Dog Sitting Winter Garden
Book a Winter Garden dog sitter to watch your dog in your sitter’s home or yours.
Over 184 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.
“Absolutely Amazing Pet Sitter! Jack did an absolutely amazing job taking care of my Pomeranian, Sassy, and my Siamese cat, Dukesa! From the very beginning, he was reliable, punctual, and incredibly caring. He truly went above and beyond, treating my pets as if they were his own. He made sure Sassy and Dukesa were well fed, received their medications on schedule, went on their walks, and most importantly, received plenty of love and attention. It gave me so much peace of mind knowing they were in such caring and responsible hands. Jack was attentive to every detail and made sure they were happy, comfortable, and well taken care of throughout his stay. You can genuinely tell how much he loves animals and how dedicated he is to providing the best care possible. I highly recommend Jack to anyone looking for a trustworthy, dependable, and loving pet sitter. Sassy and Dukesa absolutely loved him, and we will definitely be booking him again! 🐾❤️”
“Danielle was a real life-saver by taking the booking at the last minute due to another cancellation hours before I was leaving town. She was able to meet with me quickly and understood Coco’s care needs. Everything was completed as requested and I returned to find Coco calm and happy! Also enjoyed seeing the pictures and reading the notes from each visit. Great experience with Danielle!”
“The best! Sarah sent pics of our kitty, who was so happy to have her attention. She’s attentive and caring - I’ll definitely be recommending and using her in the future!”
About: I’ve been caring for dogs since I was 12 years old, and they’ve always been a huge part of my life. Over the years, I’ve had experience with dogs of all sizes, breeds, and personalities, including Pit Bulls, French Bulldogs, Yorkshire Terriers (Yorkies), Cane Corsos, and many others. My love for animals goes far beyond simply caring for them—they truly become family. I understand that every dog has their own unique personality, routine, and needs, and I take the time to make sure they feel safe, comfortable, and loved while you’re away. Whether your dog enjoys long walks, playtime, cuddles, or simply having someone nearby, I’m committed to providing the same level of care and attention that I would give my own pets. If you choose me as your pet sitter, you can have peace of mind knowing your furry family member will be treated with patience, compassion, and plenty of love every step of the way Pet care fits seamlessly into my daily routine. I currently work part-time, Monday through Friday from 9:00 a.m. to 1:00 p.m., which allows me plenty of time each day to provide attentive care before and after work. Whether your pet needs walks, playtime, feeding, medication, or simply companionship, I’m available to give them the love and attention they deserve. On the weekends, I’m completely off, giving me even more flexibility to accommodate your pet’s schedule and spend quality time with them. I understand how important it is to maintain your pet’s routine, and I’m committed to making sure they feel comfortable, safe, and well cared for while you’re away. I care for every pet as if they were my own, making their comfort, safety, and happiness my top priorities. I take the time to learn each pet’s routine, personality, and specific needs so they can feel as comfortable as possible while you’re away. In my client’s home, I strive to keep your pet on their normal schedule by providing fresh food and water, walks or potty breaks, playtime, exercise, medication (if needed and with instructions), and plenty of affection. I also make sure your home is respected and kept tidy while I’m there. To give you peace of mind, I’m happy to send regular photo and video updates so you can see how your furry family member is doing. Whether your pet is energetic and loves to play or prefers quiet companionship, I’ll provide patient, loving, and reliable care tailored to their individual needs.
“Thank you so much for the Excellent care of my fur babies. Pics were sent of drop in visit. My pups enjoyed it. I will definitely book her again when I go on vacation.”
About: With 5 years of experience as a pet sitter, I have developed a deep passion for providing loving and responsible care to animals. I treat every pet as if they were my own, making sure they feel safe, comfortable, and happy while their owners are away. I understand how important it is to maintain their routines, give them attention, and provide a calm environment. I am committed to offering dependable care built on trust, patience, and genuine love for animals! Pet care fits naturally into my routine, allowing me to provide dependable and attentive care. I keep my schedule organized so I can be flexible with visits, walks, and overnight stays whenever possible. My goal is to give every pet the time, attention, and affection they deserve while keeping owners updated for complete peace of mind. Your pet's safety and comfort are always my top priorities. I carefully follow each owner's instructions, including feeding schedules, medications, exercise routines, and any special needs. I take time to build trust with every pet, creating a calm and loving environment where they feel safe and cared for. Whether I'm caring for your pet in your home or mine, I'll treat them like a member of my own family and keep you updated with photos and messages throughout every visit.
