Dog Sitting in Winter Garden
Book a Winter Garden dog sitter to watch your dog in your sitter’s home or yours.
Every sitter passes an enhanced background check. Learn about RoverProtect
Top rated Winter Garden dog sitters
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
About: I’ve had dogs my whole life and have experience caring for over a dozen dogs ranging from puppies to seniors. I’m patient, attentive, and comfortable handling different personalities, energy levels, and routines. I genuinely love spending time with animals and miss being around dogs since moving away from home, so I’d love to give your pet lots of care, attention, and exercise while you’re away. I currently work 4 days a week, and am available most mornings and evenings. I am also available for midday visits on Mondays, Thursdays, and Saturdays. I provide care through visits to my client's homes, making sure pets stay comfortable in their normal environment and routine. During visits, I can handle feeding, fresh water, walks, playtime, bathroom breaks, and plenty of attention and companionship. I know how important updates are while you’re away, so I also make sure to communicate clearly and send photos/check-ins whenever possible
“Karen has now been my go-to pet sitter for nearly a year and a half. She took amazing care of my previous two senior kitties who have since passed away, and now she is the “cool babysitter” for my two heathen kittens. She has even walked / watched my sister’s dog when he’s visiting from out of town. No matter the species, pet age, or duration of travel, Karen is always exceptional. Thank you, Karen, for everything you do!”
“Chrys is always quick to respond to inquiries and is super great with our boy. She leaves great detailed reports cards which my husband and I love to read. Thanks so much for always taking great care of our boy.”
“Mark has been walking our large German Shepherd for almost two years now (including some long stretches when we were on vacation). We have always had really good experiences, observed impeccable reliability, have seen him go above and beyond to help us out and our dog seems to love him! The dog is 130 lbs so that can also be tricky but Mark works great with him! Would highly recommend Mark.”
“Lani was great with my two dogs. She is dependable and very reliable. Always gave great updates and provided pictures. My dogs were spoiled by Lani. I highly recommend Lani.”
About: I have two cats and two dogs. I take care of them daily and provide the correct and loving care I would with all of your pets. I worked as a kennel technician at a doggy daycare for a year and loved taking care of animals of all sizes, ages, and needs. I am experienced in grooming, medication administration, feeding schedules, cleaning and safety. I am also in a pre-vet club at my school so I often learn lots of animal anatomy and safety procedures. I love volunteering at any local clinic and animal sanctuary when I have free time. I am very passionate about my work and animals and would love the opportunity to provide care for your fur babies. I am a student at UCF, my schedule in the fall is a bit busier however I am able to set aside any time that you would need for your pets needs. As of right now I am on summer break and am available all day everyday. Pet care comes first and I am willing to work with any schedule you would need. I am very clean and love organization. If I were to stay at your home not only would I care for your pets but also your home and make sure to keep a clean and safe environment. I also love sending photos of your fur babies to make you smile during your work day or vacation. If I am pet sitting for the day or taking the animals for a walk I will make sure the proper steps are taken such as securing leashes, properly stocking what I need for the day, washing paws if dirty and checking pavement for paw safety. I am very easy to work with and love instructions and constructive criticism. No matter the instructions or the task, each pet will be safe and loved in my care.
“Tanya is absolutely the best dog and cat sitter we could ask for! She takes wonderful care of our pets, giving us complete peace of mind whenever we’re away. Our animals are always happy, well cared for, and comfortable in her hands. What really sets Tanya apart is that she goes above and beyond. Not only does she care for our pets, but she also helps with household tasks like picking up pet waste, taking our trash and recycling cans out to the curb, and bringing them back afterward. Those extra touches make such a difference and show how thoughtful and dependable she is. Thanya is reliable, caring, and incredibly helpful. We highly recommend her to anyone looking for a trustworthy pet sitter who truly treats your home and pets as if they were her own.”
“Katie was a pleasure to meet and attend to my dog's needs. She is extremely reliable and flexible, which I appreciated especially during the holiday season. She sent the cutest pics of my pup and showed her the love she needed while I was away. If I were still living in Orlando, I would book her again and again! Thanks, Katie :)”
About: I've had dogs my entire life and have experience caring for dogs of all sizes and ages. Unfortunately, my family dog recently passed away, which only deepened my appreciation for the love and companionship pets bring into our lives. I recently graduated from Florida State University and regularly volunteered at Champs Chance Rescue in Tallahassee, where I helped care for dogs of different breeds, ages, and temperaments. I also fostered a dog this past semester, which gave me valuable experience providing consistent care and helping a dog adjust to a new environment. I love spending time outdoors, going on walks, and making sure dogs get plenty of exercise, attention, and affection. As a nursing student, I'm responsible, dependable, and attentive to each pet's individual needs, and I treat every dog like they're my own. I’m currently focused on studying for my NCLEX to become a Registered Nurse, so I spend the majority of my time studying from home. I also work part-time as a Pilates instructor, which is typically only a 6–10 hour commitment each week, and my schedule is very flexible. Because of this, I have plenty of time to provide attentive care, companionship, walks, and playtime for your pet throughout the day. My home is a safe and pet-friendly environment with plenty of space for your dog to feel comfortable. I have a pet ferret who stays in his cage, and I am able to crate your dog if needed. I also have a screened-in pool area and live in a gated neighborhood with lots of green space that's perfect for walks. Additionally, there is a local dog park just a short drive away for dogs who enjoy extra exercise and socialization.
