Dog Walking Winston

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

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Over 14
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Winston, Find top rated dog walking

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: Megan D.
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Megan D.
from
$20
per walk
5.0 out of 5 stars
4 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: Marcy M.
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Marcy M.
from
$20
per walk
4.7 out of 5 stars
10 reviews
3 repeat clients
5 years of experience
Camphor, Lakeland, FL, 33803

About: Firstly, I will listen to your pet's needs that you have, and follow them accordingly. Secondly, I will play with your babies and pay attention to them, with love and affection. I will walk with them around the Lake's, and engage them, by talking to them, so that they know they are loved by me. Thirdly, I do like to play catch and engage them in different games, so their time away from you will fly by for them. Lastly, I am not trained in the Heimlich for dogs, nor CPR, but I have had to do the Heimlich on my own dog, whom was choking on food, to save her life. I look forward to playing with your babies. Thank you so very much.

Sitter Profile Image: Joshua G.
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Joshua G.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
263 reviews
49 repeat clients
15 years of experience
Lakeland, FL, 33811

We hesitated writing a review because, honestly, we’re selfish and don’t want his popularity to skyrocket, making it harder to book him! But he truly deserves it more than anyone on Rover. He’s amazing! Quick to respond, always on time, no matter the weather—whether it’s raining or ridiculously hot. We trust him 100%. He even has the code to our front door, comes in, gets the dogs, makes them happy, and brings them back exhausted (which is no easy feat with our two energetic GSPs). So, long story short—book him! You won’t regret it.

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

Ruth is so sweet not only to my dog but to me as well. She's baked doggie treats for my dog and he loves them. Ruth is on time and gives her full attention to us. She handles my dog with love and care and he loves her back! I would recommend Ruth to anyone with dog care needs.

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

Kylee took excellent care of our dog Lady and cat Scamp. She sent us pics of Lady doing her happy dance post walk and let us know each time she was arriving and departing. I would book Kylee's services again in a heartbeat.

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Aaron B.
Sitter Profile Image: Bri S.
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Bri S.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
60 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: Mirla G.
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Mirla G.
Star Sitter
from
$12
per walk
5.0 out of 5 stars
9 reviews
6 repeat clients
12 years of experience
Lakeland, FL, 33810

About: I’ve taken care of all kinds of animals ever since I was 5 years old! I’ve taken my time to learn animal behaviors and I can assure your pet will be in good hands. I have had the chance of taking care of multiple animals! Ranging from dogs, cats, goats, pigs, many kinds of birds, reptiles, amphibians and many more. Ive also taken care of many animals of many ages in life. I am mostly always free! I am a student just earning money and experience to become a future veterinarian. I have a great passion for all things animal related so I hope to have the greatest opportunity to take care of your pets! (Hablo español) (I cannot stay overnight!) I am currently a student just earning money and studying. So I am almost always free! (unless my parents planned something.) If anything comes up I will always let you know! I have a dog of my own that is very friendly! If you'd like to socialize your pet I can help! I don't mind buying things to ensure your pets needs are met. (within reason and budget of course)

Sitter Profile Image: Rachelle S.
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Rachelle S.
from
$25
per walk
5.0 out of 5 stars
85 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: Pennie A.
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Pennie A.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
10 reviews
3 repeat clients
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: Amber M.
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Amber M.
from
$10
per walk
5.0 out of 5 stars
3 reviews
15 years of experience
Plant City, FL, 33565

About: I have had a dog since I was 5, she is currently 15. I care for her greatly and will do anything to keep her happy and healthy. I would do the same for anyone else's pet while their owner is away. I am available while I am home from college all the time. I am willing to take care of an animal to the best of my abilities any time of the day. I follow the instructions given by the owner very well so the change does not harm the animal. I have a fenced in backyard and one medium sized female dog. If boarding at my home, the dog(s) would need to be good with female dogs. I will ensure the dog is very well taken care of while in my care.

Sitter Profile Image: Shelisha F.
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Shelisha F.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
28 reviews
11 repeat clients
10 years of experience
Crystal Lake, Lakeland, FL, 33801

Very reliable, takes wonderful care of my pups. Would recommend to friends and family

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Suzanne L.
Sitter Profile Image: Emma D.
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Emma D.
from
$15
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
3 years of experience
Westgate, Lakeland, FL, 33815

About: I grew up with dogs, and I used to have two cats. I have over 3 years of experience using Rover and multiple 5-star reviews. I have taken care of pets who need medication or have special needs. I am open to dog walking and pet sitting. I do not have any pets of my own to take care of daily. I drop in on one dog three days a week and walk another dog twice a week. I will follow all guidelines provided by the client. Respecting all rules in their home and ensuring that their pets will be in good hands.

