Dog Walkers in Winston, FL

Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Winston dog walkers

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Kylee E.
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Kylee E.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
176 reviews
57 repeat clients
8 years of experience
Cleveland Heights, Lakeland, FL, 33803

Kylee is awesome! I shopped around for a while and couldn't find the right match.My Sadie is very protective and she has been very sheltered so she doesn't care for too many people but she took to Kylie right away! she loves her! She is very prompt and very trustworthy ! She is capable of doing any type of service that you need! Even though I would like to keep her all to myself she could benefit other people as well! Highly recommended!

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Kris S.
Sitter Profile Image: Megan D.
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Megan D.
from
$20
per walk
5.0 out of 5 stars
3 reviews
1 repeat client
12 years of experience
Lakeland, FL, 33815

About: I am experienced, responsible, friendly and loved by pets of all ages. Get reliable pet sitting from someone who’s raised a Westie and wrangled puppies. I live and work locally in Lakeland. Available for midday walks and sitting evenings/weekends. I am happy to provide snuggles, walks, park trips, feeding and treats. I previously worked in a pet store providing care for puppies and I currently have a 12 year old Westie. She is very friendly & loves to play with other animals.

Sitter Profile Image: Joshua G.
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Joshua G.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
234 reviews
47 repeat clients
15 years of experience
Plant City, FL, 33563

I can’t thank Joshua enough for the wonderful care he’s given Melvin. He’s been incredibly patient and understanding with my pup, and it’s clear that he genuinely cares about animals. Highly recommend Joshua to anyone looking for a reliable, kind, and attentive dog walker!

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Sarah H.
Sitter Profile Image: Bri S.
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Bri S.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
57 reviews
21 repeat clients
15 years of experience
plant city, FL, 33565

Bri is great! I just moved to the area and I’m so glad I found her. Bri takes lots of photos during her visits and leaves great feedback and notes. I will continue to use Bri as my go to dog walker!

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Ashlee G.
Sitter Profile Image: Ruth M.
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Ruth M.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
188 reviews
92 repeat clients
34 years of experience
Lakeland, FL, 33801

Ruth is always quick to respond to my messages and is very reliable. She makes sure to keep my updated on my girl’s status when she walks her and always sends me pictures. She’s flexible and understanding as well. I’m very happy and lucky to have found her since I moved to a new area.

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Cherise G.
Sitter Profile Image: Rachelle S.
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Rachelle S.
from
$25
per walk
5.0 out of 5 stars
83 reviews
9 repeat clients
2 years of experience
Dixieland, Lakeland, FL, 33803

Rachelle was so responsive and made me feel so comfortable! It is my first time ever using Rover & I’m glad that she was available. Definitely will be using her services again! Highly recommend!

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Alyssia L.
Sitter Profile Image: Lauren L.
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Lauren L.
from
$12
per walk
5.0 out of 5 stars
5 reviews
10 years of experience
Parker Street, Lakeland, FL, 33801

About: I’ve grown up around animals my entire life and have experience caring for dogs, cats, and multiple pets at once. I regularly cared for a household with five dogs, so I’m very comfortable managing different personalities, routines, and energy levels. I’m also a pet owner myself (one dog and two cats), so I truly understand how important it is to have someone you trust caring for your pets. I treat every animal like my own and focus on keeping them safe, comfortable, and stress-free while you’re away. I’m reliable, very responsive, and available for last-minute bookings when needed. I’m happy to follow detailed instructions, send updates/photos, and make sure you feel completely at ease while you’re gone. I work full time but I am remote, so taking time during the day is no problem in addition to availability in the mornings and evenings. I’m happy to provide care in your home, where pets are most comfortable and can stick to their normal routines. Whether that includes feeding, walks, playtime, medications, or just companionship, I’m committed to making your time away stress-free for both you and your pets. I’m very respectful of your space and privacy, and I also provide updates and photos so you can feel at ease while you’re away. I’m also happy to help with small extras like bringing in mail or watering plants.

Sitter Profile Image: Pennie A.
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Pennie A.
from
$15
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
30 years of experience
Lakeland, FL, 33815

About: I've owned and cared for all types of dogs. I've walked and cared for large and small. I've experenced easy, well trained to the most challenging. I love them all. I'm retired, so I can easily work in walks, drop-ins, and sittings during my days. Most days I'm available after 10 A.M., but I'm flexible. I only do care at the pet parent's house, and I follow the guidelines the pet-parent sets because routines are important for consistency. I will always respect your home.

Sitter Profile Image: Alexandre S.
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Alexandre S.
from
$20
per walk
5.0 out of 5 stars
60 reviews
18 repeat clients
25 years of experience
Lakeland, FL, 33811

My dogs look forward to their walks with Alex 😍

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Calinda P.
Sitter Profile Image: Mercedes D.
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Mercedes D.
from
$20
per walk
5.0 out of 5 stars
8 reviews
1 repeat client
3 years of experience
Lakeland, FL, 33811

About: I’ve taken care of many pets whether it was mine family or friends. I really enjoy having fur babies around I live by myself so it’s good company/fun I’m home full time. I do work from home but it doesn’t get in the way of the care for your babies. I have my own and he’s very happy. I live in a gated community. Lots of trail walks inside the community also DOG PARK ! Your baby will be safe with me. Can’t wait to see them all !

