Dog Walking in Winter Garden
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Winter Garden dog walkers


“Kayla is super patient with my big baby. I appreciated the extra effort Kalya went through to help support my pup during their walk visits. I will keep Kayla in rotation as needed for us.”


“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.”


“Victoria did a fantastic job filling in while my usual walker was on vacation. It’s obvious she takes great care with her furry clients, she was very mindful of the heat outside and made sure my Sydney didn’t get too hot. Would absolutely reach out to her again if I need extra help!”


“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.”


About: We have experience with special needs dogs. We are active so we are happy to tire your puppy. A tired dog is a better behaved dog for sure. We have had dogs all our lives and love every dog, even the tough ones. Your dog or dogs will be spoiled and loved. We are not new to Rover, nor watching visiting dogs. We believe your dog will benefit from us being it's friend. My wife works from home everyday so potty breaks are plentiful. We love dogs and can't imagine life without them. Your fur baby will be in great hands and get the spoil treatment. We look forward to spoiling your puppy. You will get pictures and information throughout the stay. We know you will miss your puppies so we will do our best to bridge that gap We spend the majority of our days focused and trying to tire out the puppies every single day. Our dogs are the most important thing in our world and will treat your dog(s) like our own. Our back yard is fenced in with secure fencing and has no soft spots or gaps for small dogs to get out of. We keep a close eye on all the dogs while in the back yard.

About: I believe what sets me apart from other sitters is my extensive experience both as a dog trainer and in boarding. Over the years, I've worked with dogs of all ages and temperaments, from energetic puppies to senior dogs requiring more specialized care. My background in dog training allows me to work with your dog on behavioral issues or reinforce good habits while they're under my care. Additionally, my experience in boarding means I'm accustomed to managing multiple pets at once and ensuring each gets the attention, exercise, and care they need. Whether it’s administering medications, keeping them on a consistent schedule, or providing enrichment activities, I always ensure that pets feel safe, comfortable, and loved. With a deep understanding of canine behavior and a compassionate approach, I can offer more than just basic pet-sitting—I can be an extension of your dog’s family and contribute to their well-being, whether they're staying with me for a day or an extended period. Pet care is an integral part of my daily routine, and my experience allows me to seamlessly incorporate it into my schedule. As a dog trainer, I’m accustomed to spending time with dogs throughout the day, whether it’s for training sessions, walks, or general care. I prioritize regular exercise and mental stimulation for pets, which fits well with my structured daily plan. In addition to my training work, I also have experience with boarding, which means I’m used to managing the care of multiple dogs at once. I make sure to set aside specific times each day for feeding, walks, and attention, while also balancing the other tasks of my day. Whether I’m working with puppies, senior dogs, or dogs in need of more specialized care, I structure my routine to ensure each pet gets the individual care and attention they deserve. This flexible yet organized routine allows me to manage pet care efficiently, while maintaining a balanced schedule. Safety, trust, and a comfortable environment are always my top priorities when caring for pets in a client’s home. I respect the pet’s routine and environment, ensuring that everything stays consistent with what they’re used to. I stick to their regular feeding, walking, and play schedules, while also incorporating any necessary training or enrichment activities. For pets that need additional care—like senior dogs or those with anxiety—I create a calm, structured environment to help them feel comfortable. I also make sure the home is safe and secure, checking for any potential hazards like open windows, toxic plants, or unsecured doors. Trust is key, and I keep an open line of communication with pet owners, offering updates and photos so they feel reassured their pets are in good hands. My goal is to provide a safe, loving, and familiar environment where pets feel cared for, relaxed, and happy.

“I cannot recommend Claire and Megan highly enough! Leaving my furry baby with them was the best decision I made. They provided top-notch care, ensuring my dog felt loved and comfortable throughout the entire sitting time. Their communication was excellent, sending regular updates and photos, which really put my mind at ease. It's clear they have a genuine passion for animals, and I wouldn't hesitate to book with them again in the future. Thank you for taking such great care of my beloved pet!”


About: I have taken care of family and friend's pets for years. Plus having my own. I am retired so most of the time I am available to come and love on your fur-babies. I am very active so if your pup needs plenty of walks, I'm the person for the job. I am retired so I have most weekdays and weekends available to care for your fur-babies with pop-in visits. Unless I am out of town. I would love to do pop-in visits and walks. Unfortunately, at my home my fur-baby only loves people. She gets very jealous, and I would never want to put anyone's pups at risk.

“Amazing, we continue to use her every time. Our dog had a medical condition and she took extra care of her, giving her medication and ointments twice daily. Our pets live her!”