Sitter Profile Image: Rosemary S.
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Rosemary S.
Star Sitter
from
$17
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: Amber P.
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Amber P.
from
$18
per walk
1 repeat client
15 years of experience
Downtown, Lakeland, FL, 33801

About: I have owned dogs since was 9/10 years-old, and enjoy playing with dogs and love keeping them occupied espically puppies. For puppies, I like to help potty-train them by offering treats to understand that "outside is where we use the bathroom not inside". I also pay really close attention to due to possible getting into things. I watch out for things that could possibly hurt your dog. As a dog owener myself I will treat your dog as if it was my own dog at home, giving all the attention and play time there hearts desire. I’m currently not working so I am available during select times. I also know what it is like to need a caregiver for your pets while you are away on a business trip or just a quick get away from reality. I live in an apartment complex where everyone keeps to themselves but as for any home I would treat it as if it were my home and how I would want to make sure things are in the right place

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: Tiffany B.
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Tiffany B.
from
$20
per walk
5.0 out of 5 stars
5 reviews
1 repeat client
16 years of experience
Lakeland, FL, 33811

About: I have always had fur babies growing up, and have three dogs of my own now! I love taking care of all animals big and small and have experience with all. I can walk, play, and administer any medications that are needed as. I look forward to meeting all our fur babies! I have a pretty flexible schedule and lots of availability during the week and weekends. If you have any questions about my schedule and availability feel free to reach out. When taking care of your pets in your home I try to keep the same routine as if you were home. I will feed at specific times, walk at specific times, administer medications at specific times, and make sure they are always safe. I will keep you updated with everything and send pictures!

Sitter Profile Image: Sarah p.
Verified Enhanced Background Check
Sarah p.
from
$15
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 currently work at a dog training facility so I have experience in training and taking care of dogs in a professional manner. 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: Alexis N.
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Alexis N.
from
$15
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
8 years of experience
Lakeland, FL, 33805

About: With over 9 years of experience in the pet care industry, I've had the pleasure of working in various settings, including veterinary clinics, pet resorts, shelters, and grooming salons. My extensive experience has given me a unique understanding of the needs of animals of all shapes and sizes. I'm a patient and compassionate individual who is committed to providing top-notch care for your beloved pets. My dependability and love for animals make me an ideal candidate for pet sitting or dog walking services. I'm excited about the opportunity to bring joy and comfort to your pets as their next sitter or walker! I work full time as a veterinary assistant at a local clinic in Lakeland. I will be available at various times throughout the week to take care of your pets! I'm delighted to offer flexible services in the comfort of your home. Above all I prioritize your pets' safety and well-being, I strive to provide a fun and relaxing experience for both you and your furry companions.

Sitter Profile Image: Erika L.
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Erika L.
from
$20
per walk
5.0 out of 5 stars
85 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.
Sitter Profile Image: Alexandra B.
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Alexandra B.
from
$20
per walk
5.0 out of 5 stars
5 reviews
2 repeat clients
17 years of experience
Plant City, FL, 33563

About: I was a veterinary technician for 13 years. Fully capable and experienced in medication administration for cats and dogs. Including but not limited to insulin injections, pill administration, and SQ Fluid administration. Then, I pursued other opportunities in the veterinary field. During my tenure as a vet tech I also pet sat for clients. Experience with dogs, cats, sugar gliders, birds I have full availability for your pet. I am looking for long-term set schedules as well as flexible ones. I can give special attention or medical accommodations. I now offer in my home boarding and daycare. My dog Sirius loves other dogs and plays well. He'd love to meet your pup(s)! I also specialized in pets that can't be with others. If your dog needs a home care environment without other animals I have the experience and ability to accommodate. For special cases like this I would only board your pet for the same rate. have studied and continue to study dog behavior and working in becoming specialized.

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The median cost per walk for dog walking in Winston is $20

Dog parents share their Rover experiences - Winston

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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Meet local walkers who will treat your dogs like family

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Popular requests for dog walking - Winston

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Sitters in Winston average 3
repeat dog walking clients

FAQs for Dog Walking - Winston

Frequently asked questions about Rover

The average cost for Dog Walking in Winston on Rover is $21.8 per walk (as of August 2026). However, all sitters set their own rates based on experience, location, and availability.

Rover makes budgeting the cost of Dog Walking easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Walking. For more information on service fees, click here .

As of August 2026, there are 4,580 sitters on Rover offering Dog Walking across Winston. Enter your ZIP code to see which available sitters are closest to your home.

Whether you want a solo or group walk depends on your dog's personality. Solo walks can be beneficial for dog parents with reactive dogs, puppies, or dogs who are anxious around unfamiliar animals. Many dog walkers on Rover offer private, one-on-one walking services.

Group walks are a good fit for social dogs who enjoy structured walks. If your dog prefers the energy of a group stroll, ask your dog walker about group walks in your Winston. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.

For dog walking services, you can request a report card update with specifics about your dog’s walk. Report cards require photos and can include a map of the walking route , total walk time, poop and pee breaks, and distance traveled, so you know exactly where your dog has been walking in Winston.

Got specific details you'd like the dog walker to include? Message them in the app before your dog’s walk begins.

The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.

All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.

Every walker on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.

Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .

Yes, you can find walkers who have experience with handling special pet needs in Winston. On Rover:

  • 90% of walkers can help with special care needs
  • 95% can help with giving oral medications or injections
  • 98% can help with daily exercise

You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.

Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.

A Meet & Greet is a short introductory meeting between you, your dog, and a walker. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your walker or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your walker questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and walkers on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.

Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.

Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.

If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement walker.

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