House Sitting Highwood Estates

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

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Over 27
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.
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Jenn S.
Star Sitter
from
$70
per night
5.0 out of 5 stars
130 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.

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Jenna Z.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
51 reviews
22 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha is wonderful! Our pups are very shy but Keisha did a great job helping them warm up. She is sweet, communicative and flexible, and even sent us pics of the girls while she was watching them!

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Julianne S.
Sitter Profile Image: Sarah J.
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Sarah J.
from
$50
per night
5.0 out of 5 stars
532 reviews
96 repeat clients
5 years of experience
West allis, WI, 53219

Sarah took good care of my precious Joey and my home while I was on a vacation. She sent updates and gave him lots of love. I appreciate her professionalism .

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Michele R.
Sitter Profile Image: Elizabeth H.
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Elizabeth H.
Star Sitter
from
$75
per night
5.0 out of 5 stars
228 reviews
44 repeat clients
9 years of experience
Muskego, WI, 53150

Elizabeth watched our puppy overnight for NYE. She kept us updated and sent pictures. We appreciated the last minute help especially for the holiday!

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Hockey 2.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
103 reviews
28 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

Emily was prompt, respectful, and communicative. She sent pictures and updates and my dog seemed very comfortable and calm when I returned. I highly recommend Emily and will happily book her again in the future if I need a dog sitter!

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Meredith H.
Sitter Profile Image: Audrey N.
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Audrey N.
from
$28
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
1 year of experience
Greenfield, WI, 53228

Audrey took excellent care of my babies so I could have a mini getaway, she made my boys happy and feel loved.

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Kelly S.
Sitter Profile Image: Molly O.
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Molly O.
from
$65
per night
5.0 out of 5 stars
72 reviews
20 repeat clients
18 years of experience
Wick Field, Milwaukee, WI, 53208

Molly is the best! She is very patient and caring with our senior dogs. She takes initiative to engage and enrich our pups with lots of fun and play. Of equal, if not greater, importance is her quick thinking when unforeseen events arise. She’s shrewd, highly responsible, and I trust her in an emergency. She is always our first choice. All around, she’s a stellar human and highly capable sitter!

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Lily S.
Sitter Profile Image: Carolina G.
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Carolina G.
Star Sitter
from
$50
per night
4.9 out of 5 stars
39 reviews
8 repeat clients
9 years of experience
Cudahy, WI, 53110

We were pleased with Caroline😊 She was attentive to Petey and helped him adjust to a new person caring for him. Petey is a happy dog and Caroline was great at getting him to play and took him for several walks! We felt she kept us posted with notes and pictures. We honestly can’t think of anything she could improve-Our Petey was well cared for and given plenty of attention😊

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Richard /Katrina M.
Sitter Profile Image: Melissa F.
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Melissa F.
from
$68
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
25 years of experience
WEST ALLIS, WI, 53227

Melissa was a HUGE help, stepping in over the holidays for a long house-sitting service when a previous sitter had to cancel last-minute. She is personable and communicative, shared lots updates during the stay, and took good care of our house. Our dog and cat were in great hands, and it felt wonderful to come home to relaxed happy pets. Happy to recommend!

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Marcella M.
Sitter Profile Image: Laurie P.
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Laurie P.
Star Sitter
from
$75
per night
5.0 out of 5 stars
120 reviews
50 repeat clients
36 years of experience
Historic Third Ward, Milwaukee, WI, 53202

Laurie was great and made my first experience with Rover amazing! I felt so comfortable and relaxed knowing my fur babies were in good hands and didn't feel stressed wondering about them! The pics I received were SUCH a nice touch, like a random surprise waiting for me when I'd check my phone. I DEFINITELY recommend Laurie and will contact her in the future when she's available. ♡

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Samantha T.
Sitter Profile Image: Emily M.
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Emily M.
from
$59
per night
5.0 out of 5 stars
41 reviews
10 repeat clients
30 years of experience
Milwaukee, WI, 53213

Emily was exceptional through and through. Great communication and even better care of our home & pups. We will most certainly ask her to care for our boys again!

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Caryn L.
Sitter Profile Image: Patricia N.
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Patricia N.
Star Sitter
from
$40
per night
5.0 out of 5 stars
106 reviews
32 repeat clients
30 years of experience
Franklin, WI, 53132

Patricia was great with Jeter! He was very well taken care of and she shared pictures with us while we were away. We will definitely rebook with her in the future!

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Julie Q.
Sitter Profile Image: Holly J.
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Holly J.
from
$85
per night
5.0 out of 5 stars
41 reviews
10 repeat clients
15 years of experience
Wauwatosa, WI, 53226

Holly was great with our sweet boy and girl! She provided updates and pictures throughout the stay which we so appreciated! Would definitely recommend her!

