Dog Sitting Winter Park
Book a Winter Park dog sitter to watch your dog in your sitter’s home or yours.
Over 207 pet parents in Winter Park have booked dog sitting
Winter Park, 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.
“Noelle did a great job of caring for our kitty boys. We really appreciated the daily pictures and coming home to happy cats. Not only were they fed and litter box cleaned, but she spent time with them, giving them some play time and affection. Would definitely book her again.”
About: I'm an FSU grad with a passion for animals. Dogs have always been a huge part of my life. Growing up I lived with five dogs so I'm quite comfortable caring for multiple animals. I started dogsitting for neighbors & friends while I was in school. I have also worked with pets as a Petland associate & volunteer Tech. All sizes, breeds and ages welcome please. Your dog's safety & comfort are always my highest priorities. I always make sure to follow your instructions not to get them out of their routine and send you pictures & videos on a daily basis while you're away. I usually take the dogs on short walks 4 times a day, make one trip to the dog park a day for your dog to burn energy. I also make sure your dog gets the right amount of food you indicate and that it gets plenty of love and patting while you're away. I have experience caring for Senior pups as well as dogs of all temperaments. It's important to me that every dog feels comfortable in my home, I definitely love them like my own. *I have no problem administering pill medications. Thanks for considering me to look after your loved one, it will be my pleasure to spend time with him/her. I'm almost always working from home. I am flexible with last minute bookings. Sometimes I may already have 2 dogs booked to stay & sadly that is the limit at my house. I make sure dogs are loved & get to play & go for walks often. Even trips to the park if you're okay with it
About: You know those 20-something olds who make their pets their personality? I feel that. I’ve been a pet sitter since high school where my first experience was taking care of my neighbors dogs—three beagles, a labradoodle, and two cats—talk about a full house! Since then, I’ve taken care of an array of breeds/sizes/ages from yorkies to goldens to puppies or old souls. My personal favorite—my pandemic pupper Fred, who was a beautiful mix. It’s just not dogs! My family had a cutey orange tabby—Scout. I now own my baby Bernedoodle—Bobo. He’s a sweet heart and loves to play with everyone. If you’re looking for someone who will treat your dog or cat as my own, that’s me! *También hablo español si es tu idioma preferido. I’m currently working full time but have a flexible schedule—I’ve been puppy training for weeks. I’m more than happy to board on the weekends as they’re usually free and open. Or stop by during my lunch break for a quick walk or playtime. I live in an apartment but it has plenty of open space outside to walk pets during the day and had an open floor plan. I’m very adaptable to the needs of the pet. Ie, medication, food needs, crates vs no crates . When boarding, if you have a bed, toy, blanket that makes the pet more comfortable, I’ll gladly use it to comfort them. With cats and dogs, I’ve found that some of the best comfort, is to simply be present. It doesn’t mean always having to be active or playing, but just as we find peace in their presence, they find it in us too. With every service, I’m also happy to provide pictures or videos.
About: I’ve had two dogs since I was five-years old. Throughout those years, I have fed, walked, and bathed them. In addition, friends and family have relied on me to care for their pets. I also have had experience volunteering in Sunday School and Senior Care Centers. I swim year-round for Rollins College. However, that does not mean I do not have time for your pups! I am available everyday in the afternoon between practice and classes. I care for pets in their own home through drop-in visits or walks, following their normal routine and any instructions you provide. I make sure they’re fed, exercised, safe, and given plenty of attention, and I always send updates so you know how they’re doing.
