House Sitting In Havenwoods

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

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Top rated Havenwoods house sitters

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

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Sitter Profile Image: Catherine R.
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Catherine R.
Star Sitter
from
$70
per night
5.0 out of 5 stars
21 reviews
8 repeat clients
1 year of experience
Murray Hill, Milwaukee, WI, 53211

Catherine did a great job house sitting and pet sitting my golden retriever for 5 nights. She was extremely professional throughout the entire process and left my home clean and tidy. I would not hesitate to book with her again!

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Kirstyn W.
Sitter Profile Image: Joseph D.
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Joseph D.
from
$28
per night
10 years of experience
Wauwatosa, WI, 53213

About: I’ve been looking after fluffy frens of all shapes and sizes from a young age. My time doing a full house/dog sitting gig was for my grandparents and their French bulldog, Sugar (miss you, Sugs!). Since then I have been the go-to for my friends and family for taking care of their for legged family. I make sure your fury family gets the love and care they need, whether you just have one smol dog or a pack of greyhounds. I currently had a stretch of rough health luck, but my ails are your pups gain! I’m currently on the mend, and it’s going well, but between jobs, so my schedule is wide open. I’ll have the time to give your pups the TLC they deserve! Currently unavailable to board pets at my house, but I will make sure to treat all pets in a safe and caring way. I’ll treat them like a newborn baby, because hey, in a way they are!

Sitter Profile Image: Keisha P.
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Keisha P.
from
$45
per night
5.0 out of 5 stars
40 reviews
19 repeat clients
8 years of experience
Clarke Square, Milwaukee, WI, 53204

Keisha was amazing!! She sent lots of updates on our dog and spent really good time with her the whole 5 day trip. She was in such good hands and we would DEFINITELY use her again! Thank you!!

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Elissa G.
Sitter Profile Image: Mykala A.
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Mykala A.
from
$32
per night
4.7 out of 5 stars
8 reviews
2 repeat clients
10 years of experience
Northridge Lakes, Milwaukee, WI, 53223

Mykala did a phenomenal job watching over my Iris for this weekend. She sent pictures and videos and was very consistently available with updates and willing to stay and watch her even longer when requested. She loved her like she was hers and I came home to a VERY happy fur baby!

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Angela C.
Sitter Profile Image: Elizabeth J.
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Elizabeth J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
32 reviews
6 repeat clients
17 years of experience
Lower East Side, Milwaukee, WI, 53202

It was our second time hiring Elizabeth, another positive experience. My pooch likes his walks and we are grateful she is ok with taking him. She is great with giving updates and sending photos. Upon return the house was just as we left it.

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Carol M.
Sitter Profile Image: Kelsey H.
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Kelsey H.
from
$39
per night
5.0 out of 5 stars
80 reviews
22 repeat clients
13 years of experience
Mount Mary, Milwaukee, WI, 53222

This was the first time that we used a pet sitting service and we couldn’t have been happier. Kelsey took wonderful care of our chihuahua and elderly cat, who both can be difficult. Every day we got updates and pictures that made it possible to relax and enjoy ourselves. Kelsey was so responsive to us both before our trip and during it. If you are looking for top notch care, Kelsey is it!!

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Jill A.
Sitter Profile Image: Jackie C.
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Jackie C.
Star Sitter
from
$90
per night
5.0 out of 5 stars
140 reviews
50 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Jackie was amazing with the dogs and you could tell by how calm they were when I got home that they had a great weekend. I would recommend and will have her watch my dogs again.

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Hannah L.
Sitter Profile Image: Margaret V.
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Margaret V.
from
$50
per night
1 repeat client
8 years of experience
Whitefish Bay, WI, 53217

About: I’ve been pet sitting for many years for family and friends - young dogs, senior dogs, and cats all included! My senior dog recently passed away and I am looking forward to spending time with animals again. I recently graduated college and moved back home so I am currently working part time as a nanny as I figure out what I want to do with my life. I have lots of extra time and love to go on walks! I will care for pets in your home as I am living at home with my parents right now. I want to be respectful of whatever you/your animal needs. Depending on the day I am needed I won’t be able to stay with the animal all day but usually the longest I ever need to step out to nanny is 4-5 hours.

