Pet Sitting in Windermere
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Windermere pet sitters
“Grey was so sweet and wonderful with our three cats while we were on vacation for almost 3 weeks. She sent detailed reports, so many pictures and was very communicative. We will definitely be booking with her again in the future!”
“Karen was amazing with my sweet fur baby! She updated me everyday and even sent plenty of pictures/videos. Lots of communication and eased my nerves about leaving my sweet cat by herself. Highly recommend! Thank you Karen!!!!!!”
“Jenn was wonderful with my cat, Oakley, who was sick at the time. While his care needs were simple (feeding, checking the automated litter box, and monitoring for any sickness), I truly appreciated the level of attention and compassion she showed. Many sitters would consider this an “easy” job, but Jenn still honored the full 30 minutes of each visit—keeping Oakley company, which I was able to see both in her updates and through my Ring camera. She also went above and beyond when Oakley got sick on the carpet. Instead of just grabbing whatever was available, she reached out to ask what cleaning products were best to use—showing that she cared about both my cat and my home. Another thoughtful touch was that she offered to do a preliminary meet-and-greet ahead of time to walk through the care plan. I chose to coordinate via text instead, but I really appreciated that she made the option available—it showed how much she values communication and trust. Jenn is personable, reliable, and truly cares. I felt completely at ease leaving Oakley in her care, and I highly recommend her to anyone looking for a sitter who goes the extra mile.”
“Daijah was absolutely amazing! She took such good care of our two dogs, including a geriatric dog who wears diapers. She kept us updated everyday and sent lots of pictures. We will definitely request her again!!!”
“Jamie is awesome! I was so nervous to try Rover because I’ve never really had anyone else take care of my boy Oliver before! Jamie made me feel comfortable and from the pictures she sent me, Oliver was very comfortable and happy with her too! I would definitely recommend and I plan to book Jamie again in the future!”
“Outstanding! My little one is only 2 months old, Mark is incredibly patient with her. He is on time and sends lots of pupdates. When I get home I find my little one sleeping after all the play and attention. Very kind and caring for my little one, will be using him in the future!”
“Cassia was great with our cats while we were away. She sent us updates and pictures. She also was concerned and asked great questions when she noticed one of our cats preferred staying in the bed. When I told het that it was a normal behavior for him, she was relieved there was nothing wrong with him. Thanks for your help, Cassia.”
“We’ve hired Shelley for several bookings and highly recommend her. Every visit she sends us updates and pics of our pets. She’s always on time, follows our feeding and care schedules and provides each of our pets with individual attention.”
“She is a sweet person! And did exactly as I requested. She even got along with my black cat who really does not like ppl. She is very trustworthy as well! Definitely rebooking soon! She sent photos and communicated very well too.”
“Victoria was amazing! Very patient and understanding when we had key trouble and very informative in the after visit reports. Would recommend and rebook in a heartbeat! Thanks so much!”
“Jonathan has been our go to dog sitter anytime we are out of town and always does an amazing job with Mia. We recommend him to anyone who will be away from their pups for an extended period of time.”
About: I’ve been around dogs my whole life and have dog sat for many over the years! I’ve owned big & small dogs so nothing is new to me. Big believer in training dogs and that they are smarter than most people know. But overall I just want every pup to be loved and cared for in whatever ways the need! I currently work during the day but have a flexible schedule! I love taking walks after work in the evenings and during the day on my days off (Sunday / Monday) My dog is my everything to me but he doesn’t like kids. I have to be careful about that on walks. Every dog is different. Whether it’s on walks or in your own back yard I know dogs want to have fun and play but I’ll also ensure they stay safe. Whether it’s from other dogs, animals, running off or even from people- I understand that every dog is different and needs different care. I’ll pay attention and keep them safe, cared for and happy!
About: I have loved on and cared for many animals for over 15 years. This includes dogs, cats, hamsters…and fish if you count them! (: All sorts of sizes and ages as well. I am comfortable with puppies and elderly animals, and I treat them all with as much care as I do my own fur baby. I have plenty of toys and the dogs are allowed anywhere in the house ! I have a fenced in dog park at my apartment, and I love to walk around the close by neighborhoods and enjoy the Florida weather. I love caring for fue babies and would bring any pet into my home with the same love I give my little chocolate chunk (lab). I’m currently a medical student, and as such my schedule changes all the time! I am able to move around my hours as needed to care for a fur baby. I am going to be off some days and on other days and depending on when your pet needs to be watched or walked I may be home the whole time. I live in a dog friendly apartment with lots of greenery around. I also have a fenced in grass dog park for exercise ! At home I have a mini chocolate lab that is a loverboy and would enjoy any and all company to be best friends with. I am very active and like going on long walks and exploring new areas for the fur babies to sniff.
“Reece took the time to meet my dog and to address any concerned or question that I had. My dog can be a little hyperactive and she was able to handle him just fine. Will definitely recommend her or use her service again. Thank you Reece for taking good care of my doggy.”
About: I’ve been taking care of dogs for over 15 years. I’m friendly, love playing with them, know what they need to be happy. I have a puppy and she loves to come on all jobs with me. Please let me know if your dog is not friendly towards other dogs as I have to bring my puppy with me. I’m looking to get experience with different types of pets as my dream is to be a foster parent to dogs and create my own animal rescue to help dogs find their furever homes. Besides working full time and having a dog of my own I have plenty of free time. This makes me almost always available to take care of your pets. I can come to your house and follow your pets usual routines. I’m very flexible, love playing with animals and just spending time cuddled up together. I can bathe or do extra responsibilities based on your pet. I also have experience with giving diabetic dogs shots.
