Dog Sitting Winter Garden
Book a Winter Garden dog sitter to watch your dog in your sitter’s home or yours.
Over 199 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.
About: Dogs have been a part of my life for as long as I can remember! I grew up in a home where we always had a dog, and as soon as I graduated from college and was living on my own, I welcomed a pup of my own into my life. Today, I’m a proud dog mom to Oliver, my sweet little Maltese-poodle mix, who has been part of our family for the past year. I understand that our dogs aren’t just pets, they’re family! I know how important it is to feel confident that your furry family member is being cared for by someone who is loving, responsible, and attentive. Whether your pup needs a fun walk, some playtime, or a little extra love and attention while you’re away, I’ll treat them with the same kindness, patience, and care that I give my own dog. I’m dependable, communicative, and happy to provide updates so you can have peace of mind knowing your pup is in good hands! I’m a full-time professional and a dedicated dog mom, so caring for dogs is already a natural part of my daily routine! I enjoy spending time outdoors, going for walks, and making sure pups get plenty of attention and exercise. I’m looking forward to incorporating dog walking and pet care into my schedule during evenings, weekends, and other times when I’m available. I value being dependable and will only accept bookings when I know I can give your pup the time, attention, and care they deserve! Your pet’s safety, happiness, and comfort are my top priorities! As a dog mom myself, I understand how much trust it takes to leave your furry family member in someone else’s care. I take the time to learn each dog’s unique personality, routine, and needs so they feel comfortable and secure. Whether we’re enjoying a walk, playing, or spending time together at home, I’ll always prioritize their safety and well-being. I’m respectful of your home, attentive to instructions, and committed to keeping you informed with updates and photos. My goal is for you to feel completely at ease knowing your pup is being cared for with the same love and attention I give my own!
About: Hi there! I’m Alyssa, a TRUE animal lover. For the past 7 years, I’ve enjoyed caring for pets of all shapes, sizes, and species. Dogs, cats, bunnies, birds…you name it! I open my heart & home to animals in need through volunteer fostering, primarily caring for cats and kittens with medical needs. Full-time pet sitting has allowed me to continue doing what I love most: giving animals the care, attention, and love they deserve. Have a unique pet, or a pet with unique needs? I have extensive experience administering medication, including insulin injections, and I'm happy to meet anxious or nervous pets wherever they're at. I treat every pet as if they were my own, and I'd love nothing more than to become a trusted member of your pet's pack! Pet sitting is my full-time job! I'm flexible, and can typically make a wide variety of days and times work. Just let me know what your animal needs, and I will always do my best to accommodate! I understand some animals may need time to warm up to me! I always follow my client's instructions, and promise to take meticulous care of your fur babies. I am detail-oriented by nature!
About: I approach animals with respect and compassion. I always had kitties growing up, I also had 3 dogs a black lab, golden, and a german mutt I love dogs and I miss having them around !! I am very attentive to detail and will follow any instructions to a T :) I would want the same for my babies! Looking forward to meeting you and your Fur baby :) Currently I rent a studio in a house and the kitties love it ! They’re strictly indoor because Momo has allergies and Haru loves to eat lizards :( I feed them once a day and they’re good at pacing themselves till next feed in the AM. My kitties love me very much so i’d like to be able to stop by my house for an hour or 2 if it’s an over night stay . I am free from Thursdays 3PM - Sunday8pm for over night stays. I would be able to play, hangout, feed, walk, (poop scoop, litter box clean), any additional help I can do as well please let me know and we can work something out at booking ! :)
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
“Samantha has been amazing! She has been reliable and caring and takes great care of my puppy! Unfortunately my previous experience was not so good with another Rover cg but I decided I'd give it one more try and I am sobglad I did!!! She has been excellent and trustworthy and cares for my puppy as if it were her own.”
About: I have grown up with at least 2 dogs my whole life and I love the bond that can come with an animal. I have walked and pet sit many times. I also volunteer at the animal shelter whenever I can! I would love to help watch over or walk your dog! I am currently working part time and have a pretty open schedule and availability. Just contact me about scheduling and we can work it out! I can pretty much help with whatever the animal needs. I know everyone has different styles on how they take care of their animals, so that’s something that we can discuss!
About: I’ve taken care of small and large dogs throughout my childhood. As a pet owner, I understand the anxiety associated with leaving your pet in someone else’s hands. I am here to take that stress away and provide the best care possible for your pet! I work full time, but I have availability for late afternoons and weekends. I am happy to discuss your pet’s daily schedule to ensure their routine is followed Right now, I am offering drop in visits to feed and/or take your pet out while you are away. I will be sure to give your furry friend much love and attention during my visits!