About: I’ve taken care of dogs and cats for the past five years. Not just my own but family and friends! I love to watch pets in my home who want to have fun and play with my own two dogs and 1 cat! I work from home full time so am available to meet needs of taking out your pet when you need! My weekends are also free to enjoy play time! I have two friendly pups who constantly look for new friends! I also have a cat that likes to see who is here but doesn’t bother them! My yard isn’t fenced in but we take many walks a day for everyone’s exercise!

“Words cannot express how grateful we are to found Michele, she was super sweet, sent us beautiful pictures and videos and gave us that peace of mind that we needed. Definitely 5 stars rating is what she deserves, thank you Michele ❤️”


About: I have raised colts, goats, cats, and a couple of dogs. I believe my experience with various animals, particularly horses, has helped me connect with/ win the trust of dogs relatively quickly. I work remotely. I can give attention to your animal more frequently. I am a proud owner of a golden retriever and former owner of many animals, having grown up on a ranch. I treat your animals as if they were my own. I respect that responsibility. Animals are very special in our families and ought to be treated as such.

“Hannah is so sweet to my dottie! I was in a bind and she came through like a CHAMP! I can not tell you how thankful I am to have Hannah walk my dottie when I’m out! She is amazing!”

Loving dog walkers in your neighborhood
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Alyssa M.

“I'm starting to think my dog loves Alyssa more than me!”


Jenn H.Star Sitter

“Jenn works around my crazy schedule and is sometimes able to come at times different than when I originally booked. !”




Kayla W.Star Sitter

“Kayla is super patient with my big baby. I appreciated the extra effort Kalya went through to help support my pup during their walk visits. I will keep Kayla in rotation as needed for us.”


Darryl W.

“My dog Nami took to Darryl right away and she came back so happy from her walk!”


Reece L.Star Sitter

“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.”


Stacie W.

“First week using Stacie and she has been reliable with great communication. She’s just what LunaLou needed! I would definitely recommend her and will be using her again soon!!”


Victoria D.Star Sitter

“Victoria did a fantastic job filling in while my usual walker was on vacation. It’s obvious she takes great care with her furry clients, she was very mindful of the heat outside and made sure my Sydney didn’t get too hot. Would absolutely reach out to her again if I need extra help!”


Remy S.Star Sitter

“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.”


Tim & Tess O.
About: We have experience with special needs dogs. We are active so we are happy to tire your puppy. A tired dog is a better behaved dog for sure. We have had dogs all our lives and love every dog, even the tough ones. Your dog or dogs will be spoiled and loved. We are not new to Rover, nor watching visiting dogs. We believe your dog will benefit from us being it's friend. My wife works from home everyday so potty breaks are plentiful. We love dogs and can't imagine life without them. Your fur baby will be in great hands and get the spoil treatment. We look forward to spoiling your puppy. You will get pictures and information throughout the stay. We know you will miss your puppies so we will do our best to bridge that gap We spend the majority of our days focused and trying to tire out the puppies every single day. Our dogs are the most important thing in our world and will treat your dog(s) like our own. Our back yard is fenced in with secure fencing and has no soft spots or gaps for small dogs to get out of. We keep a close eye on all the dogs while in the back yard.


Hailey M.Star Sitter

“Cleo looks so happy in her picture ! Thank you! Great job! We will be reaching out again :)”


Nia M.
About: I believe what sets me apart from other sitters is my extensive experience both as a dog trainer and in boarding. Over the years, I've worked with dogs of all ages and temperaments, from energetic puppies to senior dogs requiring more specialized care. My background in dog training allows me to work with your dog on behavioral issues or reinforce good habits while they're under my care. Additionally, my experience in boarding means I'm accustomed to managing multiple pets at once and ensuring each gets the attention, exercise, and care they need. Whether it’s administering medications, keeping them on a consistent schedule, or providing enrichment activities, I always ensure that pets feel safe, comfortable, and loved. With a deep understanding of canine behavior and a compassionate approach, I can offer more than just basic pet-sitting—I can be an extension of your dog’s family and contribute to their well-being, whether they're staying with me for a day or an extended period. Pet care is an integral part of my daily routine, and my experience allows me to seamlessly incorporate it into my schedule. As a dog trainer, I’m accustomed to spending time with dogs throughout the day, whether it’s for training sessions, walks, or general care. I prioritize regular exercise and mental stimulation for pets, which fits well with my structured daily plan. In addition to my training work, I also have experience with boarding, which means I’m used to managing the care of multiple dogs at once. I make sure to set aside specific times each day for feeding, walks, and attention, while also balancing the other tasks of my day. Whether I’m working with puppies, senior dogs, or dogs in need of more specialized care, I structure my routine to ensure each pet gets the individual care and attention they deserve. This flexible yet organized routine allows me to manage pet care efficiently, while maintaining a balanced schedule. Safety, trust, and a comfortable environment are always my top priorities when caring for pets in a client’s home. I respect the pet’s routine and environment, ensuring that everything stays consistent with what they’re used to. I stick to their regular feeding, walking, and play schedules, while also incorporating any necessary training or enrichment activities. For pets that need additional care—like senior dogs or those with anxiety—I create a calm, structured environment to help them feel comfortable. I also make sure the home is safe and secure, checking for any potential hazards like open windows, toxic plants, or unsecured doors. Trust is key, and I keep an open line of communication with pet owners, offering updates and photos so they feel reassured their pets are in good hands. My goal is to provide a safe, loving, and familiar environment where pets feel cared for, relaxed, and happy.


