Doggy Day Care in Woodland Hills, Madison, WI

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Top rated Woodland Hills doggy day care sitters

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Sitter Profile Image: Natalie B.
Verified Background Check
Natalie B.
Star Sitter
from
$30
per day
5 out of 5.0 stars
140 reviews
43 repeat clients
15 years of experience
Hill Farms-University Neighborh, Madison, WI, 53705

Natalie took great care of Zara for us. We appreciated the added walks during her stay!

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Grace H.
Sitter Profile Image: Andrew L.
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Andrew L.
Star Sitter
from
$42
per day
5 out of 5.0 stars
165 reviews
61 repeat clients
25 years of experience
Greenbush, Madison, WI, 53715

Drew is the best!!! Wilson loves him! We have been over several times he literally drags me to the door with excitement when we arrive:) I always have peace of mind leaving Wilson with Uncle Drew, anytime we go to Madison we will definitely re book.

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Sara G.
Sitter Profile Image: Elena A.
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Elena A.
from
$30
per day
5 out of 5.0 stars
111 reviews
35 repeat clients
10 years of experience
Madison, WI, 53719

Elena provided just the best care we could imagine for our puppy. Her attention to detail and her sensitivity to our puppy’s needs and developmental stage were awesome! Marley had a great time playing with Panda and Zoe. I know she will want to return. And, we will feel confident that we will be leaving her in good hands!

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Deb L.
Sitter Profile Image: Mary Z.
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Mary Z.
Star Sitter
from
$35
per day
5 out of 5.0 stars
18 reviews
8 repeat clients
10 years of experience
Regent, Madison, WI, 53726

Wolfy had such a great day with Mary and her family. He can back very happy, and Mary sent several lovely photos of his time. Mary was also flexible with me when my plans changed after booking, which was so appreciated.

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Jeff K.
Sitter Profile Image: Gen A.
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Gen A.
Star Sitter
from
$35
per day
5 out of 5.0 stars
319 reviews
191 repeat clients
7 years of experience
Middleton, WI, 53562

Amazing! Our three pups hung out for a day while we went to an event, and they had lots of fun playing together and with Gen’s dogs! Lots of pictures of their day too ☺️

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Rachel C.
Sitter Profile Image: Julie Z.
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Julie Z.
Star Sitter
from
$36
per day
5 out of 4.9 stars
20 reviews
8 repeat clients
25 years of experience
Sunset Village, Madison, WI, 53705

Julie did great job making me and my dog Stella Watson very comfortable from meet and greet thru 1st daycare visit. Stella had wonderful time playing with Zilla and zooming around the yard and house. Will be hoping to visit again soon!

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Shelby L.
Sitter Profile Image: Kristin & Bruce M.
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Kristin & Bruce M.
Star Sitter
from
$30
per day
5 out of 5.0 stars
77 reviews
21 repeat clients
2 years of experience
Madison, WI, 53719

Kilo came back very happy and sleepy from the day with Kristin and family. I got updates without having to ask, which I really appreciated. I think she had a great time and I’d trust bringing my pup back. Thanks again!!

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Kassie L.
Sitter Profile Image: Jiayi H.
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Jiayi H.
from
$30
per day
5 out of 5.0 stars
47 reviews
14 repeat clients
2 years of experience
Verona, WI, 53593

We couldn’t be more pleased with Marley’s experience with Joyce. Joyce was very good about sending photos that really reassured us that Marley was getting along nicely. Marley was so well-cared for and had such a good time! In fact, Marley laid down outside the car, as we tried to leave, as if to say, “Aw gee, do we have to go home already?”

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Deb L.
Sitter Profile Image: Polyanna N.
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Polyanna N.
Star Sitter
from
$45
per day
5 out of 5.0 stars
35 reviews
9 repeat clients
10 years of experience
Midvale Heights Community, Madison, WI, 53711

Polyanna was good with communicating throughout the day with text, pictures, and videos. She also was able to watch our dog with a 3 days notice.

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Emalie S.
Sitter Profile Image: Robert N.
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Robert N.
Star Sitter
from
$36
per day
5 out of 5.0 stars
125 reviews
44 repeat clients
20 years of experience
Orchard Ridge Community, Madison, WI, 53711

Robert is great! Our dogs had a wonderful few days of doggy daycare at Robert's home. He was very responsive and accommodating on drop-offs and pick-ups. He sent plenty of pictures and the dogs came home happy every day.

