Dog Walkers in Windermere, FL
Book a dog walker to give your dog a 30-minute walk around your neighborhood.

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Top rated Windermere dog walkers
“Mark went out his way to help us out, making scheduling easy by being flexible and quick with communication. He even sent us a cute picture of Tilly on her walk. Feel grateful to know she was well cared for when I couldn’t be there.”

“I felt so comfortable and reassured leaving for a long work day knowing that Samantha was caring for my dog. She is reliable, professional, and treated my dog with so much love. Highly highly highly recommend.”

“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.”

“Jamie is such a kind and attentive dog sitter! I needed someone to take my corgi out for me on weekdays while I’m at work, but Jamie did a lot more than that. She played with my dog, gave her lots of love and treats, and made sure she had water. Jamie will take great care of your pup!”

“Jenn is terrific! She was very responsive to my requests. She came to my house to meet my dog and immediately got on the floor with her. My dog loves Jenn! She was on-time and provided great care to my dog. Additionally, Jenn was super-flexible when i needed her to change the time she came to do the walk. I can’t recommend Jenn highly enough! I will use her again for sure!”

“Absolutely amazing!! I wish I could give more stars but instead I will just HIGHLY recommend this amazing woman for her loving demeanor towards animals!! She truly cares for pets and my girl LOVED HER. I will 100% rebook with her and highly recommend everyone does the same!!”

About: I have owned and trained large dogs (including my two beautiful malamutes) for over 10 years! Experienced caring for animals of all sizes and temperaments and will love and care for your animals like they are my own child! Whatever your animal care needs I can make myself present and available to give 110% to your pet’s care! I love to run for our pets who need a bit more exercise than a walk 💕 Any and all animals I care for, including my own, are treated with respect, care, attention, and love. I am meticulous in observing their needs and behaviors so that their experience and yours can be joyful and peaceful!
About: Over 11 Years of Trusted Pet Care With more than a decade of experience, I’ve cared for pets of all ages—including senior pets and those needing medication like insulin for diabetes. I also offer in-home boarding in a cozy, loving environment where your pet will feel right at home. My schedule is very open and flexible, which makes it easy for me to give your pet the time and attention they need. I work a job with a lot of flexibility, so I can easily adjust my day to fit your pet’s routine—whether it’s feeding, walking, or just keeping them company. Your pup will get plenty of love, cuddles, and playtime in a calm, pet-friendly home. I offer daily walks, potty breaks, and follow your feeding/medication routines. I board dogs under 25 lbs who get along with my cat and treat every guest like family! We also have a fenced backyard.
“Sarai is fantastic! She took excellent care of my dog and made sure he had fun and was taken care of. She is very communicative and provides updates consistently. I highly recommend and will be reaching out to her in the future!”

About: HEY HEY HEY! MY NAME IS AMANDA! I WILL BE YOUR PET'S FAVORITE BABYSITTER. 🐾 ANY DOG I SEE I BELIEVE IS MY BEST FRIEND. I WORK FROM HOME SO I HAVE ALLL THE TIME IN THE WORLD TO DEDICATE, PLAY AND CARE FOR YOUR FUR BABIES. PET CARE IS MY DAY AND NIGHT JOB. I HAVE A MINI POODLE NAMED MISSY. SHE LOVES TO PLAY WITH ALL DOGS, HER ENERGY LEVEL IS SUPER HIGH AND LOVES A GOOD CUDDLE. Pet care is my only job ! So I work from home . I am able to give my undivided attention to all fur babies! I believe in Cage free doggy daycare and boarding. I have a Fenced in yard for fur babies to release energy and a controlled safe environment for potty time.
About: Hi, my name is Meera Blackstock. I’m a college student in Orlando, Florida, studying Kinesiology. I’ve had my Chihuahua, Bruno, for nine years, and he’s taught me so much about caring for dogs. My family also has dogs, and we love getting them together for playdates. With years of hands-on experience, I understand how important pets are—they’re truly family. You can trust that I’ll care for yours with the same love and attention I give my own. I currently work and have internships in the mornings, but I’m generally available on weekends at any time I’m booked. I always communicate with clients in advance to confirm availability and will do my best to accommodate your preferred time, whether that means adjusting slightly earlier or later. I always take the time to get acquainted with each dog before our walk, making sure they feel comfortable and know that I’m friendly and there to care for them.
“Ashley is amazing! She walks two of my big dogs and does a great job. She feeds them and always leaves there water bowls filled up. She even tidies up the place! Shes great :)”

