House Sitting Windermere
Find a loving house sitter to watch over your pets and your home.

Over 45 pet parents in Windermere have booked house sitting
Windermere, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Caleb did a great job sitting for our energetic 1.5 year old dog. His communication was good, and we came home to a happy dog in a very clean house. I will definitely book him again!”

“Meagan was fantastic! She shared daily updates about our senior cat, Pinot, along with pictures and videos. She also took excellent care of our house while we were away.”

“Kathleen really is the best! I’d give her 6/5 stars if I could. She was not only timely with the girls’ schedule, she sent us updates everyday along with pictures of them. We could tell how much she cared for the girls and we can’t thank her enough. Our cat was dealing with some vomiting issues, but Kathleen was on top of keeping us updated and making sure she was doing ok. We can’t recommend her enough!”


“Michelle was wonderful. i came home to 8 very happy and loved animals. She sent a picture with a message every night. Since I have several ancient pets she stayed at our house and kept it looking good. We would definitely hire her again.”

“Noah was an absolutely fantastic dog sitter! He was reliable, communicative, and treated my dog with so much genuine care and attention. I received regular updates and photos, and it was clear my pup felt comfortable and happy the entire time. I couldn’t recommend Noah more highly!”

“Karen communicates well, always leaves my place clean, and keeps my dog Reese happy while I'm away! She consistently goes above and beyond to make sure he is cared for.”

“Jasmine is a complete dream. She is caring, intuitive about pets and helped ours feel so calm and safe, even on the 4th of July when fireworks were going off. She's completely responsible, reliable, and has great communications, often sending us pictures of our pets, but beyond that, just has a beautiful way about her and a true love and affection for the pets in her care. Our dog, Ollie, can sometimes be a little shy at first but right away, from the photos she sent with his eyes shining and happy, I could tell she'd made him feel completely at ease. Anyone's pets would be lucky to be in her care.”


“Jason was stellar and we couldn't be happier! Our dog and cat loved him, and he was very organized and professional. When we got back it felt like we'd been gone for just an afternoon - the house was tidy and the pets seemed unphased by our absence! Jason was also particularly gracious working around a last-minute internet outage at our house.”

“Sofia was great! She gave us regular updates and the dogs seemed very happy. Sofia also was very conscientious and took very good care of our house. We definitely will use her again.”


“Robert was great with our dogs while we were away for a week. He left our house clean and tidy. He sent pictures and updates daily. We would absolutely book Robert again to watch our pups!”

About: I’ve taken care of all types of dogs over my years as a pet sitter. Some puppies, some elderly dogs. I have experience in emergency situations, if the need arises. This is my first time trying Rover out -I’ve usually only advertised through word of mouth. Excited to get to know you & your pet. Pet care will be my main priority. Schedule can be fit around your pet. If emergency situations arise - I have experience in that. I need to exercise so taking dogs out for walks will be welcomed. I will follow the instructions laid out for me by the employer. You let me know if your pet is allowed or not allowed on furniture and I will act accordingly.
“Jolene is awesome, she was well prepared with details about toby. She is a creative person and it was awesome to see her draw Toby! Toby loved her!!”

“Jade was the best. She was available very last minute and was wonderful with our pets. Plenty of regular updates and photos. We will definitely have Jade watch our pets in the future.”

“This was the second time Myranda watched Clyde and it was great! She sent daily updates with pictures, gave Clyde a lot of attention (including a Christmas toy), and when my flight was delayed 5 hours was able to get an extra walk in and feed him dinner. I really appreciated Myranda's help and will definitely be booking with her again!”

“It was great to have Olivia watch my two dogs during a weekend getaway. She was patient with them as they got comfortable with her and then settled in nicely. Not only were the dogs taken care of and updated provided daily but my apartment was left extremely clean and tidy. Would have Olivia watch my dogs any time.”

“Mason was amazing! I needed to go on a last-minute trip, and he was incredibly responsive, thoughtful, and accommodating. He took wonderful care of my dog, and it’s clear that he’s a natural animal lover and caregiver. What a gem!”

“Quinn did an excellent job watching my doggo Kanna. They were really responsive and I appreciated the lovely photos they sent. Kanna got to go on a really long walk at a local park which she surely loved. Quinn super exceeded my expectations in all areas and I'm grateful they could watch kanna for her first time in a new house while I was away.”

“Jiani was an amazing rover during our time away. She was super responsive, communicative and proactive in her updates to us while we were away. We felt confident that everting was taken care of, and would be happy to work with Jiani again in the future.”

“Judy is the best of the best. She goes above and beyond for you and your pet. Very good communicator and reliable. She was extremely patient with my (sometimes difficult, lol) doggo. I would recommended her to anyone in need of a pet sitter!! Thank you so much, Judy. Phoebe appreciated you🫶🏼”

The median cost per night for house sitting in Windermere is $65
Pet parents share their Rover experiences - Windermere
Michelle watched our 6 month old German Shepherd mix puppy and adult cat, and house sat for 5 days when our original sitter canceled on us a couple weeks before our trip. This was our first time using rover and we couldn’t have gotten luckier with Michelle! She was clearly a professional, taking over our pets’ daily routines seamlessly, which was so important to us given our puppy’s age. She sent daily check-ins and photos, which kept us at ease during our trip. Our home was also spotless and taken care of, making our return so much easier. We can’t wait to book her again soon!

Leslie was amazing - she watched our high maintenance corgi, Ella, for a long weekend while we had to go to a family funeral. She was so thoughtful and did such a good job. The house was immaculate and Ella was very happy and content when we got home. Leslie sent pics throughout the weekend and it was obvious that Ella fell in love with her as well! We will definitely use Leslie again and would highly recommend her!

Ashley was so wonderful! She sent us updates, was a great communicator, and really went above and beyond! The pictures she sent assured us that our pets were having fun with her. Even our very skittish cat warmed up to her! Our house was in such great condition when we got back, and it was clear she took great care of our pets. I would highly recommend her!

Noah has been a godsend relief to my anxiety about finding quality care for the furry misters while I need to travel. I have 3 young pets (cats, dog), all of which has their quirks. Even Dmitri, who can have loads of stranger trepidation, warmed to Noah sooner than expected. In fact, they all seemed drawn to him. My home was equally treated with care and his communication is top notch. I was so pleased, I quickly reserved his care again.

Amanda was so great with our 3 pups! Having to have pivoted on short notice, they brought so much comfort for a long trip away. They shared daily updates and sent lots of pictures of play time, sun soaking, and cuddles. I could really tell our pups loved Amanda. Having two senior dogs too, they did great with navigating meds and challenging eating habits as well. We can’t thank Amanda enough for keeping them happy and comfortable!

Taila was so attentive to our dachshund puppy. It was our first time leaving him but she reassured us so much and went above and beyond, staying in contact the whole day and communicating how he was doing and what he was needing. It made the day easier on all of us and I am so grateful!! Pepino was so calm and happy when we came back, and I know it was thanks to Talia’s help.

Danielle took wonderful care of Pepper for 10 days. I really appreciated her thoughtful daily notes and photos—it was reassuring to see that my dog was happy and that Danielle genuinely seems to enjoy being with her. She also takes good care of my home while I am away.

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.
How to book house sitting

1. Search
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2. Meet In Person
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3. Book & Pay
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