Dog Walking in Winter Park

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Sitter Profile Image: Ryan S.
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Sitter Profile Image: Ryan S.
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1. Ryan S.

Loving Care, When You Need It!
Baldwin Park, Orlando, FL, 32814
2.2 mi. away
Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
6 reviews
4 repeat clients
Profile image

Ryan is awesome!! He’s been taking care of my dogs for years. My dogs love him!

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Cheyenne L.
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Sitter Profile Image: Cheyenne L.
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2. Cheyenne L.

Star Sitter
I love pups of all shapes and sizes
Orlando, FL, 32807
3.7 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
16 reviews
7 repeat clients
Profile image

Fantastic! Super responsive and respectful. Cheyenne has a passion for animals and takes good care of my baby. She communicates well and take the BEST pictures! I would recommend to anyone and even additional services!

Availability updated 8 days ago
Sitter Profile Image: Rebecca A.
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Sitter Profile Image: Rebecca A.
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3. Rebecca A.

Animals Make Everyday Brighter
Maitland, FL, 32751
3.3 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
116 reviews
40 repeat clients
Profile image

Rebecca helps me with all my pets. She even went with me to pick up my Irish Setter puppy from boarding after I had surgery, since I was too weak to handle him. I really appreciated her willingness to help me with this situation.

Availability updated 10 days ago
Sitter Profile Image: Ariana M.
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Sitter Profile Image: Ariana M.
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4. Ariana M.

Rover 101
Star Sitter
Your pet's second best friend!
Casselberry, FL, 32707
2.8 mi. away
Drop-In Visits, Dog Walking
from
$16
per walk
5 out of 5.0 stars
29 reviews
11 repeat clients
Profile image

Ariana was really attentive and in constant communication with me which was really amazing. She also kept my dog company which was really sweet. Her responses are quick and she was available to help with all the little annoying requests I had like leaving the tv on for my pup, the fan, filling her water etc. I really do recommend her and I’m happy to have found someone reliable for all my future bookings! Thank you again Ariana :)

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Tatiana M.
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Sitter Profile Image: Tatiana M.
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5. Tatiana M.

Rover 101
Star Sitter
They deserve the best and more
Casselberry, FL, 32707
3.7 mi. away
Boarding, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
157 reviews
77 repeat clients
Profile image

Tatiana took care of my two senior dachshunds this week after their dental surgery. We did a meet & greet at my home one night and then booked for the following 3 days of walks. Everything went well, as expected and I plan to book with her again soon.

Availability updated 8 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Meg T.
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Sitter Profile Image: Meg T.
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6. Meg T.

Star Sitter
Loving sitter for your fur baby!
Maitland, FL, 32751
2.3 mi. away
Drop-In Visits, Dog Walking
from
$18
per walk
5 out of 5.0 stars
132 reviews
49 repeat clients
Profile image

Meg did an amazing job caring for my pups this past weekend sending photos and keeping prompt and detailed timing of her visits. I felt comfortable and that my pups were in good hands! There was a beautiful touch of printed photos of my pups waiting for me when I got home from my trip. Above and beyond is my review, in summary! I’ll be booking with her again and I highly recommend her service.

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Courtney K.
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Sitter Profile Image: Courtney K.
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7. Courtney K.

Pet lover since birth!
Winter Park, FL, 32792
3.6 mi. away
Drop-In Visits, Dog Walking
from
$14
per walk
3 reviews

I am happy to recommend Courtney Kaelin for any dog-sitting or dog-walking opportunity. Her love for animals has been shown through a variety of meaningful experiences. She grew up with two dogs, giving her a natural comfort and familiarity with pet care from an early age. To earn community service hours, she volunteered at an animal shelter working closely with dogs of all breeds and temperaments. She also cared for a horse while taking riding lessons, showing her responsibility and dedication to animal well-being. Additionally, Courtney gained valuable professional experience working at a veterinary office, where she further developed her skills in handling and caring for animals in a clinical setting. Courtney Kaelin is a hard worker who takes every responsibility seriously. She will always go the extra mile to ensure the animals in her care are safe, comfortable, and happy. Her compassion, reliability, and strong work ethic make her an excellent choice for anyone seeking a trustworthy and caring pet sitter or dog walker.

Availability updated 2 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Erin M.
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Sitter Profile Image: Erin M.
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8. Erin M.

Star Sitter
Full Time Dog-Lover
Maitland, FL, 32751
2.1 mi. away
Drop-In Visits, Dog Walking
from
$13
per walk
5 out of 5.0 stars
7 reviews
2 repeat clients
Profile image

Erin has been such a blessing for us! We both have a busy schedule right now and she has been able to help us immensely with our puppy. She’s so easy to communicate with, she always lets us know changes in schedule way in advance and she is AMAZING with Brody. We are so so happy we found her and can’t recommend her enough!!

Availability updated 3 days ago
Sitter Profile Image: Maya C.
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Sitter Profile Image: Maya C.
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9. Maya C.

Care for Pets, Anytime
Winter Park, FL, 32792
1.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$14
per walk
3 reviews
1 repeat client
Profile image

Super sweet and did great with my pup! Definitely a great choice!

Availability updated 11 days ago
Sitter Profile Image: Natalie D.
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Sitter Profile Image: Natalie D.
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10. Natalie D.

