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

Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Windermere house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Absolutely amazing - Alyson was one and considerate and helped with my little dog Daisy's severe separation anxiety. She sent so many check-ins - I was very grateful for her help and responsiveness,”

“Absolutely amazing! My girls loved Stephanie. My house was clean when I returned home after two weeks as if I’d never left and the cleaning lady had just come.”

“Nathan took wonderful care of our dog, Koda. He checked in with us regularly and sent lots of pictures. He got Koda out on lots of walks, even in the rain. We came home to a clean house and a happy dog!”

“She was excellent. I highly recommend her. We will be using her, again. Our dogs loved her. Even our timid dog snuggled her. Excellent communication. Left the house very clean and tidy.”


“Sarah did an amazing job! Our senior lab is blind and has diabetes, and previously had issues with us leaving her. Sarah was able to come in and make our pup comfortable and kept us updated on how our pup was doing!! I absolutely recommend Sarah.”

“Thank you, Nick, for another fantastic stay with Ellie and Theo! We came home after two weeks to two happy pups and everything perfectly in order at home.”

“My pup loved Brittney and she made him feel so comfortable! She had incredible communication and updates that left me no questions about my pups care and how his day was while I was away. I would absolutely use her service again and I know Argo is looking forward to it as well.”

“Sarah was absolutely amazing! She took care of our two rambunctious puppies and two older cats while house-sitting, and we couldn’t be happier with the experience. We left her a (very detailed!) schedule for the pups, and she followed it exactly—sending tons of photo updates that gave us peace of mind while we were away. Communication was super easy, and Sarah went above and beyond to make sure our pets felt loved and our home was well cared for. We came back to happy animals and a calm home, which says everything. We will definitely be booking with her again and have already recommended her to our friends and family. Thank you, Sarah!”

“So very pleased with Anastasiia‘s service! She was prompt, courteous, and kept my pup constant company . You can tell she has a real passion for pet care! And she sent daily texts with pics and an update on how my dog was doing. I would recommend her highly to anyone.”

“Ariela is a total gem, best sitter we’ve ever had! She cared for our dog Belinha at our home for five days while we were out of the country. Our dog has a history of separation anxiety, so we’re always nervous about leaving her, but from the moment we met Ariela, we felt confident she was in good hands. Throughout the stay, Ariela was a fantastic communicator. She sent us regular updates with photos that truly put our minds at ease. We came home to a happy, healthy pup and a spotless house. It’s clear that Ariela genuinely loves and understands the pets she cares for. We highly recommend her and will absolutely be a repeat customer!”

“Alexis was amazing! She sent us pictures and kept us updated. The dogs looked so happy!! She stayed at our house, and we came back to a beautiful, clean home. We’d definitely use Alexis again!”

“Yelena just joined rover, and i was her first booking. She house sat my dog for 2 days. My dog seemed happy on our return, and she communicated well while we were away, and followed his regular routine. I was looking forward to rebooking, and building a familiar dog sitter for my dog however she said she was allergic to my dog (he’s a none allergic breed, and never had issues with anyone else around him…however that being said I guess no dog really is none allergic). This was so disappointing for us as I wouldn’t expect someone with dog allergies to be signing up and doing dog sitting on Rover. For us it’s back to looking for someone we can rebook often, for you she maybe the perfect house sitter, I definitely felt calm leaving my dog with her.”

“Jonathan was recommended to me by family member and I'm glad they recommended Jonathan. Great communication for planning and during the stay. Will definitely be using Jonathan again.”

“Laura was exactly what my “needy” fur babies needed — she was patient, super attentive and provided lots of updates along the way. One of my dogs is reactive and takes time to warm up, but Laura quickly won him over! I also appreciated her flexibility in accommodating last-minute medication for my pup and an extended stay when I needed it. Definitely recommend her services!”

“Mark has taken care of our dog several times and is always wonderful to work with. He sends lots of pictures and updates, and does a great job of keeping our older dog active and having fun while we're away!”

Over 387 pet parents in Windermere have booked house sitting
How Rover works

1. Search
Read verified reviews and choose a house 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 house and 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 house sitting in Windermere is $45
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 house 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 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Windermere on Rover as of Nov 2025 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Nov 2025, there are 2,799 house sitters in Windermere. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Windermere house sitters respond in under an hour.
House sitters in Windermere have an average of 14 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Windermere.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Windermere house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.





