Dog Walking Windermere
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 108 pet parents in Windermere have booked dog walking
Windermere, Find top rated dog walking
“I highly recommend Mark. He is amazing with my not-so-easy to walk fur baby. He gave great feedback and made me feel comfortable that my dog was in the best care. I loved all the pictures he sent. Also, this is the first time I used Rover and Mark was very knowledgeable and helped me through the process.”
“Elizabeth has walked our belgian mali mix multiple times and it has gone great! She is very knowledgeable and a great person to trust with your pups. Recommend 10/10 and will be booking her again!”
About: I love dogs, I can talk about my own baby dog for days. I’m bilingual (Spanish and English), I love walking and I love pets. Mix them together and I’m there. I’m probably available when you need me so you can trust that I will take good care of your pets when you are not able :) I am a freelance photographer, so I work from home and manage my own schedule. I am available mornings, afternoons and evenings as needed :) I can walk pets, come and feed them or play with them or I can pet sit in your home. Unfortunately not available to bring pets to my own home
“⭐⭐⭐⭐⭐ Youm J. was awesome! Super friendly, reliable, and took great care of my pup. 🐾 I really appreciated the communication and updates—it definitely gave me peace of mind knowing my dog was in good hands. Great experience all around and I’ll definitely be booking with Youm again. Highly recommend! 🙌🏽”
“My second time working with Jessie. As before, communicated very professionally and showed up on time for the walk. My dog was happy, when I got home, and so I'm happy as well :)”
About: I am a vet student in school and I have been caring for my 6 animals for more than 10 years. You can trust me I will be very careful, responsible, and loving towards your animals. I work a part time job as a barista and my mornings and weekends are usually free so I will have a lot of time free to do what I love most and care for your animals! I will care for your animals at your home by feeding/walking them on time and I can put them to bed in their crate if needed or if not then they’ll have a safe space to get their zoomies out and relax!
“If I could give Sarah more than the allowed stars, I would!!! She really went above and beyond for my anxious little doggy who was in a weird hotel while my family was on vacation. She was only expected to take our dog on a 30 min walk, but when she realized how anxious she was, Sarah stayed extra time just to give her some much needed TLC. She is not only responsible and attentive, but extremely conscientious and empathetic to our pets being an extension of our own families. I couldn't recommend her more.”
About: Hi, I'm Ken! With 8 years of pet care experience, I provide top-tier dog walking, pet sitting, and drop-in check-ins tailored to your pet's exact routine. Whether your dog needs an energetic walk to shake off the "ruff" days, or your cat needs some quiet cuddle time during a check-in, I’ve got you covered. Why Choose Me? -8+ Years Experience: Deep understanding of dog and cat behaviors and body language. -Flexible Services: Available for high-energy walks, overnight sitting, or quick potty breaks and feedings. -Safety First: Reliable, fully vetted, and dedicated to keeping your pets secure and happy. I treat every dog and cat like my own family. Book a service today, and let's give your pet the smooth, stress-free day they deserve! I work a steady evening schedule, my routine is perfectly tailored for pets who need dedicated overnight care, morning routines, or daytime attention on my days off. Here is exactly how my availability breaks down: • Mondays & Thursdays (Completely Free): These are my full days off! I am available all day and night for extended playtime, daytime drop-ins, mid-day walks, or a seamless start to an overnight stay. • Wednesday, Friday, Saturday, & Sunday (Evening Workdays With Tuesday as an Occasional Morning): • Mornings & Early Afternoons: Available for morning walks and early drop-in visits before I head out for the evening. • Nights & Overnights: Perfect for overnight House Sitting! I am available to arrive in the late evening to tuck your pets into bed, stay through the night, and provide a full morning routine with breakfast and a walk before leaving. I treat your home with the utmost respect and your pets like members of my own family. Because change can sometimes be 'ruff' for animals, my primary goal is to maintain their familiar habits, scents, and routines as closely as possible while you are away. Here is exactly what you can expect when I care for your pets in your home: • Consistency & Routines: I stick strictly to your established schedule for feeding, medication, crate time, and bathroom breaks. • Active Engagement: I provide active playtime, mental stimulation, and plenty of one-on-one affection. • Thorough Clean-up: I keep all pet areas tidy, including washing food bowls, scooping litter boxes daily, and cleaning up any accidental messes immediately. • Frequent, Detailed Updates: You will receive regular photo and/or video updates through Rover Cards or Messaging along with detailed summaries of how your pet is doing, so you never have to wonder. I also offer meet and greets, so schedule yours today!
