Dog Walking in Oakwood Village, Madison, WI

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Top rated Oakwood Village dog walkers

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Sitter Profile Image: Allegra R.
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Allegra R.
Star Sitter
from
$25
per walk
5 out of 4.9 stars
75 reviews
34 repeat clients
29 years of experience
Faircrest, Madison, WI, 53705

Allegra is the best with my dogs. She is responsible, great at quick communication, and truly treats my pups well when we need her to walk the. Or stay the night. We cant say enough nice things about Allegra.

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Francesca C.
Sitter Profile Image: Melinda N.
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Melinda N.
Star Sitter
from
$25
per walk
5 out of 5.0 stars
129 reviews
22 repeat clients
25 years of experience
Leopold, Madison, WI, 53713

Melinda is a wonderful dog walker. She quickly established rapport with our dog and has been very reliable and responsive. She lets us know how each visit went and often sends photos. I recommend her highly.

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Sybil P.
Sitter Profile Image: Keezieng V.
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Keezieng V.
Star Sitter
from
$19
per walk
5 out of 5.0 stars
63 reviews
29 repeat clients
3 years of experience
Arbor Hills, Madison, WI, 53713

Keezieng has been a fantastic dog walker this past week! Very flexible and always on time, he made sure that Stella always had a nice mid-day walk.

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Colin S.
Sitter Profile Image: Mindi L.
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Mindi L.
Star Sitter
from
$18
per walk
5 out of 5.0 stars
7 reviews
4 repeat clients
4 years of experience
Greenbush, Madison, WI, 53715

Caring, my dog gets so excited when Mindi walks in, she takes time to play w/ her after the walk and give her lots of love and treats. I know my dog is in good hands w/ Mindi.

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Maggie J.
Sitter Profile Image: Ann V.
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Ann V.
Star Sitter
from
$20
per walk
5 out of 5.0 stars
89 reviews
28 repeat clients
10 years of experience
Madison, WI, 53711

Great first walk with Pete! Helped him to feel calm and connected with treats before the headed out. Felt great to know Pete was in good hands!

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Jeneen H.
Sitter Profile Image: Michelle S.
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Michelle S.
Star Sitter
from
$16
per walk
5 out of 5.0 stars
121 reviews
51 repeat clients
4 years of experience
Madison, WI, 53719

Michelle was absolutely fantastic with Kona. Our pup is nervous around new people and Michelle was amazing on her first visit/walk to meet her in advance of her house/pet sitting. After her walk and getting to know Kona, Michelle did a thorough walk through of our house and asked all the little questions and details that I’d never think to talk about before she comes to sit. I’m so confident that she will be an amazing sitter while we are away!

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Penelope D.
Sitter Profile Image: Jennifer L.
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Jennifer L.
Star Sitter
from
$28
per walk
5 out of 5.0 stars
433 reviews
144 repeat clients
30 years of experience
Madison, WI, 53705

Jennifer is great! We'd love for her to walk our dog again (in fact we already rebooked). We needed help once a week with our 8mo puppy. Jennifer always picks him up on schedule and returns him happy and well exercised! Our dog loves everyone but my husband is convinced the pup loves Jennifer extra.

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Rosanne L.
Sitter Profile Image: Kaelena K.
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Kaelena K.
from
$16
per walk
5 out of 5.0 stars
4 reviews
15 years of experience
Fitchburg, WI, 53711

About: I’ve taken care of dogs, cats, & many other animals since I was young! I currently have two English Cocker Spaniels - they are sweeties! My husband and I got them as pups and trained them ourselves. I feel very confident working with puppies and I adore them. The dogs I grew up with were all rescues, so I also feel confident in caring for rescue dogs that may have more difficult pasts or behaviors. We had a senior chihuahua up until a year ago- she was my everything! Big or small, active or couch potato, I’m happy to care for your special ones. I am happy to get out and walk, run, bike, train or play as well as cuddle up and give some loves. (: I have a flexible work schedule and can easily fit in part-time pet sitting. I’m happy to come by for an hour or two in the afternoon as well as stay the night and keep the animals active morning and evening. I typically try to avoid leaving pets for more than 5 hours- it’s typically 2-4. I have two sweet, easy going boys that are very happy to play and hang out with other dogs in the owner’s home if they would like. I am flexible- I have watched active dogs, low-key dogs, dogs that need extra love and attention, and everything in between. I’m an active person and am happy to take dogs on longer walks or runs, even. My lifestyle is such that doing activities with animals fits in well with the day-to-day.