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: Experienced dog sitter, trainer, and groomer. Fully sidwalked neighborhood for Pack walks, the dog park is only 2 miles away for excursions, round trip transportation to keep your car clean. looking forward to pampering your pooch. offer inexpensive dog bathing and full grooming can be requested so your dog always come home clean and we'll cared for. Full time stay at home avalible from 6am to 10pm dog park trips each morning are generally between 8-10am. Depending on weather I like to get the dogs well exercised early in the day so we are inside between 10am and 2pm to avoid the heat of the day Plenty of time for training, outback play, and socializing or pack walks If I have other out of the house apointments I keep my area of care to a 15/20 miles radius to do stop in care or walks so your dogs wont ever be alone for longer than a couple of hours tops I have a 8ft fenced in back yard multiple crates if needed as well as a 4 foot fenced partitioned side yard to seperate large and small dogs if needed. I own one female standard poodle excellently behaved so your dog will get socialized unless requested otherwise. Multiple food/water bowls are inside and outside. Bathing is optional but if your dog is a digger and gets particularly dirty i will to do a simple rinse and dry for free. We can arrange for full shaving/sanitary trims after shampooing, or de-shedding shampoo and brushing for double coats like huskies
About: I’ve been around animals my entire life and grew up with both cats and dogs. Caring for pets has always been a natural part of who I am. Today, I’m a proud cat parent to two senior cats, ages 12 and 13, who have taught me patience, responsibility, and the importance of personalized care. I understand that every pet has its own personality, routine, and needs. Whether it’s playtime, walks, feeding, medication, or simply providing companionship, I treat every pet as if they were my own. My goal is to make sure your furry family member feels safe, comfortable, and loved while you’re away. I look forward to meeting you and your pets! 🐾❤️ I’m not working at the moment, so I have full availability and a flexible schedule to care for pets. This allows me to give them plenty of attention, stick to their regular routines, and make sure they feel comfortable, safe, and loved while their owners are away. I can also accommodate last-minute bookings whenever possible. When caring for pets in their own home, my priority is to keep their routine as normal as possible. I’ll make sure they’re fed on schedule, have fresh water, get plenty of exercise and playtime, and receive lots of love and attention. I’ll also keep your home tidy, follow all care instructions carefully, and send regular photo updates so you can relax knowing your pet is happy, safe, and well cared for. 🐾❤️
About: I worked at a dog boarding and daycare facility for 3 years, where I completed multiple courses on canine behavior and handling. I hold a degree in Animal Behavior and have been dog sitting for friends and family for several years. Currently, I work part-time as a Zoological Specialist, and previously gained years of experience caring for and training exotic animals. I have a strong foundation in animal training techniques, and my background gives me a deep understanding of behavior, safety, and enrichment — insight I bring to every pet I care for! My own dog, Moxie, was my best friend & lived a long, happy life of 15 1/2 years. She taught me how deeply we love our pets & how much they mean to us. That’s why I treat every animal I care for as if they’re my own! I currently work 40 hours as a Zoological Specialist, with a rotating schedule. My weekend falls on Wednesday and Thursday, when I’m most available. Since my shifts vary, I often have availability during weekday mornings or evenings, depending on the week. Safety has always been a top priority in my work. While at the dog daycare, I was responsible for closely observing canine behavior to ensure safe and positive interactions within playgroups.
About: I have always loved being around animals since before I could walk. I have worked with Dogs, Cats, and Horses. In college, I worked at a Day Camp teaching children to ride horses. I love being around Cats, and dogs; they make me smile with their different personalities and quirks. I am a part time swim instructor I work during the week, and the weekends from 8am- 1:30 PM. I am available for dog walking/sitting anytime after 2:00pm during the week, and weekends. I have done pet sitting in the clients home. I fed the cats, fish, walked the dog. I once watched my friends dog over a weekend. I fed his dog on their scheduled time and walked the dog many times it was a lot of fun!!! I am very cautious when I am with a clients pet. I treat every pet as if they were my own.
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.
About: Hi! I'm Andrea and the cute pup in my photo is my dog, Disney. My experience caring for my own dog with complex needs has shaped the way I approach every pet in my care, with patience and understanding. I'm Fear Free Certified, trained to recognize canine body language and use techniques that help minimize fear, anxiety, and stress. I'm also Pet First Aid & CPR Certified and insured, so you can feel confident your dog is in good hands. My goal is to provide the same level of thoughtful care I would want for my own dog. I’m fortunate enough to have a flexible schedule which allows me to be readily available for your pets needs whether it’s going on walks, playing catch, having a yummy meal, whatever your dog desires! Your pup will be in great hands with me. I will give them my undivided attention the whole time they are in my care. I’m also Fear Free certified and CPR & first aid certified so you can rest assured they will be well taken care of.
About: I love dogs, I can talk about my own baby dog for days. I’m bilingual (Spanish and English), I love walking and I love pets. Mix them together and I’m there. I’m probably available when you need me so you can trust that I will take good care of your pets when you are not able :) I am a freelance photographer, so I work from home and manage my own schedule. I am available mornings, afternoons and evenings as needed :) I can walk pets, come and feed them or play with them or I can pet sit in your home. Unfortunately not available to bring pets to my own home
About: Hi, I am a current graduate student, and animal lover. I’ve been taking care of animals since I was young and pet-sit for my friends all the time. I am eager and willing to help out! I am currently graduated from school, so my hours are usually flexible as I look for jobs right now. Excited to help and look out for your pets. I usually pet sit for my friends when they’re out of town, so I’m open to doing drop ins and feeding and walking your pets for those times. Always making sure they are fed and their needs taken care of.
About: *Disney area Hi, I’m Jordan!! I grew up in a home surrounded by dogs, cats, reptiles, birds, etc. I have also previously worked as a veterinary assistant, so I have plenty of experience with all different types of pets and their personalities!! Currently I have a 2 year old Italian Spinone and a 4 year old cat, so I’m equipped for it all! I am a true animal lover at heart and I can’t wait to take care of your fur babies! I am available all throughout the Windermere/Winter Garden/Disney area I work part-time and only have online classes, so I am available Sunday-Wednesday at any time of day! I have plenty of time to care for & play with your pets! I am here for whatever you need! However you want me to go about caring for your pet in your home I’m able. I understand how important your pets are to you and I am determined to keep them safe, happy, and healthy!
About: Dogs have been a part of my life for more than 20 years, and caring for them is something I genuinely love. Friends and family have long trusted me as their go-to pet sitter and dog walker whenever they travel, knowing their pets will be treated like family in my care. I have experience with dogs of all ages, sizes, and temperaments, including training and rehabilitating aggressive rescue dogs. I’m comfortable administering medications such as pills, ear drops, and topical treatments, and I have firsthand experience caring for elderly dogs or dogs with complex medical needs. My beloved dog, Ralphie, bravely battled cancer for over a year, which taught me patience, attentiveness, and the importance of compassionate care during difficult times. My home features a secure, grassy fenced-in backyard where dogs can safely play and explore. Since Ralphie passed away last year after a second battle with cancer, I have all the space, supplies, and dog-friendly setup needed to comfortably care for visiting pets, but no pets of my own. This allows me to focus completely on the dogs in my care. My goal is simple: to make your dog feel safe, happy, loved, and cared for while you’re away. 🐾❤️ I am currently between jobs, which gives me a very flexible schedule and plenty of time to provide walks, playtime, companionship, potty breaks, medication administration, and lots of love and attention. I offer doggy daycare, drop-in visits, walks, and can accommodate boarding for up to two dogs at a time on a case-by-case basis to ensure every pet receives personalized care. When caring for dogs in my home, I focus on creating a safe, calm, and comfortable environment where they can maintain their normal routine as much as possible. I have a secure, grassy fenced-in backyard for supervised play and exercise, and there are no children in the home—just two responsible adults—so visiting dogs can enjoy a quieter, lower-stress environment. Because I do not currently have any pets of my own, dogs in my care receive my full attention and don’t have to adjust to sharing space with resident animals. For daycare and boarding, I provide regular potty breaks, walks, playtime, enrichment activities, plenty of affection, and close supervision. I am experienced with administering medications, including pills, ear drops, and topical treatments, and I carefully follow any instructions provided by pet parents. I also limit boarding to a small number of dogs to ensure each one receives personalized care and attention. When caring for dogs in a client’s home, I respect their established routines and work to make the experience as seamless as possible. Whether that means following a specific feeding schedule, administering medications, maintaining training practices, providing exercise, or simply offering companionship, I treat every pet as if they were my own. I understand that consistency helps dogs feel secure while their owners are away, and I make communication a priority by providing regular updates, photos, and check-ins. 🐾
About: I have been around all kinds of dogs my whole life. I had my childhood dog for 10 years (ages 8-18). I have lots of puppy experience from puppy sitting my sisters frenchie. I’ve grown up around Shih Tzus, Frenchies, Goldendoodles, Pit Bull mixes, Chihuahuas, Huskies and Great Danes. I love all kinds of animals! I currently work a part time job Sunday-Thursday. I’m available for walks/potty breaks anytime before noon on those days. Friday-Saturday I am off and have lots of flexibility to stay and play with your babies all day. I am also available for boarding any day of the week! I will care for your babies in the comfort of their own home where they will feel safe and comfortable. With parental permission I can also take them to the nearest dog park to play and socialize with other dogs. Regular updates will be given, whether it’s a text or a cute picture or video.
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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- 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?
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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 $22 per visit as of October 2026. Most bookings cost between $14 and $31 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 October 2026, there are 5,167 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 .
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 , 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 .
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 , 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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