House Sitting Midtown

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

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Midtown, 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.

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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 with our 10 year old dog! This was our first time using a sitter and it went so smoothly. We got tons of pictures updates and Keisha left the house in tip top shape. I highly recommend working with her! Best of the best!

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Riely J.
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 did a fantastic job watching Tuukka while we were traveling to India for a wedding. She sent daily updates with lots of photos and we knew our pup was well take care of when we were away!

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Anna C.
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: Jasmine R.
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Jasmine R.
from
$35
per night
5.0 out of 5 stars
85 reviews
8 repeat clients
5 years of experience
Murray Hill, Milwaukee, WI, 53211

Jasmine was so great with our cat and dog. She was thoughtful and sent lots of updates and photos. She left our place spotless and was a wonderful guest and pet sitter!

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Cassandra D.
Sitter Profile Image: Jessica Z.
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Jessica Z.
Star Sitter
from
$64
per night
5.0 out of 5 stars
222 reviews
64 repeat clients
30 years of experience
Lower East Side, Milwaukee, WI, 53202

Our family had recently experienced a loss of our other pet. It was a tough time for travel but Jessica supported our other pet while we were away. She kept us informed and made the world of difference being away during such a difficult time.

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

Ashley was So responsive and Wonderful with my boys! Thankful she was able to watch them in their house!! Will definitely book again if she is willing to watch them!!

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Dena K.
Sitter Profile Image: Jamila M.
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Jamila M.
from
$65
per night
4.9 out of 5 stars
98 reviews
29 repeat clients
27 years of experience
Washington Heights, milwaukee, WI, 53208

Jamila was awesome. Our pets were very well taken care of and the house was clean. Jamila sent tons of pics throughout the duration of our trip. We will absolutely use her again!

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Amanda G.
Sitter Profile Image: Lily S.
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Lily S.
from
$125
per night
5.0 out of 5 stars
68 reviews
18 repeat clients
25 years of experience
Milwaukee, WI, 53212

Lily was a blessing for our family!! This was the very 1st time we have used rover. We ended up adopting a dog 2 weeks before a preplanned vacation. Lily was so patient and understanding with us as we had very little information about our new family member when we booked with her. We were able to leave her with notes on training our new dog had and we gave her the ability to address and immediate concerns with positive training as she saw fit to help her week go smoothly. Lily was able to help bridge the gap with consistent training while we were gone to ensure we didn’t lose precious training time. She was also able to pivot and help address any behavioral issues or quirks that arose that we were unaware of. She even sent us videos and a great description of how she addressed them. She sent updates everyday and didn’t hesitate to reach out with questions. She put away our grocery order before we arrived and made sure to have the house cleaned up and even washed the towels I left out for her. We definitely will be booking with her again.

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Sarah R.
Sitter Profile Image: Riley L.
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Riley L.
Star Sitter
from
$43
per night
5.0 out of 5 stars
9 reviews
5 repeat clients
3 years of experience
Avenues West, Milwaukee, WI, 53233

I couldn’t have asked for a better dog sitter! She communicated wonderfully from the start and even met with me ahead of time to get to know my dog’s routine and feel comfortable with the space. While I was away, she sent daily updates with pictures of Stewart completely abandoning dad to cuddle with his new friend! 😂 I wholeheartedly recommend her to anyone looking for a trustworthy and caring sitter.

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

Jackie took such great care of Daisy for me while I was out of town for several days. I didn't worry about a thing while I was gone, she sent texts with photos and updates. Everything was fantastic and I will definitely call her again!

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Lisa K.
Sitter Profile Image: Julianna W.
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Julianna W.
from
$44
per night
5.0 out of 5 stars
17 reviews
2 repeat clients
30 years of experience
Milwaukee, WI, 53204

Julianna (and her partner Ed) were amazing with our anxious pup Winnie. She was communicative beforehand, organizing a meet and greet and asking great questions. She wanted to make sure Winnie was comfortable as possible, allowing us to walk Winnie together before entering our home. During the stay, she sent regular updates with photos. Asked some clarifying questions about our pup’s favorite activities, and ultimately let us relax and enjoy our vacation. She administered our pups meds and helped us have peace of mind. Would absolutely recommend Julianna and Ed!!!

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Jenna P.
Sitter Profile Image: Murphy N.
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Murphy N.
from
$45
per night
4.9 out of 5 stars
15 reviews
4 repeat clients
25 years of experience
Milwaukee, WI, 53208

Murphy was great with my animals. She was attentive, responsive and I felt comfortable leaving for the weekend knowing my animals were in good hands!

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

Laurie is a fantastic dog sitter and house-guest! Amazing with our dogs and very communicative. We’ve had Laurie stay with our dogs a few times now and will definitely have her again, thanks so much!!

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CJ K.
Sitter Profile Image: Celia K.
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Celia K.
from
$40
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
3 years of experience
Lower East Side, Milwaukee, WI, 53202

Celia was great with house sitting and taking care of my elderly dog and two cats!

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Patti W.
Sitter Profile Image: Margaret D.
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Margaret D.
from
$45
per night
4.9 out of 5 stars
9 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: 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

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: Flor F.
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Flor F.
Star Sitter
from
$75
per night
5.0 out of 5 stars
12 reviews
4 repeat clients
15 years of experience
Brewer's Hill, Milwaukee, WI, 53212

Flor was an EXCELLENT sitter to our dog Toast! We left on a trip for 5 days and she took amazing care of not only our dog, but our house as well! She was a great communicator and sent a ton of pictures! She also was great at giving our dog his medicine. We would absolutely book Flor again!

