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

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Top rated Windemere house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Molly was fantastic with my dogs who are not always great with strangers. My dogs fell in love with her on their first meeting. I felt so comfortable being away for a few days. She sent multiple updates throughout the day with lots of pics. I hope she will come back when I need her.”

“Samara was amazing with our Luna. She took excellent care of both our home and Luna, followed all of our care instructions, and kept us updated with photos throughout the stay. She even accepted a last-minute booking on New Year’s Eve, which we were extremely grateful for. Samara has great communication skills, and it’s clear that she truly sees and cares for dogs as if they were her own. I would highly recommend her to anyone looking for someone trustworthy, attentive, and loving. We are very grateful for her kindness and care toward Luna.”

“Had a same day request and Kenna was there in a pinch! Total lifesaver... She was excellent with my dog and super super polite. 10 out of 10 will totally book with again!”


About: I’ve been an animal lover for as long as I can remember. I grew up around dogs and have owned four dogs throughout my life, giving me experience with different personalities, energy levels, and care needs. While I wasn’t around many cats growing up because of my dad’s allergies, I quickly fell in love with them and now share my home with two cats of my own. Over the years, I’ve regularly pet sat and walked dogs for friends and family simply because I enjoy spending time with animals. Now, I’m excited to turn that passion into a side gig through Rover. I understand that being away from their family can be stressful for pets, so I always focus on making them feel comfortable, safe, loved, and cared for while you’re away. My goal is to treat every pet like they’re part of my own family and give you peace of mind knowing they’re in good hands. I do work a full-time job, about 8 hours a day Monday-Friday. However, my hours are pretty flexible through the week so I can work around a schedule. I always make sure the pets feel comfortable with me and listen to their needs! If they are feeling anxious or scared I make sure to be patient and give them the time they need. If they are super cuddly I make sure to give them all the love I can give and play with them! I can take them on walks or play with them around the house!
“Arturo was fantastic to work with! During our time away he would constantly keep us updated when he would be heading out as well as provide photos of Dottie throughout the day. From our initial meet and greet, we could tell that he and Dottie would get along and from what we heard, she was snuggled up with him all weekend! My partner and I would give him more stars if possible.”

“Elisa watched my 11 year old pitbull and was amazing! I have never left my dog with a stranger before, Elisa gave me multiple updates everyday and made sure both Lady (my dog) and I felt very comfortable. I would absolutely recommended Elise to anyone and would, without a doubt use Elisa again to watch my girl.”

“Chantell is awesome! She messaged us often with updates and took great care of our pup. We could totally relax knowing he was in great care. We will definitely book again with her for our next trip.”


“Our dogs were in good hands while we were away! We had to find someone short notice after our other pet sitter had to cancel and we appreciate Geoffrey accommodating his schedule to take care of our two pups. We received multiple updates throughout the day and were worry free on our vacation because of it! Our dogs are very needy and require a lot of attention and supervision, Geoffrey made them feel comfortable. He also took good care of our house. Highly recommend him and will be using his services again in the future.”

About: Over 25 years of experience as a devoted pet owner and pet sitter. I know how important it is to trust someone with your pets, and I take that responsibility seriously. I won’t just check in on your pets, I’ll make sure they feel safe and loved. As I approach retirement & only working part time, pet sitting is a natural fit for my flexible schedule, experience, and lifelong love of animals. This flexibility allows me to provide dependable, attentive pet care while doing something I genuinely love & enjoy! I will respect your home, follow instructions carefully, secure doors and gates, provide updates, and care for your pets with dependable, trustworthy attention. Your pet’s safety and your home’s security are my priorities.

“She is Awesome… Kaitlan kept our 4 babies for 9 days. She sent updates and pictures each day. We have one guy who is a little cranky and they were best friends after a few day’s. She took them for walks. The house was just like we left it (a nice surprise). She is now my number one and only dog sitter. Thank you Kaitlin for loving our babies like we do. You are awesome!!!”


“I highly recommend my dog sitter! She did an outstanding job taking care of Triton while I was away. She is always punctual, communicative, and very reliable. Most importantly, she is incredibly sweet, caring, and playful with Triton, which gave me great peace of mind. She followed all of my instructions carefully and kept me updated throughout the entire time. It was clear that she genuinely cared about Triton’s happiness and well-being. I came home to a happy, well-cared-for dog, and I couldn’t have asked for a better experience. Thank you for taking such wonderful care of Triton! I will definitely be using your services again and would highly recommend you to anyone looking for a trustworthy and loving pet sitter. 🐾🐾🐾🐾”

About: I’ve grown up around both dogs and cats, so caring for animals has always come naturally to me. I have experience taking care of my own dog as well as helping coworkers and neighbors by watching their pets during weekends and trips. I’m patient, attentive, and make sure each pet feels comfortable, safe, and loved while you’re away. I’m especially mindful of each pet’s routine and needs, whether that’s keeping up with feeding schedules, providing playtime, or giving extra care and attention to more anxious or older pets. I’m a teacher with summers off, which gives me a very flexible schedule to care for your pets whenever it works best for you. I am available any day or night of the week. In my client’s home, I follow each pet’s normal routine to help them feel comfortable and secure. This includes feeding on schedule, fresh water, walks, playtime, and any medication or special care instructions. I also make sure their space stays clean and tidy, and I give plenty of attention and affection so they don’t feel lonely while you’re away. My goal is to keep everything as consistent and stress-free as possible for your pet.
“Ryan is amazing and really cared for Hayze. Hayze loves it every time he comes around. He also gives us up to date information on how Hayze is doing every day and provide lovely pictures. We definitely will continue using Ryan in the future!”