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Bryan W.
Sitter Profile Image: Lidan Y.
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Lidan Y.
from
$25
per day
10 years of experience
Verona, WI, 53593

About: I’ve always loved dogs and have been best friends with many of my friends’ and family’s pups over the years. I haven’t been able to have one of my own because I already have four sweet, healthy cats at home, but my heart has plenty of room for dogs, too. I follow dog videos every day on Instagram and TikTok and “virtually” care for so many pups through Reels—it’s my favorite part of the day. I’m excited to use Rover to finally spend time with dogs in real life, give them love, care, and fun walks, and make them feel safe and happy. I truly treat every pet like family, and I’d be honored to be your dog’s sitter or walker! I’m currently home full-time, so I have a very flexible schedule for pet sitting and drop-in visits. I’m available for morning, afternoon, and evening care every day, including weekends and holidays. I’ll always make time to give your pet lots of love, attention, and play! I live in a calm, pet-friendly home with four sweet and well-behaved cats. I make sure every pet feels safe, relaxed, and loved. I follow your care instructions closely and always provide a clean, quiet space. I’m attentive, gentle, and treat every pet as if they were my own.

Sitter Profile Image: Priyanka "Pri" T.
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Priyanka "Pri" T.
from
$49
per day
5 out of 4.8 stars
176 reviews
72 repeat clients
20 years of experience
Madison, WI, 53719

Pri took care of my 9 month old for puppy daycare when I needed to get some painting done at the house. Lily can be busy so she probably kept Pri on her toes throughout the day. Pri sent adorable pictures of their walks and Lily came home tired and happy! Looking forward to booking again in the future.

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Gina C.
Sitter Profile Image: Carli D.
Verified Background Check
Carli D.
from
$30
per day
5 out of 5.0 stars
99 reviews
41 repeat clients
10 years of experience
Westmorland, Madison, WI, 53711

Carli was so great with our pup! She sent many pics and he had a great time socializing with the other dogs, we will definitely be looking to Carli for our dog sitting needs!

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Siddartha S.
Sitter Profile Image: Isabel K.
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Isabel K.
from
$25
per day
2 years of experience
Verona, WI, 53593

About: I am a dog lover who work from home, so your pup will always have care and attention. My own sweet dog Nila loves having canine friends over to play or relax with! I'm happy to set up a meet & greet sessions beforehand. I pride myself on being highly communicative—expect lots of photo and video updates throughout the day :) I stay home Thursdays-Sundays. This means your pup will never be left alone for long stretches and can enjoy frequent potty breaks, walks, and play sessions throughout the day. We usually start the morning with a potty break and outdoor time. Midday includes more walks, visit to dog park, or play with Nila. We wrap up the evening with another outdoor break and wind-down time. Whether your dog is playful or prefers a quiet spot to relax, we’ll adjust the routine to meet their needs. We live in a quiet, dog-friendly residential area surrounded by parks, grassy trails, and trees. We live on the first floor, with quick and easy access to the outdoors, including a dog run.

Sitter Profile Image: Valeria D.
Verified Enhanced Background Check
Valeria D.
Star Sitter
from
$25
per day
5 out of 5.0 stars
15 reviews
2 repeat clients
3 years of experience
Prairie Hills, Madison, WI, 53711

Excelente, muy cariñosa con mis mascotas. 100% recomendada.

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Alberto D.
Sitter Profile Image: Bevin R.
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Bevin R.
from
$25
per day
8 years of experience
Madison, WI, Madison, WI, 53717

About: I've had dogs all my life, of all shapes and sizes. Happy to work with you to meet all the needs of your little critter. I work from home so I am quite flexible and can come visit most times of the day. I also stay up late so late night visits are fine. Honestly, I am happy to work with you. Each pet is different, so if your pet has specific needs, I'm happy to do what will make them comfortable and happy.

Sitter Profile Image: Holly T.
Verified Background Check
Holly T.
from
$40
per day
5 out of 4.5 stars
12 reviews
3 repeat clients
20 years of experience
Middleton, WI, 53562

Holly was very receptive to caring for our dog on short notice when we had to be in Madison for a family member’s hospitalization. The home, fenced in yard, companionship of their dog Mocha was wonderful for our little guy. I could tell he was exercised and loved while in her care.

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Denise F.
Sitter Profile Image: Ava B.
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Ava B.
from
$28
per day
5 out of 5.0 stars
10 reviews
2 repeat clients
5 years of experience
Madison, WI, 53719

Ava was very welcoming to my dog and my dog had no problem getting along with her. She responds fast and sent updates throughout the day.

