Dog Sitting in Windermere
Book a Windermere dog sitter to watch your dog in your sitter’s home or yours.
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Top rated Windermere dog sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Reece took the time to meet my dog and to address any concerned or question that I had. My dog can be a little hyperactive and she was able to handle him just fine. Will definitely recommend her or use her service again. Thank you Reece for taking good care of my doggy.”
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!
“Grateful for Sarah accepting a last minute drop-in visit to our home to let our girls out and play with them before bed! My original travel itinerary changed last minute affecting my ability to get home before our girls bedtime. Sarah saved the day! 🙌🏽”
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.
“Karen was absolutely incredible! Little Stevie has never liked a sitter as much as she has Karen! I know that next time I go out of town Stevie will be in good hands with Karen and I will be trying to rebook with her again in the future.”
“Our pup was very well cared for while we were away. We will definitely be using Nicholas again in the future. He did and amazing job and I love that he washed the dogs bowls before he fed him each time.”
“Yelena provided outstanding care for my Giant Schnauzer, Jager. From the moment we met her, it was clear that she genuinely loves animals and takes her responsibilities seriously. She kept us updated, was attentive to Jager’s needs, and made sure he was comfortable and well cared for throughout his stay. Jager came home happy, relaxed, and clearly enjoyed the time he spent with her. Knowing that he was in such caring and trustworthy hands gave us complete peace of mind. I highly recommend Yelena to anyone looking for a reliable, compassionate, and professional dog sitter. Thank you, Yelena, for taking such wonderful care of Jager. We would gladly trust you with him again!”
“Jessie has been so great and helpful to us this week! She is on time and very good about keeping me update on the dogs activities. Will definitely be rebooking. We love her.”
“Tanya is absolutely the best dog and cat sitter we could ask for! She takes wonderful care of our pets, giving us complete peace of mind whenever we’re away. Our animals are always happy, well cared for, and comfortable in her hands. What really sets Tanya apart is that she goes above and beyond. Not only does she care for our pets, but she also helps with household tasks like picking up pet waste, taking our trash and recycling cans out to the curb, and bringing them back afterward. Those extra touches make such a difference and show how thoughtful and dependable she is. Thanya is reliable, caring, and incredibly helpful. We highly recommend her to anyone looking for a trustworthy pet sitter who truly treats your home and pets as if they were her own.”
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.
“We can’t say enough positive things about Nye and her quality of care! She visited our 2 older cats and an additional temporary cat who was still adjusting to the new environment twice per day. We were on an 8 day Cruise and are so pleased we found someone so wonderful and able to put us at ease from her very first contact. Each cat had something unique she had to deal with and she did so with flying colors. She sent at least 8 to 9 pics during each check in — more than we have their entire lives lol. Her caring energy and love for what she does was extremely obvious. We feel blessed and will most definitely employ her again for future trips out of town. Trustworthy. Safe. Loving to our “children”. Great attention to details. Able to navigate our high degree of security. What else can I say other than you should contact her for anything Rover related without hesitation! ??”
“Excellent first experience, Darryl was responsible, communicative, followed instructions to the T, and took good care of my doggo, most definitely would recommend him”
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.
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!
About: You know that girl at parties hanging out with the dog of the house instead of mingling? That’s me, I’m that girl!! I’ve grown up with all sorts of animals and have such respect & love for them, dogs in particular💜 My best fur friend Buster passed away at age 16 and it’s been an adjustment in my house, I have a lot of time on my hands, and would love to offer my services and attention to my community! I have dealt with separation anxiety and senior care (my fur baby had kidney issues in the end and required a lot of fluids injections) and am comfortable administering medications so I am willing to work with you & your needs. Upon request, I can also check your mail, bring in packages, water your plants, and do other small household tasks/chores to ensure that you have no worries while you're away. I look forward to meeting you! Spayed & neutered animals only please. I work part time, and my weeks are pretty flexible for drop ins and walks/care throughout the day so I’m available to spend as much time your pets need and give them all the lovins! I have a completely fenced yard and no current animals in my home, so your pet will get a lot of attention! I have a lot of space and can crate your pet if that’s what’s needed, and live in a gated community. Self transportation, and because I’m in a good area in Ocoee, between Windermere & Winter Garden, it’s great for drop ins as needed and I can be readily available.