“Our strong willed energetic 5 month old puppy, Yoshi, loved Katie immediately. We left her in Katie’s care for a week and didn’t have to worry about either one of them at all. It was apparent they enjoyed each other, and Yoshi got as much love and care from Katie as she would have with us at home. After we got home, Yoshi was still right by Katie, wagging her tail and eating up the attention. Thank you, Katie, for all you did to entertain and care for our pup! We’ve found a wonderful sitter for Yoshi and will refer Katie to others!”

“Sara was an amazing dog sitter to my 2 Labradors. She followed all food and medication instructions, took them on walks when it was cool, and sent me pictures! I loved getting pictures of my girls. She stayed overnight at my house, and she also collected my mail, put the trash containers at the end of the driveway on trash day, and brought any packages into the house. None of these were part of her dog sitting duties. I was very grateful to Sara for all of her help. I will definitely use her again in the future, and I highly recommend her as a responsible dog sitter.”

“Anne was great with our pup Alex and our 2 cats! Very attentive and considerate. Updated us with photos through out our vacation/honeymoon. Left us a card and thoughtful gift congratulating us on our wedding which was very nice to return to. Would highly recommend her house sitting and watching our pup again!”

“Renada was an amazing dog sitter for Lia. She was incredibly attentive to her needs, sent us lots of photos, and kept us consistently updated while we were out of town, which gave us so much peace of mind. She was also very respectful of our home and left everything exactly as we had it. We would absolutely trust her with Lia again and highly recommend her to anyone looking for a reliable and caring sitter.”

Over 187 pet parents in Windemere have booked house sitting
Windemere pet parents share their Rover experiences
Ashley was fantastic as a both a home and pet sitter. She takes the cutest little photos, my dogs looked happy and comfortable the entire stay, and she was super response to messages. I have an active dog and a senior dog and she was able to handle all of their needs. I was so relieved when I got home and my dogs seemed to have had a great time and didn't show any signs of anxiety or discomfort. Ashley was such a blessing.

She is Awesome… Kaitlan kept our 4 babies for 9 days. She sent updates and pictures each day. We have one guy who is a little cranky and they were best friends after a few day’s. She took them for walks. The house was just like we left it (a nice surprise). She is now my number one and only dog sitter. Thank you Kaitlin for loving our babies like we do. You are awesome!!!

Teresa took wonderful care of our two kitties! They are indoor/outdoor so we needed someone to put in some extra work and she really stepped up! Teresa is super friendly and a great communicator as well. I received daily updates (often more than once a day) that put my mind at ease while we were away. We will definitely use her services again and would highly recommend her to other cat owners.

I see why Woody has gotten so many positive reviews about both the care they provide for the dogs but also the person they are. I am so particular about who cares for my dogs while I’m away and woody made me feel so secure!!!! My dogs adored her and so do I!! They updated me throughout the day and sent personalized videos. They were attentive and listened carefully when I discussed my dogs and what they’re used to. You can tell she really cares. On a personal note - Woody is a bright light of a person, such a pleasure to have found them and met them for future dog sitting needs. Thank you Woody

Elisa did a wonderful job watching our 2 dogs who can take some time to warm up to strangers. She was very kind and patient with them. She kept our house organized and communicated well with us so we felt confident with her care while we were out of town. Will definitely have Elisa again!

I wish I could give 100 stars to Maggie. What an amazing petsitter. She communicated better than any sitter I’ve ever used. Plenty of updates and photos, even cute little videos. When I arrived home, both pets seemed at complete peace. I could tell they had a great week with Maggie! ❤️.

Leah & Tyler were awesome with both our puppy and house. When we got home, our Sophie was happier than she has ever been with others staying at house. They truly engaged with our pup and showed her so much love. Our dog has separation anxiety, and I can't think of any better people to stay with her. We are so happy to have found the right folks for our Sophie!

We had a wonderful experience with Nicole as our house and pet sitter, and we highly recommend her! We have one elderly dog and an oddball kitten, both of whom require lots of attention. Our trip was 10 days long and international, so we were understandably nervous about leaving them. However, after a meet-and-greet with Nicole in our home, we immediately felt confident they would be in great hands and asked her to sit for us on the spot. Nicole put us at ease by asking thoughtful questions—many covering things we had planned to mention, as well as important details we hadn’t even considered. As a person, she clearly loves and understands animals—their needs, behavior, and unique personalities. As a professional, she is thoughtful, responsible, kind, and responsive (even with a 7-hour international time difference!). We received multiple photos and updates each day, and it was clear from our pets’ normal playful behavior that they felt comfortable with her very quickly. We returned home from our long trip to a clean house, happy and healthy pets, and even two houseplants resurrected (by Nicole!). We would definitely book Nicole as a house and pet sitter again!

Chantel was super communicative and provided multiple updates and photos each day. Our home was very well cared for, even with two dogs and a string of rainy days. Our boys absolutely loved their daily walks and playtime. It is obvious Chantel really cares about others pets and homes. We would be grateful to have her stay here again!

Katie was absolutely wonderful! We had an emergency trip we had to make and were unable to guide Katie through our pup’s routine before leaving. Katie went above and beyond in figuring things out with very little guidance and making sure our pup was taken care of and loved. As a veteran and first responder, I can wholeheartedly recommend her for her reliability, trustworthiness, and professionalism.

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 Windemere is $50
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 Windemere 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 Windemere on Rover as of Jun 2026 was about $50 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 Jun 2026, there are 4,404 house sitters in Windemere. 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, 88% of Windemere house sitters respond in under an hour.
House sitters in Windemere have an average of 15 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 Windemere.
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. Windemere 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.











