Pet Sitting & Drop Ins in Highwood Estates, Milwaukee, WI

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

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Highwood Estates pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

1 / 1
Sitter Profile Image: Sarah J.
Verified Enhanced Background Check
Sarah J.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
458 reviews
85 repeat clients
5 years of experience
West allis, WI, 53219

Sarah is awesome! I recently adopted a very high maintenance half Persian cat. I had to leave town to visit family for 4 days. I found Sarah on Rover based on reviews. She came to meet my cat and his routine. She came to the house daily when I was gone. She very willingly, happily, and efficiently followed a long list of to do things (meal times with specific types of foods, food puzzles, setup automatic feeders, play time, litter box maintenance, etc) I Sarah went above and beyond to make me feel better about leaving my cat behind home alone for the first time. She did a wonderful job at taking care of the cat and making him feel safe and loved 🥰 I highly recommend Sarah with your fur babies!

Profile image
Yarin M.
Sitter Profile Image: Mallory S.
Verified Enhanced Background Check
Mallory S.
Star Sitter
from
$21
per visit
5.0 out of 5 stars
27 reviews
11 repeat clients
30 years of experience
West Allis, WI, 53719

Mallory did a great job checking in on our cat Marvin while we were away on vacation. She provided great updates with photos every visit, and was very professional & communicative overall. Thank you Mallory!

Profile image
Nick P.
Sitter Profile Image: Emily S.
Verified Enhanced Background Check
Emily S.
Star Sitter
from
$20
per visit
4.9 out of 5 stars
52 reviews
28 repeat clients
6 years of experience
West Allis, WI, 53227

Emily has been wonderful with Heisenberg! I am so grateful for her help. I was nervous to have a stranger take care of him, but I couldn't be happier with how well it has worked out.

Profile image
Talia S.
Sitter Profile Image: Katie N.
Verified Background Check
Katie N.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
62 reviews
14 repeat clients
20 years of experience
Greenfield, WI, 53220

Katie was awesome and our Luna loved her! Luna tends to be shy at first with new people but she warmed right up after a day and loved all the attention and playtime she was getting. Katie was thorough with her updates & sent great photos as well, I highly recommend and will be rebooking!

Profile image
Leandrea R.
Sitter Profile Image: LilyAnn R.
Verified Enhanced Background Check
LilyAnn R.
from
$13
per visit
5 years of experience
West Allis, WI, 53219

About: Growing up, I’ve had two dogs, a Beagle and Maltese. I’ve babysat all different types of breeds from Golden Retriever to Huskies to Border Collies. So truly no dog is too big nor too small for me to take care of! I am currently attending school online, so I have the flexibility to be there at after bark or call! I normally go for a couple hour long walk, so adding your pet in the mix would only help me! Previously, I have watched both cats and dogs in their homes, as its the best for a the transition. Furthermore, with the familiar environment, it helps the pet maintain their schedule and most times holds the tools to groom them, feed them, and play with them!

Sitter Profile Image: Leandrea R.
Verified Enhanced Background Check
Leandrea R.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
224 reviews
61 repeat clients
4 years of experience
Milwaukee, WI, 53220

Leandrea did a superb job with my kitty Sunny! I was anxious about leaving him due to him just having surgery a couple of days prior, but I was immediately put at ease with her quality of care! I would recommend her to anyone looking for care for their pet! I will definitely be booking for all my pet needs in the future! Thank you for being so wonderful!

Profile image
Allison W.
Sitter Profile Image: Jenn S.
Verified Enhanced Background Check
Jenn S.
Star Sitter
from
$24
per visit
5.0 out of 5 stars
110 reviews
32 repeat clients
40 years of experience
West Allis, WI, 53227

Jenn was great! Came before hand to meet my dog and to get to know the usual routine. She sent pictures and updates and had great communication!

Profile image
Jessica T.
Sitter Profile Image: Lexi K.
Verified Enhanced Background Check
Lexi K.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
129 reviews
37 repeat clients
10 years of experience
Cannon Park, Milwaukee, WI, 53214

Lexi & Aaron did drop-in visits for Louis, our attention needy :) cat. They were dependable and I'm sure if cats could talk, Louis would say 'they were great!' He was a happy guy when we got home & his litter box was so clean. Knowing someone was dropping in to hang out with him (& give him his wet nummy food) made our vacation more enjoyable.

