House Sitting Oakwood Village

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

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Over 40
pet parents in Oakwood Village have booked house sitting

Oakwood Village, 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: Allegra R.
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Allegra R.
Star Sitter
from
$65
per night
5.0 out of 5 stars
133 reviews
53 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

Allegra was AMAZING at pet sitting our dog and cat while we were gone for 5 nights. She sent updates and phots as often and was great at communicating. We returned to happy and healthy pets. I felt very confident leaving my somewhat high needs cat with her. 10/10 would recommend!

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

Louisa was kind, responsive and took extra care to come to our hotel to watch our dog on our wedding day. We could not recommend her more highly 💜

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Angie A.
Sitter Profile Image: Jacki J.
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Jacki J.
from
$40
per night
5.0 out of 5 stars
7 reviews
1 repeat client
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: Anna H.
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Anna H.
from
$75
per night
5.0 out of 5 stars
35 reviews
9 repeat clients
7 years of experience
Middleton, WI, 53562

Smooth meet-up & sitting experience, and great level of communication! She was reliable and trustworthy in taking care of our pups and the house. Would definitely work with you again and looking forward to it!

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Hanna E.
Sitter Profile Image: Amy U.
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Amy U.
Star Sitter
from
$65
per night
5.0 out of 5 stars
19 reviews
5 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: Amy F.
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Amy F.
from
$40
per night
5.0 out of 5 stars
13 reviews
1 repeat client
30 years of experience
Meadowood, Madison, WI, 53711

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.
Sitter Profile Image: Tucker S.
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Tucker S.
from
$42
per night
5.0 out of 5 stars
7 reviews
10 years of experience
Orchard Ridge Community, Madison, WI, 53711

Tucker was amazing — he took great care of my fur baby and provided pics regularly AND he was gracious and unflappable in the face of some unforeseen challenges. Flexible, great communicator, and left the house cleaner than he found it. Great with following directions and proactively taking care of all the things — he even noticed the light on the automatic feeder and refilled it before I even messaged him about the notification I’d received. Perhaps best of all, he saw AJ for the loving, playful kitty that he is—so I knew AJ was feeling comfortable and that he was in good, kind hands. Would definitely recommend to others and would be glad to have his help again!

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Sarah G.
Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$82
per night
5.0 out of 5 stars
123 reviews
46 repeat clients
10 years of experience
Madison, WI, 53719

Ann did a fantastic job dog sitting our very high energy and dog-reactive pup in our home for five days! She sent so many pictures and we could tell our pup was content/happy and so well taken care of. Ann also reached out to ask clarifying questions when needed and was very responsive. I highly recommend Ann!

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Claire G.
Sitter Profile Image: Justine D.
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Justine D.
from
$43
per night
5.0 out of 5 stars
9 reviews
2 repeat clients
10 years of experience
Madison, WI, 53711

Justine was so great with my pups! One of my dogs has special needs and the other is anxious and shy around new people, and Justine won them both over and made sure they were well cared for while I was away. I plan on being a repeat customer!

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Erick S.
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

Excellent, kind, considerate dog sitter. Briana sent us pictures daily of our dog, she walked him extensively and also helped to work on some training with him. Briana knew how to handle our dog who has some reactivity and anxiety. She was respectful of our home, prompt and great with communication and care !

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Amy K.
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

Great sitter - of house and dog. Friendly and kind; Chico was happy and healthy when we returned and my house was exactly as I left it. I would recommend Megan to anyone and hope to reunite Megan and Chico again!

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Alex D.
Sitter Profile Image: Andrea P.
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Andrea P.
Star Sitter
from
$47
per night
5.0 out of 5 stars
16 reviews
4 repeat clients
1 year of experience
Sauk Creek, Madison, WI, 53717

About: I love animals and truly enjoy taking care of dogs and cats. I make sure they’re well-fed, walked, and have plenty of playtime, giving them lots of love and attention. I treat every pet as part of my family, making sure they feel comfortable, safe, and happy while under my care. I’m available to care for dogs and cats on weekends. I can provide feeding, walks, and loving companionship with care and responsibility. My available hours are from Friday at 6:00 p.m. until Sunday at 9:00 p.m. I live in an apartment with my two daughters, who are very sweet and loving with animals. We have a spacious and comfortable area where your pet can feel relaxed and happy. There are plenty of natural areas nearby where I can take your dog for walks to enjoy the outdoors and nature. I’m available on weekends, from Friday at 6:00 p.m. to Sunday at 9:00 p.m., to provide loving, responsible, and personalized care for your pet.

