Pet Sitting & Drop Ins in Woodland Hills, Madison, WI

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Top rated Woodland Hills pet sitters

1 / 1
Sitter Profile Image: Kim M.
Verified Background Check
Kim M.
from
$17
per visit
5 out of 5.0 stars
98 reviews
40 repeat clients
8 years of experience
Middleton, WI, 53562

The pets are always excited to have Kim come over and we feel confident they are in good hands. She always goes above and beyond and is willing to work with us for last minute requests:)

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Angelina H.
Sitter Profile Image: Maiya W.
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Maiya W.
Star Sitter
from
$15
per visit
5 out of 5.0 stars
97 reviews
31 repeat clients
5 years of experience
Middleton, WI, 53562

Maiya is amazing and sent us pictures everyday to check in. Our cat loved her (and our cat does not like strangers). Super accommodating and professional. We highly recommend her!

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Mikala W.
Sitter Profile Image: Dietrich G.
Verified Enhanced Background Check
Dietrich G.
from
$20
per visit
5 out of 4.9 stars
67 reviews
20 repeat clients
12 years of experience
Walnut Grove, MADISON, WI, 53717

Dietrich has been a wonderful dogsitter for my dog! He is a great communicator thru the Rover App and I appreciate is daily comments and photo. I know that Coco is in great care!

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Brittany H.
Sitter Profile Image: Cleda W.
Verified Background Check
Cleda W.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
192 reviews
78 repeat clients
11 years of experience
Madison, WI, 53705

Thank you for watching felix! Cleda communicates well, very thoughtful and loves animals:) she always leaves a thorough summary each day about your pet and how the visit went. I definitely would recommend Cleda hands down no worries with her at will. Thanks again!

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Ali H.
Sitter Profile Image: Jennifer L.
Verified Background Check
Jennifer L.
Star Sitter
from
$21
per visit
5 out of 5.0 stars
415 reviews
135 repeat clients
30 years of experience
Madison, WI, 53705

We were incredibly grateful that Jennifer was able to accept a last-minute request when our family experienced an unexpected emergency and my husband was suddenly hospitalized. I reached out to her around 10:30 p.m., and she responded right away with understanding and flexibility. During such a stressful time, knowing Missy was in safe, capable hands brought us tremendous peace of mind. Jennifer followed our care instructions closely, including giving Missy her daily medication, and managed feeding and litter box. Missy is shy around new people, especially during stressful changes, but Jennifer was calm and patient. Her gentle approach helped Missy feel comfortable and secure in our absence. It’s clear that she is not only experienced but also genuinely compassionate and attentive to each animal’s needs. As pet owners, we value someone who is dependable, communicative, and truly cat-savvy—and Jennifer exceeded every expectation. We feel very fortunate to have found her at the last minute and will absolutely be booking her again!!!

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Jennifer V.
Sitter Profile Image: Sidney R.
Verified Enhanced Background Check
Sidney R.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
51 reviews
15 repeat clients
20 years of experience
Middleton, WI, 53562

Sidney was so professional work with, and we appreciated her responding to us so quickly when we needed help on short notice. Layla loved her! We will definitely use Sidney again.

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Brian K.
Sitter Profile Image: Allegra R.
Verified Enhanced Background Check
Allegra R.
Star Sitter
from
$25
per visit
5 out of 4.9 stars
72 reviews
33 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!

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Francesca C.
Sitter Profile Image: Sarah S.
Verified Enhanced Background Check
Sarah S.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
119 reviews
35 repeat clients
7 years of experience
Sunset Village, Madison, WI, 53705

Thank you again to Sarah for a wonderful sitter experience! Was sad to leave my cat at home during the holidays, but was happy to have Sarah keep her company and give her lots of love :)

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Jasmine M.
Sitter Profile Image: Yvonne L.
Verified Enhanced Background Check
Yvonne L.
Star Sitter
from
$17
per visit
5 out of 5.0 stars
16 reviews
5 repeat clients
16 years of experience
Madison, WI, 53705

Yvonne’s a great pet sitter. She is super responsive and goes the extra mile with my cat. My cat has asthma and required a daily inhaler dose. Yvonne was kind and patient to provide my cat with her daily inhaler. When my auto feeder failed, she stayed back to help to reset it so my cat didn’t starve. She also provided me with daily update. When I came home, my cat was happy and well cared for. I highly recommend her because she truly cares about pets! I would totally rebook her.