Profile image
Clare S.
Sitter Profile Image: Angie B.
Verified Background Check
Angie B.
from
$20
per visit
5.0 out of 5 stars
34 reviews
9 repeat clients
30 years of experience
West Allis, WI, 53219

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

Profile image
Becky D.
Sitter Profile Image: Adrienne N.
Verified Enhanced Background Check
Adrienne N.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
57 reviews
10 repeat clients
14 years of experience
Milwaukee, WI, 53220

Adrienne, as always, brings so much comfort when I have to leave my voids, especially when I’m going off the grid. She’s very communicative and gives me the silliest pictures of my cats! She’s my go to gal, always going above and beyond.

Profile image
CeCe L.
Sitter Profile Image: Maya M.
Verified Enhanced Background Check
Maya M.
from
$18
per visit
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Greenfield, WI, 53228

Maya was excellent with Rosie and Rudy. I knew they were well cared for while I was away, which gave me peace of mind during my travels!

Profile image
Emily A.
Sitter Profile Image: Lisa N.
Verified Enhanced Background Check
Lisa N.
from
$15
per visit
5.0 out of 5 stars
2 reviews
2 repeat clients
35 years of experience
West Allis, WI, 53151

Lisa was very communicative and sent updates while I was away. Will book again!

Profile image
Lisa V.
Sitter Profile Image: Lilly C.
Verified Background Check
Lilly C.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
73 reviews
20 repeat clients
5 years of experience
Milwaukee, WI, 53227

Lilly always comes through in a pinch and having her be able to check in on my kitties so close to Christmas took so much stress off! I’m so happy to have found a regular sitter who is awesome with cats!

Profile image
Allie T.
Sitter Profile Image: Kelly M.
Verified Enhanced Background Check
Kelly M.
from
$20
per visit
5.0 out of 5 stars
40 reviews
12 repeat clients
15 years of experience
Greenfield, WI, 53227

Kelly did an amazing job with Canelo!! We received a detailed update of her time with him and would definitely contact her again!

Profile image
Sonia R.
Sitter Profile Image: Kelsey W.
Verified Enhanced Background Check
Kelsey W.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
13 reviews
4 repeat clients
2 years of experience
West Allis, WI, 53227

Kelsey was so great keeping in contact with me before and asking questions and information I forgot to let her know. Very pleased! Got lots of cute check ins!

Profile image
Sara S.
Sitter Profile Image: Courtnee S.
Verified Enhanced Background Check
Courtnee S.
from
$17
per visit
4.0 out of 5 stars
3 reviews
19 years of experience
Woodland Court, Milwaukee, WI, 53220

About: I have 16+ years pet care experience with Dogs, and 20+ years experience with dogs. I treat my pet companions like family, always. My dog Marley gets walked, bathed and has daily playtime. My cat Katara has daily playtime and even plays with me and my pup. They are two peas in a pod and love each others time. I have experience administering pets meds as well as bathing cats and dogs. Pet care falls into my daily routine naturally. My pet babies know when I get home they get 1 treat, Marley knows he goes out to use the bathroom and goes for his daily walk. When Marley and I get back from our walk its playtime for all three of us. I have a very nice pet friendly apartment complex, as well as many safe areas for us to explore! I can provide animal care services on an as needed basis, I will just need to be notified ahead of time of meds, allergies, pet specific foods etc.