Sitter Profile Image: Brenda S.
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Brenda S.
from
$40
per night
4.9 out of 5 stars
33 reviews
11 repeat clients
9 years of experience
Waunakee, WI, 53597

Brenda was amazing!!! She took great care of our house and our cats. Sent pictures and updates, and left the house cleaner than she found it. 😁 We needed last minute help, and she was so flexible and accommodating! I would not hesitate to hire her again!

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Alicia S.
Sitter Profile Image: Julia M.
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Julia M.
from
$60
per night
5.0 out of 5 stars
3 reviews
2 repeat clients
8 years of experience
University Apartments, Madison, WI, 53705

Julia was great in every way possible. Very responsive, flexible and communicative. Chip and Beau loved her. She sent many pictures of them enjoying her visit.

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Adam D.
Sitter Profile Image: Annalesse B.
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Annalesse B.
from
$35
per night
5.0 out of 5 stars
4 reviews
5 years of experience
Madison, WI, 53719

Annalesse did a great job taking care of my dog while I was out of town at a wedding. It was my first time leaving my dog with stranger and I was nervous but annalesse did a great job of ensuring Bandit was well cared for! I received plenty of pictures and my girl had a great time!

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Jett M.
Sitter Profile Image: Hanna P.
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Hanna P.
from
$40
per night
5.0 out of 5 stars
2 reviews
1 repeat client
6 years of experience
Madison, WI, 53719

Hanna communicated regularly and left the space as she found it.

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Wade U.
Sitter Profile Image: Madalyn M.
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Madalyn M.
from
$50
per night
5 years of experience
Middleton, WI, 53562

About: I enjoy caring for energetic dogs and love keeping them active through games like fetch and tug-of-war. I am a dependable and attentive pet sitter who is comfortable administering medications and providing any additional care your pet may need. I strive to build trust with every pet I care for, and I’m proud that many of my clients have chosen me as their recurring pet sitter. My goal is to ensure every pet feels safe, comfortable, and well cared for while their owners are away. I am currently available through the beginning of August and am happy to discuss scheduling to find a time that works for you. Please feel free to message me with any questions about my availability. I typically provide care in your home to help keep your pets comfortable in their familiar environment. I can also welcome your furry family members into my home for stays of up to two days, if needed. While I do not have a fenced yard, I make sure every dog gets plenty of exercise through long walks and trips to local parks. If your dog enjoys socializing with other dogs and you approve, I’d be happy to take them to a dog park for additional play and enrichment. Your pet’s safety is always my top priority. I carefully follow your care instructions and make sure every dog in my care receives plenty of love, attention, exercise, and responsible supervision. My goal is for every pet to feel safe, happy, and well cared for while you’re away.

Sitter Profile Image: Evelin C.
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Evelin C.
from
$42
per night
5.0 out of 5 stars
15 reviews
4 repeat clients
3 years of experience
Verona, WI, 53593

Great experience! Our sitter took wonderful care of our two Labrador puppies—playing with them in the yard, giving them a special treat, and keeping them happy and content. We loved receiving photos of them playing and resting peacefully. Highly recommend!

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Ben D.
Sitter Profile Image: Jennifer G.
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Jennifer G.
from
$41
per night
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Madison, WI, 53705

Jennifer did a fantastic job taking care of Indy. Indy needed extra attention with his medications and health situation. Jennifer was very thoughtful and caring in giving attention to Indy to make him feel comfortable. We sincerely appreciate the care given by Jennifer for Indy.

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Vinoth G.
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 took excellent care of our dogs and our home. We felt very comfortable with her and the dogs took to her right away. She took them for walks and sent pictures too! Thank you Katie!

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Dawn S.
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The median cost per night for house sitting in Oakwood Village is $50

Pet parents share their Rover experiences - Oakwood Village

1 / 1
5.0 out of 5 stars

Allegra gave us so many updates and photos while we were away. She made our pets be so safe and comfortable while we were away on vacation.

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Holly F.
House Sitting
5.0 out of 5 stars

Pets always have a great time with Ann! She’s super communicative and send lots of photos! Never have to worry when she watches out pets!