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Heather D.
Sitter Profile Image: Alexandra I.
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Alexandra I.
Star Sitter
from
$80
per night
5.0 out of 5 stars
31 reviews
6 repeat clients
11 years of experience
Juneau Town, Milwaukee, WI, 53202

Alex recently stayed in my condo and watched my french bulldog, Hazel. I cannot say enough great things about Alex! She took Hazel out on numerous adventures and always sent photo updates. Alex would be sure and text if she had any questions as well. She was absolutely wonderful and I know Hazel misses her already. I will definitely book with Alex again.

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Lorna D.
Sitter Profile Image: Rebecca M.
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Rebecca M.
Star Sitter
from
$38
per night
5.0 out of 5 stars
12 reviews
5 repeat clients
5 years of experience
Kilbourn Town, Milwaukee, WI, 53203

Rebecca was phenomenal with my little critters! Excellent communication throughout the week and she was able to adjust last minute to needing to give my dog extra TLC and medication. I highly recommend her for your pet-sitting needs!

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Kristina P.
Sitter Profile Image: Joseph D.
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Joseph D.
from
$28
per night
4.8 out of 5 stars
7 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!

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Candy P.
Sitter Profile Image: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
34 reviews
7 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

Elizabeth was amazing. We need a last minute dog sitter and she came through and saved vacation! She provided plenty of updates, photos, and videos. Our dog sometimes is a little shy coming out of her crate but she loved Elizabeth. We will definitely use Elizabeth's services again!!

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Shaun M.
Sitter Profile Image: Fatima B.
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Fatima B.
from
$35
per night
5.0 out of 5 stars
8 reviews
1 repeat client
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!!!

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Alex S.
Sitter Profile Image: Ashley S.
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Ashley S.
from
$50
per night
5.0 out of 5 stars
21 reviews
9 repeat clients
13 years of experience
Juneau Town, Milwaukee, WI, 53202

Ashley took absolutely excellent care of our cat while we were out of the country for a week! I knew from the moment she met our cat during our meet and greet that our little girl was going to be in great hands. Throughout the trip, Ashley reached out with check-ins and photos reflecting how well she was being taken care of. She also responded quickly to any messages and went above and beyond watching our place. We (and our cat) look forward to seeing her again in the future!

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Jeremiah W.
Sitter Profile Image: Alissa A.
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Alissa A.
Star Sitter
from
$80
per night
5.0 out of 5 stars
14 reviews
3 repeat clients
20 years of experience
Greenfield, WI, 53221

Excellent communication from the start. Came for a greet and meet and easy to be with and obvious knew dogs well. Ended up a friend of mine knows Alissa so a double excellent reference. She communicated with me constantly throughout the stay. My dog is a senior and she did well with him and when I returned he kept roaming into where she was staying in my place. Would have back again as she is available.

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Cindy S.
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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

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.

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Catherine K.
House Sitting
5.0 out of 5 stars

Mallory was great. She house sat for me with my two dogs I got regular updates and pictures. Great communication will definitely use her again.

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Mandy P.
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!!

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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.

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Hannah T.
House Sitting
5.0 out of 5 stars

Alyssa was absolutely amazing. When we had the meet and greet, I loved her from the very start. We have two Maltese, which are tightly bonded to my husband and I, not wanting anyone in our space. But with her great communication skills, loving and kind personality, she had them cuddling up on the sofa soon into the day. We enjoyed messaging her and receiving pictures from her. she is a wonderful person and would love becoming a friend of hers! I highly recommend her, she would be my first choice having her as a caregiver for my dogs.

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Audrey H.
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!

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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!

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Angela G.
House Sitting
5.0 out of 5 stars

We had been having a hard time finding a reliable sitter for our pets but this last weekend with Stephanie was such a relief! Our dog and cat looked well taken care of. Our dog can be a little tricky to handle at times (huskys…)and we felt she did great!

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Tiffany M.
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!

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Jenna Z.
House Sitting
5.0 out of 5 stars

Fatima sat with our two Australian Shepherds for a few hours while I was out of the house. She was terrific to work with, from the meet-and-greet to the stay, and we've already booked her for another stay. Thanks, Fatima!

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Dave P.
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!

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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!

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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!

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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.

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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.

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Joette R.
House Sitting
5.0 out of 5 stars

Stephany was great! She updated us when she arrived and kept us updated with pictures throughout. The dogs were happy when we got home and the house was clean. Highly recommend.

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Lyndsay Z.
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!

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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 ❤️

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Kathleen K.
House Sitting
5.0 out of 5 stars

Rachel was great with Howie and I loved all the photo updates she provided. Really appreciated her patience with my puppy!

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Amanda K.
House Sitting
5.0 out of 5 stars

As with last time, everything was perfect! Amazing communication throughout the stay. Sharing everything from updates on our moody dog’s tummy issues to funny anecdotes! Even our most shy cat deems Emily a quality caretaker! So much so that he makes his presence known and allow for pets!

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Jensen M.
House Sitting
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