Sitter Profile Image: Nariya W.
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Nariya W.
from
$28
per night
5 years of experience
Garden Homes, Milwaukee, WI, 53209

About: I currently work at a dog daycare where I care for multiple dogs daily, managing different temperaments and energy levels. I’m experienced in supervising play, maintaining safety, and keeping dogs calm, comfortable, and well cared for. I’ve also owned dogs and cats in my lifetime as well! Genuinely an animal lover. I’m available for morning and evening visits on weekdays, and I have open availability on weekends. I offer flexible scheduling for walks, drop ins, and pet sitting, and I do my best to accommodate each pet’s routine. I prioritize a safe, calm, and clean environment. I’m attentive to each pet’s behavior and needs, follow routines closely, and make sure every pet feels comfortable, secure, and well cared for.

Sitter Profile Image: Katelyn A.
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Katelyn A.
Star Sitter
from
$85
per night
4.9 out of 5 stars
35 reviews
17 repeat clients
8 years of experience
Bayside, WI, 53217

As always, Katelyn works magic with Otis. She recently sat for a night when we had to go away for a wedding, and instead of being his usual skittish self when we aren't around, he relaxed and spent much of the time relaxing and cuddling. Thank you, Katelyn!

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Zack G.
Sitter Profile Image: Stephen & Wipawee D.
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Stephen & Wipawee D.
from
$95
per night
5.0 out of 5 stars
51 reviews
19 repeat clients
5 years of experience
Dineen Park, Milwaukee, WI, 53216

Stephen and Amelie provided exemplary care for our dogs, Cameron and Colby. Their kindness, coupled with their commitment to regular exercise and clear communication, put us completely at ease. They frequently updated us with photos and videos, and their prompt responses to our questions were much appreciated. In addition to taking great care of our dogs, they kept our house in perfect condition. We wholeheartedly recommend Stephen and Amelie to anyone needing reliable and loving pet sitters. We can't thank them enough for their top-notch service!

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Elliott R.
Sitter Profile Image: Anna S.
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Anna S.
from
$50
per night
5.0 out of 5 stars
31 reviews
9 repeat clients
12 years of experience
Fenway-Kenmore, Fox Point, WI, 53217

Anna was fantastic! She was great with my very energetic and large dog; she was very responsive and left my place spotless! Would definitely book again!

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Bri M.
Sitter Profile Image: Charles B.
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Charles B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
103 reviews
17 repeat clients
17 years of experience
Fox Point, WI, 53217

Charley was amazing with our pup Maisy! She was calm and happy when we got home from an 8 day trip. PLUS - our house was spotless! Fantastic job, we will use him again.

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Eliz G.
Sitter Profile Image: Tegra R.
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Tegra R.
from
$40
per night
5.0 out of 5 stars
49 reviews
16 repeat clients
30 years of experience
Milwaukee, WI, 53223

Tegra was amazing with our quirky doggo. We couldn't have asked for a better experience. Tegra provided updates and loved on our pup while we were away for almost two weeks. Upon returning home, we could tell puppers was anxiety free and our home was in excellent order. 1000% would use Tegra again.

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Bret K.
Sitter Profile Image: Lenys H.
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Lenys H.
from
$50
per night
4.9 out of 5 stars
26 reviews
11 repeat clients
12 years of experience
Kyle Canyon, Bayside, WI, 53217

Lenys was wonderful with Tucker! She was super flexible and understanding with a scheduling miscommunication on my end, I super appreciated that. She was also very responsive and kept me updated the whole time I was out

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nathan m.
Sitter Profile Image: Riley N.
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Riley N.
from
$60
per night
5.0 out of 5 stars
25 reviews
4 repeat clients
10 years of experience
Milwaukee, WI, 53212

Riley continues to be our first choice - our high maintenance and not super friendly boys love her, and we really appreciate the extra stuff she does for us like watering the plants!