Sitter Profile Image: Austin C.
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Austin C.
Star Sitter
from
$18
per walk
5 out of 5.0 stars
23 reviews
9 repeat clients
5 years of experience
Madison, WI, 53719

Austin was fantastic walking Mazie! Great communication, lots of pictures, and she was tired and seemed very comfortable and happy. I recommend to everyone!

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Cailin C.
Sitter Profile Image: Annie J.
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Annie J.
Star Sitter
from
$20
per walk
5 out of 5.0 stars
60 reviews
20 repeat clients
6 years of experience
Midvale Heights Community, Madison, WI, 53711

Really appreciated Annie walking my sweet dog for me! She’s very trustworthy and great!

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Genevieve H.
Sitter Profile Image: Ashley E.
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Ashley E.
Star Sitter
from
$28
per walk
5 out of 5.0 stars
492 reviews
124 repeat clients
13 years of experience
Madison, WI, 53705

Ashley is wonderful! She's on time, communicative, and great with my dog. I love using her and will continue to for as long as she'll have me!

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Jessica L.
Sitter Profile Image: Chenghao X.
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Chenghao X.
from
$14
per walk
4 years of experience
Middleton, WI, 53590

About: I’ve been caring for pets for years, starting with walking dogs for my neighbors — from tiny terriers to big, energetic labs. That hands-on experience taught me how to handle different sizes, breeds, and personalities with confidence and care. What sets me apart is my calm, reliable nature and genuine love for animals. I’m comfortable with leash training, reading dog body language, and keeping even the most energetic pups engaged and happy. I’m also attentive to each pet’s needs — whether that means a brisk walk, a slow stroll for a senior, or extra cuddle time. Your pet’s safety, routine, and happiness always come first with me. I have a very flexible schedule and am available anytime — weekdays, weekends, and even holidays. Pet care fits perfectly into my routine because I truly enjoy spending time with animals and can easily adjust my day around their needs. Whether it's an early morning walk, midday visit, or evening check-in, I’m ready whenever your pet needs me. When caring for pets in a client’s home, I treat it as my own. I follow all routines closely from feeding times to walks and medication and always prioritize your pet’s comfort and safety. I keep a calm, clean environment and make sure pets feel secure, whether they’re outgoing or shy. I pay close attention to details like locked doors, clean water bowls, and tidy spaces. I’m also happy to send regular updates and photos, so you can feel confident and connected while you're away.

Sitter Profile Image: Anna N.
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Anna N.
from
$15
per walk
5 out of 5.0 stars
8 reviews
2 repeat clients
5 years of experience
Madison, WI, 53705

Great job

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Andy O.
Sitter Profile Image: Megan B.
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Megan B.
from
$19
per walk
5 out of 5.0 stars
3 reviews
8 years of experience
Madison, WI, 53719

Megan did a great job with Sami while we were away! We would definitely use her again!

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Andy O.
Sitter Profile Image: Rex E.
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Rex E.
from
$15
per walk
5 out of 5.0 stars
3 reviews
1 repeat client
1 year of experience
Midvale Heights Community, Madison, WI, 53711

About: I have been pet/house sitting for about a year but have had pets and taken care of animals my whole life. I am open to watching any animals and even doing chores while you’re away! I am available for weekends and afternoons during the school year and all days of the week during summer! I might be out for an hour or two to go to the gym but otherwise can hang with furry buddies all hours of the day. I can be around your pets to watch them at all times if needed. I can crate dogs and make sure they stay where they should be.

Sitter Profile Image: Alisyn L.
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Alisyn L.
from
$25
per walk
5 out of 5.0 stars
65 reviews
17 repeat clients
9 years of experience
Madison, WI, 53717

Alisyn has been wonderful with our dog, Indy! We would highly recommend her for dog walking. She is professional, dependable, and communicative. Most importantly, she made Indy feel very comfortable right away. We greatly appreciate the Rover (Report) Cards and photos after every walk. Thank you, Alisyn!

