House Sitting In Oakwood Village

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Top rated Oakwood Village house sitters

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Sitter Profile Image: Louisa M.
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Louisa M.
Star Sitter
from
$60
per night
5.0 out of 5 stars
88 reviews
24 repeat clients
3 years of experience
Midvale Heights Community, Madison, WI, 53711

Louisa and Sammy did an excellent job of taking care of our 7 month old puppy! They spent time playing with her and working with her on training so she is prepared for her puppy class tomorrow! Thank you!

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Ben D.
Sitter Profile Image: Sidney M.
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Sidney M.
from
$45
per night
5.0 out of 5 stars
4 reviews
2 repeat clients
6 years of experience
Madison, WI, 53711

Sidney was amazing! She sent me pics and updates of my pup and took great care of him while I was away, I would 100% recommend her!!

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Hannah M.
Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
125 reviews
51 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

I interact with you very well, and vice versa. You are our go-to sitter of all time, now with Teddy as with Cindy. You are so tender and wise with our dogs.

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Dietrich G.
Sitter Profile Image: Nicole W.
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Nicole W.
from
$35
per night
5.0 out of 5 stars
10 reviews
4 repeat clients
5 years of experience
Madison, WI, 53705

We (and our dogs) loved having Nicole sit for us. She is an excellent communicator and took care of our pups like they were her own. I’d absolutely have her stay with our dogs again—and based on their lukewarm reaction to us coming home, I think they’d like to see her again too. 🤣

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Kim B.
Sitter Profile Image: Jacki J.
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Jacki J.
from
$40
per night
5.0 out of 5 stars
5 reviews
25 years of experience
Maple-Prairie, Madison, WI, 53719

Jacki is amazing!!!! I cannot say enough good words about her! She provides constant updates with great information about the my pets and lots of very cute photos! She made me feel super confident that my pets are well taken care of so I don’t have to worry about them. There’s always an update coming my way right when I wanted to check. She also has great attention to details and noticed that I had a perishable package delivered. She checked in with me to get my permission for next steps and I really appreciate how she approached that situation. It is an amazing experience having Jacki as a sitter. I would highly recommend her to anyone considering.

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Maggie L.
Sitter Profile Image: Katie T.
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Katie T.
from
$60
per night
5.0 out of 5 stars
42 reviews
9 repeat clients
5 years of experience
Westmorland, Madison, WI, 53711

Katie was great with my dog. You can tell she really cares about my guy and appreciates his quirkiness! I will definitely have Katie watch him again. In fact, she is watching him again next weekend!

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Micha M.
Sitter Profile Image: Kaitlyn J.
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Kaitlyn J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
25 reviews
6 repeat clients
15 years of experience
Madison, WI, 53705

Katy is so wonderful that I have to leave a second review. We’ve been going through a big transition and Katy continues to meet each of my boys where they are at. Her hyper awareness, consideration, and kindness allow me to travel and not stress about any of the boys.

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Robyn S.
Sitter Profile Image: Daseanna M.
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Daseanna M.
from
$42
per night
5.0 out of 5 stars
12 reviews
7 repeat clients
4 years of experience
Madison, WI, 53711

Daseanna was absolutely wonderful, she took care of our dog and cat for 4 days at our house and sent photo updates several times a day. It was so nice to come home to happy pets and a house exactly as we left it. She was very communicative and respectful of our space. Our dog had previously stayed with Daseanna for one night at her place, so that was a good trial run for our anxious dog.

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Katie S.
Sitter Profile Image: Raymar F.
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Raymar F.
from
$40
per night
5.0 out of 5 stars
4 reviews
10 years of experience
Madison, WI, 53705

Ray did a great job with both our dogs, but especially with our older thunder-phobic dog during a week in which many storms were predicted and a few happened. Her willingness to communicate, and her good questions made her a great choice for our dogs. And our dogs were clearly happy, comfortable and well-cared for in our absence. We would definitely book her again.

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Karen L.
Sitter Profile Image: Amy U.
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Amy U.
Star Sitter
from
$65
per night
5.0 out of 5 stars
18 reviews
3 repeat clients
30 years of experience
Regent, Madison, WI, 53726

It was so nice to know we had a reliable, kind and experienced pet sitter! Amy took care of our two dogs, cat, and gecko and sent great pictures during her stay. We were lucky to have her!

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Beth R.
Sitter Profile Image: Julia M.
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Julia M.
from
$60
per night
5.0 out of 5 stars
3 reviews
1 repeat client
8 years of experience
University Apartments, Madison, WI, 53705

Julia was so pleasant and professional! She asked great questions to prepare for her time with Princeton, and you could tell she really cared - Princeton warmed up to her immediately :) I highly recommend Julia and would definitely hire her again!

