House Sitting Highwood Estates

Find a loving house sitter to watch over your pets and your home.

End
Search

Over 24
pet parents in Highwood Estates have booked house sitting

Highwood Estates, Find top rated house sitting

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

1 / 1
Sitter Profile Image: Jenn S.
Verified Enhanced Background Check
Jenn S.
Star Sitter
from
$68
per night
5.0 out of 5 stars
• 132 reviews
35 repeat clients
40 years of experience
West Allis, WI, 53227

“Another great experience with Jenn!! Came home to a happy pup and tiddy home. In addition, I was out of town and a snow storm hit! My flight was cancelled. Jen was a saint for being able to take care of my dog with my extended leave.”

Profile image
Jenna Z.
Sitter Profile Image: Keisha P.
Verified Enhanced Background Check
Keisha P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
• 56 reviews
25 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

“Keisha was amazing! She helped us out when another sitter cancelled. She took amazing care of our 2 dogs while we were away! She was very responsive, sent lots of pictures, and kept us posted the whole weekend! She truly understood and embraced my dog’s personalities! I would highly recommend her and will be using her again in the future!”

Profile image
Janine P.
Sitter Profile Image: Emily M.
Verified Enhanced Background Check
Emily M.
from
$59
per night
5.0 out of 5 stars
• 45 reviews
12 repeat clients
30 years of experience
Milwaukee, WI, 53213

“Emily was great at communicating with us the entire stay, and we could tell from all her updates and pictures that our pups loved having her around. Our flight ended up getting delayed because of the blizzard rolling through Wisconsin this past weekend, and Emily was able to help make sure our pups were let out and fed while we figured out how to get back to Milwaukee. I would absolutely recommend Emily to anyone else looking for expert and friendly care for their pups on Rover. Thank you again!”

Profile image
Creighton B.
Sitter Profile Image: Fatima B.
Verified Enhanced Background Check
Fatima B.
Star Sitter
from
$35
per night
5.0 out of 5 stars
• 9 reviews
2 repeat clients
2 years of experience
West Allis, WI, 53214

“Fatima was amazing to work with. I booked her on short notice before the holiday when my original plans fell through. She offered and made it a priority to come do a meet & greet on days notice. I’m always a little nervous when using a new sitter especially when they stay at mine, but my mind was at ease immediately when I met her. I could tell she has a big heart and really cares for animals. She followed all instructions and she went above and beyond spending time with Diesel doing his favorite activities (walks, playing fetch, swimming, etc.). She was incredibly communicative and sent a lot of pictures and videos which was much appreciated. As a former Rover sitter and a frequent user of Rover’s services, I can confidently say that Fatima is one of the best sitters I’ve come across. I will definitely be using her in the future and have already recommended her to others looking for sitters. Thank you Fatima!!!”

Profile image
Alex S.
Sitter Profile Image: Diana M.
Verified Enhanced Background Check
Diana M.
from
$50
per night
5 years of experience
Milwaukee, WI, 53215

About: I love all pets, big and small! I’ve pet sat for family and friends (from puppies to tripod cats) over the last few years. I don’t have any pets of my own so I always enjoy meeting new dogs/cats :) I work 9-5 (mon-friday) and typically work from home once a week. I’m available when I wfh, weeknights and weekends! Would love to use some of my free time to take care of your pets. For overnight stays, I’ available to stay at your house. I know every pet has their own personality, routine and quirks - I do my best to stick to what makes them feel comfortable. I’ll follow your care instructions and treat your pet the way I’d want someone to treat my own. Whether that’s a long walk, trip to the park, pup cup or being a house hippo, I’m happy to accommodate.

Sitter Profile Image: Stephen & Wipawee D.
Verified Enhanced Background Check
Stephen & Wipawee D.
from
$100
per night
5.0 out of 5 stars
• 51 reviews
19 repeat clients
6 years of experience
West Allis, WI, 53227

“Stephen and Wipawee watched our dog for the second time. They took excellent care of him. They kept us informed with pictures and updates throughout our trip. They were very respectful of our home and even brought in our mail and took our trash out to the curb. 100% recommend them and will definitely ask them to dog sit again in the future!”