“I have never left my cats in the care of anyone I did not directly know before, but this time I had to, with late notice at that, and moving forward when I have to do so again I will absolutely choose Jocelyn every time! She is incredibly caring, concise, punctual, communicative, attentive, and trustworthy. One of my cats never comes out from hiding for strangers, and even rarely for close friends who he has met before, but with Jocelyn he was out and about! She sent great pictures of our cats and their food, water, and litter. There is absolutely no question of the quality of care she provides, even on brief visits! If you are in a similar boat, I highly recommend Jocelyn!”
About: I’ve taken care of dogs since I was 14. I’ve watched family and friends furry friends while they went out of town. I also had an amazing dog that passed recently and I miss everyday. I currently work full time so I will be out of the house between 8 and 5. I have every other Friday off and I am able to spend the full day with your dog on those Fridays and then every Saturday and Sunday I follow instructions diligently and will ensure your dog is taken care off with all of there needs being met plus all of the cuddles
Windermere dog parents share their Rover experiences
Elizabeth was absolutely wonderful. She is so friendly and personable. I knew from the moment we met her that our furry family members would be in great hands. She did a great job keeping everyone happy and healthy while we were away. She provided daily photos (that had us laughing) and I loved getting the drop in report cards to see how our babies were doing. She leaves great comments on the report cards as well for extra communication. I highly recommend Elizabeth and will definitely book her again.
I highly recommend Taylor! She is reliable, professional, and clearly cares about the animals she works with. Communication is excellent, and I appreciate the updates and photos during walks. It's a relief knowing my dog is in good hands, and I highly recommend her to anyone looking for a trustworthy and caring individual to take care of their pets!
Tanya is absolutely the best dog and cat sitter we could ask for! She takes wonderful care of our pets, giving us complete peace of mind whenever we’re away. Our animals are always happy, well cared for, and comfortable in her hands. What really sets Tanya apart is that she goes above and beyond. Not only does she care for our pets, but she also helps with household tasks like picking up pet waste, taking our trash and recycling cans out to the curb, and bringing them back afterward. Those extra touches make such a difference and show how thoughtful and dependable she is. Thanya is reliable, caring, and incredibly helpful. We highly recommend her to anyone looking for a trustworthy pet sitter who truly treats your home and pets as if they were her own.
Samantha was amazing! We were so fortunate to have Haze in her care. I have a 3 year old German Shepherd with a lot of energy, and she handled him so well. Samantha was attentive, communicative, and took great care of him. I really appreciated the frequent updates and photos too! Would definitely book with her again. Highly recommend! 🐾
Popular requests near you
Select a filter and find qualifying Windermere sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs while you’re away
3. Book & Pay
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The median cost per night for dog sitting in Windermere is $20
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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Windermere average 6 repeat dog sitting clients
Dog Sitting FAQs
Frequently asked questions about Rover
Dog sitters on Rover are free to set their rates. The median cost to hire a dog sitter in Windermere on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A dog sitter’s rate may also change as you customize your booking to fit your and your dog’s needs.
As of Jun 2026, there are 5,252 dog sitters in Windermere. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog sitter near you. As a reminder, dog sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, 88% of Windermere dog sitters respond in under an hour.
Dog sitters in Windermere have an average of 15 years of experience. Dog sitters with repeat customers have an average of 6 repeat clients. Experience can vary from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Windermere.
Rover makes it easy to find Windermere dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog sitter’s pets
There are 5,252 dog sitters in Windermere on Rover, so you’re sure to find the perfect match for your dog! In Windermere, 98% of dog sitters offer daily exercise, 97% offer medication administration, and 91% 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 sitter near you. As a reminder, dog sitters joining Rover must pass background checks for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter 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 sitter 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 sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.
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