both April and Brad had become good buddies with Carson. They treated him like he was their own dog. I highly recommend April and Brad for sleepovers with your pet!

Sitter Profile Image: Karen & Toy
Verified Background Check
Sitter Profile Image: Karen & Toy
Verified Background Check

6. Karen & Toy

Rover 101
Ready to play and cuddle
Alverno, Greenfield, WI, 53220
2.4 mi. away
Boarding
5.0 out of 5 stars
81 reviews
40 repeat clients
from
$35
per night

Karen and Toy were great. Our dog seemed to have a great time and came home happy and tuckered out. She kept us updated and feeling comfortable.

Sitter Profile Image: Katherine B.
Verified Enhanced Background Check
Sitter Profile Image: Katherine B.
Verified Enhanced Background Check

7. Katherine B.

Star Sitter
Dogs are happiness 😊
West Allis, WI, 53219
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
22 reviews
9 repeat clients
from
$50
per night

I never like to leave a review the first time my dogs go to a new sitter’s house, since they can’t tell me how it went and I have no real way of knowing. I can say for sure now, though, that Bailey and Walter LOVE going to Katherine’s house! Both times we’ve brought them back, they have gotten SUPER excited when we pull up to her house (like dog park excited). I can tell that they love her and her dog by the way they run up with doggie smiles and wagging tails to say hello. They also seem really comfortable in her fenced- in yard, so I know they’ve spent happy times there. Highly recommend!

Sitter Profile Image: Sarah J.
Verified Enhanced Background Check
Sitter Profile Image: Sarah J.
Verified Enhanced Background Check

8. Sarah J.

I’m awkward with humans.
West allis, WI, 53219
0.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
117 reviews
38 repeat clients
from
$25
per night

Gizmo loves Sarah! He loves going to play and they are so good with him. He always comes home happy and tired. Definitely recommend her as a sitter!

Sitter Profile Image: Stacey M.
Verified Enhanced Background Check
Sitter Profile Image: Stacey M.
Verified Enhanced Background Check

9. Stacey M.

Genuine pet lover
Fairview, Milwaukee, WI, 53219
1.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care
5.0 out of 5 stars
6 reviews
from
$25
per night

Stacey and her family did a great job taking care of Buddy for a week. He seemed happy and fit in well with the family pets. I would love for Stacey to take care of Buddy again.

Sitter Profile Image: Alberto V.
Verified Background Check
Sitter Profile Image: Alberto V.
Verified Background Check

10. Alberto V.

Rover 101
Welcome to our home 🤍🏡
Fair Park, Milwaukee, WI, 53407
2.9 mi. away
Boarding
5.0 out of 5 stars
31 reviews
10 repeat clients
from
$33
per night

Alberto & Chance were so sweet and took great care of Kirby while I was away for an extended weekend! They sent updates and were very patient when my flight got delayed. Would definitely book them again!!

Sitter Profile Image: Angela & Justin M.
Verified Enhanced Background Check
Sitter Profile Image: Angela & Justin M.
Verified Enhanced Background Check

11. Angela & Justin M.

We're a family of dog lovers!
Wauwatosa, WI, 53226
4.1 mi. away
Boarding, Dog Walking
5.0 out of 5 stars
35 reviews
8 repeat clients
from
$30
per night

Angela and Justin have been the best dog sitters I’ve ever had! My dogs seriously loved them! If I wasn’t leaving milwaukee they’d watch them all the time! I got daily updates and stories about their day. They went on walks and had the best time. I couldn’t ask for anything more.

Sitter Profile Image: Jill F.
Verified Background Check
Sitter Profile Image: Jill F.
Verified Background Check

12. Jill F.

Star Sitter
Dog lover work from home
West Allis, WI, 53214
2.3 mi. away
Boarding, Doggy Day Care
5.0 out of 5 stars
68 reviews
20 repeat clients
from
$55
per night

Jill was wonderful with my dog Ramona and I know Ramona was happy to have someone with her all day. She took great care of my dog and it was great not to have to worry about her while my family was on vacation.

