Dog Walking Windermere
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 110 pet parents in Windermere have booked dog walking
Windermere, 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.
“Jamie is amazing as always!! She really gets to know your pet, and it shows. You can tell that she really cares and wants to do what’s best for your pup. Jamie is my first choice every time!!”
“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!”
“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.”
“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.”
“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 !”
“⭐⭐⭐⭐⭐ 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: After loving animals for more than 20 years and having more free time open up, I’d love to base my free time around helping other pet owners. I am here to help if your pet needs a walk around the neighborhood, drop ins while you’re at work, or multiple while you’re out of town. I am open everyday of the week except for Wednesdays. I am free from 9 Am to 8 Pm but, can work around any other hours needed or for overnights. I want you to feel 100% safe about leaving your pet to be cared for by me whether it’s for drop ins in your space or a quick in-and-out to take your pet on a walk. I will follow instructions thoroughly and will make myself as available as possible to answer any questions and send as many photos when you’re out of town!
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!
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 for Dog Walking in Windermere on Rover is $22.2 per walk (as of September 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 September 2026, there are 5,287 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 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 Windermere.
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 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 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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