Profile image
Kristin L.
Sitter Profile Image: Alexis G.
Verified Enhanced Background Check
Alexis G.
from
$47
per night
5.0 out of 5 stars
• 13 reviews
9 repeat clients
6 years of experience
Greenfield, WI, 53221

“Oliver enjoyed his time with Alexis!!”

Profile image
Cindy A.
Sitter Profile Image: Samantha B.
Verified Background Check
Samantha B.
from
$60
per night
4.9 out of 5 stars
• 15 reviews
4 repeat clients
13 years of experience
Milwaukee, WI, 53215

“Samantha did a wonderful job during an overnight say with my Sasha. She came to meet Sasha beforehand and get a quick tour of the house and rundown of Sasha's schedule. During her stay, she sent lots of pictures and updates. She also left my home cleaner than when I had left! I am extremely appreciative of Samantha's care that she put towards watching my fur baby.”

Profile image
Alyssa T.
Sitter Profile Image: Sarah J.
Verified Enhanced Background Check
Sarah J.
from
$60
per night
5.0 out of 5 stars
• 551 reviews
98 repeat clients
5 years of experience
West allis, WI, 53219

“I am a repeat consumer of Sarah’s pet sitting. She is phenomenal. For this house sitting visit, I was out of the country and there was a snow storm back home. I was super concerned, but didn’t need to be. Sarah still made every visit and the sleep overs punctual and full of fun for my dog. Sent tons of pictures and details notes. Recommend Sarah hands down!”

Profile image
Jenna Z.
Sitter Profile Image: Carolyn G.
Verified Enhanced Background Check
Carolyn G.
from
$35
per night
5.0 out of 5 stars
• 4 reviews
2 repeat clients
17 years of experience
West Allis, WI, 53214

“Cary was an excellent dog sitter! She cared for my dog for 7 days while I was out of the country, and this was my first time being away from my dog. She was very thoughtful about sending regular updates throughout the day, which gave me so much peace of mind. Cary stayed at my home and took great care of both my dog and my space. She kept everything clean and even washed my sheets before I returned, which I truly appreciated after a long day of traveling. It’s clear she genuinely cares and treats your pet like her own. I highly recommend her to anyone looking for a reliable and caring dog sitter!”

Profile image
Seryna G.
Sitter Profile Image: Evita E.
Verified Enhanced Background Check
Evita E.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 22 reviews
4 repeat clients
10 years of experience
Sunset Heights, Milwaukee, WI, 53216

“While Evita watched our pup Molly overnight at our house, she was punctual and communicated well. She also took Molly on a nice long walk each day that pleasantly tuckered her out. Molly seemed calm and happy when we returned home.”

Profile image
Alia E.
Sitter Profile Image: Adrianne R.
Verified Enhanced Background Check
Adrianne R.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 20 reviews
2 repeat clients
20 years of experience
Franklin, WI, 53132

“This was my first time leaving our puppy Fritz and first time using Rover. I couldn’t be happier with our experience with Adrienne! I appreciated the daily check ins and pics/videos and I could tell that Fritz was happy and content and well cared for. I would recommend Adrienne and will use her again the next time we go out of town without the pup.”

Profile image
Holly Y.
Sitter Profile Image: Patricia N.
Verified Enhanced Background Check
Patricia N.
Star Sitter
from
$40
per night
5.0 out of 5 stars
• 110 reviews
32 repeat clients
30 years of experience
Franklin, WI, 53132

“Patricia was very attentive and detail oriented, and she made sure to cover all of her bases when preparing to care for our pup. She is experienced and professional. I would absolutely hire her again and recommend her to others!”

Profile image
Lauren P.
Sitter Profile Image: Joseph D.
Verified Enhanced Background Check
Joseph D.
from
$28
per night
4.9 out of 5 stars
• 9 reviews
2 repeat clients
10 years of experience
Wauwatosa, WI, 53213

“Joe was great with our Fifi, he was really a lifesaver! He stayed at our house as our rescue dog can be a little clingy. I received the cutest pictures and was really able to enjoy myself on vacation knowing she was at home!”

Profile image
Candy P.
Sitter Profile Image: Daija H.
Verified Enhanced Background Check
Daija H.
from
$45
per night
11 years of experience
Milwaukee, WI, 53226

About: From working/volunteering at shelters to pet sitting for friends and family, I have 10+ years of experience caring for furry friends of all ages, personalities, and sizes! Most all of my pet care has been limited to cats and dogs, but I am willing to work with small critters, birds and reptiles with the right care instructions/tutorials. I am not typically squeamish, so I am open to handling clean up and medication - please message me for specifics. As a dog mom myself, I understand that each pet requires different levels of care and attention, and am willing to meet them where they’re at! However, I do not offer training services and might not be the most compatible caretaker for pets that exhibit aggressive behaviors (I am open to discussing). Additionally, I am a full time graduate student, so care in the early morning and evenings will work best for my week day schedule. I will be available some holidays (i.e., Thanksgiving). My availability may also change from time to time, so please be sure to check my profile or message me. Choosing me means your pet will receive quality care, and that all the updates you receive will include cute pics! As a full time student, my weekday availability might mean limited check-ins, but your pet is always the priority! - Monday & Tuesday: 6:00 AM - 7:30 AM; after 5 PM - Wednesday: 6:00 AM - 7:30 AM; after 7 PM - Thursday: 6:00 AM - 7:30 AM; after 5 PM - Friday: 6:00 AM - 8:00 AM; after 3:00 PM - Saturday & Sunday: Flexible! I will need a few hours in the morning and some afternoons to volunteer. For pet sitting, I can provide the following: - Feeding and hydration - Exercise and play - Maintenance and cleaning of pets environment (e.g., litter box, crate, etc.) - Medication administration - Light housekeeping (e.g., bringing mail in, watering plants, taking out trash, etc.) - Text/photo/video updates

Sitter Profile Image: Amanda S.
Verified Enhanced Background Check
Amanda S.
from
$55
per night
5.0 out of 5 stars
• 43 reviews
11 repeat clients
10 years of experience
West Allis, WI, 53219

“Amanda watched my golden retriever Murphy from Wednesday to Sunday. She was fantastic! Communication was great. She sent multiple updates throughout the day including photos. She left my house in exactly the same condition it was in before I left and even grabbed my mail for me. I highly recommend Amanda. I will be using her again!”

Profile image
Kristin K.
Sitter Profile Image: Maya M.
Verified Enhanced Background Check
Maya M.
Star Sitter
from
$55
per night
5.0 out of 5 stars
• 13 reviews
4 repeat clients
10 years of experience
Greenfield, WI, 53228

“Maya was so great with our two dogs! She’s incredibly trustworthy, kind, helpful, and communicative. Her dog, Mello, is also such a gem. We really appreciated all her help over the long weekend, and would rebook in a heartbeat!”

Profile image
Audrey J.
Sitter Profile Image: Ryan T.
Verified Enhanced Background Check
Ryan T.
from
$50
per night
5.0 out of 5 stars
• 4 reviews
10 years of experience
West Allis, WI, 53214

“Ryan was fantastic! He took great care of our very large dog, who can be reactive at times. I completely trusted him while we were away for a week. We received lots of updates like we asked. He gave our dog medicine without any issues. We came home to a very happy pup and a spotless house. Ryan even got our mail and watered our flowers while we were away, which was super nice. We highly recommend him and already have our next trips booked with him!”

Profile image
Leah G.
Sitter Profile Image: Quazaye K.
Verified Enhanced Background Check
Quazaye K.
from
$55
per night
4.8 out of 5 stars
• 37 reviews
17 repeat clients
10 years of experience
Franklin, WI, 53132

“What a lovely human! Absolutely loved our experience with Quazaye - she sent pics every day and was always very responsive while we were away :) My pups were happy and well cared for & my house was in the same condition I left it in! Would definitely use her services again! Don’t think twice <3”

Profile image
Stephanie F.
Sitter Profile Image: Sarah G.
Verified Enhanced Background Check
Sarah G.
from
$28
per night
8 years of experience
Milwaukee, WI, 53220