Lena C.

“Lena was great! She was reliable and able to accommodate my last minute dog walk need. She communicated frequently and based on the pictures provided, our dog had a blast!”


Claire G.

“I cannot recommend Claire and Megan highly enough! Leaving my furry baby with them was the best decision I made. They provided top-notch care, ensuring my dog felt loved and comfortable throughout the entire sitting time. Their communication was excellent, sending regular updates and photos, which really put my mind at ease. It's clear they have a genuine passion for animals, and I wouldn't hesitate to book with them again in the future. Thank you for taking such great care of my beloved pet!”


Tracy W.
“I can’t say enough good things about Tracy! I feel completely at ease knowing my pets are in loving and capable hands with her, treating them like her own. She goes above and beyond - frequent updates, adorable photos, and thoughtful touches to show how much she truly cares. It’s such a relief to have someone I trust completely while I’m away.”


Kellie-Lynn R.Star Sitter

“Amazing, we continue to use her every time. Our dog had a medical condition and she took extra care of her, giving her medication and ointments twice daily. Our pets live her!”


Imani Z.
“Imani was prompt and communicated with me as necessary. She followed the instructions for my pups and took good care of them.”


Sara H.
About: I’ve taken care of dogs and cats for the past five years. Not just my own but family and friends! I love to watch pets in my home who want to have fun and play with my own two dogs and 1 cat! I work from home full time so am available to meet needs of taking out your pet when you need! My weekends are also free to enjoy play time! I have two friendly pups who constantly look for new friends! I also have a cat that likes to see who is here but doesn’t bother them! My yard isn’t fenced in but we take many walks a day for everyone’s exercise!


Michele B.

“Words cannot express how grateful we are to found Michele, she was super sweet, sent us beautiful pictures and videos and gave us that peace of mind that we needed. Definitely 5 stars rating is what she deserves, thank you Michele ❤️”


Jason K.
About: I have raised colts, goats, cats, and a couple of dogs. I believe my experience with various animals, particularly horses, has helped me connect with/ win the trust of dogs relatively quickly. I work remotely. I can give attention to your animal more frequently. I am a proud owner of a golden retriever and former owner of many animals, having grown up on a ranch. I treat your animals as if they were my own. I respect that responsibility. Animals are very special in our families and ought to be treated as such.


Hannah R.

“Hannah is so sweet to my dottie! I was in a bind and she came through like a CHAMP! I can not tell you how thankful I am to have Hannah walk my dottie when I’m out! She is amazing!”
Over 534 pet parents in Winter Garden have booked dog walking
Winter Garden dog parents share their Rover experiences
Rafael is the perfect person to walk my Sadie. He was firm with her and managed to train her on their walks. Sadie thinks he is her best friend and stares at the door awaiting his arrival. He is knowledge in dog behavior and was able to give me some pointers on how to get Sadie to obey. Rafael is very professional, always on time, and communicates well. I will definitely hire him again!!!

How Rover works
1. Search
Read verified reviews and choose a dog walker who’s a great match for you and your dog2. Meet & Greet
Meet either virtually or in-person with a walker to discuss the level of care needed for your dog3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per walk for dog walking in Winter Garden is $18
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 dog walker has to cancel, we’ll work with you to find a new walker.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winter Garden 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 Winter Garden on Rover as of Aug 2025 was about $18 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.
As of Aug 2025, there are 4,684 dog walkers in Winter Garden. 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, 86% of Winter Garden dog walkers respond in under an hour.
Dog walkers in Winter Garden 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 Winter Garden.
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 4,684 dog walkers in Winter Garden on Rover, so you’re sure to find the perfect match for your dog! In Winter Garden, 89% 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.
