Pet Sitting & Drop Ins In Windermere
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Windermere pet sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

“Isabella took exceptionally great care of my little kitty! The notes she always left after each check-in were very thorough, and I loved all of the pictures she sent. She was very accommodating and helpful, and really went the extra mile! I would absolutely recommend her as a sitter for anyone who wants complete peace of mind while they are away on a trip 😁”

“Our pup seemed to really enjoy visits from Brittany! She was punctual and very easy to communicate with and we enjoyed the pictures that she left after each visit.”

“Elli was absolutely wonderful in her care, feeding and walking of my sweet dog Ramona. She’s very thorough, attentive and caring. I especially enjoy her creating multiple photos of Ramona during and after her walks with her! I had been out of town when she was taking care of Ramona and seeing those photos brightened my day. I highly recommend Elli.”

About: I have extensive experience caring for senior pups and administering medications. I’ve cared for all types of dogs, from nine to ninety pounds! I love pets and I’d love the opportunity to care for your four legged friend!. I currently work part-time and I’m off school for the summer! My schedule is very flexible and easy to work around. I have no conflicts which can’t be worked around! I’d prefer to care for your pet in your own home, as I have a pup of my own and she can be a little persnickety!
“Working with Bonnie has been great this past week. Our dog Sadie can be finicky with her walkers and also with other dogs, but Bonnie won Sadie over really fast. Sadie looked happy at every walk and was super happy when we came home. Thanks, Bonnie!”

About: Hi! I’m an experienced dog walker and lifelong dog lover who understands that every dog has unique needs and personalities. As the owner of a rescue dog, I have hands-on experience working with nervous, shy, and anxious dogs, and I know the importance of building trust and creating a calm, positive environment. I prioritize safety, patience, and plenty of love and attention during every walk or visit. Whether your dog is energetic and playful or prefers a slower pace, I’ll make sure they feel comfortable and cared for. I look forward to treating your pup like one of my own! I’m home from college for the summer, so I have plenty of availability for pet care. As a dog owner, caring for pets is already a regular and enjoyable part of my routine. I follow each pet’s routine closely, including feeding, walks, playtime, and any special instructions. I provide a safe, comfortable environment, plenty of attention, and ensure pets feel secure and well cared for.
“Madysen is the best! I’ve continued to book with her and she exceeds expectations and takes such good care of my kitties while I’m away! My plants are doing great too! Thank you Madysen!”

“Ashley was great! She was very responsive and extremely helpful with her updates. We were stuck from a delayed flight and she was able to help check on Piper while we were stuck. I know I would highly recommend her and use her again in the future! Thank you again Ashley!”

“Caitlyn took great care of our anxious kitty while we were away. She made it to our house in the snow (!!) and gave her meds. It was a relief knowing she was in good hands while we were away. Thank you Caitlyn!”


About: Hello, thank you for checking out my profile! I LOVE dogs, I’ve had them my entire life! I grew up around mostly small dogs, however I have lived with 50+ lb dogs and a couple cats 😊 Ensuring your dog is taken care of is my biggest priority, and many belly rubs will be made along the way. I WFH Mon.-Fri. and so my schedule is pretty flexible. I tend to have free evenings, and can step off of work whenever needed. My weekends are usually free! I will always respect the safety of your fur friends and you. I will ensure doors are locked upon entering and exiting, the leash is securely fastened, and any alarms are set. Additionally, if your dog has any aggression/anxiety around other dogs, I will ensure your pup is given the space they need.
About: My entire life has been spent in the presence of all kinds of different animals! I have a very open schedule and would love to take care of any pet responsibilities. I have a very good relationship with every animal I come across. I like to be very active and loving with my animals, I encourage walking, hiking or a simple trip to the park with your loved one! I am a grad student studying my master’s in Seattle and would love the opportunity to help out with your pet! I never feel a dull moment when I am around animals and would love the opportunity to share an exciting moment with yours. Whether you need a walker, sitter or check-ins I can be very flexible to your needs! Thank you very much and I hope you can consider me. I am working towards my masters ant the moment and working part-time as a behavior therapist. I have a good amount of free time during the day and can be flexible! I always keep the dogs I watch close by and leashed to ensure their safety while going on walks. I will be trustworthy in keeping homes safe as well as tidy since I’m a bit of a neat freak!
“Andrea was fantastic with my elderly kitty, doing a meet and greet and carefully reviewing instructions for care and medication. She went above and beyond, and got my cranky kitty to feel comfortable with her quickly. Appreciate you, Andrea!”

“Nicolas is a fantastic cat sitter! I got photos and updates after each visit and my anixous kitty warmed right up to him. My cat had a slight dental emergency while I was away and he kept me updated”

“Bethan was absolutely great. I highly recommend if you are looking for a fantastic sitter that will treat your pet well and show it lots of love. Overall very thankful she was available for the 5 days I was gone for.”

About: I’ve been a pet owner my whole life and have experience taking care of pets of all ages. Animals bring me so much happiness. Since I cannot have a pet of my own while in college, I will give all my love and attention to your pets to provide excellent care. As a college student on summer break, I will have plenty of time to spend with your pets. Im available all weekdays and most weekends, I can stop by whatever time is best for your furry friend! I will be unable to house your dog overnight in my home, but I am more than willing to stay extended periods with your pets if needed.

About: What sets me apart is my reliability, attention to detail, and genuine love for animals. I understand that every pet has a unique personality and needs individualized care, so I take the time to learn each pets routine, preferences, and comfort level. I am patient with puppies who are still learning good habits and attentive to senior pets who may need extra care, slower walks, medication administration, or additional comfort. I prioritize communication and provide updates, photos, and check-ins so owners can feel confident that their pets are safe, happy, and receiving the same level of care they would get at home. I treat my clients pets the same way I would want my dogs to be treated! Pet care fits naturally into my daily and weekly routine because I am organized, responsible, and I enjoy spending time with animals. I plan my schedule carefully to ensure pets receive consistent attention, exercise, feeding, and companionship throughout the day. I care for pets by following their normal routine as closely as possible to help them feel comfortable and secure. In both my home and clients homes, I provide fresh water, meals according to their schedule, exercise, playtime, companionship, and any medications or special care instructions. I also keep pet areas clean and provide regular updates to owners so they know their pets are happy and cared for!
Over 55 pet parents in Windermere have booked pet sitting
Windermere pet parents share their Rover experiences
Jiani has cat sit for my kitties twice now and has done a phenomenal job both times! She is great at sending pictures from each visit and I can tell they really enjoy her visits which makes it so nice to travel and know their in good hands!! Highly recommend Jiani⭐️⭐️

Teresa watched my two cats for two weeks while I was out of the country and was wonderful. She actually spent time with them rather than just doing food-and-litter visits, and sent so many photos throughout. It made being that far from home much easier. She's incredibly easy to work with and went out of her way to water my plants and bring in my mail, even though neither was part of the service. Highly recommend. I'll absolutely book her again.

Camille was great! She stayed with our dog for two drop-in visits over a weekend. We did a meet and greet ahead of time and felt extremely comfortable having Camille look after our dog. She does great updates and extensive Card summaries. Wouldn't hesitate to book her again!

Popular requests near you
Select a filter and find qualifying Windermere sitters!How Rover works

1. Search
Read verified reviews by pet parents like you and choose a 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 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!
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 pet 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.
Pet Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, pet sitters on Rover respond in under an hour.
Experience can vary widely from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when comparing pet sitters available in Windermere.
Rover makes it easy to find Windermere pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:
- Pets of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Pets who’d love to socialize with their pet sitter’s pets
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.

















