House Sitting in Oakwood Village, Madison, WI

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Top rated Oakwood Village house sitters

1 / 1
Sitter Profile Image: Katie T.
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Katie T.
Star Sitter
from
$60
per night
5 out of 4.9 stars
25 reviews
3 repeat clients
5 years of experience
Marquette, Madison, WI, 53703

Katie was wonderful with my dog and a great communicator. She sent lots of updates and I could tell she was taking great care of him. She went above and beyond! I would definitely utilize her again.

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Susana S.
Sitter Profile Image: Annie J.
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Annie J.
Star Sitter
from
$55
per night
5 out of 5.0 stars
49 reviews
19 repeat clients
6 years of experience
Midvale Heights Community, Madison, WI, 53711

Annie took great care of our dog and guinea pig! She gave me frequent updates and was very attentive to our anxious dog’s needs. Thank you!!!

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Genevieve H.
Sitter Profile Image: Julie A.
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Julie A.
Star Sitter
from
$45
per night
5 out of 5.0 stars
15 reviews
2 repeat clients
16 years of experience
Verona, WI, 53593

Julie is an amazing dog sitter. Best we have had through Rover yet. She watched our two dogs, one of which is a senior dog with health issues and requires medication. I couldn't recommend her more highly!

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

Louisa and her daughter did a great job of communicating with me, though their stay was short. My cat loved the attention they gave her. Her coat was beautifully soft and clean from all the brushing. I would definitely schedule them again when I am out of town.

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Judy B.
Sitter Profile Image: Kaitlyn B.
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Kaitlyn B.
Star Sitter
from
$40
per night
5 out of 5.0 stars
16 reviews
5 repeat clients
20 years of experience
Madison, WI, 53719

Kaitlyn has been so patient with my anxious dog! I feel so good leaving him in her care because I know he'll be well taken care of and allowed to adjust at his own pace. She always leaves my home spotless and communicates promptly when I reach out. Highly recommend!

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Sarah S.
Sitter Profile Image: Erika K.
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Erika K.
from
$45
per night
5 out of 5.0 stars
10 reviews
12 years of experience
Middleton, WI, 53562

Erika was great. She is a delightful person who gleefully mixed with my two furry sweet beasts. When I returned home, everything was in fine shape and the dogs were very happy. I will surely contact her in the future when I travel.

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Timothy H.
Sitter Profile Image: Hannah I.
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Hannah I.
Star Sitter
from
$50
per night
5 out of 5.0 stars
97 reviews
32 repeat clients
5 years of experience
Wexford, Madison, WI, 53717

This was our first time leaving our dog “Gracie” with a sitter. Hannah arrived on time and it was a very early morning arrival!! Gracie is an anxious dog around strangers, but Hannah knew instinctively to let Gracie approach her and get comfortable. We were gone for 12 hours and came home to a happy well cared for puppy. Hannah sent pictures and updated us throughout the day. We felt very comfortable knowing she was in good hands and will definitely call on Hannah again. Thank you, Hannah!!

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Kevin & Mary V.
Sitter Profile Image: McKenna B.
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McKenna B.
from
$40
per night
5 out of 5.0 stars
5 reviews
20 years of experience
Madison, WI, 53711

McKenna, was great. She sent pictures of our dogs. They seemed very happy. Our house was in the exact same shape when we got home as we left it. Would definitely recommend.

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Ashley B.
Sitter Profile Image: Ann A.
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Ann A.
Star Sitter
from
$75
per night
5 out of 5.0 stars
54 reviews
19 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: Sidney R.
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Sidney R.
Star Sitter
from
$50
per night
5 out of 4.9 stars
59 reviews
19 repeat clients
20 years of experience
Middleton, WI, 53562

Sidney took great care of my house and dogs while I was away for a few days. I will definitely work with Sidney again if I get the opportunity to!

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Cale H.
Sitter Profile Image: Jolie Zevallos
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Jolie Zevallos
Star Sitter
from
$23
per night
5 out of 5.0 stars
6 reviews
4 repeat clients
8 years of experience
Madison, WI, 53715

Jolie is great. Good communication and goes above and beyond to spend quality time with our two large dogs. Very happy, will book again if possible.

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Rachel H.
Sitter Profile Image: Sophie H.
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Sophie H.
from
$60
per night
5 out of 5.0 stars
55 reviews
16 repeat clients
3 years of experience
Regent, Madison, WI, 53726

Sophie jumped in and helped us so last minute & she was great! Gave our dog time to warm up, sent pics and gave her lots of love. Thanks Sophie!