About: I am a cat mom to two lovable cats that are my World, and have owned dogs in the past (my black lab passed away in March). I am currently in college to become a Vet Tech (I graduate in June), so I am very passionate about helping animals, providing excellent care, and of course having lots of fun with them! I have 8+ years of experience dog and cat sitting for various families as well as experience working at a Doggy Daycare for 4 years. Lastly, I am Veterinary CPR certified and can administer medications, including insulin injections. Being that I am a full time student, I will be unavailable mornings, Mon-Fri between 7am-noon. If I sit for your dog or cat, I will be at your home the rest of the time. If you have any questions don't hesitate to reach out and I look forward to meeting your fluffy friend! I am currently a full time Vet student, so I will be unavailable from 7am-noon on weekdays. I will be available to be with your pet outside of those hours at all times. I am CPR certified for dogs and cats, and can administer oral and SQ medications. . . .. . . . . . . .

1 / 1
View more

The median cost per night for house sitting in Highwood Estates is $50

Pet parents share their Rover experiences - Highwood Estates

1 / 1
5.0 out of 5 stars

Whenever we need a pet/house sitter Emily is our top choice. He always makes leaving our home and pets an easy experience without worry that everyone will be taken care of.

Profile image
Jensen M.
House Sitting
5.0 out of 5 stars

Mallory is so great! My dog has never been so calm and content after we have been away. Mallory was responsive, shared great updates, and made him feel so comfortable while we were out of town. Would book with her again in a heartbeat!

Profile image
Anna K.
House Sitting
5.0 out of 5 stars

Stephany did a phenomenal job watching my dogs overnight. I was nervous at first as it was my first time leaving them with someone besides family. However, stephany went above and beyond. Following their usual daily schedules, taking them for walks, and updating me regularly with photos and videos. I could tell that they were comfortable with her and really liked her! I will absolutely re book stephany again in the future, she will take wonderful care of your pets and home while you are away. Thank you Stephany!

Profile image
Erika R.
House Sitting
5.0 out of 5 stars

Kerry watched our two girls for 5 days at our home. We have an Aussie and a Terrier mix and the Aussie can be anxious when we are away. Kerry was awesome and we could tell when we returned that the girls were calm and well taken care of. She asked thoughtful questions to make sure she knew about their preferences/routine and gave us updates along the way. Highly recommend!

Profile image
Kay M.
House Sitting
5.0 out of 5 stars

Fatima was great! Very kind, caring and communicative. We would definitely recommend and will be looking forward to having her back!

Profile image
Erica S.
House Sitting
5.0 out of 5 stars

Maiah was great to work with! She was quick to respond and communicate with. Our doggos enjoyed her company and she took great care of them! Would definitely rebook with her again!

Profile image
Rebekah J.
House Sitting
5.0 out of 5 stars

Alissa was awesome with Walter! She definitely was able to meet his high energy breed’s needs and sent us great updates throughout her stay. Our home was left very clean, which we hugely appreciate. Thank you!

Profile image
Livia A.
House Sitting
5.0 out of 5 stars

Katlynn followed my detailed instructions and I felt very comfortable with her caring for Mink. She watched him carefully to make sure he did not have a recurrence of his medical condition.

Profile image
Catherine K.
House Sitting
5.0 out of 5 stars

Lexi was wonderful to work with! She was on time, sent pictures and updates, and did a great job caring for our dogs while we were away. I am looking g forward to using Lexi’s services in the future- thank you!!

Profile image
Sarah D.
House Sitting
5.0 out of 5 stars

Sarah is an absolute star - we’re so lucky to have found her on Rover! Our dogs are so happy and comfortable with her, and we know we can rely on her 100%. Consistent photos and updates, and when we get home, the dogs are so chill that it’s like we never left.

Profile image
Hannah T.
House Sitting
5.0 out of 5 stars

Katherine is incredible! Our pets receive so much attention and she is so caring for each of their needs. We return home to an extremely clean house. Everything from the care of our pets and home, her attention to detail is above and beyond!