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Ting Hei Dilys Y.
Sitter Profile Image: Helen S.
Verified Enhanced Background Check
Helen S.
Star Sitter
from
$28
per day
5 out of 5.0 stars
17 reviews
6 repeat clients
5 years of experience
Hill Farms-University Neighborh, Madison, WI, 53705

Helen and her mom were so great to my pup Rooster. They took him on two walks and sent several pictures, which put my mind at ease. Definitely recommend!

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Grace H.
Sitter Profile Image: Naomi M.
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Naomi M.
from
$25
per day
5 out of 5.0 stars
4 reviews
1 repeat client
2 years of experience
Middleton, WI, 53562

About: I regularly walk and check in on a dog four times a week and have pet sat for several families. I’ve also helped care for my grandma’s dog over the years. I’m reliable, patient, and always make sure pets feel safe and cared for. I am currently on summer break, so I have a pretty high availability to care for pets — through boarding, quick walks, drop in visits, etc! I provide a calm, safe environment and always follow care instructions closely. Though I don’t have a fenced yard, I’m comfortable caring for dogs and cats — supervising pets carefully to ensure their safety and comfort at all times.

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Sitter Profile Image: Natalie B.
Verified Background Check
Sitter Profile Image: Natalie B.
Verified Background Check

Natalie B.
Star Sitter

Stress-Free Trips Start with Me!
Hill Farms-University Neighborh, Madison, WI, 53705
1.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$30
per day
5 out of 5.0 stars
140 reviews
43 repeat clients
Profile image

Natalie took great care of Zara for us. We appreciated the added walks during her stay!

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

Andrew L.
Rover 101
Star Sitter

Looking for a fur baby to love! 💜
Greenbush, Madison, WI, 53715
5.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$42
per day
5 out of 5.0 stars
165 reviews
61 repeat clients
Profile image

Drew is the best!!! Wilson loves him! We have been over several times he literally drags me to the door with excitement when we arrive:) I always have peace of mind leaving Wilson with Uncle Drew, anytime we go to Madison we will definitely re book.

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

Elena A.

Loving Canine Care
Madison, WI, 53719
4.0 mi. away
Boarding, Doggy Day Care
from
$30
per day
5 out of 5.0 stars
111 reviews
35 repeat clients
Profile image

Elena provided just the best care we could imagine for our puppy. Her attention to detail and her sensitivity to our puppy’s needs and developmental stage were awesome! Marley had a great time playing with Panda and Zoe. I know she will want to return. And, we will feel confident that we will be leaving her in good hands!

Availability updated 2 days ago
Sitter Profile Image: Mary Z.
Verified Enhanced Background Check
Sitter Profile Image: Mary Z.
Verified Enhanced Background Check

Mary Z.
Star Sitter

Dog-loving home
Regent, Madison, WI, 53726
3.9 mi. away
Boarding, Doggy Day Care
from
$35
per day
5 out of 5.0 stars
18 reviews
8 repeat clients
Profile image

Wolfy had such a great day with Mary and her family. He can back very happy, and Mary sent several lovely photos of his time. Mary was also flexible with me when my plans changed after booking, which was so appreciated.

Availability updated 5 days ago
Sitter Profile Image: Gen A.
Verified Background Check
Sitter Profile Image: Gen A.
Verified Background Check

Gen A.
Rover 101
Star Sitter

Not your average pet care service!
Middleton, WI, 53562
4.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 5.0 stars
319 reviews
191 repeat clients
Profile image

Amazing! Our three pups hung out for a day while we went to an event, and they had lots of fun playing together and with Gen’s dogs! Lots of pictures of their day too ☺️

Availability updated 9 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Julie Z.
Verified Enhanced Background Check
Sitter Profile Image: Julie Z.
Verified Enhanced Background Check

Julie Z.
Star Sitter

I let dogs be dogs!
Sunset Village, Madison, WI, 53705
2.7 mi. away
Boarding, Doggy Day Care
from
$36
per day
5 out of 4.9 stars
20 reviews
8 repeat clients
Profile image

Julie did great job making me and my dog Stella Watson very comfortable from meet and greet thru 1st daycare visit. Stella had wonderful time playing with Zilla and zooming around the yard and house. Will be hoping to visit again soon!