Sitter Profile Image: Zachary S.
Verified Enhanced Background Check
Zachary S.
Star Sitter
from
$22
per visit
4.9 out of 5 stars
16 reviews
2 repeat clients
15 years of experience
Fairview, Milwaukee, WI, 53219

About: I grew up with pets my whole life - ferrets, fish, cats, and primarily bigger dog breeds (cocker spaniels and Labradors). I'm the kind of person who will show up to a party and hang out with your dog instead of the people for 3 hours. It is a given that I love animals, and ever since I moved from my family after covid, I am not able to have a long-term pet in my living situation. I do sometimes take care of my neighbors cat, however I'd like to spend more time with dogs as they are my favorite. I currently work doing pizza delivery around 30+ hours a week. I can come home once or twice a shift between deliveries, but Id say that your pet needs to be comfortable being alone for at **LEAST** 4 hours at any given time. I've already had issues with a clients dog not handling my schedule well and damaging property as a result -- so I need to be clear on this. I am not home 24/7, but I can try my best. I also prefer a minimum 2 day notice for requests. You can still attempt to request boarding if its last minute, I get it, life happens. But I cannot guarantee a confirmation on anything less than 2 days. I have a fenced in backyard and currently no other animals or people in my home. I can provide a safe and comfortable living space for a dog. I do not mind if they are on my furniture or if they want to sleep in my bed at night.

Sitter Profile Image: Justine R.
Verified Enhanced Background Check
Justine R.
from
$20
per visit
20 years of experience
Euclid Park, Milwaukee, WI, 53227

About: I have owned pets my entire life. I have one chocolate lab of my own. She is my baby and my best friend. I have one cat as well and I love her so much! I love all animals and I know what it’s like to leave them and worry when you aren’t there. I will treat your dogs like my own and make sure they get plenty of attention and treats. I will update you with photos to help put your mind at ease as well. I work from home so I do usually have enough flexibility to do drop in visits just depends on my schedule that particular day. I hope to work with you in the future and make sure you feel comfortable leaving your animals in my care. I work from home and have a decently flexible schedule. I have a young son and pets of my own but thankfully I share these responsibilities with my rockstar husband so I will be able to care for your fur babies. I understand that having a stranger in your home can be a little uncomfortable. I will 💯 respect your space and keep things clean in order for your while you are gone. Please let me know your preferences for my stay.

Sitter Profile Image: Mary C.
Verified Enhanced Background Check
Mary C.
from
$18
per visit
5.0 out of 5 stars
71 reviews
22 repeat clients
30 years of experience
GREENFIELD, WI, 53220

Mary is a great communicator - she let me know when she was at my house and sent pics during her visit. Overall, she was a caring, attentive friend to my furries! I would absolutely partner with Mary again. 😊

Profile image
Althea W.
Sitter Profile Image: Stephanie M.
Verified Enhanced Background Check
Stephanie M.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
7 reviews
3 repeat clients
15 years of experience
Greenfield, WI, 53228

Stephanie was great! She was responsive and communicative and I was able to be worry-free when out of town!

Profile image
Cheryl E.
1 / 1
View more sitters

Highwood Estates pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Another great drop in day with Sarah! Spent time playing and being outside. Came home to a happy pup!

Profile image
Jenna Z.
Drop-In Visits
5.0 out of 5 stars

Lexi has always been great with our two kitties, super responsive and kind. She goes above and beyond every time we are out of town and couldn’t recommend her more!

Profile image
Auburn L.
Drop-In Visits
5.0 out of 5 stars

Was able to accommodate a last-minute booking due to unexpected surgery and was super-accommodating over the weekend hospital stay updates. The pups looked super happy in every pic! Thanks so much.

Profile image
Dave B.
Drop-In Visits
5.0 out of 5 stars

Katie always goes above and beyond to make us comfortable while we’re away. In addition to taking great care of our kitty, she grabbed packages on our stoop for us to help with peace of mind. Will continue to have her in the future!

Profile image
Katy M.
Drop-In Visits
5.0 out of 5 stars

Maya was excellent with Rosie and Rudy. I knew they were well cared for while I was away, which gave me peace of mind during my travels!

Profile image
Emily A.
Drop-In Visits
5.0 out of 5 stars

Cosmo was in really great shape. Emily gave lots of feedback, and really eased my concerns. Cosmo had Diarrhea when she started taking care of him, but Emily was very good at taking care of him, and he was fine when we got home. She was great at giving me updates.

Profile image
Ronald S.
Drop-In Visits
5.0 out of 5 stars

This is the third time I have used Mallory to vacation visit my 2 cats. She is the best. The bowls were cleaned and the pictures showed happy cats. She is easy to work with a generally loves taking care of my cats.

