Dog Sitting Winter Garden
Book a Winter Garden dog sitter to watch your dog in your sitter’s home or yours.
Over 188 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.
“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: greetings✨:) i am currently in school studying to become a veterinary assistant. i would like to gain more experience & knowledge of the behavior of different breeds of animals.i have much experience with different dog breeds such as yorkies, frenchies , chihuahuas , golden doodles, even larger breeds like pitbulls and rotweilers & more. i also have experience in handling exotics such as snakes, frogs ,rabbits, chameleons ,etc. :) I have vet school during the end of the day from 6pm - 10pm on tuesdays and thursdays. Around those hours i am dedicated to taking care of the beautiful fur babies 💪🏽❤️ I have a 2 bedroom townhome with a fenced dog park area roughly about 30 feet away large enough for any breed to rome comfortably while still being safe & secure. I also have a 6 year old very friendly & vaccinated make pitbull that loves to make new friends and will glady keep your fur baby entertained!!💖 My mission is to take care of Gods animals, the way he intended and treated them with the upmost love, empathy and care.
“Excellent first experience, Darryl was responsible, communicative, followed instructions to the T, and took good care of my doggo, most definitely would recommend him”
“It was our first time to use Rover in a new city. We were nervous. Ariella was fantastic. She’s a natural with dogs, and we got regular updates during our absence. I would definitely hire her again.”
“Reece was very responsible, and communicated well throughout the sitting hours. If any changes on the time was needed, she made sure to check first. I could tell she took this seriously and made me feel at ease. My dog is giant and not many people can handle it. But she did well with Mocha.”
About: For over 15 years, I have provided comprehensive, high-quality care for both dogs and cats. My experience ranges from high-energy playtime to specialized senior care and positive reinforcement training. I pride myself on creating a safe, structured, and joyful environment for every pet. What I Offer- Medical & Senior Care: Confident in administering oral medications and skin topicals, as well as managing specialized routines for aging pets. Positive Training: Skilled in teaching basic manners, tricks, and reinforcing good behavior using force-free methods. Play & Enrichment: Expert at reading animal body language to deliver the perfect balance of physical exercise and mental stimulation. Feline Expertise: Experienced in managing cat behavior, specialized diets, and giving space to timid or anxious felines. Whether your pet needs basic puppy training, gentle elder care, or just a fun day of structured play, I adapt my approach to their unique personality. Because my work schedule varies week-to-week, I am highly adaptable and can often accommodate non-traditional times, last-minute requests, and mid-day visits that standard 9-to-5 sitters cannot. I manage my calendar tightly to ensure that when your pet is booked, they get my 100% undivided attention, medical care, and training focus. As a seasoned pet professional specializing in medical administration and behavioral training, I look at safety through a clinical and preventative lens. I do not just watch your pet; I actively monitor their health, behavior, and physical surroundings to prevent accidents before they happen. You can travel with total peace of mind knowing an expert is at the helm.
“Steffanie did a wonderful job! She was great communicating with and sent me photos of my fur babies to ease my mind! My dogs loved her and I will definitely hire her again!! :) thank you so much Steffanie!!”
“Skye was great at communication and sending pictures of my fur babies! By looking at the pictures I can tell that my dogs adored her and that alone speaks for itself! Skye was able to watch them on short notice too, so that’s a plus! Even when she had car troubles, she still made it to check in! I would rebook her again! :)”
“We just returned from a 5-day trip and couldn't be happier with Tathyana's care for our cats. She was attentive and understood their different personalities. It was heartwarming to see even our shy cat start to warm up to her through the updates! It's such a relief knowing they were well taken care of when we missed them terribly. Tathyana is warm, friendly, and trustworthy. We 100% recommend her for your pet’s care!”
“Ani’yah was such a wonderful person to work with! She was so good with our pup and very communicative! We will absolutely be recommending her to our friends! Thank you so much Ani’yah!”
“Yolanda is a fantastic communicator and wonderful caretaker for our fur babies. She goes above and beyond to ensure their comfort and fun and came through on a last minute request!”
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.
