Dog Sitting Winter Garden
Book a Winter Garden dog sitter to watch your dog in your sitter’s home or yours.
Over 163 pet parents in Winter Garden have booked dog sitting
Winter Garden, Find top rated dog sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Taylor looked after my sweet baby, Tofu, for a week, and I never once felt worried. Tofu looked like she was having the best time, and it was clear she was well loved and cared for. Taylor is so sweet, kind, and trustworthy. I highly recommend her to anyone looking for someone to care for their furry friend!”
“Wonderful! Always left details and photos in each Rover Card. Was a nice enough to set up a meet and greet before we left to get the lay of the land and introduce herself to our Tony. Thank you!!”
“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!”
“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!”
“So great with both our dogs - even our younger dog who normally is distrustful of everyone. Reliable. Always on time and dogs love her so nothing much else to say. Highly recommend.”
“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 had animals my entire life I can take care of any fur baby with instructions special needs, puppy,daily meds, schedule just let me know My routine is scheduled around your baby. I like to do my best to not interrupt daily life of your fur baby. It’s my pleasure. I have a big backyard and I know the neighborhood around me like the back of my hand. It’s Important that I treat your babies like my own and give them all the love in the world while they are in my care
“I have used Shelley twice and loved how she cared for my two kitties!! I would recommend her to anyone!! I’m hoping she will be able to care for them again next month!!”
About: What sets me apart is that my dedication to providing personalized senior care, ensuring every pet feels safe, comfortable, and loved in their golden years." I’m currently working two part time jobs so my schedule isn’t the same every week but I work either from 9am-2pm or 2pm-5 and 5pm-7pm, but you can let me know in advance and we can work something out!. In my home, I have a secure fence for safe outdoor play and a crate for providing a cozy, secure den. With my experience caring for my two cats, I understand the importance of creating a comfortable environment for all pets, whether in my home or yours. Each pet's unique needs are met with personalized care, ensuring their happiness and well-being.
About: I’m patient with older dogs and pups just learning, as well as those missing their people and are scared. Grand mom to 4 sweet puppers. Lifetime pet family, we have guinea pigs, hamsters and every kind of dog and cat. I always helped neighbors when the needed pet care as well as years of volunteer work in shelters. Pets are family. I am a retired teacher due to injury and have a home based business so my hours are flexible. With enough notice I will do my best to accommodate care needed. I am unable to care for other pets in my home, we have 7 cats. I will follow all instructions given to lovingly care for your pets at your home
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
“Jaya is incredibly responsive, communicative and - above all - genuinely concerned with the well being of my dog. I cannot recommend her more strongly if you want to feel confident and secure in being away from your pet. She will go out of her way to address any unplanned need that may come up and is always available to talk in real time. A delight to work with.”
About: You know that girl at parties hanging out with the dog of the house instead of mingling? That’s me, I’m that girl!! I’ve grown up with all sorts of animals and have such respect & love for them, dogs in particular💜 My best fur friend Buster passed away at age 16 and it’s been an adjustment in my house, I have a lot of time on my hands, and would love to offer my services and attention to my community! I have dealt with separation anxiety and senior care (my fur baby had kidney issues in the end and required a lot of fluids injections) and am comfortable administering medications so I am willing to work with you & your needs. Upon request, I can also check your mail, bring in packages, water your plants, and do other small household tasks/chores to ensure that you have no worries while you're away. I look forward to meeting you! Spayed & neutered animals only please. I work part time, and my weeks are pretty flexible for drop ins and walks/care throughout the day so I’m available to spend as much time your pets need and give them all the lovins! I have a completely fenced yard and no current animals in my home, so your pet will get a lot of attention! I have a lot of space and can crate your pet if that’s what’s needed, and live in a gated community. Self transportation, and because I’m in a good area in Ocoee, between Windermere & Winter Garden, it’s great for drop ins as needed and I can be readily available.
“Elizabeth was absolutely amazing! I had a last minute request and needed help getting my dog home from daycare. She was so responsive and amazing to work with. She took great care of my pup getting her all settled in and included plenty of photos! Made my busy day so much smoother and lighter. Will definitely work with her again”
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.
“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.”
The median cost per visit for dog sitting in Winter Garden is $20
Dog parents share their Rover experiences - Winter Garden
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!
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.
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 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.
How Rover works
1. Search
Browse profiles of sitters near you who offer dog sitting
2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winter Garden sitters!Sitters in Winter Garden average 6 repeat dog sitting clients
FAQs for Drop-In Visits - Winter Garden
Frequently asked questions about Rover
The average cost for Dog Sitting in Winter Garden on Rover is $24.42 per visit (as of July 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Dog Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for Dog Sitting. For more information on service fees, click here .
As of July 2026, there are 5,180 sitters on Rover offering Dog Sitting across Winter Garden. Enter your ZIP code to see which available sitters are closest to your home.
A pet sitter can provide focused care sessions, help your pet’s routine stay on track, or keep you updated on your pet’s mood and energy levels.
Whether you’re at the office for the day or traveling for a few nights, a pet sitter can offer potty breaks during a Winter Garden stroll, cleaning the litter box, or making sure your pet has on-time food or water refills. For daytime services like walking and drop-ins, you can also request sitters to send a report card with every visit.
Tip: You can discuss your specific arrangements with a pet sitter on Rover to what fits you, your pet, and your sitter’s needs. To find what their special skills are, look at the "Skills" and "Pet care experience" sections on their profile.
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winter Garden choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit Rover's Trust & Safety page .
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the Rover Guarantee , which provides up to $25,000 in eligible veterinary care reimbursement.
A Meet & Greet is a short introductory meeting between you, your dog, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter or the new environment. During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
While Rover doesn’t offer traditional subscription services, some sitters offer recurring bookings for services like home visits and dog walking. Recurring services come with their own perks, such as flexibility to modify services (up to five weeks in advance), automatic billing, Rover Card updates, and same-day cancellations.
To find sitters in Winter Garden with recurring or weekly availability, select "Repeat Weekly" and which days you’d like them to care for your pet.
Yes, you can find sitters who have experience with handling special pet needs in Winter Garden. On Rover:
- 91% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 98% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works with you to find a replacement sitter.
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