Dog Walking Winter Garden
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 78 pet parents in Winter Garden have booked dog walking
Winter Garden, 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.
“Tracy is a life saver. I always get nervous introducing my dog to new people but she is so patient and kind, my dog took to her right away. Tracy sent photos, updates and kept communication top tier each day. I feel so much peace of mind thanks to Tracy, DEFINITELY recommend.”
About: My name is Skye, I’m 27 and l’ve owned and cared for dogs and cats in a variety of sizes, temperaments and breeds for most of my life. I've been pet sitting for 5 years as a part time job and for fun since I was younger. As a passionate animal lover, I promise to provide a fun and safe environment for your pet as they walk, eat and play. Hope to meet your pets soon! I’m currently working part time, so I’ll have plenty of time to play with your pets! Please see my schedule for availability! My schedule is mostly consistent but has some rotation. I will keep your pets safe, happy, and healthy while enjoying their time on their walk, in their play time, or on their play dates.
“Karen was great! She was very responsive and communicative. She even helped us with a UPS delivery while at the house which we really appreciate. We will definitely use her again!”
“Reece was punctual and very attentive with my dog. She made sure he was comfortable, gave him a treat, and refreshed his water. I really appreciated her care and attention to detail.”
About: After losing my 14 year old Lola I want to be close and offer love and care to other pups. Can’t wait to meet yours My schedule is very flexible at the moment. I do have some commitments in the early morning and early afternoon but I can work around them. I try to adjust to the clients needs first of all. That is the most important thing to me. I want to make sure I follow all the rules and your pet feels safe and cared for.
“Remy was great! Very reliable, professional and took great care of my dog! She even brought my packages inside and made sure my dog had enough fresh water before leaving. Highly recommend.”
“We’ve had such a wonderful experience with Rebecca. She is incredibly sweet, gentle, and clearly cares deeply about the dogs she works with. Our pup absolutely loves her! She’s always punctual, very communicative, and keeps us updated, which gives us so much peace of mind. It’s clear that she treats our dog like her own. We’re so grateful to have found someone so reliable, kind, and trustworthy. Highly recommend!”
“Darryl is very caring, and loving towards Mocha. He's considerate and communicates with me beforehand and during his services. He's very reliable and professional. Definitely recommend”
“Ani'yah did an excellent job walking my dog. As soon as i opened the door she welcomed me with a big smile was so kind to bring chocolates. She was very calm and polite throughout the walk. I recommend her 100%”
“Tathyana is amazing! She's so responsible and flexible. My elder dog had an accident and she helped me clean up. She is so loving and caring for Mocha. Definitely 100% recommend !”
“Most amazing service, she was able to come an extra time to help when we had a delay. Very sweet to my dog Luna and played with her so she wouldn’t feel alone. Most definitely recommend.”
“Danielle did great with taking care of my two dogs and cat while we were away. She went above and beyond with her communication, sending pics and taking her time walking and feeding the pets. She even helped clean up with one of my dogs who had a poopy situation which was not at all expected, I felt bad my dog got runs while I was away. But she helped give him sweet potato so he felt better and even bought peewee pads, which just kept my mind at ease knowing my dog was being cared for. I would definitely rehire her again, she was just the best!”
“Yanran had been taking my pup for a walk several days a week. She gives lots of feedback and takes plenty of pictures. She also spends some time playing with her after the walk. I have been very happy wher services.”
“Jenn is such a rockstar. She walked, trained, played, and fed our dog while I had to go into office for the week. She provided great notes and pictures. She stuck to the schedule i provided but did lean on Nias temperament where necessary. Jenn is so careful and considerate. She is officially my go to for puppy sitting or walking.”