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Sabrina C.
Sitter Profile Image: Anna H.
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Anna H.
from
$20
per visit
5 out of 5.0 stars
27 reviews
7 repeat clients
7 years of experience
Middleton, WI, 53562

Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!

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Sabrina M.
Sitter Profile Image: Ann V.
Verified Enhanced Background Check
Ann V.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
78 reviews
23 repeat clients
10 years of experience
Madison, WI, 53711

Ann was willing to learn how to administer insulin to my diabetic cat which was above and beyond! She was also great at communicating and clearly an animal lover. Thanks again for taking care of our cats!

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Jesse
Sitter Profile Image: Anna N.
Verified Enhanced Background Check
Anna N.
from
$15
per visit
5 out of 5.0 stars
7 reviews
2 repeat clients
5 years of experience
Madison, WI, 53705

Anna was wonderful with our dog Panda and I highly recommend her to take care of your pets. Our request was different but she was responsive and super communicative. Thanks for taking great care of Panda for us!

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Wendy M.
Sitter Profile Image: Seán & Leticia W.
Verified Enhanced Background Check
Seán & Leticia W.
Star Sitter
from
$18
per visit
5 out of 5.0 stars
96 reviews
24 repeat clients
20 years of experience
Maple-Prairie, Madison, WI, 53719

Seán and Leticia are always so quick to respond when I put in an inquiry and I’ve never had an issue with communication. They always send more photos than expected and it is so nice to be able to leave my pup at home without fear for her care and wellbeing. I haven’t used anyone else since meeting them.

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Kevin B.
Sitter Profile Image: Lydia S.
Verified Background Check
Lydia S.
from
$20
per visit
5 out of 5.0 stars
115 reviews
36 repeat clients
10 years of experience
Middleton, WI, 53562

This was our 2nd time hiring Lydia and we were glad for it. The first night we ran into some complications and Lydia was there to help us problem solve it, taking initiative and going out of her way. Communication is 10 out of 10! And sends us daily pics of our little guy. Thanks Lydia!

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Meg N.
Sitter Profile Image: Annie J.
Verified Enhanced Background Check
Annie J.
Star Sitter
from
$20
per visit
5 out of 5.0 stars
48 reviews
17 repeat clients
6 years of experience
Midvale Heights Community, Madison, WI, 53711

Annie was great with my cat, Cleo! She sent over lots of pictures and a detailed account of their time together, which was appreciated. She was flexible and accommodating with coming by before the check in dates to pick up my spare key. Recommend!

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Kaitlin H.
Sitter Profile Image: Corinne B.
Verified Enhanced Background Check
Corinne B.
from
$20
per visit
5 out of 5.0 stars
18 reviews
6 repeat clients
25 years of experience
Madison, WI, 53719

Corinne is quick to respond to messages and very personable. She did a great job with our almost 12 yo rescue dog!

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Kathleen M.
Sitter Profile Image: Taylor B.
Verified Enhanced Background Check
Taylor B.
Star Sitter
from
$15
per visit
5 out of 4.8 stars
22 reviews
5 repeat clients
20 years of experience
Prairie Hills, Madison, WI, 53711

Thank you so much, Taylor, for the great and smooth check in for our guys. We’re excited to have connected & to use you in the future as well! 🤗

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Emily B.
Sitter Profile Image: Alisyn L.
Verified Enhanced Background Check
Alisyn L.
from
$25
per visit
5 out of 5.0 stars
65 reviews
17 repeat clients
9 years of experience
Madison, WI, 53717

Would absolutely recommend Alisyn!! She has been wonderful with our older dog, Indy, over the last year. When we added a second dog (a young rescue with heartworm disease), I knew I could trust Alisyn to take great care of Eeva and keep her safe during treatment, too. We are so grateful to have such a dependable, experienced, and compassionate person watching and walking our pups!

