Dog Walking Windermere
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 115 pet parents in Windermere have booked dog walking
Windermere, Find top rated dog walking
“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.”
“Jamie regularly watches and walks my pup for me while I’m at work, and she’s been so caring! She’s so attentive, and she communicates with me a lot. Very trustworthy sitter!”
“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 !”
“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!”
“Solomon is a great asset, my dog Bandit looks forward to seeing him. Solomon is a good guy who is timely and good at what he does. I'm very impressed with him and this service.”
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
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!
About: I have grown up with at least 2 dogs my whole life and I love the bond that can come with an animal. I have walked and pet sit many times. I also volunteer at the animal shelter whenever I can! I would love to help watch over or walk your dog! I am currently working part time and have a pretty open schedule and availability. Just contact me about scheduling and we can work it out! I can pretty much help with whatever the animal needs. I know everyone has different styles on how they take care of their animals, so that’s something that we can discuss!
About: I have always been the "go to" person to care for friend and family pets. Mostly dogs and cats but willing to learn if you need any other kind of pet watched :) I currently work from home. I am home all day with the pets and will be able to tend to anything they might need. :) I have a large living room and am able to keep an eye on all pets at all times along with provide the required amount of walks your pet might need
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
The median cost per walk for dog walking in Windermere is $20
Dog parents share their Rover experiences - Windermere
Taylor has to be one of the best people to take care of my Zoe. She walked Zoe everyday for two weeks and was always on time, made sure Zoe was well exercised and well fed.Taylors love for animals and her work is very evident and I️ will definitely be using her again.
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 - 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 on Rover is $22 per walk as of October 2026. Most bookings cost between $17 and $28 per walk. 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 5,312 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 a map of the walking route , 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 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 Windermere. On Rover:
- 90% of walkers can help with special care needs
- 95% 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 Meet & Greet .
walkers on Rover set their own cancellation policy , 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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