About: Animal lover, pet-less at the moment, but with lots of animals in my life. I have plenty of love, patience, cuddles, and care to give to your furry family member, big or small. I know how important and stressful finding a reliable place or a trustworthy person is. For over 20 years now neighbors, friends, and family have trusted me to take care of their beloved pets at their house or mine. I have a very welcoming home with couches to surf, plenty of laps to sit on, lots of treats(or not), walks and playtime. My backyard is enclosed and the community has lots of green areas, several parks, fun walks and a dog park just a car ride away. I don’t mind traveling. I have taken care of two potbelly pigs, two donkeys, a squirrel, and two cats up in Archer, FL. Five cats and an African Gray parrot in Orlando. Several cats and dogs at their homes and mine, and whenever I can, I escape to my friend’s farm to help with the care of their horses. My grand-dog, April, loves to visit and get spoiled! Give me the opportunity to show you how well and at home your baby will feel! I work part-time from home so I have plenty of time to play with your pups! I’m available for boarding 7 days a week. I set up beds in the living room and in my office. I also do pottery, and I have my wheel in an enclosed patio with a rug right next to it for my special helpers! I do a walk in the morning and another one about an hour after breakfast followed by some playtime. Then I do bathroom breaks every two hours or as needed. After noon, I work on my pottery and do some gardening in my fenced backyard. Rest assured your pet will never be outside unsupervised. Late afternoon I take them for a longer walk, a bathroom break after dinner, and again before bed. I make sure your baby is active and well exercised, with plenty of time for play, rest, and cuddles! And of course, I will also follow any schedule or routine they may have. I have a pet friendly home with an enclosed patio and fenced backyard, but rest assured your pup will never be left outside unsupervised. Your pet is welcomed on our couches, our laps, and any part of the house they wish to be in. If I have to go out, and no one else is home, I will leave the TV on with relaxing music or pet friendly content playing. I don’t own a crate, but you’re welcome to bring one if your baby is used to staying or sleeping in one. They are welcome to sleep in any of our bedrooms. I usually don’t allow them on my bed but my daughter will be ever so happy to oblige! If I’m caring for your beloved at your home, I will follow any rules you have set up for them, even sleeping with them if necessary!
About: I’ve had the privilege to take care of dogs of all personalities thanks to my family and friends. On top of their basic necessities I’ve learned how to bond with hyper energy-filled doggies to the relaxed and snuggly kind! I’m currently in summer break after my graduation so I will be available any day, and at all times, from 12 AM to 11:59 PM Whenever I dog-sit for a new dog I always ensure to ask for any information on grumpy neighbors, or animals in the area to ensure the dogs walks are as enjoyable and stress-free for everyone as possible!
About: I’m patient with older dogs and pups just learning, as well as those missing their people and are scared. Grand mom to 4 sweet puppers. Lifetime pet family, we have guinea pigs, hamsters and every kind of dog and cat. I always helped neighbors when the needed pet care as well as years of volunteer work in shelters. Pets are family. I am a retired teacher due to injury and have a home based business so my hours are flexible. With enough notice I will do my best to accommodate care needed. I am unable to care for other pets in my home, we have 7 cats. I will follow all instructions given to lovingly care for your pets at your home
About: I’ve taken care of dogs of every kind since I was 8. Neighbors, friends, and family have been able to rely on me to feed, walk, and sit their pets. I also am great with cats. I’m currently working a full time job but I’m more than happy to work around my schedule! I’m off on Wednesday and Thursday with alternating times. I am a very dependable person and you should know your pet is in good hands when you work with me. I’ll make sure to spend plenty of time with your pet, playing with them and making sure to walk them often. I will also be sure to feed them on time.
The median cost per walk for dog walking in Winter Garden is $20
Dog parents share their Rover experiences - Winter Garden
Delanie is a gem!! She walked and kept our very needy goldendoodle with severe separation anxiety company, her communication is level 10. She is very accommodating and definitely goes the extra mile! We absolutely will be calling her back for help! Thank you Delanie!
Jezabell is exceptional! I have both a dog and a bunny that she cared for and both had very different needs. She went above and beyond to make sure they both had their individual play time, and were both cared for individually specific to their needs. She is also extremely sweet, kind, caring, and goes above and beyond her duties. Our sensitive babies loved her! Highly recommend and will be booking again with her for sure!
Tracy is a life saver. I always get nervous introducing my dog to new people but she is so patient and kind, my dog took to her right away. Tracy sent photos, updates and kept communication top tier each day. I feel so much peace of mind thanks to Tracy, DEFINITELY recommend.
Kayleigh arrived a few minutes ahead of the scheduled 60 minute walk to become acquainted with Rhea. During the walk, she sent several pics of Rhea exploring her surroundings (enthusiastic ground sniffing). When they returned, Rhea demonstrated her signature affection behavior of licking and rubbing her head against Kayleigh’s leg. Rhea and I look forward to Kayleigh’s return.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
Why Choose Rover?
Cashless payments
Book and pay through Rover’s secured platform—no cash or checks required.
Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.
Meet local walkers who will treat your dogs like family
1. Search
Browse profiles of walkers near you who offer dog walking
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests for dog walking - Winter Garden
Select a filter and find qualifying sitters offering dog walking.Sitters in Winter Garden average 3 repeat dog walking clients
FAQs for Dog Walking - Winter Garden
Frequently asked questions about Rover
The average cost for Dog Walking in Winter Garden on Rover is $21.09 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 5,196 sitters on Rover offering Dog Walking across Winter Garden. 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 Winter Garden. 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 Winter Garden.
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 Winter Garden. 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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