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Mariya T.
Sitter Profile Image: Julie A.
Verified Enhanced Background Check
Julie A.
from
$13
per visit
5 out of 5.0 stars
12 reviews
1 repeat client
16 years of experience
Verona, WI, 53593

Julie is awesome. She is kind and patient with senior dogs. She’s reliable and jumps in to assist in even if n situations where there is a short notice. Thank you Julie

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Tracy S.
Sitter Profile Image: Anna O.
Verified Enhanced Background Check
Anna O.
from
$18
per visit
5 out of 5.0 stars
15 reviews
4 repeat clients
23 years of experience
Madison, WI, 53711

Anna does such a good job! She sends a ton of pictures of all the girls and they all look happy and are having fun. She makes sure they have food, water, and receive a treat! Best dog sitter we've ever had!

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Ashley T.
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Loving pet sitters in your neighborhood

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Sitter Profile Image: Kim M.
Verified Background Check
Sitter Profile Image: Kim M.
Verified Background Check

1. Kim M.

Loving and experienced Dog Mom!
Middleton, WI, 53562
1.2 mi. away
Boarding, Drop-In Visits
from
$17
per visit
5 out of 5.0 stars
98 reviews
40 repeat clients
Profile image

The pets are always excited to have Kim come over and we feel confident they are in good hands. She always goes above and beyond and is willing to work with us for last minute requests:)

Availability updated 8 months ago
Sitter Profile Image: Maiya W.
Verified Background Check
Sitter Profile Image: Maiya W.
Verified Background Check

2. Maiya W.

Star Sitter
I'll love them like you love them!
Middleton, WI, 53562
1.6 mi. away
Drop-In Visits
from
$15
per visit
5 out of 5.0 stars
97 reviews
31 repeat clients
Profile image

Maiya is amazing and sent us pictures everyday to check in. Our cat loved her (and our cat does not like strangers). Super accommodating and professional. We highly recommend her!

Availability updated today
Sitter Profile Image: Dietrich G.
Verified Enhanced Background Check
Sitter Profile Image: Dietrich G.
Verified Enhanced Background Check

3. Dietrich G.

Dietrich is a dog's delight
Walnut Grove, MADISON, WI, 53717
0.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per visit
5 out of 4.9 stars
67 reviews
20 repeat clients
Profile image

Dietrich has been a wonderful dogsitter for my dog! He is a great communicator thru the Rover App and I appreciate is daily comments and photo. I know that Coco is in great care!

Availability updated 4 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Cleda W.
Verified Background Check
Sitter Profile Image: Cleda W.
Verified Background Check

4. Cleda W.

Rover 101
Star Sitter
Dogs & Cats LOVE me!
Madison, WI, 53705
1.3 mi. away
Boarding, Drop-In Visits
from
$20
per visit
5 out of 5.0 stars
192 reviews
78 repeat clients
Profile image

Thank you for watching felix! Cleda communicates well, very thoughtful and loves animals:) she always leaves a thorough summary each day about your pet and how the visit went. I definitely would recommend Cleda hands down no worries with her at will. Thanks again!

Availability updated today
Sitter Profile Image: Jennifer L.
Verified Background Check
Sitter Profile Image: Jennifer L.
Verified Background Check

5. Jennifer L.

Rover 101
Star Sitter
AVAILABLE THIS WEEKEND! TOP RATED!
Madison, WI, 53705
1.5 mi. away
Drop-In Visits, Dog Walking
from
$21
per visit
5 out of 5.0 stars
415 reviews
135 repeat clients
Profile image

We were incredibly grateful that Jennifer was able to accept a last-minute request when our family experienced an unexpected emergency and my husband was suddenly hospitalized. I reached out to her around 10:30 p.m., and she responded right away with understanding and flexibility. During such a stressful time, knowing Missy was in safe, capable hands brought us tremendous peace of mind. Jennifer followed our care instructions closely, including giving Missy her daily medication, and managed feeding and litter box. Missy is shy around new people, especially during stressful changes, but Jennifer was calm and patient. Her gentle approach helped Missy feel comfortable and secure in our absence. It’s clear that she is not only experienced but also genuinely compassionate and attentive to each animal’s needs. As pet owners, we value someone who is dependable, communicative, and truly cat-savvy—and Jennifer exceeded every expectation. We feel very fortunate to have found her at the last minute and will absolutely be booking her again!!!