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Kristin & Bruce M.
Verified Enhanced Background Check
Sitter Profile Image: Kristin & Bruce M.
Verified Enhanced Background Check

Kristin & Bruce M.
Star Sitter

100% Pawtastic dog sitting
Madison, WI, 53719
5.4 mi. away
Boarding, Doggy Day Care
from
$30
per day
5 out of 5.0 stars
77 reviews
21 repeat clients
Profile image

Kilo came back very happy and sleepy from the day with Kristin and family. I got updates without having to ask, which I really appreciated. I think she had a great time and I’d trust bringing my pup back. Thanks again!!

Availability updated 3 days ago
Sitter Profile Image: Jiayi H.
Verified Enhanced Background Check
Sitter Profile Image: Jiayi H.
Verified Enhanced Background Check

Jiayi H.

Welcome to Pooch Paradise!
Verona, WI, 53593
3.4 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5 out of 5.0 stars
47 reviews
14 repeat clients
Profile image

We couldn’t be more pleased with Marley’s experience with Joyce. Joyce was very good about sending photos that really reassured us that Marley was getting along nicely. Marley was so well-cared for and had such a good time! In fact, Marley laid down outside the car, as we tried to leave, as if to say, “Aw gee, do we have to go home already?”

Availability updated 2 days ago
Sitter Profile Image: Polyanna N.
Verified Enhanced Background Check
Sitter Profile Image: Polyanna N.
Verified Enhanced Background Check

Polyanna N.
Star Sitter

Giant fun!
Midvale Heights Community, Madison, WI, 53711
2.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per day
5 out of 5.0 stars
35 reviews
9 repeat clients
Profile image

Polyanna was good with communicating throughout the day with text, pictures, and videos. She also was able to watch our dog with a 3 days notice.

Availability updated 2 days ago
Sitter Profile Image: Robert N.
Verified Enhanced Background Check
Sitter Profile Image: Robert N.
Verified Enhanced Background Check

Robert N.
Star Sitter

I'll do the walking!
Orchard Ridge Community, Madison, WI, 53711
3.2 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$36
per day
5 out of 5.0 stars
125 reviews
44 repeat clients
Profile image

Robert is great! Our dogs had a wonderful few days of doggy daycare at Robert's home. He was very responsive and accommodating on drop-offs and pick-ups. He sent plenty of pictures and the dogs came home happy every day.

Availability updated 8 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Lidan Y.
Verified Enhanced Background Check
Sitter Profile Image: Lidan Y.
Verified Enhanced Background Check

Lidan Y.

Your Dog’s New Best Friend
Verona, WI, 53593
3.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per day
10 years of experience

About: I’ve always loved dogs and have been best friends with many of my friends’ and family’s pups over the years. I haven’t been able to have one of my own because I already have four sweet, healthy cats at home, but my heart has plenty of room for dogs, too. I follow dog videos every day on Instagram and TikTok and “virtually” care for so many pups through Reels—it’s my favorite part of the day. I’m excited to use Rover to finally spend time with dogs in real life, give them love, care, and fun walks, and make them feel safe and happy. I truly treat every pet like family, and I’d be honored to be your dog’s sitter or walker! I’m currently home full-time, so I have a very flexible schedule for pet sitting and drop-in visits. I’m available for morning, afternoon, and evening care every day, including weekends and holidays. I’ll always make time to give your pet lots of love, attention, and play! I live in a calm, pet-friendly home with four sweet and well-behaved cats. I make sure every pet feels safe, relaxed, and loved. I follow your care instructions closely and always provide a clean, quiet space. I’m attentive, gentle, and treat every pet as if they were my own.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Priyanka "Pri" T.
Verified Background Check
Sitter Profile Image: Priyanka "Pri" T.
Verified Background Check

Priyanka "Pri" T.

Poodle Paws love and care for pups!
Madison, WI, 53719
4.0 mi. away
Boarding, Doggy Day Care
from
$49
per day
5 out of 4.8 stars
176 reviews
72 repeat clients
Profile image

Pri took care of my 9 month old for puppy daycare when I needed to get some painting done at the house. Lily can be busy so she probably kept Pri on her toes throughout the day. Pri sent adorable pictures of their walks and Lily came home tired and happy! Looking forward to booking again in the future.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Carli D.
Verified Background Check
Sitter Profile Image: Carli D.
Verified Background Check

Carli D.

Home full time pet lover
Westmorland, Madison, WI, 53711
3.0 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5 out of 5.0 stars
99 reviews
41 repeat clients
Profile image

Carli was so great with our pup! She sent many pics and he had a great time socializing with the other dogs, we will definitely be looking to Carli for our dog sitting needs!

