Dog Walking Windermere
Book a dog walker to give your dog a 30-minute walk around your neighborhood.
Over 97 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.
“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.”
“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 !”
“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 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!!”
“Ani'yah did an excellent job walking my dog. As soon as i opened the door she welcomed me with a big smile was so kind to bring chocolates. She was very calm and polite throughout the walk. I recommend her 100%”
“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!”
“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.”
About: I’ve grown up with dogs my whole life and am very comfortable with daily pet care routines like walks, feeding, playtime, and giving them attention! I have also cared for dogs and cats for family friends while they were away. I am back home from college for the summer, so I have plenty of time! My schedule is pretty flexible outside of practices and workouts which are usually from around 9 AM-2 PM. Other than that, I’m available for walks, drop-ins, playtime, and overnight care! In a client’s home, I make sure pets stay comfortable by keeping them on their normal routine with feeding, walks, playtime, bathroom breaks, and lots of attention!
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
About: My name is Skye, I’m 27 and l’ve owned and cared for dogs and cats in a variety of sizes, temperaments and breeds for most of my life. I've been pet sitting for 5 years as a part time job and for fun since I was younger. As a passionate animal lover, I promise to provide a fun and safe environment for your pet as they walk, eat and play. Hope to meet your pets soon! I’m currently working part time, so I’ll have plenty of time to play with your pets! Please see my schedule for availability! My schedule is mostly consistent but has some rotation. I will keep your pets safe, happy, and healthy while enjoying their time on their walk, in their play time, or on their play dates.
About: I’ve been around dogs my whole life and have dog sat for many over the years! I’ve owned big & small dogs so nothing is new to me. Big believer in training dogs and that they are smarter than most people know. But overall I just want every pup to be loved and cared for in whatever ways the need! I currently work during the day but have a flexible schedule! I love taking walks after work in the evenings and during the day on my days off (Sunday / Monday) My dog is my everything to me but he doesn’t like kids. I have to be careful about that on walks. Every dog is different. Whether it’s on walks or in your own back yard I know dogs want to have fun and play but I’ll also ensure they stay safe. Whether it’s from other dogs, animals, running off or even from people- I understand that every dog is different and needs different care. I’ll pay attention and keep them safe, cared for and happy!
“Danielle did great with taking care of my two dogs and cat while we were away. She went above and beyond with her communication, sending pics and taking her time walking and feeding the pets. She even helped clean up with one of my dogs who had a poopy situation which was not at all expected, I felt bad my dog got runs while I was away. But she helped give him sweet potato so he felt better and even bought peewee pads, which just kept my mind at ease knowing my dog was being cared for. I would definitely rehire her again, she was just the best!”
The median cost per walk for dog walking in Windermere is $19
Dog parents share their Rover experiences - Windermere
Gina was absolutely wonderful. We had some last minute issues come up and needed a walker for two days at the literal last minute. Gina stepped in and took great care of our two pups. She was very communicative, punctual, and friendly. We will definitely be using her again in the future..hopefully with more notice!
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.
Kayleigh arrived a few minutes ahead of the scheduled 60 minute walk to become acquainted with Rhea. During the walk, she sent several pics of Rhea exploring her surroundings (enthusiastic ground sniffing). When they returned, Rhea demonstrated her signature affection behavior of licking and rubbing her head against Kayleigh’s leg. Rhea and I look forward to Kayleigh’s return.
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 near you
Select a filter and find qualifying Windermere sitters!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 July 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 July 2026, there are 5,321 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
- 96% can help with giving oral medications or injections
- 98% 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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