Availability updated 6 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Sidney R.
Verified Enhanced Background Check
Sitter Profile Image: Sidney R.
Verified Enhanced Background Check

6. Sidney R.

Star Sitter
They call me “The Pal Gal”!
Middleton, WI, 53562
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
51 reviews
15 repeat clients
Profile image

Sidney was so professional work with, and we appreciated her responding to us so quickly when we needed help on short notice. Layla loved her! We will definitely use Sidney again.

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Allegra R.
Verified Enhanced Background Check
Sitter Profile Image: Allegra R.
Verified Enhanced Background Check

7. Allegra R.

Rover 101
Star Sitter
Dog person for life.
Faircrest, Madison, WI, 53705
1.2 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 4.9 stars
72 reviews
33 repeat clients
Profile image

My dogs really like Allegra and she seems to be great with them too. She was great during our meet and greet and spent time to get to know the pups. Will hire again for sure!

Availability updated today
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Sarah S.
Verified Enhanced Background Check
Sitter Profile Image: Sarah S.
Verified Enhanced Background Check

8. Sarah S.

Star Sitter
Hoping I can meet your fur babies!
Sunset Village, Madison, WI, 53705
2.7 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
119 reviews
35 repeat clients
Profile image

Thank you again to Sarah for a wonderful sitter experience! Was sad to leave my cat at home during the holidays, but was happy to have Sarah keep her company and give her lots of love :)

Availability updated 2 days ago
Sitter Profile Image: Yvonne L.
Verified Enhanced Background Check
Sitter Profile Image: Yvonne L.
Verified Enhanced Background Check

9. Yvonne L.

Star Sitter
I take pet care very seriously!
Madison, WI, 53705
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$17
per visit
5 out of 5.0 stars
16 reviews
5 repeat clients
Profile image

Yvonne’s a great pet sitter. She is super responsive and goes the extra mile with my cat. My cat has asthma and required a daily inhaler dose. Yvonne was kind and patient to provide my cat with her daily inhaler. When my auto feeder failed, she stayed back to help to reset it so my cat didn’t starve. She also provided me with daily update. When I came home, my cat was happy and well cared for. I highly recommend her because she truly cares about pets! I would totally rebook her.

Availability updated 23 days ago
Sitter Profile Image: Anna H.
Verified Enhanced Background Check
Sitter Profile Image: Anna H.
Verified Enhanced Background Check

10. Anna H.

The best care for your best friend!
Middleton, WI, 53562
1.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
27 reviews
7 repeat clients
Profile image

Anna has been so great with Peanut and has been so flexible with scheduling! Would definitely recommend to anyone!

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

11. Ann V.

Star Sitter
Animal Lover and Law Student
Madison, WI, 53711
3.8 mi. away
Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
78 reviews
23 repeat clients
Profile image

Ann was willing to learn how to administer insulin to my diabetic cat which was above and beyond! She was also great at communicating and clearly an animal lover. Thanks again for taking care of our cats!

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

12. Anna N.

Professional student who loves dogs
Madison, WI, 53705
1.4 mi. away
Drop-In Visits, Dog Walking
from
$15
per visit
5 out of 5.0 stars
7 reviews
2 repeat clients
Profile image

Anna was wonderful with our dog Panda and I highly recommend her to take care of your pets. Our request was different but she was responsive and super communicative. Thanks for taking great care of Panda for us!

Availability updated 23 days ago
Sitter Profile Image: Seán & Leticia W.
Verified Enhanced Background Check
Sitter Profile Image: Seán & Leticia W.
Verified Enhanced Background Check

13. Seán & Leticia W.

Rover 101
Star Sitter
Take Care Of Your Best Friend!
Maple-Prairie, Madison, WI, 53719
4.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
96 reviews
24 repeat clients
Profile image

Seán and Leticia are always so quick to respond when I put in an inquiry and I’ve never had an issue with communication. They always send more photos than expected and it is so nice to be able to leave my pup at home without fear for her care and wellbeing. I haven’t used anyone else since meeting them.

Availability updated yesterday
Sitter Profile Image: Lydia S.
Verified Background Check
Sitter Profile Image: Lydia S.
Verified Background Check

14. Lydia S.

Here to help with your schedule
Middleton, WI, 53562
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
115 reviews
36 repeat clients
Profile image

This was our 2nd time hiring Lydia and we were glad for it. The first night we ran into some complications and Lydia was there to help us problem solve it, taking initiative and going out of her way. Communication is 10 out of 10! And sends us daily pics of our little guy. Thanks Lydia!

Availability updated 21 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Annie J.
Verified Enhanced Background Check
Sitter Profile Image: Annie J.
Verified Enhanced Background Check

15. Annie J.

Rover 101
Star Sitter
Active & communicative pet lover!
Midvale Heights Community, Madison, WI, 53711
2.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
48 reviews
17 repeat clients
Profile image

Annie was great with my cat, Cleo! She sent over lots of pictures and a detailed account of their time together, which was appreciated. She was flexible and accommodating with coming by before the check in dates to pick up my spare key. Recommend!

Availability updated 3 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Corinne B.
Verified Enhanced Background Check
Sitter Profile Image: Corinne B.
Verified Enhanced Background Check

16. Corinne B.

Animal Lover
Madison, WI, 53719
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per visit
5 out of 5.0 stars
18 reviews
6 repeat clients
Profile image

Corinne is quick to respond to messages and very personable. She did a great job with our almost 12 yo rescue dog!

Availability updated 4 days ago
Sitter Profile Image: Taylor B.
Verified Enhanced Background Check
Sitter Profile Image: Taylor B.
Verified Enhanced Background Check

17. Taylor B.

Star Sitter
Affectionate & Energetic Caretaker
Prairie Hills, Madison, WI, 53711
3.1 mi. away
Drop-In Visits
from
$15
per visit
5 out of 4.8 stars
22 reviews
5 repeat clients
Profile image

Thank you so much, Taylor, for the great and smooth check in for our guys. We’re excited to have connected & to use you in the future as well! 🤗

Availability updated 5 days ago
Confirmed availability for Memorial Day Weekend
Sitter Profile Image: Alisyn L.
Verified Enhanced Background Check
Sitter Profile Image: Alisyn L.
Verified Enhanced Background Check

18. Alisyn L.

Veterinary Technician & Adventurer
Madison, WI, 53717
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per visit
5 out of 5.0 stars
65 reviews
17 repeat clients
Profile image

Would absolutely recommend Alisyn!! She has been wonderful with our older dog, Indy, over the last year. When we added a second dog (a young rescue with heartworm disease), I knew I could trust Alisyn to take great care of Eeva and keep her safe during treatment, too. We are so grateful to have such a dependable, experienced, and compassionate person watching and walking our pups!

Availability updated 12 days ago
Sitter Profile Image: Julie A.
Verified Enhanced Background Check
Sitter Profile Image: Julie A.
Verified Enhanced Background Check

19. Julie A.

Mature, skilled and flexible
Verona, WI, 53593
3.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$13
per visit
5 out of 5.0 stars
12 reviews
1 repeat client
Profile image

Julie is awesome. She is kind and patient with senior dogs. She’s reliable and jumps in to assist in even if n situations where there is a short notice. Thank you Julie

Availability updated 5 days ago
Sitter Profile Image: Anna O.
Verified Enhanced Background Check
Sitter Profile Image: Anna O.
Verified Enhanced Background Check

20. Anna O.

Will treat your sweet pet as my own
Madison, WI, 53711
3.0 mi. away
Drop-In Visits, Dog Walking
from
$18
per visit
5 out of 5.0 stars
15 reviews
4 repeat clients
Profile image

Anna does such a good job! She sends a ton of pictures of all the girls and they all look happy and are having fun. She makes sure they have food, water, and receive a treat! Best dog sitter we've ever had!

Availability updated 10 days ago

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