Profile image
Cheryl K.
Drop-In Visits
5.0 out of 5 stars

Lilly did a fantastic job of checking in on our cat Marvin while we were away! She provided great updates and was very professional & communicative overall. Thank you Lilly!

Profile image
Nick P.
Drop-In Visits
5.0 out of 5 stars

Ashley is the sweetest! Loves my pup like her own and gives awesome updates & photos from her visits.

Profile image
Nitalia D.
Drop-In Visits
5.0 out of 5 stars

Amanda was great as always- our cats quickly became comfortable with her, and it was wonderful to know they were well taken care of!

Profile image
Meredith W.
Drop-In Visits
5.0 out of 5 stars

Stephanie was great! She was responsive and communicative and I was able to be worry-free when out of town!

Profile image
Cheryl E.
Drop-In Visits
5.0 out of 5 stars

Liz is so sweet & follows directions very well! Our two boys absolutely love her as she goes above and beyond to make sure they are taken care of while we are out of town. I was so happy Liz was available to watch them as she knows their routine and always willing to help more if needed. Cannot recommend enough!

Profile image
Hope C.
Drop-In Visits
5.0 out of 5 stars

Caitlyn is an amazing cat sitter! I hired her while I was away for a work trip and she dropped in multiple times a day and medicated one of my cats (who gets several meds throughout the day). On top of that, her updates were phenomenal! She gave me up descriptions of my cats activities that were very consistent with their personalities, so I could tell she was really paying attention to their moods and needs. One of the best cat sitters on here and I would easily hire her again! So flexible to work with, sends amazing photos, and responds quickly.

Profile image
Virginia S.
Drop-In Visits
5.0 out of 5 stars

I have used her multiple times for my first dog, and with my second now. She is wonderful especially since I am night shift and she is able to accommodate those night time hours. She is wonderful with the dogs. I recommend her 100%🤗

Profile image
Gaby S.
Drop-In Visits
5.0 out of 5 stars

Nicole was excellent! When she came for the meet and greet, she asked excellent questions to really get to know our girls and set expectations. She was calm and let our girls come to her. Then, when she came for the visit, she took excellent care of our kitties and was able to pill our calico successfully! Throughout the whole experience she communicated super well, which is something that we value. We will absolutely recommend and rebook!! Thanks Nicole!

Profile image
Amy S.
Drop-In Visits
5.0 out of 5 stars

Amanda has been helping us since we first got our puppy last November. She has been GREAT with her. Communicative, flexible, and caring are just a few words that describe Amanda! Couldn't have asked for better help.

Profile image
Emily P.
Drop-In Visits
5.0 out of 5 stars

Serena did an excellent job with our dogs, on-time and went above and beyond. Provided updates and pics for each visit so we felt totally at ease they were happy and well taken care of. Would happily book again.

Profile image
Kaytee S.
Drop-In Visits
5.0 out of 5 stars

Khersa was just so nice to have. Our cat loved her and the care Khersa gave to our fur baby was just superb. Def will be going back to her for future trips.

Profile image
Delanie F.
Drop-In Visits
5.0 out of 5 stars

Faith helped out while we were gone for a long day and was a great communicator and also sent us photos of the fur babies! We plan to use her again for future needs!

Profile image
Emily S.
Drop-In Visits
5.0 out of 5 stars

This is our second time booking with Emily, and we’ve loved her so much that we’ve referred friends to her who confirm the same sentiment: She is just fantastic at what she does. Her experience with young children as an elementary school teacher certainly translates to being phenomenal with furry friends! We were concerned that our shy calico would hide, but she was happily making friends within a few visits. Rover reports were detailed (and so sweet!) each day. Cannot continue recommending Emily enough!

Profile image
Hannah S.
Drop-In Visits
1 / 1
Find pet care near you

Popular requests near you

Select a filter and find qualifying Highwood Estates sitters!

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for pet sitting in Highwood Estates is $18

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Highwood Estates on Rover as of Mar 2026 was about $18 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Highwood Estates pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.

Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Highwood Estates.

Rover makes it easy to find Highwood Estates pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.