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Santiago M.
Sitter Profile Image: Carrianne L.
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Carrianne L.
Star Sitter
from
$85
per night
5.0 out of 5 stars
214 reviews
53 repeat clients
20 years of experience
Milwaukee, WI, 53209

Carrianne did a wonderful job caring for my dog when I went out of town for a weekend. Penny takes some time to warm up to people and Carrianne was very patient and understanding throughout that process. She followed the care instructions I left and sent daily updates with important information (e.g., walks, eating habits, general behavior) with photos. She also stayed overnight in my apartment and left everything really tidy. I couldn't be happier with the care Penny received and will definitely rebook for future travel plans!

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Angela M.
Sitter Profile Image: Rebecca M.
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Rebecca M.
Star Sitter
from
$45
per night
5.0 out of 5 stars
13 reviews
8 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
4.9 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.
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The median cost per night for house sitting in Midtown is $50

Pet parents share their Rover experiences - Midtown

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5.0 out of 5 stars

Evita was absolutely amazing with both of our dogs. She took great care of them and even pivoted during unforeseen circumstances to ensure our dogs stayed loved on and safe while we were gone. We will definitely use her again in the future!

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Frances T.
House Sitting
5.0 out of 5 stars

Laurie was AMAZING! She kept us updated on how our girls (Luna & Fig) were doing during our trip, followed their routine, and left our home in pristine condition! We would book Laurie again and again. Your dogs will be in great hands.

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Hannah M.
House Sitting
5.0 out of 5 stars

Our dog Rosie is a bit of a weirdo and Elizabeth made our trip stress free for Rosie and my family. Will book with Elizabeth again in the future!

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Paul K.
House Sitting
5.0 out of 5 stars

Jessica is 100% reliable and cares for my dogs with love and attentiveness. I felt completely confident in leaving for five days with my dogs in her care. She sent me updates and pictures to put me at ease. When I returned home the dogs were happy and that makes me happy. I cannot recommend Jessica highly enough.

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Amy N.
House Sitting
5.0 out of 5 stars

Wish we could leave more than 5 stars! Alex was an amazing Rover find. She came to us and stayed at our house, keeping our dog comfortable and house safe and clean while we were away. She was extremely responsive and communication was so great, we got tons of pics and she even let us know if she’d be leaving for short stretches and when she was back (which was above and beyond!). We were all over the place with our plans (travel with kids, IYKYK)- possibly leaving later than planned and ended up coming back earlier than planned, and she was super flexible and pivoted with everything. Our dog LOVED her and they cuddled and went for plenty of walks. We were so appreciative to find someone like her and it made our time away so much easier, will definitely book again! Thanks Alex!

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Abby G.
House Sitting
5.0 out of 5 stars

Ivy is amazing with our dogs who are sometimes quite challenging! We trust her to handle any situation that comes up.

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Brent W.
House Sitting
5.0 out of 5 stars

Keisha is an absolute wonder sitter! Our little pup was very anxious about us leaving and Keisha was so very kind, patient and loving. She took extra special care to help our pup feel safe, loved and secure. We will always ask Keisha to come watch our pup anytime we leave or even just to hang out for an afternoon. Trust Keisha to be the best care giver!

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Jamelyn H.
House Sitting
5.0 out of 5 stars

I was out of the country and needed a reliable person to help care for Olive during the daytime hours as my partner works long hours. Becca took the best care of Olive and she's so incredibly reliable!! She was always on time, took Olive on her walks, played with her, fed her and I didn't have to worry about anything. She also sent pics and videos of Olive which made being away from her a little bit easier. I can also tell in all of the pictures that Olive loves Becca and there's nothing better than knowing your pup is happy while you're out of town! Highly recommend Becca!!!

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Aleka C.
House Sitting
5.0 out of 5 stars

Talor recently stayed at my home and watched my French bulldog while I was on a work trip. She was amazing and sent the cutest pictures and updates on how things were going back home. I would definitely recommend Talor for your housesitting needs. Hazel cannot wait for her to come over again. :)

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Lorna D.
House Sitting
5.0 out of 5 stars

Ashley took such great care of our cats while we were away! She sent us pictures and an update everyday. She even printed out some of the photos and left them for us which was so sweet and unexpected! We will definitely be booking with Ashley again in the future!

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Janelle N.
House Sitting
5.0 out of 5 stars

Mikalanne took amazing care of my two dogs and was amazing with her communication. Would definitely book again

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Hannah L.
House Sitting
5.0 out of 5 stars

Great service and very well communicating with me throughout the day. The pup most definitely had fun and enjoyed her time with Kyla

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Jules T.
House Sitting
5.0 out of 5 stars

Cindy is amazing. She takes great care of Bear when we are away. Everyday she sends a picture so we know how our baby is doing.

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Craig R.
House Sitting
5.0 out of 5 stars

Tabitha was fantastic! She made the process seamless and took excellent care of Newt. I will certainly request her services again!

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Erin L.
House Sitting
5.0 out of 5 stars

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.
House Sitting
5.0 out of 5 stars

Marley does such a wonderful job and if she ever decides to change a career, she could make a meant as an animal photographer!

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Eric M.
House Sitting
5.0 out of 5 stars

The best house/cat sitter! Our cat was very happy, and she left our house so nice and clean. Amazing.

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Nancy & Daniel N.
House Sitting
5.0 out of 5 stars

Nina stayed with our two dogs for a night. We came home to two happy and well cared for pups and a clean house. I would definitely recommend her!

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Sarah M.
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

The best Rover sitter I have had. Communicative, clean, great with Gertie, and an all around kind, responsible, and trustworthy person. Thank you Acacia! It means the world to me 🥰

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Naomi S.
House Sitting
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