About: *Disney area Hi, I’m Jordan!! I grew up in a home surrounded by dogs, cats, reptiles, birds, etc. I have also previously worked as a veterinary assistant, so I have plenty of experience with all different types of pets and their personalities!! Currently I have a 2 year old Italian Spinone and a 4 year old cat, so I’m equipped for it all! I am a true animal lover at heart and I can’t wait to take care of your fur babies! I am available all throughout the Windermere/Winter Garden/Disney area I work part-time and only have online classes, so I am available Sunday-Wednesday at any time of day! I have plenty of time to care for & play with your pets! I am here for whatever you need! However you want me to go about caring for your pet in your home I’m able. I understand how important your pets are to you and I am determined to keep them safe, happy, and healthy!
“Mauricio is great and truly cared about dogs. He did great handling my senior dog and treated him with great care. I’ll definitely be using his services again in the future!”
About: I have pet and house sat over the last ten years. I have grown up with and cared for dogs, cats, fish, free range chickens and even an African grey parrot. I am dependable and trust-worthy. I will love your pet(s), have the utmost respect for your home, and bring a strong work ethic. Please disclose all specifics for care and training of your fur babies. I will be sure to provide my best care, ensuring continuity to help keep your pet(s) the most at ease during your absence. You don’t have to worry about me leaving daily to work. I’m employed with a temp agency, and I don’t have any assignments at this time. When contacted, my assignments are typically hybrid or remote. I have a 2018 Sedan with leather seats, which is consistently cleaning, serviced, and maintained. I have a clean driving record and drive very cautiously.
“Highly recommend! Remy is reliable, responsible, caring and goes above and beyond to take great care of my dog during walks. Her communication, updates and photos are great! She even brings my packages inside from the porch.”
“Shelley, was prompt and kind. I felt very comfortable with her and our pup! This was a meet n greet as build up to a longer house/dog sitting adventure in a couple months!! Excellent communucation, honesty and very easy going personality! Highly recommend.”
About: With 5 years of experience as a pet sitter, I have developed a deep passion for providing loving and responsible care to animals. I treat every pet as if they were my own, making sure they feel safe, comfortable, and happy while their owners are away. I understand how important it is to maintain their routines, give them attention, and provide a calm environment. I am committed to offering dependable care built on trust, patience, and genuine love for animals! Pet care fits naturally into my routine, allowing me to provide dependable and attentive care. I keep my schedule organized so I can be flexible with visits, walks, and overnight stays whenever possible. My goal is to give every pet the time, attention, and affection they deserve while keeping owners updated for complete peace of mind. Your pet's safety and comfort are always my top priorities. I carefully follow each owner's instructions, including feeding schedules, medications, exercise routines, and any special needs. I take time to build trust with every pet, creating a calm and loving environment where they feel safe and cared for. Whether I'm caring for your pet in your home or mine, I'll treat them like a member of my own family and keep you updated with photos and messages throughout every visit.
About: I’ve taking care of dogs and cats for my whole life. My whole family owns dogs and cats and I all always volunteer to take care of them. I have two rescued puppies that are my entire life I am an orthodontist assistant. My job is five minutes away from my house. I work 3 days a week and the rest of the days I am free and at home I have a 2 acres house, the whole yard is fenced and it has a lot of space for your dog to run and play. I also have two rescued puppies that are extremely friendly that love to play.
“Ariella is simply the best! We have several pets with totally different personalities and she is so good with picking up on their individual traits. We fully trust her with our babies and always feel at ease when away!”
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!
The median cost per walk for dog walking in Windermere is $20
Dog parents share their Rover experiences - Windermere
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?
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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.
How to book dog walking
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 - Windermere
Select a filter and find qualifying sitters offering dog walking.Sitters in Windermere average 3 repeat dog walking clients
FAQs for Dog Walking - Windermere
Frequently asked questions about Rover
The average cost of Dog Walking in Windermere is $22 per walk as of October 2026. Most bookings cost between $17 and $28 per walk. On Rover, walkers set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 5,263 sitters on Rover offering Dog Walking across Windermere. 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 Windermere. Since all dog walkers are local, they may have a neighborhood dog who is a good walking companion to yours.
For dog walking bookings, your dog walker can send a Rover Card with details about your dog’s walk. Rover Cards require at least one photo and may include , the total walk time and distance, and any pee or poop breaks recorded by the walker.
The route map lets you review where your dog was walked in Windermere after the booking. It is not live GPS tracking.
Have specific details you would like included? Message your dog walker in the app before the 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 , 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 .
Yes, you can find walkers who have experience with handling special pet needs in Windermere. On Rover:
- 89% of walkers can help with special care needs
- 93% can help with giving oral medications or injections
- 97% 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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your walker interacts with your pet 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. Meet & Greets are a great way to prepare your pet and walker for longer stays or first-time bookings. Read our tips for your first .
walkers on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement walker.
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