About: What sets me apart is my hands-on experience with senior and special-needs dogs, shaped by caring for my own senior pup who requires dietary and lifestyle adjustments. I spent three years working in a veterinary office, giving me minor medical training and confidence with medications and health monitoring. I come from a lifelong family of animal lovers, work from home, and have a large, secure yard—so your pet receives knowledgeable, attentive, and loving care in a calm environment. Pet care fits seamlessly into my daily routine since I work from home and structure my days around the animals in my care. I’m able to provide consistent feeding, playtime, litter maintenance, medications if needed, and plenty of companionship throughout the day. Caring for pets isn’t something I squeeze in—it’s part of my everyday life. I care for pets by following their normal routine as closely as possible to keep them comfortable and stress-free. In my home, pets receive a calm environment, regular feeding, playtime, enrichment, and rest, along with supervision throughout the day since I work from home. In a client’s home, I focus on maintaining their familiar schedule, providing attentive care, administering medications if needed, and keeping their space clean and secure. I always prioritize safety, comfort, and individualized care based on each pet’s needs and personality.
“Ava was wonderful caring for my girls! She is communicative and sent updates/pictures so I never had to worry. I definitely recommend booking with her and will be a repeat customer 🤍”
About: I’ve watched family and friends pets over the years when they need a hand. I even worked with a dog trainer for a summer! I currently have two part time jobs and I’m also an actor. I can provide pet care before and after work. I can drop in and give your dog a walk when needed! Or that little bit of exercise to get their energy out. I will stick to your dogs tried and true routine! Provide them with extra care and ensure a safe and fun environment whilst you’re away or busy.
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.
“I cannot say enough how wonderful our experience with Angelina was! She was great with communication, was super respectful, kind, and incredibly sweet! She always made sure to send videos & pictures of our cats which made us so happy. :-) On top of the care we asked for (food, water, litter box) she played with our boys and gave them lots of loving - she even took our trash out for us! We don't have many friends in Orlando yet, so Rover & Angelina truly put our anxieties to rest when we had to leave town for a while. Thank you so much Angelina!!”
About: I'm so excited to welcome, play with and care for your furry love. Please read the following: I am accessible by phone all the time, and I love taking pictures, so you can expect to get lots of updates of how your dog is doing! Your dog’s stay will not overlap with other dogs so your dog will receive the care and attention he or she deserves! - DAYCARE: The neighborhood is very pet friendly. Doggy bags nearby. - WALKS: Can personally walk your dog up to 2 miles. We stay active! Give your dog the walk he/she deserves while you're away at work or on vacation. - DOGGY BAGS / DOGGY BOWLS: Please provide the necessary items your dog needs while away. It's a good idea to reserve dates as soon as you know you need me! We can schedule a time to meet briefly before the first stay so we can discuss details and get you familiar with my home. In your booking request, please include your drop off and pick up times. Check out my rate and time guidelines above. I'm very flexible on times with a couple exceptions, which can be discussed. Please send your dog with their food (either pre-portioned or with a measuring scoop/cup), their treats, leash and collar and any other items such as toys. If your dog is crate trained, please bring that too. Please message me for any questions. I'm so excited to get to know you and looking forward to sitting your furry one. Weekly routine includes waking up, several walks during the day, constant updates to clients and ensuring there's a happy exciting day every day. The day varies as the client or pet! Pets are spoken to, walked, and given proper attention. For previous clients during week long stays, they were played with, fed and given baths in addition to constant updates!
“I’ve used Adriana two times now, and will continue to use her in the future! She did a great job taking care of my beloved kitties and my apartment, she is very conscientious. (And I am very particular!) Thank you so much!”
About: I have been a huge animal lover and caretaker ever since I was a child. I have a multitude of experiences with animals from all walks of life through my own personal pets and volunteering experiences with local rescues. I am currently a foster for a local rescue (Husky Haven) and I have experience with dogs of all ages (from puppy to senior) and have worked on house-training, proper leash manners, crate-training, socializing, and loving the dogs to get them adopted into their forever home. As someone who owns two dogs, I know it can be stressful finding someone to take care of your furry family members. I will do everything I can to give your pets the best care and communicate with you/send loads of pictures so you have an ease of mind! I have a job where I always work evenings, so I am free every day of the week from the morning to the afternoon (6 am-3pm). I also have weekend availability! If you have a fenced-in yard, I will monitor your dog make sure your dog does not escape or get into anything that would harm them. If you do not have a fence, I will make sure the dog is in a secure environment at all times and be careful to harness and leash them before taking them out.