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Aisha B.
Sitter Profile Image: Nate G.
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Nate G.
Star Sitter
from
$60
per night
5.0 out of 5 stars
216 reviews
75 repeat clients
15 years of experience
Capitol, Madison, WI, 53703

Nate house sat for our 2 dogs and 1 cat while we were away for a week. He was really wonderful - sent regular photos and updates, took the dogs to the dog park several times, and left the house in great shape. We absolutely recommend him and will definitely rebook with him in the future!

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Jackie B.
Sitter Profile Image: kylie l.
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kylie l.
from
$58
per night
5.0 out of 5 stars
87 reviews
26 repeat clients
1 year of experience
Madison, WI, 53719

Kylie was very communicative and really helped us out with a last minute booking on a holiday. She was punctual, sent great updates, and instantly put our senior dog at ease. We were nervous using Rover for the 1st time, but we would highly recommend her services and will absolutely call her again the next time we need someone.

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Sean P.
Sitter Profile Image: Briana L.
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Briana L.
from
$40
per night
4.9 out of 5 stars
28 reviews
8 repeat clients
10 years of experience
Madison, WI, 53711

Thanks again! Briana stepped in at the last minute when we needed to leave town for a funeral. She took good care of Frankie. We’re grateful.

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Zayna T.
Sitter Profile Image: Anna H.
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Anna H.
from
$75
per night
5.0 out of 5 stars
34 reviews
9 repeat clients
7 years of experience
Middleton, WI, 53562

Anna is a fantastic dog sitter who goes above and beyond for her clients. Before having Anna sit for us for the first time, she made the effort to come by and visit our pup. This was so important for there reasons: 1. Gave our pup the opportunity to become friends with Anna; 2. Allowed our dog to feel comfortable in her home with this new friend; and 3. Gave us the opportunity to show Anna where the important things for our dog are in the house. Anna is prompt and communicative. She gave us photo and text updates throughout her visit. She is clearly a kind and respectful person and dogs seem to love her immediately. I will most definitely reach out to Anna again for any dog sitting/house sitting occasions.

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Lesli M.
Sitter Profile Image: Natalie M.
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Natalie M.
from
$50
per night
5.0 out of 5 stars
3 reviews
6 years of experience
Regent, Madison, WI, 53726

Natalie was wonderful! This was our first time having her sit for us and she was very punctual, communicative, and respectful. We came home to happy girls. Would love to have her house sit for us again in the future ☺️

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Ariel N.
Sitter Profile Image: Megan B.
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Megan B.
from
$65
per night
5.0 out of 5 stars
10 reviews
8 years of experience
Madison, WI, 53719

Megan took excellent care of my pups while I was away. One of my dogs became ill right before I left. She kept me updated on his condition and her concerns, as well as handling my sassy girl! I will definitely use her services again! My pups loved her.

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Leah H.
Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$82
per night
5.0 out of 5 stars
120 reviews
42 repeat clients
10 years of experience
Madison, WI, 53719

Ann (again) did a great job watching our dog and house while we were on an 8 day vacation!! She sent us plenty of pictures along the way and we have high confidence in her to do it again for us next time we need her.

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Gregory B.
Sitter Profile Image: Maureen H.
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Maureen H.
Star Sitter
from
$65
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
20 years of experience
Madison, WI, 53705

Maureen left our pup and house better than when we headed off for vacation. Great communication — responsive, but also gave us space to focus on our trip. I recommend her.

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Raphaella F.
Sitter Profile Image: Michelle S.
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Michelle S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
135 reviews
55 repeat clients
4 years of experience
Madison, WI, 53719

Michelle was great with our 2 Goldens!! She was truly concerned with their needs and routine!! Asked questions and kept us informed of their well-being while we were away!! We will definitely be asking her to come back! ??

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Julie L.
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Oakwood Village pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Allegra was great with our dog! Very responsive, genuine care, left our dog happy and home clean and tidy. Can’t wait to have her back!

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Abbey L.
House Sitting
5.0 out of 5 stars

Emma was a great sitter! We will definitely use her again! She sent lots of updates and our guy was very happy the whole time. She also kept our house very clean.

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Laurel S.
House Sitting
5.0 out of 5 stars

Sophie is the Best! She was able to come on short notice to dog-sit while we were out for a long evening. She was very responsive to our texts with directions and timing. Our spirited 15 month old doodle immediately connected with her. Although we didn't expect her to, Sophie took him out for a walk to work off some of his energy. Afterward, she sent us a photo of him relaxed and content. Five stars for Sophie!