About: 🐶 Instead of simple pet sitting, dog walking or drop-in’s, you are investing in a well-mannered companion during enriching activities with a certified professional dog trainer. 🏠 HOUSE SITTING w/ TRAINING The ultimate luxury training package: While a House Sitting stay on Rover does not include an active, full-scale training curriculum, your dog will benefit from my expert background. I offer a premium, structured alternative to standard pet sitting. I stay overnight in your home to provide 24/7 comprehensive training in your dog's natural environment! What's Included: • Daily structured training sessions covering your specific goals. • Intensive behavior modification and management (separation anxiety, house rules, manners). • Daily video progress reports and a comprehensive hand-off workshop. 💎 Every immersive stay is completely tailored to your behavior goals and includes a complimentary hand-off training lesson at conclusion of stay. Having this expertise assures optimal experience in real world proofing. *Select "House Sitting" on my profile to book a premium board & train! 🏡 IN-HOME PRIVATE TRAINING LESSONS Get professional behavior coaching right where the issues happen! Perfect for backyard recall, doorbell barking, or crate training. What's Included: • 30 or 60 minutes of intensive one-on-one behavior work with brain breaks & rest. • Real-world coaching in your home or immediate neighborhood. • Clear homework steps to keep your progress on track. *Select "Drop-In Visits" on my profile to book your private lesson! 🐾 STRUCTURED LEASH MANNERS WALKS No more pulling! Turn your dog's daily walk into a professional training session focused on calm outdoor focus. What's Included: • 30 or 60 minutes of active loose-leash training. • Real-world practice with distractions (dogs, cars, squirrels). • Immediate feedback & simple handling tips for owners. *Select "Dog Walking" on my profile to book a training walk! 🐾 DAY TRAINING CAMP 🐾 Skip standard daycare. Drop off your dog for a structured day of professional behavior training! What's Included: • 3 Focused One-on-One Training Sessions (30 mins each) • Real-World Practice (Leash manners, distraction proofing, impulse control) • Behavioral Targets: Loose-leash walking, jumping, basic obedience, focus, recall & socialization. • Video Updates & End-of-Day Hand-off Consultation *Select "Doggy Daycare" on my profile to book your day training camp! 🙋♀️ A NOTE ABOUT ME: Aside from being a dog trainer, I am an active volunteer with Pet Alliance as a in-shelter bark buddy, and a foster dog parent. I participate in local events, fundraising and Hound Around Town monthly. I have since expanded my efforts with Husky Haven of Florida as a transport for rescues. I’ve worked at Disney’s pet resort & dog daycare in downtown Orlando. 💯 My base rate listed on my profile covers standard, high-quality care (feeding, potty breaks, and companionship). Since I am a certified dog trainer, the context described above is offered as an active Training Add-On Package for an extra $15 per day. Just be sure to brief me in your contact message and we can discuss together further in detail. With dog training as my core, and having an Executive Assistant professional background of over 20 years, calendar maintenance comes natural and my availability is easily workable around varying schedules. If I’m not at the dog park or training, I can be available for services as necessary. I focus on science-backed methods that are mindful and effective, while integrating enrichment, affection, stimulation (both mentally and physically), rest breaks, sniffy walks, play time and cuddles. I prioritize the pet parents requests and instructions, aligned with fulfillment that meets the dog’s foundational needs.
“I have had Ziva since she was 4 months old. She is the last of my trio of pugs. Now at 16 she has survived surgeries, anemia where we almost lost her, she is my ride or die. I say all that bc I don't trust many people with her. I can count on my hand how many I woukd trust with her. Now I can add a 2nd hand. Lynn was FANTASTIC. I have 4 furbos in my house & every moment I watched was a joy. He talked to her, gave her cuddles, and even did some of her physical therapy exercises. Which I am grateful for bc today is a long work day. When he walked her he used her sling & had patience with her I will absolutely be reaching out to him for future bookings. Thank you from the bottom of my heart. Again Phenomenal job.”
“James was wonderful with my birds! He was reliable and clearly cared about making sure they were well taken care of while I was away. He also watered my plants which was such a thoughtful extra. I came home knowing everything had been taken care of, and I really appreciated his help. I would definitely recommend James and would be happy to have him watch my birds again! 🐤🐤”
“Lindsey has been a godsend and the perfect sitter for our two crazy boys! From drop-ins to housesitting, Lindsey is always incredibly communicative, thoughtful, and professional, and treats our pups and our home as her own. We couldn’t be more grateful to have connected with her, and we always know our boys are in the best of hands.”
“First time using Taylor and we are very happy with her communication and how she treated our cat-Koko. We will definitely book her again during our upcoming trips. Thanks!”
“Alexis was amazing - my pets (dog & cat) immediately warmed up to her and were comfortable with her. Will definitely utilize her services again and recommend her to neighbors.”
“Katherine is absolutely wonderful! She was very responsive and reliable. I also appreciate that she would grab our packages if we had any sitting and bring them in. I will absolutely schedule care with Katherine again in the future!”
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.
We had an awesome experience with Tori! She had a great initial meeting with Coco and asked lots of questions to make sure he was well cared for while we were out of town. There was great communication after each visit and pictures to let us know he was doing well. We never had a worry while we were away and returned to find him happy and relaxed. Very pleased with Tori and the care she provides!
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!!!
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.
Meet local sitters who will treat your dogs like family
1. Search
Browse profiles of sitters near you who offer dog sitting
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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 Drop-In Visits - Winter Garden
Frequently asked questions about Rover
The average cost for Dog Sitting in Winter Garden on Rover is $22.2 per visit (as of August 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 August 2026, there are 5,117 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:
- 90% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 97% 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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