House Sitting Highwood Estates

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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: Samantha S.
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Samantha S.
Star Sitter
from
$33
per night
5.0 out of 5 stars
• 9 reviews
3 repeat clients
10 years of experience
Bay View, Milwaukee, WI, 53207

“Sam was great with our rambunctious pup! She was so attentive to Walter, sent daily updates and photos, and left our home in stellar shape. Thank you!”

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Livia A.
Sitter Profile Image: Sarah J.
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Sarah J.
from
$60
per night
5.0 out of 5 stars
• 540 reviews
97 repeat clients
5 years of experience
West allis, WI, 53219

“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.
Sitter Profile Image: Evita E.
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Evita E.
Star Sitter
from
$50
per night
5.0 out of 5 stars
• 18 reviews
3 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.”

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

“Andrianne was wonderful! She was communicative throughout her time with Tex. Pictures often! She Not only took good care of our precious dog, but Our Home as well! I would highly recommend Adrianne for your pet sitting needs! We will definitely be using her again! Words I would use to describe her: kind, trustworthy,friendly!”

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Pamela W.
Sitter Profile Image: Jenn S.
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Jenn S.
Star Sitter
from
$70
per night
5.0 out of 5 stars
• 132 reviews
35 repeat clients
40 years of experience
West Allis, WI, 53227

“We were very pleased on how well Jenn took care of our fur baby Zoey. Jenn sent us pictures and updates daily. We will definitely book Jenn again for future dog sitting.”

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Mark S.
Sitter Profile Image: Emily M.
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Emily M.
from
$59
per night
5.0 out of 5 stars
• 43 reviews
11 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!”

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Creighton B.
Sitter Profile Image: Emily R.
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Emily R.
Star Sitter
from
$77
per night
5.0 out of 5 stars
• 104 reviews
29 repeat clients
20 years of experience
Story Hill, Milwaukee, WI, 53213

“We love having Emily stay with our dog and cat when we go out of town! She’s so great with them, we never have to worry about a thing. We always come home to happy animals! She’s also very quick to respond to messages. We love Emily!”

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Kathleen P.
Sitter Profile Image: Keisha P.
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Keisha P.
Star Sitter
from
$50
per night
4.9 out of 5 stars
• 54 reviews
24 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!”

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Janine P.
Sitter Profile Image: Joseph D.
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Joseph D.
from
$28
per night
4.9 out of 5 stars
• 8 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: Fatima B.
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Fatima B.
from
$35
per night
5.0 out of 5 stars
• 9 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: Stephen & Wipawee D.
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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

“Stepen and Amelie took great care of our 1 year old dog and our home. They took our dog on multiple walks, played with him and made sure he was comfortable. They were great about keeping us up to date with pictures, videos and messages about how our dog was doing. We came home to a detailed list of what our dog did each day, how much he ate, when he used the bathroom and when he slept. We were very impressed and would recommend Stephen and Amelie.”

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Kristin L.
Sitter Profile Image: Margaret D.
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Margaret D.
from
$45
per night
5.0 out of 5 stars
• 8 reviews
4 repeat clients
20 years of experience
Cooper Park, Milwaukee, WI, 53222

“She was amazing with Russell and Cora! I felt so comfortable leaving them for so long when she was caring for them!”

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Beth G.
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: Maiah D.
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Maiah D.
Star Sitter
from
$100
per night
5.0 out of 5 stars
• 94 reviews
28 repeat clients
16 years of experience
West Allis, WI, 53214

“We had a wonderful experience with Maiah and would absolutely recommend her. Our beagle can be a bit high-maintenance, but Maiah was so great with her. It gave us peace of mind knowing our pup was in trustworthy, kind, and capable hands. Maiah was also an excellent communicator--we received regular updates, photos, and quick responses, which made it easy to relax while we were away. We wouldn’t hesitate to book with her again!”

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

“Alissa was great! She really came through for us at the last minute so we were able to enjoy our concert stress free! She kept us updated, and was prompt with her communication! The boys loved her!”

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Cue T.
Sitter Profile Image: Margaret M.
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Margaret M.
from
$55
per night
5.0 out of 5 stars
• 3 reviews
1 repeat client
35 years of experience
Bluemound Heights, Milwaukee, WI, 53213

“Wow! What can I say? Margaret exceeded every expectation I had for Uecker’s care today! As a new puppy mom who’s only had him for three weeks, leaving him with someone for the first time was a little nerve-wracking. But Margaret made me feel completely at ease. She didn’t just watch him—she played with him, loved on him, reinforced the commands we’ve been working on, and treated him like he was her own. The best part? Walking through the door and finding Uecker snuggled up right next to her. My heart absolutely melted. It was obvious he felt safe, loved, and completely comfortable. I truly couldn’t be happier with the care Margaret provided. Book her before I do, because with my busy schedule, I’ll definitely be calling her again! Thank you so much, Margaret. Uecker already adores you, and so do I!”

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Jackie G.
Sitter Profile Image: Alexis G.
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Alexis G.
from
$47
per night
5.0 out of 5 stars
• 12 reviews
8 repeat clients
6 years of experience
Greenfield, WI, 53221

“Alexis was super communicative and took great care of our dog while we were away!”

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K M.
Sitter Profile Image: Amanda S.
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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

“It was awesome to feel confident that she could handle my energetic puppy. She also provided multiple updates with pictures :) would book again”

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Emily H.
Sitter Profile Image: Ryan T.
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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!”

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Leah G.
Sitter Profile Image: Alexis W.
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Alexis W.
from
$57
per night
5.0 out of 5 stars
• 3 reviews
10 years of experience
Jackson Park, Milwaukee, WI, 53219

“We came home clean house and my Esther was taught a trick and very disciplined on the leash in backyard. Alexis is so loving and I highly recommend her. She checked in with us throughout our trip. She is the best!”

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Michaelchad B.
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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

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

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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!

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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!

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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.

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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

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

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
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