About: I’ve taken care of my pets my whole life, including my cat Gracie Lou, chow sharpie mix Sunshine and my ball python Klaus for the past eight years. I’ve fostered kittens, volunteered at the animal shelter and pet sit for friends cats growing up. I love animals and I’m happy to care for them! Everyday I make sure my three pets have clean water and food (except the ball python they only eat once a month) I play with my cat and dog every day. I work Friday & Saturday at 6PM but other than that I have full availability. I would make sure they get clean water, food and play time as those are essential. I love to take dogs on walks as many times are needed. I’d make sure that the kitty litter box is clean.
About: Hello, I am 25 yrs old, I have cared for family dogs for the past 5 years, very flexible with scheduling, and lenient with each dog's needs. Will do my very best to make your dog feel at home while they are away from their home. I love animals, especially dogs, any breed or size. I am lenient so if your dog likes to sleep on the sofa or on the bed, no problem. If your dog likes an extra treat during the day, why not? But just as I am lenient, if your dog needs special care or restrictions I will 100% respect that and make sure your pup is on the right track. Each dog has plenty of room to play and lounge outside with a large fenced backyard. Toys are plentiful so every dog can have some, or if they have their own that is just as good too. I no longer have dogs of my own because they grew old and passed away, so dog care is my way of giving all of the dog love I have stored up. I currently do online university, so my schedule is very much open, so I am able to give your pup all the time in the world. As stated before I do University online so I am very open and flexible in terms of my schedule so I am able to give your dog all the attention and time that it deserves. I am home 99% of the time to be with your doggo and give it all the love it needs. i’m very flexible so your pet is allowed anywhere in my home and can pretty much do whatever they want as long as it’s not destructive as long as they are comfortable and happy that’s what matters. I am at home all day other than maybe groceries or to get food here & there so I have all the time for your dog! I have a fenced in yard so they can safely free roam & explore without any risk. If needed for any reason or sleep I have a jumbo sized crate they can use for any reason.
About: I have had dogs and cats my whole life and my happiest memories involve animals. I know your pets are your children, and I will treat them as such. I’ve had experience with everything from pet frogs to kittens to a 150 pound Great Pyrenees. I loved them all and I will love your pets, too. I am happy to swing by to check on your pets, or to stay the night to make sure they and your home is okay while you’re away. Please don’t hesitate to message me if you have any questions or comments, I’d be happy to answer them! I work remotely from home in Winter Garden, so I am happy to stay the day with your fur babies and work from your home or stop by throughout the day - whatever you prefer! I have three cats at home and, unfortunately, they do not love dogs as much as I do, so I will need to care for your canine friends from your home. I love animals and I would love to care for your pets as I care for my own!
“Our pup was very well cared for while we were away. We will definitely be using Nicholas again in the future. He did and amazing job and I love that he washed the dogs bowls before he fed him each time.”
About: Hi! I’m Devin, a lifelong animal lover with a soft spot for dogs of every size, shape, and personality. I’ve spent years caring for pets for friends, family, and neighbors — and now I’m opening my doors (and my heart!) to pups on Rover. Whether your dog is a high-energy goofball or a snuggly couch companion, I make sure every dog feels safe, loved, and at home. I've trained my own little pup from 8 weeks old and he's a Shiba (well known for their stubborn personality) I dont work weekends or holidays, plus my lunch breaks are typically on the longer side (1 to 3 hrs). Fitting in check ins, potty breaks and walks are a piece of cake. I believe in positive reinforcement, gentle guidance, and keeping each pet’s individual comfort level in mind. I pay attention to body language and energy, and I always go slow with nervous or shy dogs so they can warm up at their own pace.
“Laura was a life saver. We were going to be be very busy, out and about for 2 days. We forgot to plan for someone to come in the afternoon to give our dogs a break outside the house since we will be out for more than 10 hours of the day. We found Laura and she was incredible. Fast response, easy to book and update us with how our dogs did with the visits. Greatly appreciated her. I will recommend and use her services again.”