About: I got my first dog when I was in 6th grade and he was a shitzu. He was the calmest dog I ever had and people told me he kind of resembled me. That was 14 years ago and I have learned a lot of patience, love, and care throughout that time. After he passed 6 years ago, I’ve continued to love animals through fostering (longest was 2 months) and dog sitting both short term and long term. While your pet stays in my home overnight, I will give all my attention to whatever needs they have. I will play with your dog as if they were my own because that is how much I I love them. My special skill is that I am patient with pretty much everything I do so when it comes to your pets, I will keep a cool head when things get “hairy”. I am currently working part time and will have plenty of time to give them attention and company. I also live in a dog friendly neighborhood with plenty of walking trails that will be perfect to explore! I try my best to treat all pets as if they were my own. I also don’t mind if they snuggle next to me on the bed or if they want to relax on the couch.
About: I've been a dog dad for 5 years and a pet sibling for over 20. I've had cats, dogs, fish, and other pets in my life for almost all of it. When I hang out with your pets, it's just that -- we talk, we vibe, we chill, we play. I've had experience caring for dogs and cats of all types, personalities, and ages. From keeping up with young, playful pups to feeding liquid diets to old, tired, and frail kitties, I am up to any challenge. Your pet will very quickly learn to love me! I work for myself, so my days are flexible and adaptable -- I can build my schedule around your pets' needs! I prefer at least three days notice for job requests and cancelations. I am happy to come to your house and keep your pet comfortable with their familiar environment. When in your home, I will be respectful and make sure to keep your space clean and organized.
“⭐⭐⭐⭐⭐ This was my first time using Rover, and I couldn’t have asked for a better experience! The sitter did an outstanding job taking care of my dog and went above and beyond to make sure everything went smoothly. She kept me updated, took great care of my dog, and made me feel completely comfortable while I was away. My dog was happy and well cared for when I got home. I highly recommend Alyssa to anyone looking for a trustworthy, caring, and reliable sitter. I will definitely be rebooking with her again!”
The median cost per visit for dog sitting in Winter Park is $20
Dog parents share their Rover experiences - Winter Park
Havana was absolutely amazing! She was so attentive and kept us updated throughout the entire stay, which gave us so much peace of mind. You can genuinely tell how much love she has for animals because she cared for our doggies like they were her own. 🥹🤍 Our youngest pup has been struggling a little with socializing, and Havana was incredibly patient, gentle, and understanding with her. By the end of the stay, our girl had even made a new bestie, Ballpark! 🐾 We couldn’t be more grateful for the love and care she showed our babies. We would absolutely recommend her!
Lyle & Karen helped me with feeding my dog Cody who had suddenly developed an aversion to food, also administered medication that is nearly impossible to do by myself. It's especially helpful to have 2 people assisting me instead of just one. They were very patient and caring. I really appreciate them coming to see Cody, and want to apologize about the sloppy "canine cookies" instead of the liquid meal that I originally had planned to feed him. I hope to see them again for another visit. It's especially convenient how close they live to us. Thank you for everything.
Carolina was great! She dropped in to check on my 10 month old pup following a spay. Following the spay, my puppy’s incision became infected and required emergency care. Given the situation, I wanted an experienced individual checking in and monitoring. Carolina was more than just experienced — she was friendly, communicative, timely, and caring. I would recommend her without reservation.
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 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
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for dog sitting - Winter Park
Select a filter and find qualifying sitters offering dog sitting.Sitters in Winter Park average 6 repeat dog sitting clients
FAQs for Dog Sitting - Winter Park
Frequently asked questions about Rover
The average cost of Dog Sitting in Winter Park is $20 per visit as of November 2026. Most bookings cost between $14 and $37 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 5,351 sitters on Rover offering Dog Sitting across Winter Park. 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 Park 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 Park 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 Park. On Rover:
- 88% 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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