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Brianne M.
House Sitting
5.0 out of 5 stars

Super awesome and lovely to interact with! Tube loved her and we can’t wait to book with her again 💕

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Jill T.
House Sitting
5.0 out of 5 stars

Isabel was wonderful! She sent a lot of great pictures to keep us up to date on how the cats were doing. She also took wonderful care of the house. Don't hesitate to book Isabel!

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Amy W.
House Sitting
5.0 out of 5 stars

Maya did a wonderful job with our very senior dog. She took care of all his needs while we’re gone and even did a nail trim. Communication was great. Looking forward to having her help us out again.

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Karen R.
House Sitting
5.0 out of 5 stars

Joel was excellent with our dogs and even made them a pillow fort when they were scared of the fireworks. We will definitely book with him again!

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Travis T.
House Sitting
5.0 out of 5 stars

Annalesse did a great job taking care of my dog while I was out of town at a wedding. It was my first time leaving my dog with stranger and I was nervous but annalesse did a great job of ensuring Bandit was well cared for! I received plenty of pictures and my girl had a great time!

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Jett M.
House Sitting
5.0 out of 5 stars

Tucker did a great job watching Zoe & Mocha - regularly sent photos, provided updates from each visit, and was very communicative in providing care.

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Eric L.
House Sitting
5.0 out of 5 stars

Anna is the best! She’s a great communicator and our cats love her. That’s why she’s been our go-to sitter for several years now!

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Claire W.
House Sitting
5.0 out of 5 stars

My dogs both were very happy in Jesse's care. She communicates frequently with pictures. Would use again.

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Brenda W.
House Sitting
5.0 out of 5 stars

Helen stayed at our home and took wonderful care of our pets. She was a great communicator before, during and after her stay. We received regular updates and photos of our pets, which was really comforting. Helen was conscientious and careful about following the instructions we provided. She left our house and animals in great condition! We'd love to have her back to sit again!

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Susie M.
House Sitting
5.0 out of 5 stars

Jolie goes above and beyond to make sure my pups are doing well while I'm away. Especially appreciate her navigating July 4 with them!

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Erick S.
House Sitting
5.0 out of 5 stars

Jacki provided great care to our English bulldog. Provided regular updates and pictures and was proactive in her communication. We’d love to have her again!

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Allison B.
House Sitting
5.0 out of 5 stars

Alliyah did a great job with our furbabies while we were on a 2 week vacation. We appreciate returning to our home and knowing they were cared for. Thank you!

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Heather R.
House Sitting
5.0 out of 5 stars

We are so glad to have met Sophie! In addition to being a strong communicator, Sophie has a genuine desire to ensure your fur baby is well taken care of. She asks great questions, is detail-oriented, and is great about sending updates while you're away. I highly recommend Sophie and would definitely book her again!

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Aisha B.
House Sitting
5.0 out of 5 stars

Louisa did a wonderful job taking care of our two Labrador pups. She let them play in the yard, took them for a walk, gave them their evening treats, and shared some great photos for us to enjoy. It was another excellent experience, and we appreciated the care and attention she gave our dogs. We would be happy to book with Louisa again!

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Ben D.
House Sitting
5.0 out of 5 stars

Thank you for taking great care of JJ! He was so happy while his regular humans were away. We appreciate the professionalism and detail that you put into your work. Take care and see you next time!

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Katie B.
House Sitting
5.0 out of 5 stars

Aislinn was absolutely wonderful!!! She is great with communication and took the time going above and beyond to care for my pup! I’d highly recommend and hope she can help out in the future! Even my neighbor commented on how much time she spent throughout the weekend playing with Henry in the yard and making sure he was tired out before leaving :-) Thank you!

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Brenna D.
House Sitting
5.0 out of 5 stars

Amy took great care of our pups..she stayed with them and left out house as clean as when she got there. She gave us periodic reports and pictures and was willing to be flexible when we thought our flight would be canceled.

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Rory Hemp B.
House Sitting
5.0 out of 5 stars

Taylor just finished pet and housesitting for us and she is wonderful! Responsive, easy to work with, and great with our pups (one of whom is a super needy baby). So glad we found her! Thank you, Taylor!

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Emily L.
House Sitting
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Sitters in Oakwood Village average 4
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