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

Prices are estimates per walk. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: MARK B.
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MARK B.
Star Sitter
from
$20
per walk
5.0 out of 5 stars
243 reviews
48 repeat clients
3 years of experience
Windermere, FL, 34786

Mark does an amazing job with Mo especially in the heat. He is very aware of the health of my pup and makes sure he is hydrated on these very hot days.

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Barbara T.
Sitter Profile Image: Lindsay L.
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Lindsay L.
Star Sitter
from
$19
per walk
5.0 out of 5 stars
61 reviews
20 repeat clients
22 years of experience
Orlando, FL, 32819

Lindsay is fantastic! She is a kind and compassionate pet lover. Great communication all the way through and wouldn’t hesitate to book her again!

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Marty K.
Sitter Profile Image: Alexis P.
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Alexis P.
from
$12
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
12 years of experience
Windermere, FL, 34786

About: I've had dogs my entire life and have experience caring for dogs of all sizes and ages. Unfortunately, my family dog recently passed away, which only deepened my appreciation for the love and companionship pets bring into our lives. I recently graduated from Florida State University and regularly volunteered at Champs Chance Rescue in Tallahassee, where I helped care for dogs of different breeds, ages, and temperaments. I also fostered a dog this past semester, which gave me valuable experience providing consistent care and helping a dog adjust to a new environment. I love spending time outdoors, going on walks, and making sure dogs get plenty of exercise, attention, and affection. As a nursing student, I'm responsible, dependable, and attentive to each pet's individual needs, and I treat every dog like they're my own. I’m currently focused on studying for my NCLEX to become a Registered Nurse, so I spend the majority of my time studying from home. I also work part-time as a Pilates instructor, which is typically only a 6–10 hour commitment each week, and my schedule is very flexible. Because of this, I have plenty of time to provide attentive care, companionship, walks, and playtime for your pet throughout the day. My home is a safe and pet-friendly environment with plenty of space for your dog to feel comfortable. I have a pet ferret who stays in his cage, and I am able to crate your dog if needed. I also have a screened-in pool area and live in a gated neighborhood with lots of green space that's perfect for walks. Additionally, there is a local dog park just a short drive away for dogs who enjoy extra exercise and socialization.

Sitter Profile Image: Jamie L.
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Jamie L.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
46 reviews
11 repeat clients
20 years of experience
Orlando, FL, 32819

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!!

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Ashley W.
Sitter Profile Image: Taylor C.
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Taylor C.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
12 reviews
5 repeat clients
11 years of experience
Orlando, FL, 32819

About: I have taken care of animals my entire life and I would love to help take care of your fur babies! I have taken care of my own animals as well as friends/ family’s animals since 13 years old. I currently have 3 fur babies of my own as well as an entire colony of feral cats that I take care of. I treat every pet like family and give them the care and attention they are used to when you are home. I have a very flexible schedule as a fitness instructor and typically work for a few hours a day with long breaks in between. Whether you need a long term pet sitter or someone to stop in for short breaks, I am available to help you! I will care for all pets as if they were my own. I have a deep love for all animals. I don’t just show up to check on your pet, I will make sure they feel safe, loved and happy while you are away. Your baby deserves more than just a quick walk.

Sitter Profile Image: Tathyana  F.
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Tathyana F.
from
$15
per walk
5.0 out of 5 stars
106 reviews
35 repeat clients
5 years of experience
Windermere, FL, 34786

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 !

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Sheng Yi L.
Sitter Profile Image: Elizabeth R.
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Elizabeth R.
Star Sitter
from
$18
per walk
5.0 out of 5 stars
26 reviews
10 repeat clients
11 years of experience
Winter Garden, FL, 34787

Great service!!!

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Patricia M.
Sitter Profile Image: Reece L.
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Reece L.
Star Sitter
from
$14
per walk
5.0 out of 5 stars
65 reviews
20 repeat clients
10 years of experience
Ocoee, FL, 34761

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.

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Jordan M.
Sitter Profile Image: Sarah H.
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Sarah H.
Star Sitter
from
$25
per walk
4.9 out of 5 stars
174 reviews
72 repeat clients
12 years of experience
Ocoee, FL, 34761

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!

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Angel S.
Sitter Profile Image: Morgan G.
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Morgan G.
from
$13
per walk
9 years of experience
Orlando, FL, 32835

About: I have watched dogs, cats, houses, and even chickens! I have almost 10 years of paid experience walking, watching, and house/pet sitting. I am friendly, reliable, and organized and have multiple repeat sitter requests. I also have experience of watching/walking multiple pets at once. I have grown up with pets my entire life and I am very comfortable around cats and dogs. I'd love to help make your life easier whether it be daily check ins or just filling in while you are out of town. I am currently working part time, so I usually work 4 days a week and have off 3 days. On my off days I am available all day. When working, I can be available early mornings and most late afternoons/evenings. Working or not, I can be a available for house sitting or pop in visits. I frequently monitor the food/water levels as well as checking the litter box multiple times a day. I like to get a minimum of 2-3 walks in a day when i’m working. When I’m off, I’m available for longer walks or dog park visits. I always make sure to leave my client’s house cleaner than when I arrived and make sure the animal’s needs are fully met.

Sitter Profile Image: Jenn H.
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Jenn H.
Star Sitter
from
$23
per walk
5.0 out of 5 stars
117 reviews
40 repeat clients
10 years of experience
Orlando, FL, 32835

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.

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Felicia R.
Sitter Profile Image: Megan W.
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Megan W.
from
$22
per walk
5.0 out of 5 stars
83 reviews
18 repeat clients
8 years of experience
Orlando, FL, 32819

Always such a wonderful experience having Megan as our dog walker!

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Rebecca M.
Sitter Profile Image: Taylor A.
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Taylor A.
from
$15
per walk
5.0 out of 5 stars
6 reviews
3 repeat clients
20 years of experience
Lake Copeland, Winter Garden, FL, 34787

Thank you very much for your great service! I hope wasn't too difficult with such hot days. I'll look at your availability 'cause I might need your help again soon😀

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Marissa H.
Sitter Profile Image: Ani'yah G.
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Ani'yah G.
from
$10
per walk
5.0 out of 5 stars
2 reviews
1 repeat client
15 years of experience
Winter Garden, FL, 34787

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%

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Danlex B.
Sitter Profile Image: Christopher F.
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Christopher F.
Star Sitter
from
$22
per walk
5.0 out of 5 stars
9 reviews
3 repeat clients
24 years of experience
Orlando, FL, 32819

Chris was fantastic. He was on time and Bear loved him!

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Suzette R.
Sitter Profile Image: Jacqueline G.
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Jacqueline G.
from
$16
per walk
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Windermere, FL, 34786

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!

Sitter Profile Image: Sherry A.
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Sherry A.
from
$20
per walk
5.0 out of 5 stars
3 reviews
2 repeat clients
9 years of experience
Ocoee, FL, 34761

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.

Sitter Profile Image: Taryn N.
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Taryn N.
Star Sitter
from
$25
per walk
5.0 out of 5 stars
50 reviews
18 repeat clients
23 years of experience
ORLANDO, FL, 32819

Taryn is fantastic. So caring and responsible. So happy to find her.

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Theresa C.
Sitter Profile Image: Paula L.
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Paula L.
Star Sitter
from
$15
per walk
5.0 out of 5 stars
4 reviews
2 repeat clients
10 years of experience
Orlando, FL, 32835

About: Hi! I’m a true animal lover with a big heart for both dogs and cats. I understand that pets are family, and I treat every animal in my care with the same love, patience, and attention I would give my own. Whether your pup needs long walks and playtime or your cat prefers quiet companionship and gentle care, I’m happy to match their unique personality and routine. I currently work part-time and have a flexible schedule, which allows me to accommodate drop-in visits and pet sitting in your home. Whether your puppy needs patience, playtime, and consistency, or your senior dog needs a slower pace and extra TLC, I have experience providing attentive, compassionate care for both. I’m happy to follow your pet’s routine closely, provide regular updates and photos, and make sure they feel safe, comfortable, and loved while you’re away. My goal is to give you peace of mind and keep your furry family members happy in their own familiar environment.

Sitter Profile Image: Georgiana M.
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Georgiana M.
from
$20
per walk
5 years of experience
Windermere, FL, 34786

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!

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Over 97
pet parents in Windermere have booked dog walking

Windermere dog parents share their Rover experiences

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5.0 out of 5 stars

Jamie has been very helpful with my last minute needs for a dog walker! She is very caring and makes sure my puppies are not walking on hot summer pavement. I really appreciate her and highly recommend!

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Matthew O.
Dog Walking
5.0 out of 5 stars

Madison was a great communicator and took care of my pups very well! Thank you for taking the time to message and follow all directions. 🐾🐾

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Ginger F.
Dog Walking
5.0 out of 5 stars

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.

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chandni_010@hotmail.com
Dog Walking
5.0 out of 5 stars

Lena is so kind and gentle, My pup, Drew, was smitten from the start! Thank you Lena for coming to help with such short notice!

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Amy R.
Dog Walking
5.0 out of 5 stars

Cassia is the absolute BEST! I trust her completely with the care and training of my pup. She’s accommodating and able to work with my schedule - I had a last minute ask to add a walk and she connected with me right away.

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Patricia C.
Dog Walking
5.0 out of 5 stars

It was great knowing our dogs were taken care of while we were out for the day. I loved that Maria was close too. She was able to meet up the day before. Definitely will use her our next trip.

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Jennifer W.
Dog Walking
5.0 out of 5 stars

Donna did a great job with Draco. He missed us and had a little interest in eating. Donna knew exactly what to do to make him eat.

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sherene h.
Dog Walking
5.0 out of 5 stars

Hailey is awesome! Arrives on time, communicates, and does everything we need for our dogs. Thanks Hailey!

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Caroline P.
Dog Walking
5.0 out of 5 stars

Samantha is agreat communicator, very reliable and very kind! She has been regularly walking my dog for a few months now and I highly recommend her as a dog walker!

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Cassandra T.
Dog Walking
5.0 out of 5 stars

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.

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John H.
Dog Walking
5.0 out of 5 stars

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!

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Patricia C.
Dog Walking
5.0 out of 5 stars

Corisa was great with our senior dog. She was prompt and very professional. Communication was great. I would definitely recommend Corisa to anyone.

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Rita C.
Dog Walking
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How Rover works

  1. 1. Search

    Read verified reviews and choose a dog walker who’s a great match for you and your dog
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  3. 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 $20

Why Choose Rover?

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  • 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 Jun 2026 was about $20 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.

If you’re searching for a Windermere dog walker for the first time, visit the dog walker’s profile and select the Contact button.

If you have an active request or have booked a service with a dog walker before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 5,264 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 5,264 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.