Profile image
Todd S.
House Sitting
5.0 out of 5 stars

Nicole is absolutely phenomenal! She took such great care of our Siberian kitten. Nicole is very professional, communicative, and you can tell how much she loves what she does! The whole time we were gone she sent us updates and photos. We would 110% recommend Nicole!

Profile image
Angela G.
House Sitting
5.0 out of 5 stars

Stephanie was a great sitter. She helped me out when I was in a pinch due to last minute cancellation. She was able to get a meet and greet in timely and sit for me that weekend. She was prompt, professional, all around great! Will forsure use her services again!

Profile image
Jenna Z.
House Sitting
5.0 out of 5 stars

Ryan was fantastic! He took great care of our very large dog, who can be reactive at times. I completely trusted him while we were away for a week. We received lots of updates like we asked. He gave our dog medicine without any issues. We came home to a very happy pup and a spotless house. Ryan even got our mail and watered our flowers while we were away, which was super nice. We highly recommend him and already have our next trips booked with him!

Profile image
Leah G.
House Sitting
5.0 out of 5 stars

Scott was FABULOUS with our dog, Rocket! Rocket is a bit picky, but he wholeheartedly loved Scott, too. Scott had wonderful communication--he gave enough so that I felt reassured that Rocket was doing well, but he also let me just relax while on our trip. He made me feel confident that Rocket was in good hands, and that means the world to me. Scott also took in our mail and watered our garden. Thanks for everything, Scott!

Profile image
Jen C.
House Sitting
5.0 out of 5 stars

Aubrey was amazing. My doggies were comfortable with her right away. She treated my home with respect and it was even cleaner when I got back. Will be hiring her again!

Profile image
Antonia R.
House Sitting
5.0 out of 5 stars

As always, Caitlyn was amazing! Great updates of our pets, handles giving meds like a champ, and leaves our place nice and clean every time.

Profile image
Riley H.
House Sitting
5.0 out of 5 stars

Jenn was a wonderful over-night sitter for my two cats. She took great care of them while I was out of town for a few days. She sent photos each day, sent updates and communicated well. When I returned she left the house just as she found it, and she also made sure my plants / tomatoes were watered outside. She is responsible and trustworthy and she was good company for my two kitties while I was gone. I will definitely use her again if she is available.

Profile image
Joette R.
House Sitting
5.0 out of 5 stars

We feel so incredibly lucky to have found Justine! She watched our 10 month old puppy, Rumi, for the weekend and truly went above and beyond. Leaving your pup and your home in someone else's hands can be stressful, but Justine gave us total peace of mind - we knew right away he was in the best hands! She kept us connected the entire time with constant updates and photos. Rumi even got to meet her family briefly, and I can tell he absolutely loved it, especially hanging out with her son! To top it off, when Rumi had a minor issue with an itchy ear, Justine stepped right in with excellent preventative care, keeping him comfortable until we could get him to the vet on Monday. Rumi clearly had a fantastic weekend. We couldn't ask for a more trustworthy, communicative, and caring sitter - highly recommended!

Profile image
Sofia K.
House Sitting
5.0 out of 5 stars

I can't speak highly enough about Melissa and the care she gave my pets (2 dogs, 2 cats, and a 🐸). She asked thoughtful questions about their care and spent so much time loving on them during her stay! 12/10 recommend! I can't wait to invite her back for our next trip out of town! It will give me peace of mind knowing she is watching over my fur kids ❤️

Profile image
Kathleen K.
House Sitting
1 / 1
Find pet care near you

Book with peace of mind

  • Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
  • Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
  • 24/7 support from the Rover team–here to help if you ever need someone to talk to.

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 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.

Meet local sitters who will treat your pets like family

  1. 1. Search

    Browse profiles of sitters near you who offer house sitting
  2. 2. Meet In Person

    Schedule a free in-person Meet & Greet to find the perfect fit
  3. 3. Book & Pay

    It's that easy! All payments are processed through Rover's secured platform

Popular requests for house sitting - Highwood Estates

Select a filter and find qualifying sitters offering house sitting.

Sitters in Highwood Estates average 4
repeat house sitting clients

Connect anywhere with the Rover app

Download on the App Store BadgeGet it on Google Play Badge