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

Over 55 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.
“Mandy was very responsive and timely with all communication. We weren't home when she arrived or left but the pets were all happy and the home was clean.”


“Aryana is wonderful and I will 100% be hiring her again for dog sitting! She sent great updates and my dog Ash looked SO happy and comfortable with her in photos. She went above and beyond to give my dog enriching days that included all his favorite things. Aryana was comfortable staying with Ash who has some special needs and sensitivity to being handled. She is clearly very intuitive with dogs and built trust immediately with him. She sent me a picture of him lying on his back on the couch in a state of total bliss. I knew he was in good hands!”

“Anna was great with Wednesday! We are so thankful. Took great care of her as a last second request. Sent lots of photos. We felt so at ease. We will definitely request her services again. Thank you!”

“Adrian was a wonderful companion to Kiska during our trip! He sent great updates and took him on long walks every morning. Kiska is an anxious boy but Adrian had a very gentle energy and handled Kiska really well. Our home was left in great condition. Our other Rover cancelled last minute and Adrian was able to come for a meet and greet right away and is clearly very capable with animals. Would definitely hire Adrian again!”

“Robert was ABSOLUTELY fabulous! He was patient, thoughtful, and really communicative. From the moment we requested a sitter until after the service was complete, he was swift to respond, sent lots of pictures, and kept us updated on all the pet care rituals. He did not flinch when the breaker needed to be reset during a housesit, and he took such wonderful care of our tankgirl, Bailey. 5 stars, 2 thumbs way up, and a 3 snaps in Z formation! Highly recommend.”

“Melissa is just fantastic!!! This is our second time to ask her to take care of a cat, a dog, plants and the house for two weeks. She took care of them with love. Our pets are so accustomed with her. She sent us frequent photos and videos, which made us feel easy while away from home.”

“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!”

“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!”

“Jessica was amazing! Our pups were very happy and cared for in the three days we were away, and she sent us lots of updates and pics! Would absolutely book her again!”

“Egor was fantastic with our anxious dog, and we would not hesitate to book him to stay with Virgil again! He sent cute updates throughout his stay at our house, and it is clear our dog loves him. And, our house looked great when we returned. Thank you so much, Egor!!”

“Caleb loooked after our 7-month old Golden Retriver puppy and pet rabbit for 4 days and did a fantastic job! He spent tons of quality time with the animals (lots of walks and time playing outside for the puppy, and pets for the bunny) the house was spotless when we returned home. We would recommend Caleb and will certainly look to book him again when we have a need for a house sitter!”

“Kira was an amazing dog sitter! One of our dogs has separation anxiety, and Kira did a great job keeping her calm and cared for. They also asked a lot of great questions to make sure they had all of the information they needed about our dogs while we were gone. They sent us pictures of the dogs and gave status updates while we were gone which was really appreciated! They were very flexible with time too, I was able to book them with just a few days notice, and had to stay out later than expected which was no problem for them. Overall it was a great experience, our pups seemed very happy. Thanks Kira! <3”


“Stacey was great! She is a very prompt responder and very professional, sending helpful updates at least twice a day. She did great with our large, shy dog, who can sometimes be weird around new people. She left the house very clean and left a lovely note. Thanks again Stacey!”

“Allison did an amazing job watching for our dogs, who are starting to get old. Our bigger dog (husky/malamute mix), has bad separation anxiety and reactivity and she had no problems giving medication and taking care of him. Both of our dogs have high energy and she did a fantastic job taking them out. She also did a great job taking care of our house while sitting for the week we were gone. Very friendly and understanding, highly recommend!”

“Jolene was a dream come true. She went above and beyond. She took care of our little one as if it were her own dog. She kept us updated with lots of pictures. She was responsible and meticulous about every detail. We're already signed up to use her again! Highly, highly recommend.”

“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.”

“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.”

“We feel so lucky to have had Sofia stay at our home and care for our pets. She did a truly wonderful job. The animals were happy, relaxed, and clearly well loved, and we came home to a house that was spotless and beautifully cared for. She sent lots of photos and updates, which gave us such peace of mind while we were away, and her communication was always prompt, thoughtful, and kind. It made the whole experience completely stress-free. Sofia is responsible, trustworthy, and has a natural way with animals. We would hire her again in a heartbeat and recommend her without hesitation to anyone looking for exceptional pet and house care.”

The median cost per night for house sitting in Windermere is $65
Pet parents share their Rover experiences - Windermere
We had Emma watch our 13 year old (still very active) chocolate lab Kayak for 10 days while away on vacation. Kayak is a bit shy and can take a bit to warm up - but with Emma they had an almost magical bond right away. Emma just knows how to be present, and connect - as well as being extremely good at meeting our and our pup's needs. She managed complicated medications including chemo pills, gave walks and played ball - and provided numerous photos during our time away to put our minds at ease that all was well with Kayak during our absence. If you are looking for an extremely capable, mature, and fun-loving care-taker for your pet - we can't recommend Emma enough! Thanks Emma for a job well-done.

Judy did fabulously with our very different dogs. Marge who tends to be a bit more wary with strangers immediately felt comfortable with Judy. Smyth who is a lover to all and especially those who give him cookies adored her as well. This was longest we were away and both dogs while excited to see us seemed like they were well adjusted to the routine with Judy. Overall a wonderful experience with lots of pictures and videos of our dogs throughout our vacation.

Mackenzie was absolutely amazing with our dog Hank! She was extremely thorough and detail oriented about his care. I received daily pictures, video and text updates while we were away. The whole experience was above and beyond. We will be booking with her again!!

Tessa did an amazing job watching our wild pup, Baker for five days! She was very attentive, walked him every day, took care of a hot spot that he had, and gave us updates every day! She left our house super clean as well. We would definitely work with her again!

Kaitlyn was so flexible when we had a plumbing issue right before leaving town making our kitchen sink unusable for her stay and having a plumber working in yard. She handled it cheerfully and professionally. Dogs cats and house were all in great shape on our return. Highly recommend this sitter!
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.
Meet local sitters who will treat your pets like family

1. Search
Browse profiles of sitters near you who offer house sitting
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform