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Abbey L.
Sitter Profile Image: Christina H.
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Christina H.
from
$70
per night
5 out of 4.9 stars
17 reviews
1 repeat client
30 years of experience
Madison, WI, 53719

Christina was very attentive to Kya and sent lots of updates and pictures.

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Liz M.
Sitter Profile Image: Anna H.
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Anna H.
from
$65
per night
5 out of 5.0 stars
27 reviews
7 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: Robert N.
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Robert N.
Star Sitter
from
$60
per night
5 out of 5.0 stars
116 reviews
37 repeat clients
20 years of experience
Orchard Ridge Community, Madison, WI, 53711

Robert did an excellent job taking care of my high energy dog and 2 cats. He communicated very well and let me know what they were up to during the days I was away. He left my house just as clean as when I left it.

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Christina M.
Sitter Profile Image: Ashley E.
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Ashley E.
Star Sitter
from
$80
per night
5 out of 5.0 stars
480 reviews
121 repeat clients
13 years of experience
Madison, WI, 53705

Ashley was so great with our two pups. She shared pictures and updates during our time away and was really patient with our energetic puppy and also made sure to care for our older senior dog individually. So thankful for Ashley so we could take time away from our pets.

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Daniel P.
Sitter Profile Image: Sarah T.
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Sarah T.
from
$45
per night
5 out of 5.0 stars
9 reviews
6 repeat clients
2 years of experience
Madison, WI, 53719

Sarah was very calm and understanding when meeting our anxious and nervous dog Halla for the first time. Halla took treats from her and let her pet him, which usually doesn’t happen when he meets a new person. During our walk outside Halla was a bit of a jerk but she handled him very nicely. Hopefully Halla behaves better next time and matches Sarah’s calmness and kindness.

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Eliisa R.
Sitter Profile Image: Sara H.
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Sara H.
from
$55
per night
5 out of 5.0 stars
2 reviews
1 repeat client
24 years of experience
Sauk Creek, Madison, WI, 53717

Sara was great with a last minute booking when my regular sitter had an emergency. I appreciated her willingness to look after Ollie on short notice. She was great with him and I wouldn't hesitate to recommend her to anyone!

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Angi K.
Sitter Profile Image: Katia W.
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Katia W.
from
$80
per night
5 out of 5.0 stars
6 reviews
1 repeat client
15 years of experience
Madison, WI, 53705

About: I have experience caring for pets of all kinds and ages. I am an active runner and love long walks and will make sure your dog returns home ready for a nap! I work a 8-4 day job as an engineer but would love to give your friends some attention before or after work or on the weekends! I am happy to take care of your pets at your home. I am dependable and responsible and look forward to developing a bond with your pet. If applicable I also can explore your neighborhood on a *shhh* walk!

Sitter Profile Image: Stephany D.
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Stephany D.
from
$45
per night
5 out of 4.9 stars
46 reviews
14 repeat clients
10 years of experience
madison, WI, 53719

Stephany was a great house sitter! She was super friendly and respectful, and our dog got along with her great! She took him on lots of walks and we came home from our weekend away to a very happy pup. Will book her again!

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Katie H.
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Sitter Profile Image: Katie T.
Verified Enhanced Background Check
Sitter Profile Image: Katie T.
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1. Katie T.

Star Sitter
ACTIVE, FLEXABLE, DOG LOVER
Marquette, Madison, WI, 53703
6.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 4.9 stars
25 reviews
3 repeat clients
Profile image

Katie was wonderful with my dog and a great communicator. She sent lots of updates and I could tell she was taking great care of him. She went above and beyond! I would definitely utilize her again.

Availability updated yesterday
Sitter Profile Image: Annie J.
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Sitter Profile Image: Annie J.
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2. Annie J.

Rover 101
Star Sitter
Active & communicative pet lover!
Midvale Heights Community, Madison, WI, 53711
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
49 reviews
19 repeat clients
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Annie took great care of our dog and guinea pig! She gave me frequent updates and was very attentive to our anxious dog’s needs. Thank you!!!

Availability updated yesterday
Sitter Profile Image: Julie A.
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Sitter Profile Image: Julie A.
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3. Julie A.

Star Sitter
Mature, skilled and flexible
Verona, WI, 53593
3.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 5.0 stars
15 reviews
2 repeat clients
Profile image

Julie is an amazing dog sitter. Best we have had through Rover yet. She watched our two dogs, one of which is a senior dog with health issues and requires medication. I couldn't recommend her more highly!