About: I’ve been caring for dogs for over a decade, starting with my sister’s senior pup who I’ve helped to watch regularly through the years. I’ve also had a dog of my own, and I frequently care for friends’ dogs - often for overnight stays and multi-day stays. Whether it’s a playful puppy or a mellow, older dog, I provide attentive, loving care tailored to each pets needs. I’m comfortable with routines, medications, and making sure your dog feels safe, happy, and at home while you’re away. I currently work part-time as a pharmacy technician. I am in graduate school fully online, so I have plenty of availability for pet-sitting. I am unavailable on Wednesdays, and flexible all other days. When caring for a pet in someone’s home, I prioritize, safety, consistency, and comfort. I follow routines closely to ensure your pet feels secure and relaxed in their familiar environment. My goal is to build trust with both you and your pet, offering attentive, loving care that feels like home. I also provide regular updates, including photos and messages, so you can feel confident and connected while your pet is in my care.

“Sarah was incredibly accommodating, adjusting her schedule for a last-minute booking to walk Alexander. She always maintains a positive attitude, sending me photos throughout the walk and going the extra mile by leaving the house clean for me. Thank you Sarah!”

About: My top priority is making sure your fur babies are safe while I am caring for them. I will feed, love, and spoil your pets as if they were my own. I also provide my clients the best care for their home so they can have peace of mind while they are away by taking care of daily household tasks such as taking out the trash, bringing mail / packages inside, doing the dishes, watering plants, laundry, cleaning up after animals and myself, etc. Every animal is different so I am very experienced with all different types of situations and can follow instructions to adapt to the animals needs accordingly. I have cared cared for many pets that have special needs such as seizures, special diets, medication administration, vet appointment transportation, and more. I am also very active so I have no issue going for walks, to the dog beach, etc. As well as I know many parks and trails in the area that I would love to take your dog to! Your pup will always be supervised and never feel alone as long as I am around. I can drop in for visits, as well as pick them up, take them out for a walk or adventure, or I am willing to stay over and house sit as well as dog sit. I absolutely love all animals, especially dogs! I have always had one my entire life growing up. Right now I have just one small dog that I have raised myself now for 11+ years. She loves company, or if yours doesn't then it can have my full attention when needed! My rates may vary for larger amounts of animals, possibly a deal for a bulk amount including pets such as fish, birds, reptiles, small mammals, etc. Please contact me for further information or any questions you may have! :) I have a very open and flexible schedule! I am a licensed Real Estate Agent and I own a small business that I work part time from at home as well, so I make my own schedule, and have plenty of time to take care of your pets. Some days I can stay all day and hangout with them, while others I may have errands to run or appointments for work, but I can assure you I will always be back in time for feeding, walking, and staying the night with them. Your pets will be safe with me as I am a lifetime pet owner who has never put an animal in harm's way. I adore all animals, and assure you they will have a great time with me. They will have my full attention while in my care!
About: My friends call me Alex and I’m a college student working part-time! I’ve taken care of cats and dogs since I was 10. Neighbors, friends, and family have relied on me to walk, feed and bathe their pets. I’m also very reliable and caring. :) I currently work part-time, which gives me a flexible schedule and plenty of availability to care for your pets. I'm able to adjust to their routine and provide them with the attention and companionship they need. Whether I’m caring for pets in my home or my client’s, I prioritize creating a safe, calm, and comfortable environment that mirrors their usual routine as closely as possible. I make sure they have fresh water, regular meals, daily exercise, and plenty of playtime and affection. I also pay close attention to their behavior and any signs of stress or discomfort, and I keep the owners updated with regular photos and messages. If I’m in the client’s home, I respect their space, follow all instructions closely, and ensure their pet feels secure in their familiar surroundings.
Over 320 pet parents in Windermere have booked dog walking
How Rover works

1. Search
Read verified reviews and choose a dog walker who’s a great match for you and your dog
2. Meet & Greet
Meet either virtually or in-person with a walker to discuss the level of care needed for your dog
3. 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 Windermere is $19
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 Windermere 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 Windermere on Rover as of Dec 2025 was about $19 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 Dec 2025, there are 4,946 dog walkers in Windermere. 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 Windermere dog walkers respond in under an hour.
Dog walkers in Windermere 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 Windermere.
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 4,946 dog walkers in Windermere on Rover, so you’re sure to find the perfect match for your dog! In Windermere, 90% 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.