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Mariya T.
Sitter Profile Image: Ava H.
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Ava H.
from
$16
per walk
6 years of experience
Madison, WI, 53719

About: Hi, my name is Ava! I am looking to provide dog walking & check in services in the West Madison area. I am committed to providing individualized care, strong attention to detail, and genuine interest and compassion for animals. I grew up in a family that took in a variety of pets to provide a safe home. I am a strong believer in your fuzzy friends being your best friends! They deserve to be treated with care and love while you're away, just as I would want for my dog. I rescued my miniature pinscher 6 years ago and she is now 15 years old! She is both an old lady and still my little baby. I love all animals and I'm so excited to meet yours! I have experience working with children and youth with diverse needs, and that level of care and patience extends naturally to animals with anxiety, behavioral challenges, or special routines. My background in caregiving and support work has taught me to be highly responsible, communicative, and reliable. I’m organized, dependable, and quick to respond — qualities that give pet owners peace of mind. I also go the extra mile with photo updates, customized activities, and keeping pets happy and stress-free while their humans are away. I’m active and love outdoor time — whether it’s long walks, playing fetch, or trail adventures, I’m happy to match your dog’s energy level. I work from home so I have a flexible schedule from 7am-5pm, but it is not consistent every day. I am able to work my schedule around visits and walks if I have enough time to plan. Just message me with details! I could board pets during the day if it's a small dog with no aggression. I have a 15 year old miniature pinscher that gets anxious around medium-large dogs that have anxiety as well and/or some aggression. I am happy to do drop ins and walks throughout the day!

Sitter Profile Image: Shaina N.
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Shaina N.
from
$25
per walk
5 out of 5.0 stars
8 reviews
2 repeat clients
20 years of experience
Midvale Heights Community, Madison, WI, 53711

Shaina is the best! She takes great care of our two fluffballs - they love her. She’s also incredibly friendly and considerate. Would highly recommend!

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Jon W.
Sitter Profile Image: Ella O.
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Ella O.
from
$16
per walk
20 years of experience
madison, WI, 53705

About: I have had dogs my entire life. They ranged from puppies all the way to them becoming senior dogs, and they all came from very different backgrounds. I am especially good with senior dogs. My childhood dog eventually had severe arthritis and needed medication and some extra help. I would do anything for her that helped her feel more comfortable! I also puppysit for some family members so I am also used to the craziness a puppy can bring! I am currently available most days at any time until August 11. My cat does need medication at 8pm, but any other time of the day works for me! I can care for your pets however you need in your home! Whether it's going on a walk, playing outside, or staying inside, whatever is best for them is doable!

Sitter Profile Image: Meeka M.
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Meeka M.
Star Sitter
from
$20
per walk
5 out of 5.0 stars
58 reviews
17 repeat clients
10 years of experience
Madison, WI, 53717

Meeka was amazing! She was very thorough and made sure that Sadie had a good time on her walks! She sent lots of pictures and gave me a detailed summary of her cares. Would definitely recommend ☺️

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Katie H.
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Sitter Profile Image: Allegra R.
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Sitter Profile Image: Allegra R.
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Allegra R.
Rover 101
Star Sitter

Dog person for life.
Faircrest, Madison, WI, 53705
0.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 4.9 stars
75 reviews
34 repeat clients
Profile image

Allegra is the best with my dogs. She is responsible, great at quick communication, and truly treats my pups well when we need her to walk the. Or stay the night. We cant say enough nice things about Allegra.

Availability updated yesterday
Sitter Profile Image: Melinda N.
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Sitter Profile Image: Melinda N.
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Melinda N.
Star Sitter

Sorry, I was late. I saw a dog!
Leopold, Madison, WI, 53713
4.0 mi. away
Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
129 reviews
22 repeat clients
Profile image

Melinda is a wonderful dog walker. She quickly established rapport with our dog and has been very reliable and responsive. She lets us know how each visit went and often sends photos. I recommend her highly.

Availability updated 3 days ago
Sitter Profile Image: Keezieng V.
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Sitter Profile Image: Keezieng V.
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Keezieng V.
Star Sitter

A dog person through & through
Arbor Hills, Madison, WI, 53713
3.3 mi. away
Drop-In Visits, Dog Walking
from
$19
per walk
5 out of 5.0 stars
63 reviews
29 repeat clients
Profile image

Keezieng has been a fantastic dog walker this past week! Very flexible and always on time, he made sure that Stella always had a nice mid-day walk.

Availability updated 6 months ago
Sitter Profile Image: Mindi L.
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Sitter Profile Image: Mindi L.
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Mindi L.
Star Sitter

Dog-Loving Grad in Madison!
Greenbush, Madison, WI, 53715
4.0 mi. away
Drop-In Visits, Dog Walking
from
$18
per walk
5 out of 5.0 stars
7 reviews
4 repeat clients
Profile image

Caring, my dog gets so excited when Mindi walks in, she takes time to play w/ her after the walk and give her lots of love and treats. I know my dog is in good hands w/ Mindi.

Availability updated 2 days ago
Sitter Profile Image: Ann V.
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Sitter Profile Image: Ann V.
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Ann V.
Star Sitter

Animal Lover & Recent Graduate
Madison, WI, 53711
3.0 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
89 reviews
28 repeat clients
Profile image

Great first walk with Pete! Helped him to feel calm and connected with treats before the headed out. Felt great to know Pete was in good hands!

Availability updated yesterday
Sitter Profile Image: Michelle S.
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Sitter Profile Image: Michelle S.
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Michelle S.
Rover 101
Star Sitter

I love walking & playing for hours
Madison, WI, 53719
2.5 mi. away
Drop-In Visits, Dog Walking
from
$16
per walk
5 out of 5.0 stars
121 reviews
51 repeat clients
Profile image

Michelle was absolutely fantastic with Kona. Our pup is nervous around new people and Michelle was amazing on her first visit/walk to meet her in advance of her house/pet sitting. After her walk and getting to know Kona, Michelle did a thorough walk through of our house and asked all the little questions and details that I’d never think to talk about before she comes to sit. I’m so confident that she will be an amazing sitter while we are away!

Availability updated 5 days ago
Sitter Profile Image: Jennifer L.
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Sitter Profile Image: Jennifer L.
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Jennifer L.
Rover 101
Star Sitter

AVAILABLE THIS WEEKEND! TOP RATED!
Madison, WI, 53705
0.9 mi. away
Drop-In Visits, Dog Walking
from
$28
per walk
5 out of 5.0 stars
433 reviews
144 repeat clients
Profile image

Jennifer is great! We'd love for her to walk our dog again (in fact we already rebooked). We needed help once a week with our 8mo puppy. Jennifer always picks him up on schedule and returns him happy and well exercised! Our dog loves everyone but my husband is convinced the pup loves Jennifer extra.

Availability updated today
Sitter Profile Image: Kaelena K.
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Sitter Profile Image: Kaelena K.
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Kaelena K.

Doggies are my besties! (:
Fitchburg, WI, 53711
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$16
per walk
5 out of 5.0 stars
4 reviews

We really appreciated Kaelena’s care and attention she gave to our senior dog. We would highly recommend her to watch & care for other people’s pets.

Availability updated 3 days ago
Sitter Profile Image: Austin C.
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Sitter Profile Image: Austin C.
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Austin C.
Star Sitter

I love all animals!
Madison, WI, 53719
2.4 mi. away
Drop-In Visits, Dog Walking
from
$18
per walk
5 out of 5.0 stars
23 reviews
9 repeat clients
Profile image

Austin was fantastic walking Mazie! Great communication, lots of pictures, and she was tired and seemed very comfortable and happy. I recommend to everyone!

Availability updated 11 days ago
Sitter Profile Image: Annie J.
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Sitter Profile Image: Annie J.
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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
$20
per walk
5 out of 5.0 stars
60 reviews
20 repeat clients
Profile image

Really appreciated Annie walking my sweet dog for me! She’s very trustworthy and great!