“Shelley took such good care of my two kitties and sent their mom pictures everyday. She went above and beyond when one of them barfed on the rug and cleaned it. She brought in a package that was at my door.”
“Lisa has been absolutely amazing and a very great help! She is very good with my high energy dog and my kitty. She is very punctual and thourough and will take great care of your pets. I would highly recommend!”
“Zoe was great with our puppy! I was nervous to leave him for the first time but she did a great job sharing everything she did with him along with pictures. She was so communicative and understanding of me being overly nervous!”
“Taylor is an excellent sitter. She was so sweet to my kitty and she provides tons of excellent pictures and great summaries of each visit. She is also great at communicating and quick at responding. Highly recommend!!!”
About: I long for the day I can have a pet of my own, but in the mean time I will treat your fur baby like family! I work full-time in the healthcare field however I am available before and/or after shifts as well as on the weekends! My schedule is relatively consistent. My current living situation has space constraints, therefore I would be better suited to maintain the environment your pet is already accustomed to! This offers a level of heightened convenience and comfort to you and your pet.
Winter Garden dog parents share their Rover experiences
First time using a sitter on Rover (we've boarded in the past) and Katie was amazing for us! She tucked our girl into bed, and checked on her the following morning. We got tons of pictures and updates with the Rover card and texts. We would definitely use her again. Thanks Katie!
Karen was wonderful with Baxter! She took great care of him during her visits, made sure he was fed and walked, and spent quality time playing with him. It was clear Baxter was happy and comfortable with her. I really appreciated the updates and attention she gave him, and I’d absolutely recommend her to anyone looking for a caring and reliable sitter.
Tracy was truly phenomenal with our dogs while we were out of state for a few days. From the very beginning, she was professional, reliable, and incredibly kind. She followed every instruction perfectly—including carefully administering medication to one of our dogs—and made us feel completely at ease knowing our boys were in such capable hands. Tracy went above and beyond by sending regular updates and adorable photos at each visit, which meant so much to us while we were away. It was clear from the pictures and notes that our boys were not just being cared for, but were genuinely happy, comfortable, and loved. We are very particular about who we trust in our home and with our dogs, and Tracy exceeded every expectation. Having her stay in our home allowed our boys to remain in their normal routine, and we could tell they felt safe and relaxed with her. We are so grateful to have found someone we trust so completely with the two dogs we hate leaving behind. We would absolutely book Tracy again and highly recommend her to anyone looking for a caring, attentive, and dependable dog sitter.
If you’re looking for a pet sitter who is somehow more responsible than me AND my actual pet combined, Briana is your girl. She showed up prepared like she was about to take the SATs, stayed longer than she had to like she was getting paid overtime (she wasn’t), and went so above and beyond that my pets are now lowkey disappointed I came home. Pretty sure my dog tried to file adoption papers. My puppy packed a tiny suitcase. 10/10 would hire again before my pets start leaving Yelp reviews about wanting Briana back.
Remy is an A+ Star sitter! I highly recommend their services! I was visiting from out of town and Remy knocked out out of the park. Followed directions to a T, sent pictures and updates, and took time out to love on my furbababies. I highly recommend Remy's services and I hope I visit the Orlando area again to use them!!!
Rafael was absolutely phenomenal. He handled drop-ins and walks for my Great Dane—who’s not the easiest dog to walk given her size and past trauma, especially in an area crawling with other dogs—and he did it like a total pro. He clearly was mindful, kept her calm, and made sure everything went smoothly. I got regular updates and felt completely at ease the whole time. I’d absolutely rebook his services and would recommend him to anyone needing reliable, thoughtful care for their dog.
Popular requests near you
Select a filter and find qualifying Winter Garden sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs 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 dog sitter has to cancel, we’ll work with you to find a new sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Dog Sitting FAQs
Frequently asked questions about Rover
Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.
Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Winter Garden.
Rover makes it easy to find Winter Garden dog sitters to provide loving care from their own home. The background-checked, 5-star dog sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog sitting is great for:
- Dogs of all ages and abilities, including puppies
- Dog parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their dog 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 dog sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your dog sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your dog is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.
Connect anywhere with the Rover app