Availability updated 9 days ago
Sitter Profile Image: Louisa M.
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Sitter Profile Image: Louisa M.
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4. Louisa M.

Star Sitter
Your pet’s new friend! 🐶🐱🐰🐔🐠
Midvale Heights Community, Madison, WI, 53711
1.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$60
per night
5 out of 5.0 stars
61 reviews
19 repeat clients
Profile image

Louisa and her daughter did a great job of communicating with me, though their stay was short. My cat loved the attention they gave her. Her coat was beautifully soft and clean from all the brushing. I would definitely schedule them again when I am out of town.

Availability updated 5 days ago
Sitter Profile Image: Kaitlyn B.
Verified Enhanced Background Check
Sitter Profile Image: Kaitlyn B.
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5. Kaitlyn B.

Star Sitter
Your Go-To Sitter
Madison, WI, 53719
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
16 reviews
5 repeat clients
Profile image

Kaitlyn has been so patient with my anxious dog! I feel so good leaving him in her care because I know he'll be well taken care of and allowed to adjust at his own pace. She always leaves my home spotless and communicates promptly when I reach out. Highly recommend!

Availability updated yesterday
Sitter Profile Image: Erika K.
Verified Enhanced Background Check
Sitter Profile Image: Erika K.
Verified Enhanced Background Check

6. Erika K.

Loving care for your furry family
Middleton, WI, 53562
2.4 mi. away
House Sitting
from
$45
per night
5 out of 5.0 stars
10 reviews
Profile image

Erika was great. She is a delightful person who gleefully mixed with my two furry sweet beasts. When I returned home, everything was in fine shape and the dogs were very happy. I will surely contact her in the future when I travel.

Availability updated today
Sitter Profile Image: Hannah I.
Verified Background Check
Sitter Profile Image: Hannah I.
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7. Hannah I.

Rover 101
Star Sitter
Dogs love to run and play with me!
Wexford, Madison, WI, 53717
1.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 5.0 stars
97 reviews
32 repeat clients
Profile image

This was our first time leaving our dog “Gracie” with a sitter. Hannah arrived on time and it was a very early morning arrival!! Gracie is an anxious dog around strangers, but Hannah knew instinctively to let Gracie approach her and get comfortable. We were gone for 12 hours and came home to a happy well cared for puppy. Hannah sent pictures and updated us throughout the day. We felt very comfortable knowing she was in good hands and will definitely call on Hannah again. Thank you, Hannah!!

Availability updated 12 days ago
Sitter Profile Image: McKenna B.
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Sitter Profile Image: McKenna B.
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8. McKenna B.

Reliable, Responsible, and Fun!
Madison, WI, 53711
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$40
per night
5 out of 5.0 stars
5 reviews
Profile image

McKenna, was great. She sent pictures of our dogs. They seemed very happy. Our house was in the exact same shape when we got home as we left it. Would definitely recommend.

Availability updated today
Sitter Profile Image: Ann A.
Verified Enhanced Background Check
Sitter Profile Image: Ann A.
Verified Enhanced Background Check

9. Ann A.

Star Sitter
Attentive and reliable pet sitter
Madison, WI, 53719
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$75
per night
5 out of 5.0 stars
54 reviews
19 repeat clients
Profile image

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!

Availability updated today
Sitter Profile Image: Sidney R.
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Sitter Profile Image: Sidney R.
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10. Sidney R.

Star Sitter
They call me “The Pal Gal”!
Middleton, WI, 53562
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$50
per night
5 out of 4.9 stars
59 reviews
19 repeat clients
Profile image

Sidney took great care of my house and dogs while I was away for a few days. I will definitely work with Sidney again if I get the opportunity to!

Availability updated 13 days ago
Sitter Profile Image: Jolie Zevallos
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Sitter Profile Image: Jolie Zevallos
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11. Jolie Zevallos

Star Sitter
I love the fur babies so much
Madison, WI, 53715
4.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$23
per night
5 out of 5.0 stars
6 reviews
4 repeat clients
Profile image

Jolie is great. Good communication and goes above and beyond to spend quality time with our two large dogs. Very happy, will book again if possible.

Availability updated 2 days ago
Sitter Profile Image: Sophie H.
Verified Enhanced Background Check
Sitter Profile Image: Sophie H.
Verified Enhanced Background Check

12. Sophie H.

I would love to love your pets!
Regent, Madison, WI, 53726
3.4 mi. away
House Sitting
from
$60
per night
5 out of 5.0 stars
55 reviews
16 repeat clients
Profile image

Sophie jumped in and helped us so last minute & she was great! Gave our dog time to warm up, sent pics and gave her lots of love. Thanks Sophie!