Rover 101
Vet Tech + Clinic Supervisor 🐾
Winter Park, FL, 32789
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per walk
5 out of 4.9 stars
77 reviews
29 repeat clients
Profile image

Natalie was great. Meet with us the night prior for a meet & greet! Took great care of Luna and kept us up to date with A+ photos!

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Julie L.
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Sitter Profile Image: Julie L.
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11. Julie L.

Star Sitter
Teacher, pet pal, remote worker
Fern Park, FL, 32730
3.4 mi. away
Drop-In Visits, Dog Walking
from
$15
per walk
5 out of 5.0 stars
9 reviews
5 repeat clients
Profile image

We couldn’t ask for a better dog walker than Julie! She’s been walking our dog Jovie for a couple weeks now, and it’s clear how much she truly cares. Julie is reliable, kind, and always goes the extra mile—whether it’s making sure Jovie gets a good walk, keeping us updated with adorable photos, or just giving her a little extra love and attention. Jovie absolutely adores her, and we have total peace of mind knowing she’s in such good hands.

Availability updated 22 days ago
Sitter Profile Image: Kimberly H.
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Sitter Profile Image: Kimberly H.
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12. Kimberly H.

Star Sitter
Experienced and Caring
Orlando, FL, 32804
3.2 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$19
per walk
5 out of 5.0 stars
4 reviews
3 repeat clients
Profile image

Kimberly is fantastic! Very communicative and attentive. She spent time playing with my dog after walks and sent great photos. I didn’t have to worry about a thing! I would definitely recommend her to anyone!

Availability updated 7 days ago
Sitter Profile Image: Sally O.
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Sitter Profile Image: Sally O.
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13. Sally O.

Tail-Wagging Care for Your Fur Baby
Winter Park, FL, 32789
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
24 reviews
8 repeat clients
Profile image

Sally is great!! Lily loves her! She always spends time with Lily and takes the best pictures! Definitely recommend!

Availability updated today
Sitter Profile Image: Victoria A.
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Sitter Profile Image: Victoria A.
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14. Victoria A.

Keeping your pets safe and happy!
Winter Park, FL, 32792
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$13
per walk
2 reviews

Victoria treated my dog like it was her own - and I'm VERY particular. She is communicative, sends photos, and is punctual. Truly can't say enough good things about the way she cares for my baby.

Availability updated 3 days ago
Sitter Profile Image: Renee P.
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Sitter Profile Image: Renee P.
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15. Renee P.

Star Sitter
caring for pets is my passion
maitland, FL, 32751
2.4 mi. away
Drop-In Visits, Dog Walking
from
$20
per walk
5 out of 5.0 stars
33 reviews
9 repeat clients
Profile image

Renee was really nice and responded to messages quickly. She showed up on time and took really cute pictures of my dog while they were walking and playing together. The report cards were really cute and I was so happy to receive them while I was at work. Thank you for caring for my poodle girl Renee

Availability updated today
Sitter Profile Image: Roxsanna P.
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Sitter Profile Image: Roxsanna P.
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16. Roxsanna P.

All around animal lover !
Winter Park, FL, 32789
1.7 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
from
$38
per walk
5 out of 5.0 stars
24 reviews
8 repeat clients
Profile image

Savannah and I love Roxsanna!

Availability updated today
Sitter Profile Image: Kyle G.
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Sitter Profile Image: Kyle G.
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17. Kyle G.

Will love your baby like my own!
Winter Park, FL, 32792
1.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$18
per walk
5 out of 5.0 stars
9 reviews
Profile image

Kyle was a perfect fit for our needs in taking care of our pups. I had the feeling of dependability right from the start. I received photos right on time. I would recommend Kyle and look forward to having him sit for our dogs again in the future.

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: David W.
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Sitter Profile Image: David W.
Verified Enhanced Background Check

18. David W.

Star Sitter
Dog and cat whisperer
Winter Park, FL, 32789
0.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
from
$25
per walk
5 out of 5.0 stars
88 reviews
37 repeat clients
Profile image

David was great with our guys! In addition he was always on time & kept us posted on everything we needed to know of their time together. We definitely felt our they were in good hands!

Availability updated 9 days ago
Sitter Profile Image: Megan P.
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Sitter Profile Image: Megan P.
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19. Megan P.

Lifelong pet owner and lover!
Winter Park, FL, 32789
0.4 mi. away
Drop-In Visits, Dog Walking
from
$15
per walk
7 years of experience

About: I’ve taken care of pets since I was 13. My family has needed me to take care of my pets that required special attention such as medicines and shots. Family and friends have asked me to take care and walk their dogs frequently. I’m currently a college student at home for the summer and looking to make some extra money for when I go back to campus. I am free during the week and weekends, allowing flexibility for time and days. I would love to take your dogs for a walk or hang out with them! In my own home, I take care of my dog every day. I take her out, play with her, and take her on walks while my parents are at work. I love giving my dog a lot of attention as well. I would treat your dogs as my own.

Availability updated 5 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Brittany P.
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Sitter Profile Image: Brittany P.
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20. Brittany P.

Cozy home, Giant Yard, Lots of Love
Winter Park, FL, 32789
0.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$20
per walk
5 out of 4.8 stars
207 reviews
98 repeat clients
Profile image

It was comforting having Brittany check in our or new pup during our work days. Also, loved that she has experience with training. Our dog was in good hands. 5 stars and a definite for booking Brittany in the future.

Availability updated today
Confirmed availability for Juneteenth Weekend

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