Sitter Profile Image: Rosemary S.
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Rosemary S.
Star Sitter
from
$15
per walk
4.9 out of 5 stars
13 reviews
9 repeat clients
50 years of experience
Plant City, FL, 33563

Rosemary has been an incredibly dependable and caring dog walker for my senior dog, Lola. She shows up on time, communicates clearly, and handles Lola’s aging needs with such patience and compassion. Her gentle bedside manner gives me real peace of mind, knowing Lola is in thoughtful and capable hands. I’m truly grateful for the care she provides and highly recommend her to anyone with an older or special-needs pup.

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Gabriel A.
Sitter Profile Image: Mattison K.
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Mattison K.
from
$13
per walk
5 years of experience
Cleveland Heights, Lakeland, FL, 33803

About: I grew up with animals my whole life. I know how to read body language, I have experience taking care of puppies and senior dogs! As well as cats. I know how to meditate them as well! I’ve worked at a vet clinic for a little over a year. I also am a pet sitter for friends, family, mutual friends, stuff like that! I’m very experienced in the animal field! I loveeee animals!! I’m currently looking for a new animal job! So my schedule would be completely open! I have open availability, whether you guys would want me to overnight watch your babies, or early morning, and or mid day! I’m open to anything that fits my clients schedule!! I strive to keep your pet’s routine as normal and stress-free as possible while you’re away. I will follow all care instructions, provide plenty of love, attention, exercise, and playtime, and make sure your pet feels safe and comfortable in their own environment. I also provide regular updates and photos so you can have peace of mind while you’re away!

Sitter Profile Image: Olivia S.
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Olivia S.
from
$10
per walk
8 years of experience
Plant City, FL, 33563

About: I have had animals my entire life and caring for them has always been a huge part of who I am. Over the years, I've cared for pets of all sizes, personalities, and energy levels-from high energy pups who need lots of playtime to older pets who prefer a slower pace and extra TLC. I'm well versed in basic pet first aid and always pay close attention to behavior, appetite, and overall well-being, so you can feel confident your pet is in safe capable hands. I know how important peace of mind is when you're away, and i take that responsibility seriously. At home, I have a very full (and very spoiled) house-one dog, two cats, and a guinea pig- so I'm used to managing different routines personalities and needs. Whether your pet needs long walks, playtime, or just someone to keep them company, I'll treat them like one of my own-with plenty of attention, care and extra belly rubs! This is currently my main focus so i have a completely open schedule to accommodate pet parents that may need me at all hours based on their needs I have access to several dog friendly parks and trails near my home as well as a crew cab truck so even the largest dogs can enjoy a ride. I also keep a dog seatbelt and pet friendly steps in the truck in case anyone needs a little extra hand getting in

Sitter Profile Image: Zachary H.
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Zachary H.
from
$18
per walk
15 years of experience
Lakeland, FL, 33811

About: I have had pets my entire life. From puppies to old dogs all shapes and sizes. Love all animals and will care for your pet like it’s my own. I am currently home for summer as a college kid. I have a dog of my own so I take care of her. Your pet will be my first priority. I will take care of the pet by following the owners instructions and knowledge from years of caring for my own pets. Making sure that they are comfortable and having fun.

Sitter Profile Image: Nicole P.
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Nicole P.
from
$18
per walk
5.0 out of 5 stars
13 reviews
7 repeat clients
10 years of experience
Lakeland, FL, 33815

Nicole is awesome! She took amazing care of our puppy and didn’t mind the big puppy energy lol

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Nicholas N.
Sitter Profile Image: Serenah V.
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Serenah V.
from
$21
per walk
5.0 out of 5 stars
87 reviews
28 repeat clients
6 years of experience
Lakeland, FL, 33811

Serenah was excellent! She is great with my baby ?she followed my instructions, communicated well with me, and she went above and beyond and accommodated a last minute time change I needed and instructions changes. I will be calling opon her regularly to watch my doggie thank you! ?

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Mary E.
Sitter Profile Image: Sabrina G.
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Sabrina G.
from
$15
per walk
5.0 out of 5 stars
24 reviews
7 repeat clients
5 years of experience
Lake Bonnet, Lakeland, FL, 33815

About: I’ve had hamsters, dogs, cats. They were mainly family pets but I also taken care of pets on another website. I’m excited to learn about your pet and gain more experience! I’ve also volunteered for spca and love all kinds of pets. I am also a mother of an 8 month old and pets should be no different. I have taken care of snakes, turtles, Guinea pigs, hamsters, cats, dogs, and birds! I work as well as pet sitting so we can discuss if my schedule is good for you. I’m available even for last minute bookings as long as I have an opening. I have a fenced back yard and a large crate. Dogs bowls and lick pads for your animals! Fresh water and food is always available.