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Josie H.
Sitter Profile Image: Chelsea R.
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Chelsea R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
69 reviews
31 repeat clients
20 years of experience
Cooper Park, Milwaukee, WI, 53222

Chelsea stayed at my place and took excellent care of my fur babies. She took care of all of their needs and loved them as if they were her own. I would definitely recommend Chelsea for all your pet sitting needs!

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Kenneth D.
Sitter Profile Image: Montserrat R.
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Montserrat R.
from
$50
per night
10 years of experience
Golden Valley, Wauwatosa, WI, 53222

About: I’m the designated dog walker for family and friends because I love going on walks, and dogs love coming with me! I grew up with a dog but only have two cats of my own— so I miss having that four-legged friend to go with me! I’d love to take your dog out for a walk/run, or just let them stretch their legs. Cat owners, I’m happy to give your kitties as much or as little space as they need while making sure they feel the love :) I don’t work Fridays or Saturdays, so I am free to help anytime then! Definitely looking to fill my Fridays up with some time outside, and I’d love to take your dog with me - or check in on your cat! I usually walk my parent’s and brother’s dogs (about 80 lbs each) so I know how to handle bigger dogs on leashes who tend to stray from the sidewalk. I can clean up after them, feed them, and give them all the pets! For my cats at home, I love to play with strings or catnip - and can cater to their personality as need be.

Sitter Profile Image: Alyssa B.
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Alyssa B.
from
$50
per night
5.0 out of 5 stars
9 reviews
3 repeat clients
10 years of experience
Glendale, WI, 53209

I loved Alyssa's help taking care of my dog ​​Tango. She did everything I asked her to do. She was very responsible and my dog ​​Tango loved her. During my trip, she sent me photos of Tango's walks with her in the park. 100% recommended.

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Paulo A.
Sitter Profile Image: Jlene B.
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Jlene B.
from
$50
per night
4.8 out of 5 stars
18 reviews
2 repeat clients
18 years of experience
Silver Spring, Milwaukee, WI, 53218

Jae is amazing!! She went above and beyond caring for our 17 month old Golden doodle. She sent updates and photos everyday, played ball with him, & cared for him as her own. We felt so comfortable knowing that our Blu & our home were well cared for while we were away! I highly recommend Jar to anyone needing someone to care for their pets while out of town. Jae is the BEST!!

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Kelly T.
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Havenwoods pet parents share their Rover experiences

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5.0 out of 5 stars

Katie was an amazing sitter for Remi! Before the stay, Remi had a medical condition come up, and Katie made us feel completely comfortable and confident leaving her in her care while we were away. She was attentive, caring, and kept us updated, which gave us so much peace of mind. It’s clear she genuinely loves animals and treated Remi like her own. We will absolutely be booking with her again for future stays. We — and especially Remi — love Katie!

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Yasari W.
House Sitting
5.0 out of 5 stars

Rachelle was a very nice, considerate and tidy sitter to have in my home. She let us know all was well and responded quickly to our texts. When we returned home Kikki came downstairs to greet me and went and sat near Rachelle ‘s feet. So she was definitely Kikki approved.

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Janet W.
House Sitting
5.0 out of 5 stars

Jeff did a great job taking care of Franzia and Bella. We were lucky he was available at the last minute and on a holiday. He sent pictures and was very good at communicating with us.

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Stephanie B.
House Sitting
5.0 out of 5 stars

Angelina was amazing! Very communicative before and during the trip. Also very flexible with any changes. She stayed in our home and the place was very clean when ww got back. My pets loved having her here.

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Erin L.
House Sitting
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house 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 house and 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 house sitting in Havenwoods is $50

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 house 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.

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Havenwoods on Rover as of May 2026 was about $50 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

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

If you have an active request or have booked a service with a house 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 house sitters about your booking. Typically, house sitters on Rover respond in under an hour.

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

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Havenwoods house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.