About: I’m a dependable and attentive caregiver with experience caring for both my own pets and pets belonging to friends and family! I’ve provided pet sitting and drop-in care numerous times, including feeding, refreshing water, cleaning up after pets, playtime, and following their normal routines. I also have a healthcare and caregiving background, so I’m comfortable following detailed instructions and understand the importance of being reliable, observant, and respectful of someone’s home. I’ll always treat your pet and their space with the same care I would want for my own! 💜 I’m starting nursing school on October 12th and for that schedule I will be occupied Monday through Thursday from 8 AM–4 PM, but I’m available for quick drop-in visits and check-ins before or after class on those days. My weekends are much more flexible, making them great for house sitting, longer visits, and additional care. About once a month, I also have a Saturday clinical from around 6:30 AM–2 PM. Outside of those commitments, I’m happy to work with your cat’s normal routine and will always communicate my availability ahead of time! :) I’ll care for your cat in their own home where they’re most comfortable and familiar with their surroundings. I’ll carefully follow any instructions you provide for feeding, water, litter boxes, medication, playtime, and their usual routine. I’m comfortable cleaning up messes and keeping their space tidy, and I’ll always respect your home. I also understand that every cat has different boundaries, so I’ll let them approach and interact with me at their own pace. I’m also happy to provide regular photos and updates so you can see how your cat is doing while you’re away!! :)
About: I’m the kind of person who can’t walk past a dog without saying hello. I genuinely love spending time with animals and treat every pet like they’re part of the family. Whether your pup wants an adventure, a game of fetch, or just someone to snuggle up with, I’m happy to match their energy and routine. I’ll keep you updated with plenty of photos and messages, so you can relax knowing your furry best friend is getting lots of love, attention, and belly rubs while you’re away. ❤️🐾 One thing pet parents love is that my schedule gives me a lot of flexibility. I work three appointments a week (10, 2, and 6), and I’m typically only out for 1–2 appointments a day, which means I spend a lot of time at home. I also have alternating weekends off (Saturday/Sunday, then Sunday/Monday), giving me even more availability for quality time with your pet. I have a dog of my own, Honey, so I’m used to keeping a consistent routine with walks, potty breaks, meals, playtime, and lots of love. I know how important consistency is for pets, especially when their owners are away, and I do my best to make them feel safe, comfortable, and right at home. Honey is my world, so I completely understand how nerve-racking it can be to leave your pet in someone else’s care. Our days are built around walks, meals, playtime, and plenty of cuddle time, and I love keeping her routine consistent because I know how much dogs thrive on that. Caring for Honey has taught me to pay attention to the little things—whether it’s noticing a change in behavior, knowing when they need extra comfort, or just figuring out what makes their tail wag the most. When your pet is with me, I want them to feel just as loved and cared for as they do at home. I’ll treat them like one of my own, stick to their routine, and keep you updated with photos and messages so you can relax knowing they’re happy, safe, and getting lots of love while you’re away.
“We couldn’t be happier with the care Stormy and Baker receive. Michael is reliable, caring, and treats them like family. It gives us peace of mind knowing they are in such good hands. Stormy and Baker always come home happy and well cared for. Highly recommend!”
The median cost per visit for dog sitting in Winter Garden is $20
Dog parents share their Rover experiences - Winter Garden
Katie is absolutely amazing! She goes above and beyond every time she visits my dogs. She has taken the time to get to know each of them individually, gives them plenty of attention and pets, and makes sure they get some time outside. Her updates are always detailed and include lots of great photos, which gives me so much peace of mind while I’m away. She consistently makes sure they have plenty of food, water, and treats, and she is incredibly thoughtful about the little things. She also makes sure the doors are locked when she leaves and even brings in my mail. I couldn’t ask for a better pet sitter. Katie is dependable, caring, communicative, and clearly loves animals. I highly recommend her to anyone looking for someone they can completely trust with their pets!
When we came home, Latte was calm, happy, and clearly very well cared for. That gave us so much peace of mind. Darryl went above and beyond what was expected. Not only did he take amazing care of Latte, but he also left our home incredibly clean and organized, which we truly appreciated. We are so grateful for the care and attention he gave Latte. We would absolutely book with Darryl again and would recommend him without hesitation to anyone looking for someone trustworthy, caring, and reliable.
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.
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- 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.
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Reservation protection
It doesn’t happen often, but if your sitter has to cancel, we’ll work with you to find a new sitter.
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How to book dog sitting
1. Search
Browse profiles of sitters near you who offer dog sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
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Popular requests for dog sitting - Winter Garden
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winter Garden average 6 repeat dog sitting clients
FAQs for Dog Sitting - Winter Garden
Frequently asked questions about Rover
The average cost of Dog Sitting in Winter Garden is $24 per visit as of November 2026. Most bookings cost between $14 and $33 per visit. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of November 2026, there are 5,162 sitters on Rover offering Dog Sitting across Winter Garden. Enter your ZIP code to see which available sitters are closest to your home.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first Meet & Greet.
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:
- 89% of sitters can help with special care needs
- 93% can help with giving oral medications or injections
- 96% 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 contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
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