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Maree E.
House Sitting
5.0 out of 5 stars

Ray did a great job with both our dogs, but especially with our older thunder-phobic dog during a week in which many storms were predicted and a few happened. Her willingness to communicate, and her good questions made her a great choice for our dogs. And our dogs were clearly happy, comfortable and well-cared for in our absence. We would definitely book her again.

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Karen L.
House Sitting
5.0 out of 5 stars

Josie was awesome taking care of our sweet little Brella and she even watered plants and changed sheets for us! We will definitely be booking her again in the future!!!

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Kelly R.
House Sitting
5.0 out of 5 stars

Super communication and easy to work with. Kept us updated through text messages and pictures. Would love to work with her again and highly recommend!

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Ben B.
House Sitting
5.0 out of 5 stars

Ann took great care of our dogs over a long weekend, including our elderly dog. Would definitely hire again!

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Stacey B.
House Sitting
5.0 out of 5 stars

Jacki is amazing!!!! I cannot say enough good words about her! She provides constant updates with great information about the my pets and lots of very cute photos! She made me feel super confident that my pets are well taken care of so I don’t have to worry about them. There’s always an update coming my way right when I wanted to check. She also has great attention to details and noticed that I had a perishable package delivered. She checked in with me to get my permission for next steps and I really appreciate how she approached that situation. It is an amazing experience having Jacki as a sitter. I would highly recommend her to anyone considering.

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Maggie L.
House Sitting
5.0 out of 5 stars

Annalesse did so great with our 2 cats and 2 dogs. She is reliable and came on time. An expert at following instructions; everyone got their supplements with meals and treats daily. She sent us picture updates every day & was able to medicate and take time to let our shy/finicky cat eat as well which meant a lot. 10/10 would book with her again!

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Jasmyne S.
House Sitting
5.0 out of 5 stars

Ruby was great! We got back a tired, happy pup and a house as clean as we left it. We’ll definitely hire her again when we need a house sitter.

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Scott K.
House Sitting
5.0 out of 5 stars

Great job with our two dogs. Spent lots of time at our house over a long weekend. Sidney was flexible with our schedule (even when I scheduled for the wrong weekend). 10/10 would book again.

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Duncan P.
House Sitting
5.0 out of 5 stars

Had Sophia chill with our velcro kiddos at our hotel while we went to dinner. She updated us and was patient with their anxiety about us leaving. Will be booking with her again next time we are in town.

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Kaylyn R.
House Sitting
5.0 out of 5 stars

We couldn't have asked for a better experience with our recent Rover sitter! She was absolutely fantastic while watching our dog, Scooby, for the week. From the start, she excelled at being adaptable, seamlessly adjusting to Scooby’s routine and needs without any issues. We also truly appreciated the frequent, reassuring text messages and photos she sent throughout the week, which gave us total peace of mind while we were away. Most importantly, she provided Scooby with an incredible amount of love, affection, and exercise—he was a very happy pup when we returned. We highly recommend her services to anyone looking for a caring and reliable sitter!

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Zachary M.
House Sitting
5.0 out of 5 stars

Thanks to Helen for taking wonderful care of Keon while we were gone! Helen did a great job communicating, shared tons of photos of Keon, and it was obvious that Keon was feeling happy and relaxed.

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Brandon F.
House Sitting
5.0 out of 5 stars

Hannah met our Ziggy on short notice and provided excellent care of him and our home while we were away. We highly recommend Hannah and hope she will house sit for us in the future.😁

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John H.
House Sitting
5.0 out of 5 stars

Corinne was wonderful - great updates, pictures, and came home to a happy pup. Love that she was with him during the work day too.

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Kelsey T.
House Sitting
5.0 out of 5 stars

Our home & animals were well cared for and the place was left in better shape than we left it. Daily pics and happy animals. We’re sad Kaitlyn isn’t staying in the area for long because we’d definitely book her again.

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Forrest D.
House Sitting
5.0 out of 5 stars

Isabel did a great job with our somewhat challenging dog. She was positive when giving us updates and sent lots of pics while we were gone. We would definitely use her again.

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Jenifer R.
House Sitting
5.0 out of 5 stars

Megan took excellent care of my pups while I was away. One of my dogs became ill right before I left. She kept me updated on his condition and her concerns, as well as handling my sassy girl! I will definitely use her services again! My pups loved her.

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Leah H.
House Sitting
5.0 out of 5 stars

Jesse was great while she stayed overnight with my cat while I was on vacation. She sent pictures and videos, kept my place clean, and washed the sheets when she left. Thanks, Jesse!

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Chelsea B.
House Sitting
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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!

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

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 Oakwood Village.

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. Oakwood Village 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.