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.
“Elizabeth was great! She was very accommodating when I needed to update the time for the drop in. She communicated promptly and was very sweet and caring with Luna. She made sure Luna ate and had lots of bathroom breaks while walking her. I will definitely book with her again.”

“This is our second time asking Megan to watch our cats while we’re out of town— and won’t be our last! 😎 Megan is always very communicative, about everything! She’s proactive with questions, leaves a great and detailed communication card at the end of each check in, and sends the best pictures of our kitties that really captures how well she takes care of them. Always responsive and went above and beyond to help us by assisting with little extra tasks we asked of her while she was checking on our pets. Thanks for everything Megan!”
“I can not say enough good things about or express how much we appreciate Danielle. On several occasions now, she has checked in on and taken excellent care of our two feline girlies. It is so nice to be able to go away and feel sure that they are safe, secure, and well-cared for. Thank you again, Danielle!”

“You will absolutely love the expert care that Samantha will give to your pet. As a pet owner herself, she knows what's involved to keep your pet happy in your absence. I trust Samantha with my Persian and my kitty loves when Samantha visits. Don't delay...hire her today!!!”

“Jenn was great with our playful cat! She sent pictures everyday and kept me updated. I will definitely use her again. She also quickly let me know when our door battery was low and when there was a change in our cats litter box. I knew our girl was in great hands!”

“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!”
“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!”

“She was great in keeping Pumpkin fed and was able to accommodate some extra stays when we had a delay in flights, which we really appreciated! Shelley is very nice and attentive, with good communication as well.”

“Poliana is fantastic!!! She treats my pets as her own ❤️ I highly highly recommend her for her kindness and care and attention to details regarding special needs pets as well 🐶🐟😻🦎especially as our fur babies who start to get older ❤️”

“As always Karen was amazing taking care of my babies! Our cats 🐈⬛ absolutely love Karen and I know they are being taken great care of! My mind is at ease having you watch the kitties, thank you again for an amazing experience!”

“I hired Taryn for a drop-in midday to let out and play with our Goldendoodle. She was on-time, communicative, took lots of pictures, and very easy to deal with! Would highly recommend!!”

“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.”

“I booked Samanntha to look after my cat Sam for a week while I was on holiday. We emailed back and forth a few times to discuss what I was looking for and when she came to meet Sam he fell in love with her, even offering her his belly for rubs by the end of the meeting. Right then I knew she was the one!! Plus she and I had a wonderful conversation as well! She was great at communicating, cleaned his litter every day, played with him, and sent pics and videos each day, even doing a video chat one day! I would definitely recommend her services, as she is friendly, kind and clearly loves animals!! Thank you, Samanntha!!”

“Tracy did an excellent job caring for my achnauzers. She was attentive, responsible, and went above and beyond by keeping the crate area clean and organized after every visit. I truly appreciated her professionalism, communication, and the care she showed to my pets and my home. I would absolutely recommend Tracy to anyone looking for a reliable and thoughtful pet sitter.”

Over 420 pet parents in Windermere have booked pet sitting
Windermere pet parents share their Rover experiences
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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 Mar 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 Mar 2026, there are 1,302 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, 89% 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 1,302 pet sitters in Windermere on Rover, so you’re sure to find the perfect match for your pet! In Windermere, 98% of pet sitters offer daily exercise, 94% offer medication administration, and 90% 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.















