Pet Sitting & Drop Ins in Highwood Estates, Milwaukee

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

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

Search Results

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Katherine B.
Dogs are happiness 😊West Allis, WI, 53219
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Thorough with my crazy pups scheduled -and mine- and very communicative! We adore her. (more)

from
$15
per visit
Calendar Recently Updated
Nicole C.
2.
Communicative and caring pet sitterNational Park, Milwaukee, WI, 53215
House Sitting, Drop-In Visits, Dog Walking

Nicole was great with my pug (who can be anxious with new people). Good communication, arrived early, and sent me pictures. Highly recommend! (more)

from
$20
per visit
Confirmed availability: Labor Day
Stephen & Wipawee D.
Pawfessional w/love & care <3West Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking

It is such a pleasure to watch Amelie interact with doggies! She is knowledgeable but what makes her particularly good is her natural ability to connect with th… (more)

from
$20
per visit
Danielle D.
Animals Over AnythingMilwaukee, WI, 53214
Drop-In Visits, Dog Walking

Danielle was so great with our puppy! She left detailed feedback and snapped some great pictures which always makes one feel at ease when leaving their dog behi… (more)

from
$14
per visit
Confirmed availability: Labor Day
Deanna S.
5.
I will provide unconditional love.Greendale, WI, 53130
Drop-In Visits, Dog Walking

Deanna was very sweet to our puppy. We can tell by the photos she sent of them playing, that he had a good time at her visits. (more)

from
$15
per visit
Calendar Recently Updated
6.
25 year veteran of animal careWest Allis, WI, 53214
House Sitting, Drop-In Visits, Dog Walking

Aimee is the absolute best! Very professional and courteous, and was on top of communications so that I was in the loop while I was out of town. She gave my fur… (more)

from
$18
per visit
Calendar Recently Updated
Long time pet owner! Walk for fun!Highwood Estates, Milwaukee, WI, 53219
House Sitting, Drop-In Visits, Dog Walking

Rebecca was amazing with our Golden! From the first meeting she sparked energy in our old dog and they became instant friends! We couldn’t have asked for a bett… (more)

from
$16
per visit
Calendar Recently Updated
8.
Here kitty kitty (and doggies too!)Greendale, WI, 53129
Drop-In Visits, Dog Walking

Katie was fantastic! She always provided updates every visit as well as photos. Gwar seemed to love her and just knowing he was in good hands eased a lot of my … (more)

from
$19
per visit
9.
Have loved animals since birth.Greenfield, WI, 53220
House Sitting, Drop-In Visits, Dog Walking

Amanda is Super Nice and She kept me updated on everything with Shana (14) and Simba (15) She Really Cares About My Furbabies. I Will Definitely Ask Amanda to t… (more)

from
$14
per visit
Confirmed availability: Labor Day
10.
Come! Stay! Play!West Allis, WI, 53129
Dog Boarding, Drop-In Visits, Dog Walking

About: I have grown up with animals my entire life including cats, dogs, fish, and even a turtle. I have experience caring for different breeds, sizes and … (more)

from
$20
per visit
Calendar Recently Updated
11.
I'll love them like my ownWest Allis, WI, 53227
House Sitting, Drop-In Visits, Dog Walking

Was prompt and continuously kept me updated about my fur babies. Excellent communication and loving care. 5 ? we will be using Erica in the future. (more)

from
$15
per visit
Confirmed availability: Labor Day
12.
Energetic Pet Sitter! Cats & Dogs!West View, Milwaukee, WI, 53227
Drop-In Visits, Dog Walking

Our dog loves Monica! (more)

from
$18
per visit
Confirmed availability: Labor Day
13.
The dude with a cool attitudeWest Allis, WI, 53214
Drop-In Visits, Dog Walking

James is a family member of mine who was my go to whenever I needed my dog walked!!! I knew I could trust him with my baby girl-dog! My dog had a lot of energy … (more)

from
$20
per visit
Calendar Recently Updated
14.
I love taking fur babies on walks!Morgan Heights, Milwaukee, WI, 53228
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

We feel so fortunate to have found Aimee to watch over our boy while we were gone. Aimee knows a lot about dogs and their behavior and how to manage them from w… (more)

from
$15
per visit
Responsible and reliable dog lover!West Allis, WI, 53219
Drop-In Visits, Dog Walking

Michelle is a huge dog-lover. Not only is she patient and kind, she appreciates each dog’s personality. She will cuddle with the cuddly ones, be calm with the n… (more)

from
$20
per visit
Pet love girl here at your service!West Allis, WI, 53227
Dog Boarding, Drop-In Visits, Doggy Day Care, Dog Walking

Glad I found Jennifer. She does great with my pup, communication is excellent, and she is reliable. Grateful to have her care for my dog when I can’t. (more)

from
$20
per visit
Calendar Recently Updated
17.
Available for lunch walks!Lyons Park, Milwaukee, WI, 53219
Drop-In Visits, Dog Walking

Allison was amazing, we will be repeat customers for sure. Allison came to our house three times a day while we were on vacation to care for our dog, who is hyp… (more)

from
$20
per visit
Calendar Recently Updated
18.
Dog mom who loves all animals!Greenfield, WI, 53220
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Janice is by far my first choice when I've needed a dog sitter. Janice is friendly, trustworthy and the dogs always love her. I've never had to worry a minute a… (more)

from
$30
per visit
Calendar Recently Updated
19.
Loving Family to Care for your DogWest Allis, WI, 53219
Dog Boarding, Drop-In Visits, Dog Walking

Angie was wonderful with communication and photos. I would highly recommend and would use again. Thank you! (more)

from
$20
per visit
20.
Trustworthy All-Animal LoverRiver Bend, Milwaukee, WI, 53219
House Sitting, Drop-In Visits, Dog Walking

Vesna is our go-to dog watcher! We have three large doodles (65lb, 75lb and 100 lb). They can be mischievous for many who watch them, but they are always so wel… (more)

from
$38
per visit

Dog owners in Highwood Estates, Milwaukee, WI love booking pet sitting with sitters on Rover.com. Over 1,089 pet owners have reviewed pet sitters in Milwaukee, giving them an average rating of 5.0/5 stars. Booking pet sitting can be super affordable, no matter where you live. Trust us, we think you'll be pleasantly surprised. Curious what it might cost to book pet sitting with Rover? Check out our average pet sitting rates to get an idea before reaching out and starting a conversation with a pet sitter near you in Highwood Estates.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Highwood Estates pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Highwood Estates, Milwaukee, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). 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 house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Highwood Estates pet sitters and avoid the kennel.

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: