Pet Sitting in Windermere
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Windermere pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“This was our first time using a pet sitter instead of traditional boarding. It was an amazing experience and we will 100% do pet sitting again in the future. Cassia always gave detailed reports after her visits and we got lots of photos each time which was a huge plus. Our cat seemed much happier when we returned home this time vs our last trip when we boarded him. Cassia was absolutely amazing and we are thrilled to have found her!”
“Christopher is amazing! Our dogs got comfortable with him very fast and they enjoy spending time playing with him. Christopher is very punctual, responsible and communicative.”
“Victoria was amazing! Very patient and understanding when we had key trouble and very informative in the after visit reports. Would recommend and rebook in a heartbeat! Thanks so much!”
“It was my first experience with Rover, and I honestly don’t think I could find a better sitter than Lindsey. My cats had never been apart from me for this long, so I was quite worried at first. But thanks to her wonderful care, I was able to focus on my trip without any concern. I only asked her for basic care, but she gladly gave her best. She always played with my cats with so much love and sent me plenty of photos showing how happy they were. Even in unexpected situations, she didn’t hesitate to visit and help them. I’m deeply grateful to her and truly recommend her to everyone! Let’s make sure the whole world knows that Lindsey is the best sitter ever!”
“Taylor is an excellent sitter. She was so sweet to my kitty and she provides tons of excellent pictures and great summaries of each visit. She is also great at communicating and quick at responding. Highly recommend!!!”
“Madison followed the written instructions I left for her, was respectful of my home and time, and always pleasant when communicating. My cat loved Madison’s company. She left my apartment clean and neat. I came back to a fluffier cat - thanks for the brushing! You will not worry about leaving your pets with Madison!”
“She is a sweet person! And did exactly as I requested. She even got along with my black cat who really does not like ppl. She is very trustworthy as well! Definitely rebooking soon! She sent photos and communicated very well too.”
“We’ve hired Shelley for several bookings and highly recommend her. Every visit she sends us updates and pics of our pets. She’s always on time, follows our feeding and care schedules and provides each of our pets with individual attention.”
“Jonathan was an amazing life saver for our last minute trip. He took amazing care of our girl and treated her like family making sure she had everything she needed while we were away. I would highly recommend him to anyone who needs a pet sitter and we will definitely be using him again in the future!”
“Great experience!! She was great at communicating and my pups loved her. She stopped by to do a meet and greet before the drop in visit which I greatly appreciated. I will definitely be using this rover walker again!”
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.
“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.”
“Samantha was a hit with Mulder when they first met! I saw how he immediately accepted Samantha. It gave me peace of mind while we were away for an extended period of time. We have your number Samantha and we will call you again when needed. Thank you!”
“Karen has been an absolute lifesaver for our family! She took care of our Shih Tzu, Layla, while we were away, and we couldn’t have asked for a better dog sitter. Karen is incredibly reliable, attentive, and treated our dog as her own. Karen kept us updated with daily photos and messages, which gave us great peace of mind. Layla was happy, well-fed, and enjoyed her walks. We came back to a content dog, thanks to Karen’s exceptional care. If you’re looking for someone who will treat your pet like their own, Karen is the one to go to. Highly recommend her services!”
“Michael did a great job taking care of my dogs! He was on time for each visit and very respectful of the house. He sent many photos and videos of the dogs which we appreciated very much. Would definitely hire Michael again to watch our dogs!”
“Poliana is a dream come true. She is extraordinary thorough, and even goes out of the way to clean and tidy up our cat’s space - surrounding litter, food, and EVEN cleaning up a hairball incident. Poliana is a true animal enthusiast with a huge heart. We will be using her services for the rest of the year!”
Over 436 pet parents in Windermere have booked pet sitting
Windermere pet parents share their Rover experiences
I had Taylor cat sit for my super scaredy anxious sick kitty that needed medication administered while I was gone. It’s always nerve wracking leaving our sick fur babies but after meeting Taylor I knew I picked the right sitter. While we were gone, she was able to give my difficult to medicate kitty her meds. She spent quality time with kitty and was super punctual (We needed punctuality because of medication timing). She’s definitely warm and loving and treating my fur baby like it was her own. She sent pictures every day and communicated every single time she came to see my kitty.
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.
Megan was a wonderful sitter for our two cats! She sent lots of pictures and gave them as much attention as they would let her. She’s clearly an animal lover and we enjoyed our vacation so much more knowing our pets were well cared for! I’d highly recommend Megan to anyone and we absolutely plan to use her services again in the future.
Lillian was AMAZING! Caring, sweet, kind and obviously loves animals. She came to visit us even before booking to make sure it was a good fit and discuss how to take care of my cat. Great updates, speedy replies and some really cute pictures. This was the first time I left my cat alone and Lillian really helped ease my anxiety of this. Already looking toward my next trip and booking Lillian again. Thank You!
Popular requests near you
Select a filter and find qualifying Windermere sitters!How Rover works
1. Search
Read verified reviews by pet parents like you and choose a sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your pets while you’re away
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 night for pet sitting in Windermere is $20
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 pet 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.
Sitters in Windermere average 6 repeat pet sitting clients
Pet Sitting FAQs
Frequently asked questions about Rover
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Windermere on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Jun 2026, there are 1,362 pet sitters in Windermere. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 87% of Windermere pet sitters respond in under an hour.
Pet sitters in Windermere have an average of 15 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet 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 pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
There are 1,362 pet sitters in Windermere on Rover, so you’re sure to find the perfect match for your pet! In Windermere, 100% of pet sitters offer daily exercise, 98% offer medication administration, and 94% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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