Availability updated today
Sitter Profile Image: Ashley E.
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Sitter Profile Image: Ashley E.
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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
$28
per walk
5 out of 5.0 stars
492 reviews
124 repeat clients
Profile image

Ashley is wonderful! She's on time, communicative, and great with my dog. I love using her and will continue to for as long as she'll have me!

Availability updated 2 days ago
Sitter Profile Image: Chenghao X.
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Sitter Profile Image: Chenghao X.
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Chenghao X.

pet owner, pet lover
Middleton, WI, 53590
2.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$14
per walk
3 reviews

Chenghao is a pet-lover through and through. He is incredibly kind, patient, and caring with not only our cat, but he also would offer to help take care of our friends’ and neighbors’ pets just because he enjoys spending time with our furry friends. I would recommend him for anyone who needs a pet sitter!

Availability updated 2 days ago
Sitter Profile Image: Anna N.
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Sitter Profile Image: Anna N.
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Anna N.

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

Great job

Availability updated 24 days ago
Sitter Profile Image: Megan B.
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Sitter Profile Image: Megan B.
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Megan B.

Friendly, Dependable, Caring
Madison, WI, 53719
1.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$19
per walk
5 out of 5.0 stars
3 reviews
Profile image

Megan did a great job with Sami while we were away! We would definitely use her again!

Availability updated 2 days ago
Sitter Profile Image: Rex E.
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Sitter Profile Image: Rex E.
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Rex E.

Looking to make some furry friends!
Midvale Heights Community, Madison, WI, 53711
1.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
3 reviews
1 repeat client

Rex is an amazing pet caregiver. He took care of my menagerie of two dogs and two cats in my home while I was away. My shy cat who usually hides when someone is on the house he doesn’t know came out and cuddled with Rex the first night. Rex is responsible, reliable, caring, kind and completely trustworthy. I recommend him without reservation.

Availability updated 15 days ago
Sitter Profile Image: Alisyn L.
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Sitter Profile Image: Alisyn L.
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Alisyn L.

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

Alisyn has been wonderful with our dog, Indy! We would highly recommend her for dog walking. She is professional, dependable, and communicative. Most importantly, she made Indy feel very comfortable right away. We greatly appreciate the Rover (Report) Cards and photos after every walk. Thank you, Alisyn!

Availability updated 76 days ago
Sitter Profile Image: Ava H.
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Sitter Profile Image: Ava H.
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Ava H.

Friendly & Flexible Dog Walker!
Madison, WI, 53719
1.4 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$16
per walk
2 reviews

Ava is a wonderful caregiver for any creature. Working with special needs families and having pets all her life make her more than qualified to handle any loved one. She is highly organized, always kind, and very dependable. You can count on Ava!

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

Animal-loving Madisonian
Midvale Heights Community, Madison, WI, 53711
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
8 reviews
2 repeat clients
Profile image

Shaina is the best! She takes great care of our two fluffballs - they love her. She’s also incredibly friendly and considerate. Would highly recommend!

Availability updated yesterday
Sitter Profile Image: Ella O.
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Sitter Profile Image: Ella O.
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Ella O.

Life is so much better with pets!
madison, WI, 53705
1.5 mi. away
Drop-In Visits, Dog Walking
from
$16
per walk
1 review

Ella has lived with pets her entire life. She has actively assisted in the care of her families 3 dogs and 2 cats. Whether it was feeding, playing, walking, or simply cuddling with them, she did it all! Ella loves all animals, is trustworthy and dependable. Ella has a soft spot for senior pets, and she even adopted a senior cat from a shelter. You can trust that your pet will get all the love and attention with Ella as their caretaker!

Availability updated 8 days ago
Sitter Profile Image: Meeka M.
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Sitter Profile Image: Meeka M.
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Meeka M.
Star Sitter

No extra charge for multiples!
Madison, WI, 53717
0.8 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
58 reviews
17 repeat clients
Profile image

Meeka was amazing! She was very thorough and made sure that Sadie had a good time on her walks! She sent lots of pictures and gave me a detailed summary of her cares. Would definitely recommend ☺️

Availability updated 40 days ago

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