Sitter Profile Image: Mary G.
Verified Enhanced Background Check
Sitter Profile Image: Mary G.
Verified Enhanced Background Check

13. Mary G.

I have a big fenced in yard and luv
Greenfield, WI, 53228
1.4 mi. away
Boarding
5.0 out of 5 stars
50 reviews
18 repeat clients
from
$45
per night

Thanks for taking care of Bud! He loves all the attention and loving he gets from Mary, Fernando and his brothers Matteo and Roland! Bud and I are so lucky to have you in our lives! See you again in April!

Sitter Profile Image: Nathaniel D.
Verified Enhanced Background Check
Sitter Profile Image: Nathaniel D.
Verified Enhanced Background Check

14. Nathaniel D.

I love all the Animals!
West Allis, WI, 53219
2.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
27 reviews
7 repeat clients
from
$40
per night

Amazing job as always, Jasper is always so excited to see his friends and they do such a great job caring for him and for Charlie, even as moody as she is. Thanks again!

Sitter Profile Image: Blythe R.
Verified Background Check
Sitter Profile Image: Blythe R.
Verified Background Check

15. Blythe R.

Star Sitter
Every animal makes me smile!
Bay View, Milwaukee, WI, 53207
6.0 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
142 reviews
63 repeat clients
from
$45
per night

Blythe watched my pup for over a week and it was an awesomely positive experience for both me and Juno. Blythe was communicative, sent daily updates with pictures, and made me feel at ease. I will absolutely be recommending her to others and be re-booking services in the future.

Sitter Profile Image: Kelle B.
Verified Enhanced Background Check
Sitter Profile Image: Kelle B.
Verified Enhanced Background Check

16. Kelle B.

Trustworthy, dependable, caring
Honey Creek Parkway, Milwaukee, WI, 53214
3.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
56 reviews
9 repeat clients
from
$50
per night

Kelle is an excellent care taker of my two little dogs. She is experienced, and sets my mind at ease that she knows what she's doing, and takes really great care of her charges. Kelle is very responsive, and keeps in touch during the dogs' stay. I feel lucky to have her as my dogs' sitter!

Sitter Profile Image: Maggie S.
Verified Enhanced Background Check
Sitter Profile Image: Maggie S.
Verified Enhanced Background Check

17. Maggie S.

I'll Treat Your Dog Like My Own
Milwaukee, WI, 53213
4.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$45
per night

Maggie is the best!! She took such great care of our pup. She spoiled her with walks and snuggles. Our dog had a great time, and came back happy and relaxed! She can't wait to see Maggie again! ❤️

Sitter Profile Image: Christine H.
Verified Enhanced Background Check
Sitter Profile Image: Christine H.
Verified Enhanced Background Check

18. Christine H.

Experienced Dog Foster
Greenfield, WI, 53221
3.6 mi. away
Boarding, Drop-In Visits
5.0 out of 5 stars
28 reviews
9 repeat clients
from
$50
per night

Christine H. Is kind and flexible. Took several pictures of my dog to put me at ease while away. Made sure dog had activity and care. Would highly recommend her and will use her again in the future.

Sitter Profile Image: Jes B.
Verified Background Check
Sitter Profile Image: Jes B.
Verified Background Check

19. Jes B.

Rover 101
The Hardy-Berndt Ranch
Kensington, New Berlin, WI, 53151
3.8 mi. away
Boarding
5.0 out of 5 stars
75 reviews
43 repeat clients
from
$32
per night

Jes was great! She treated our Libby like her own. Our dog loved her little girls as well...I was told Libby gave them lots of kisses! I was very happy with the communication and updates I received. We just loved hearing how Libby was doing and seeing pics of her time there. I highly recommend Jes!

Sitter Profile Image: Marilynn M.
Verified Enhanced Background Check
Sitter Profile Image: Marilynn M.
Verified Enhanced Background Check

20. Marilynn M.

You KNOW Marilynn Mee LOVES Pets!
White Manor, Milwaukee, WI, 53219
1.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
41 reviews
22 repeat clients
from
$30
per night

This was the first time I used Rover and was extremely nervous. Marilyn made me feel so comfortable. She was wonderful. It's obvious she loves animals. My dog actually seemed sad to have to go home. I will definitely be using her for any future needs.

Search Map

Rover also offers Dog Boarding in these neighborhoods:

Rover also offers other services in Highwood Estates:

When it comes to dog boarding, dog owners in Highwood Estates, Milwaukee, WI love Rover.com. Over 1089 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.

Boarding