Availability updated today
Sitter Profile Image: Christina H.
Verified Enhanced Background Check
Sitter Profile Image: Christina H.
Verified Enhanced Background Check

13. Christina H.

Professional animal lover
Madison, WI, 53719
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$70
per night
5 out of 4.9 stars
17 reviews
1 repeat client
Profile image

Christina was very attentive to Kya and sent lots of updates and pictures.

Availability updated today
Sitter Profile Image: Anna H.
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Sitter Profile Image: Anna H.
Verified Enhanced Background Check

14. Anna H.

The best care for your best friend!
Middleton, WI, 53562
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$65
per night
5 out of 5.0 stars
27 reviews
7 repeat clients
Profile image

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.

Availability updated yesterday
Sitter Profile Image: Robert N.
Verified Enhanced Background Check
Sitter Profile Image: Robert N.
Verified Enhanced Background Check

15. Robert N.

Star Sitter
I'll do the walking!
Orchard Ridge Community, Madison, WI, 53711
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$60
per night
5 out of 5.0 stars
116 reviews
37 repeat clients
Profile image

Robert did an excellent job taking care of my high energy dog and 2 cats. He communicated very well and let me know what they were up to during the days I was away. He left my house just as clean as when I left it.

Availability updated yesterday
Sitter Profile Image: Ashley E.
Verified Background Check
Sitter Profile Image: Ashley E.
Verified Background Check

16. Ashley E.

Star Sitter
Treating Your Furbabies Like My Own
Madison, WI, 53705
2.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$80
per night
5 out of 5.0 stars
480 reviews
121 repeat clients
Profile image

Ashley was so great with our two pups. She shared pictures and updates during our time away and was really patient with our energetic puppy and also made sure to care for our older senior dog individually. So thankful for Ashley so we could take time away from our pets.

Availability updated 7 days ago
Sitter Profile Image: Sarah T.
Verified Enhanced Background Check
Sitter Profile Image: Sarah T.
Verified Enhanced Background Check

17. Sarah T.

Trustworthy, available pet lover!
Madison, WI, 53719
1.5 mi. away
House Sitting, Drop-In Visits
from
$45
per night
5 out of 5.0 stars
9 reviews
6 repeat clients
Profile image

Sarah was very calm and understanding when meeting our anxious and nervous dog Halla for the first time. Halla took treats from her and let her pet him, which usually doesn’t happen when he meets a new person. During our walk outside Halla was a bit of a jerk but she handled him very nicely. Hopefully Halla behaves better next time and matches Sarah’s calmness and kindness.

Availability updated 17 days ago
Sitter Profile Image: Sara H.
Verified Enhanced Background Check
Sitter Profile Image: Sara H.
Verified Enhanced Background Check

18. Sara H.

Huge animal lover, huge heart
Sauk Creek, Madison, WI, 53717
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$55
per night
5 out of 5.0 stars
2 reviews
1 repeat client
Profile image

Sara was great with a last minute booking when my regular sitter had an emergency. I appreciated her willingness to look after Ollie on short notice. She was great with him and I wouldn't hesitate to recommend her to anyone!

Availability updated 6 days ago
Sitter Profile Image: Katia W.
Verified Enhanced Background Check
Sitter Profile Image: Katia W.
Verified Enhanced Background Check

19. Katia W.

I’ll care for them like my own
Madison, WI, 53705
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$80
per night
5 out of 5.0 stars
6 reviews
1 repeat client

Katia has been a wonderful sitter for us for the last 4 years. Always professional and loving with our pets. She goes a great job communicating while we are away letting us know how it’s going and you can tell she has a passion for pets.

Availability updated 2 days ago
Sitter Profile Image: Stephany D.
Verified Background Check
Sitter Profile Image: Stephany D.
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20. Stephany D.

I'll be your dog's other bestie!
madison, WI, 53719
1.4 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$45
per night
5 out of 4.9 stars
46 reviews
14 repeat clients
Profile image

Stephany was a great house sitter! She was super friendly and respectful, and our dog got along with her great! She took him on lots of walks and we came home from our weekend away to a very happy pup. Will book her again!

Availability updated yesterday

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

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Sitters in Oakwood Village average 3 repeat house sitting clients

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