Sitter Profile Image: Sarah p.
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Sarah p.
from
$17
per walk
8 years of experience
Lakeland, FL, 33811

About: Hi! I'm Sarah, and passionate and experienced dog and animal lover who has been caring for dogs since I was 10 years old. I treat every pet like family and always make sure they feel comfortable, safe, and loved while you're away. I have experience with dogs of all ages including puppies as young as 7 weeks and senior dogs who are blind, deaf, and require frequent medication. I am very patient and attentive, and I'm happy to follow your pets routine closely-whether that includes exercise, feeding, medication, or special care instructions. I have cared for a wide variety of breeds including labs, miniature schnauzers, yorkies, chihuahuas, pitbulls, rottweilers, german shepherds, golden retrievers and more. Im comfortable with dogs of all sizes and energy levels, from high-energy pups to relaxed and calm dogs. You can expect regular updates about your pet which include photos and communication so you always know how your pet is doing. I am available on weekends and have a flexible schedule. I would love to meet and greet your pet- feel free to reach out anytime if you would like to set that up! I am currently working part time- so I am available most of the time including weekends! The only day I have obligations is Sunday until 1pm- but if needed that can change. I am able to crate dogs if needed, I am able to take care of dogs in any home type- I can accommodate any requirements.

Sitter Profile Image: Nicole R.
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Nicole R.
from
$15
per walk
3 years of experience
Lake Hollingsworth, Lakeland, FL, 33803

About: As a senior UCF and a passionate animal lover, I bring hands-on experience with both dogs and cats to every pet sitting in opportunity. I am also involved in STEP UCF, a club that is dedicated to training future service dogs and has given me valuable skills in reinforcing commands and working with puppies. Using I learned in my club I am able to practice obedience training, ensuring your pets receive consistent care and positive reinforcement. With a flexible schedule and genuine love for animal, I’m committed to providing attentive trustworthy care for your furry friends. I am currently taking online summer classes, so I have full availability to take your pets on long walks and play all day. Regardless if your pup has lots of energy that needs to be let out or just needs company I am available. I love to really get to know both pet and owner. Whether it’s that there is a specific location they like to go on walks or they have a special routine for eating. I make sure to clean whatever I’m using to prepare the meal. And I am very patient with shy animals that need some time to warm up to strangers.

Sitter Profile Image: Erika L.
Verified Enhanced Background Check
Erika L.
from
$20
per walk
5.0 out of 5 stars
84 reviews
25 repeat clients
13 years of experience
Plant City, FL, 33566

Wonderful, obviously a dog lover and charmer. So thankful and appreciative. Got lots of pictures showing how much fun he had with Erika, definitely recommend 🙂

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Jessica H.
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Winston dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Alison was punctual for the visits with Holly which was a huge relief for me while being away. She sent daily pictures and administered Holly’s medication. My house was just as I left it when I returned. I would use Alison for future visits without hesitation.

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Kathy B.
Dog Walking
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The median cost per walk for dog walking in Winston is $20

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Sitters in Winston average 3
repeat dog walking clients

Dog Walking FAQs

Frequently asked questions about Rover

Dog walkers on Rover are free to set their rates. The median cost to hire a dog walker in Winston on Rover as of Jun 2026 was about $20 per walk, after factoring in Rover’s service fees. A dog walker’s rate may also change as you customize your booking to fit your and your dog’s needs.

If you’re searching for a Winston dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 2,526 dog walkers in Winston. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, dog walkers joining Rover must pass a background check for you and your dog’s safety.

Rover makes it easy to reach out to multiple dog walkers about your booking. Typically, 87% of Winston dog walkers respond in under an hour.

Dog walkers in Winston have an average of 14 years of experience. Dog walkers with repeat customers have an average of 3 repeat clients. Experience can vary from dog walker to dog walker, but you can view reviews, years of experience, and number of repeat clients when you compare dog walkers in Winston.

You can’t always predict a super busy day at work, but you can anticipate your dog’s needs. Instead of rushing home at lunch, book a dog walker to give your dog a 30- or 60-minute dog walk. Your dog walker can stop by as many times as you need—on whatever days you need them. With the Rover app, get a comprehensive Rover Card from your dog walker that includes:

  • Start and stop times
  • A map of their walk with total distance
  • Pee, poo, food, and water breaks
  • Cute photos and a personalized note

There are 2,526 dog walkers in Winston on Rover, so you’re sure to find the perfect match for your dog! In Winston, 91% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog walker near you. As a reminder, all dog walkers on Rover have been background checked for you and your dog’s safety.

Yes! Dog walkers joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog walker through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog walker has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your dog walker requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your dog walking service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog walker’s cancellation policy.