Availability updated today
Sitter Profile Image: Isabel K.
Verified Enhanced Background Check
Sitter Profile Image: Isabel K.
Verified Enhanced Background Check

Isabel K.

WFH + Social Pup + Updates!
Verona, WI, 53593
3.3 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per day
2 reviews

I couldn’t be more grateful for the care and love Isabel gives to pets! She’s incredibly attentive and genuinely passionate about animals. She takes care of everything, from meals and playtime to the little quirks that make my Luna unique. It’s such a relief knowing my pet is in loving, capable hands. I can clearly see how much Luna adores her, and that kind of bond doesn’t happen by chance. It comes from kindness, patience, and true affection. I highly recommend Isabel to anyone looking for someone who will care for their pet as if it were her own!

Availability updated 3 days ago
Sitter Profile Image: Valeria D.
Verified Enhanced Background Check
Sitter Profile Image: Valeria D.
Verified Enhanced Background Check

Valeria D.
Star Sitter

Dog: Best friend you'll ever have💘
Prairie Hills, Madison, WI, 53711
3.2 mi. away
Boarding, Doggy Day Care
from
$25
per day
5 out of 5.0 stars
15 reviews
2 repeat clients
Profile image

Excelente, muy cariñosa con mis mascotas. 100% recomendada.

Availability updated 3 months ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Bevin R.
Verified Enhanced Background Check
Sitter Profile Image: Bevin R.
Verified Enhanced Background Check

Bevin R.

Any pet is ok.
Madison, WI, Madison, WI, 53717
0.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$25
per day
8 years of experience

About: I've had dogs all my life, of all shapes and sizes. Happy to work with you to meet all the needs of your little critter. I work from home so I am quite flexible and can come visit most times of the day. I also stay up late so late night visits are fine. Honestly, I am happy to work with you. Each pet is different, so if your pet has specific needs, I'm happy to do what will make them comfortable and happy.

Availability updated 5 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Holly T.
Verified Background Check
Sitter Profile Image: Holly T.
Verified Background Check

Holly T.

Dog lover my whole life!
Middleton, WI, 53562
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care
from
$40
per day
5 out of 4.5 stars
12 reviews
3 repeat clients
Profile image

Holly was very receptive to caring for our dog on short notice when we had to be in Madison for a family member’s hospitalization. The home, fenced in yard, companionship of their dog Mocha was wonderful for our little guy. I could tell he was exercised and loved while in her care.

Availability updated today
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Ava B.
Verified Enhanced Background Check
Sitter Profile Image: Ava B.
Verified Enhanced Background Check

Ava B.

I love animals and makin em smile
Madison, WI, 53719
2.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$28
per day
5 out of 5.0 stars
10 reviews
2 repeat clients
Profile image

Ava was very welcoming to my dog and my dog had no problem getting along with her. She responds fast and sent updates throughout the day.

Availability updated 2 days ago
Confirmed availability for Labor Day Weekend
Sitter Profile Image: Helen S.
Verified Enhanced Background Check
Sitter Profile Image: Helen S.
Verified Enhanced Background Check

Helen S.
Star Sitter

Flexible Madison sitter😸❤️
Hill Farms-University Neighborh, Madison, WI, 53705
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$28
per day
5 out of 5.0 stars
17 reviews
6 repeat clients
Profile image

Helen and her mom were so great to my pup Rooster. They took him on two walks and sent several pictures, which put my mind at ease. Definitely recommend!

Availability updated 2 days ago
Sitter Profile Image: Naomi M.
Verified Enhanced Background Check
Sitter Profile Image: Naomi M.
Verified Enhanced Background Check

Naomi M.

Reliable Dog Walker & Boarder!
Middleton, WI, 53562
1.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per day
5 out of 5.0 stars
4 reviews
1 repeat client

About: I regularly walk and check in on a dog four times a week and have pet sat for several families. I’ve also helped care for my grandma’s dog over the years. I’m reliable, patient, and always make sure pets feel safe and cared for. I am currently on summer break, so I have a pretty high availability to care for pets — through boarding, quick walks, drop in visits, etc! I provide a calm, safe environment and always follow care instructions closely. Though I don’t have a fenced yard, I’m comfortable caring for dogs and cats — supervising pets carefully to ensure their safety and comfort at all times.

Availability updated today

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