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

Over 53 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.
“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.”

About: Hi, I’m Angie (they/she)! I’m a dog parent and PhD student with 4+ years of walking and caring for my own reactive dog, and 17 years of petsitting dogs, cats, small mammals, and lizards. My goal in pet care of any kind is making sure your pets feel as safe, loved, and happy as possible while you’re away. I’m very comfortable working with reactivity in dogs and will ask all dog owners what their dog’s limits and preferences are regarding common triggers during walks. I also have experience with senior dog and cat care and medication administration. I’m a PhD student with a flexible work schedule during the school year and full daytime availability during the summer. This allows me to accommodate most care requests. The safety and comfort of your pets is my most important priority. I commit to following the “leave no trace” rule when visiting in client’s homes.
“Margaret’s got great energy, my dog chills out quickly even with his separation anxiety and goes back to being one with the couch (his usual home behavior). Will absolutely book again!”

“Kathleen did a great job with house sitting for our dog. She was communicative and sent us a lot of updates that made us feel good about our dog while we were traveling”

“Junbo is kind, reliable, and communicative. She took care of my dog and place for over a week. My 7 year old dog loved her from day 1. Junbo followed the care instructions I left, sent lots of photos, and was generous with her time, the long walks, and day adventures she took my dog on. On the way back, my dog looked happy and healthy, and my place was clean and well taken care of. I’m happy to have found a great sitter. Thank you for your great work, Junbo!”

“Caleb did such an amazing job with our two cats, and high energy golden retriever. He spent quality time with all the animals, sent us updates and communicated great with us every day of our five day trip. We came home to a spotless house and happy animals!”

“I appreciated Mandy's quick responses (before, during and after the sit), willingness to come over prior to the sit for a meet n' greet with me, a quick orientation to home, kitty and her medication routine (insulin injections). Mandy was at ease and confident with all. The sit went as expected with a daily photo and quick message to reassure me that all was well during my 4 nights away. All was in order and tidy on my return and kitty content.”

“Adrien’s care of Linus (both physical and emotional) and thoughtful updates were just wonderful. The biggest sign to me of a top-notch dog sitter is how my dog is when I am back and walking him again on leash as he can be a frustrated greeter and reactive on leash, and my dog had improved! Already booking Adrian again.”

“Cassidy is so great! She was very communicative during our trip, sending photos, etc., giving our little pup all the cuddles and attention she wanted. Can't recommend her enough. Thank you Cassidy!”

“Noah was great, he was very patient in getting to know Abby and kept us up to date on the progress. Abby did warm up and they became good buddies. Noah was very low impact, the house was as neat as it was when we left. I would gladly have him come back!”

About: I started working with animals in high school, accruing hundreds of volunteer hours at my local animal shelter, where I honed in on my passion for pet care. As I transitioned to university life, I started walking dogs on the weekends, and really enjoy getting to hang out and provide for other people's pets. I have open availability through most of the week, and for late-evening drop ins over the weekends. This allows me a lot of time and flexibility to devote to caring for your pets. Communication is key, and I strive to ensure all preferences are met during my visit/walk with your pet! I will frequently send updates, such as photos from during my visit/walk, and a little blurb about what your pet and I got up!
“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.”

“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!”


“Jason was highly communicative and sent us plenty of photos while he watched our dog! Our pup seemed to have a great time while Jason was here and our house was left clean”

“Rhiannon took amazing care of my 6 year old border collie and made sure he had lots of exercise. She left my apartment spotless and was super communicative with pictures and videos daily. Highly recommend and will be booking her again soon.”

“I really enjoyed having Brittany care for Junebug! She brought great energy, authenticity, thoughtfulness as well as groundedness to caring for June. I had a lot of instructions and she was great about following them. I also really appreciated that she was so communicative while I was on vacation -- which I don't experience a lot with other Rover sitters; communication is something that I highly value when I'm an anxious parent leaving my my baby behind -- especially with someone I don't know at first so she put me at ease and I felt safe and secure leaving my dog Junebug behind. I would definitely use her again as a sitter!”
“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!!”


“Leo adores Chelsea! I know she is one of his favorite people. She left the house cleaner than when she arrived and took such care of Leo and my house. I would recommend her to anyone! She is gem.”

The median cost per night for house sitting in Windermere is $63
Pet parents share their Rover experiences - Windermere
Emma was amazing and took great care of my 60Ibs pittie mix (with some dog reactivity considerations, meds, and enrichment needs) for two weeks! Great to coordinate in advance with, very communicative and on time. While I was away, Emma offered updates and was responsive when I checked in. I came home to a healthy and happy pup and my home in good condition! Also mindful of building / security rules of my building. Emma went above and beyond staying later with my dog over Fourth of July evening. I had peace of mind while Emma was here. Kiska misses Emma already…

Hillary was wonderful! Leaving my dog in a strangers hands last minute is always nerve racking…but Hillary showed kindness, intuitiveness, and an ease that made me feel confident leaving my space and Nova in good hands. When I returned the space was clean, Nova was calm and happy, and Hillary asked great questions / was commutative throughout the stay. So grateful and would absolutely book again!

Kaitlyn is a great sitter, she stayed in my home over the weekend and took great care of my older dog. He needs medicine on a regular schedule and she was able to handle that no problem. Apartment was in great shape when I returned. She is responsible, flexible, and communicative. Thanks, Kaitlyn!

It's been an extremely smooth and easy process working with Tessa over the holiday weekend! Tessa was very communicative, patient and took great care of Beanie and Alfie. She also went above and beyond to get me updates for some new behaviors during the last walk with Beanie along with some stubborn behaviors resulting in a sloght change of plans for end of evening activities. Really appreciate your flexibility, communication and help over the weekend! Will plan to book care for Alfie and Beanie with Tessa again, thank you!!

Noah watched my three dogs for four nights. My pitbull has serious anxiety and can be a little unpredictable. Noah knew how to behave around more difficult dogs and was endlessly patient. I felt comfortable leaving them in his care after our first meeting. My dogs couldn't have cared less when I got home which is certainly an indication that they got plenty of attention while I was gone! Noah kept in touch regularly and sent me lots of pictures. I'm very excited to have found a pet sitter I can trust with my dogs and my home.

Leaving our dogs in dabs, Debs and Paul's care gave us such peace of mind while we were away. The daily update and pictures let us know that the dogs were being well cared for. Especially for our dog with epilepsy, updates about his medication schedule allowed us to have a stress-free vacation.

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?
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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