Loving pet sitters in your neighborhood
Search Results
Grey G.Star Sitter
“Grey was so sweet and wonderful with our three cats while we were on vacation for almost 3 weeks. She sent detailed reports, so many pictures and was very communicative. We will definitely be booking with her again in the future!”
Samantha Y.Star Sitter
“Sam was so amazing!!! Our pup loved her! She made sure our pup got all the love he deserved!! Provided all the pictures and feedback!”
Karen R.
“Karen was amazing with my sweet fur baby! She updated me everyday and even sent plenty of pictures/videos. Lots of communication and eased my nerves about leaving my sweet cat by herself. Highly recommend! Thank you Karen!!!!!!”
Jenn H.Star Sitter
“Jenn was wonderful with my cat, Oakley, who was sick at the time. While his care needs were simple (feeding, checking the automated litter box, and monitoring for any sickness), I truly appreciated the level of attention and compassion she showed. Many sitters would consider this an “easy” job, but Jenn still honored the full 30 minutes of each visit—keeping Oakley company, which I was able to see both in her updates and through my Ring camera. She also went above and beyond when Oakley got sick on the carpet. Instead of just grabbing whatever was available, she reached out to ask what cleaning products were best to use—showing that she cared about both my cat and my home. Another thoughtful touch was that she offered to do a preliminary meet-and-greet ahead of time to walk through the care plan. I chose to coordinate via text instead, but I really appreciated that she made the option available—it showed how much she values communication and trust. Jenn is personable, reliable, and truly cares. I felt completely at ease leaving Oakley in her care, and I highly recommend her to anyone looking for a sitter who goes the extra mile.”
Darryl W.
“Excellent first experience, Darryl was responsible, communicative, followed instructions to the T, and took good care of my doggo, most definitely would recommend him”
Daijah B.Star Sitter
“Daijah was absolutely amazing! She took such good care of our two dogs, including a geriatric dog who wears diapers. She kept us updated everyday and sent lots of pictures. We will definitely request her again!!!”
Jamie L.Star Sitter
“Jamie is awesome! I was so nervous to try Rover because I’ve never really had anyone else take care of my boy Oliver before! Jamie made me feel comfortable and from the pictures she sent me, Oliver was very comfortable and happy with her too! I would definitely recommend and I plan to book Jamie again in the future!”
Nikki W.
“Nikki did a great job watching our pup, she was happy on our return and you can tell she got lots of attention!”
MARK B.
“Outstanding! My little one is only 2 months old, Mark is incredibly patient with her. He is on time and sends lots of pupdates. When I get home I find my little one sleeping after all the play and attention. Very kind and caring for my little one, will be using him in the future!”
Cassia V.
Star Sitter
“Cassia was great with our cats while we were away. She sent us updates and pictures. She also was concerned and asked great questions when she noticed one of our cats preferred staying in the bed. When I told het that it was a normal behavior for him, she was relieved there was nothing wrong with him. Thanks for your help, Cassia.”
Poliana D.Star Sitter
“Poliana is dependable and professional. She takes excellent care of our cat. We’ve booked multiple times and will continue to do so, she’s excellent!”
Shelley R.
“We’ve hired Shelley for several bookings and highly recommend her. Every visit she sends us updates and pics of our pets. She’s always on time, follows our feeding and care schedules and provides each of our pets with individual attention.”
Danielle H.Star Sitter
“She is a sweet person! And did exactly as I requested. She even got along with my black cat who really does not like ppl. She is very trustworthy as well! Definitely rebooking soon! She sent photos and communicated very well too.”
Victoria P.Star Sitter
“Victoria was amazing! Very patient and understanding when we had key trouble and very informative in the after visit reports. Would recommend and rebook in a heartbeat! Thanks so much!”
Jonathan W.Star Sitter
“Jonathan has been our go to dog sitter anytime we are out of town and always does an amazing job with Mia. We recommend him to anyone who will be away from their pups for an extended period of time.”
Jacqueline G.
“My pups love Jaci! I always have peace of mind when she is watching them while we travel. She is reliable and trustworthy. My pups are senior dogs that are extra needy and she does whatever they need to be comfortable and relaxed.”
Taylor N.
“I can’t recommend Taylor enough as a dog sitter! They’ve looked after my dog multiple times, and each time I’ve come home to a happy, calm, and well-cared-for pup. She is incredibly responsible, attentive, and clearly loves animals. She always goes above and beyond with daily walks, playtime, and even facetimes me to see my pup, which always put my mind at ease. It’s such a relief to know my dog is in such loving and capable hands when I’m away. Five stars every time!”
Reece L.Star Sitter
“Reece took the time to meet my dog and to address any concerned or question that I had. My dog can be a little hyperactive and she was able to handle him just fine. Will definitely recommend her or use her service again. Thank you Reece for taking good care of my doggy.”
Corisa S.
“Thank you so much!! Corisa was great when she checked in on Vinny! Would highly recommend!”
Rachel M.
“I have known Rachel for well over 2 years now and she is nothing short of spectacular. She is extremely kind, patient, and loving. Her love for her fury baby, Markie, is unmatched and she always goes out of her way to make sure he is taken care above anything else. A very passionate lover of all animals, and will certainly make sure any special considerations, diets, or other needs are recognized and accomadated. Don't think twice about letting Rachel watch your furry friends. She is careful and attentive all the time, not too mention super intelligent, beautiful, and a very close friend of mine.”
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
Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Windermere on Rover as of Aug 2025 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.
As of Aug 2025, there are 1,073 pet sitters in Windermere. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.
Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 89% of Windermere pet sitters respond in under an hour.
Pet sitters in Windermere have an average of 13 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters 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
There are 1,073 pet sitters in Windermere on Rover, so you’re sure to find the perfect match for your pet! In Windermere, 98% of pet sitters offer daily exercise, 88% offer medication administration, and 88% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.
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.
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