Pet Sitting Winter Park
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.
Over 1,261 pet parents in Winter Park have booked pet sitting
Winter Park, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“David did a wonderful job helping care for my new dog who has separation anxiety while I was at work. He is very trustworthy, flexible and you can tell he really cares about your pet. I feel in just a few short days he made a difference helping my dog adjust to her new life. I highly recommend him.”
“Natalie is always a very great rover. She is kind, caring, responsive and takes care of our little guy every time without fail. I would recommend Natalie to anyone who needs a reputable rover.”
“Nina was absolutely amazing and quick to respond! I usually don’t trust people without getting to meet them but Nina was truly amazing with my pups and will rebook again :)”
“Tori was great! She dropped in daily to check on our dogs, feed them and have them go potty while I was doing long stretches of work with my husband out of town. She was communicative, respectful, and took some great pictures of our pups. We will be booking again!”
“Cheyenne went above and beyond to take care of our little zoo. She spent quality time with them, sent us the most precious photos and videos, and took care of them better than anyone we've ever trusted with the lot. With four cats and a big doggo, she had her hands full! Would absolutely recommend her to care for you babes.”
“Emma was absolutely wonderful with my pets! She provided drop-in visits twice a day on the days when my boyfriend or neighbor wasn’t able to be there, and she handled all of their complicated little routines so easily. I was honestly a little nervous about finding someone who could keep up with everything, but Emma was fantastic. Her daily reports were incredibly detailed, and I really appreciated knowing how each visit went and how my pets were doing throughout my trip. She made me feel completely comfortable knowing they were being checked on, cared for, and getting everything they needed while I was away. I would absolutely recommend Emma and would happily book her again! ❤️”
“Rebecca was amazing! She was so accommodating to our last minute booking due to a death in the family. She took all notes for our pup with a couple new ailments. She was awesome about sending pictures and updates. Our pup clearly felt comfortable with her and helped ease any extra anxiety. We've already booked again for an upcoming vacation - highly recommend!”
“Zoe was awesome with our two Golden’s. She took great care in helping us. The dogs were happy. Zoe shares pictures and provides an outstanding report. Zoe is our “go to” for help!”
“Absolutely love Jereny. She is very sweet, sends great pics, and actually spends time with the cats. She actually listens to special considerations with cat behavior and we were thrilled to see our slightly wary cat open up to her with time.”
“Peter is wonderful to work with. He has sat our pittie a few times now and is loved by our pup! Peter was on time and this time I forgot to leave instructions out so he confirmed our pups care prior to anything. We will definitely use his services again thank you Peter!”
“She took great care of Nudy while I was away. I really appreciated the detailed updates, photos, and notes after each visit. Nudy looked happy, comfortable, and well cared for, and I could tell she gave him lots of attention. I would definitely book with her again!”
About: Your pets deserve more than just someone to stop by and fill a food bowl—they deserve someone who truly cares. With professional veterinary hospital experience since 2020 and training in canine and feline CPR, your pets are in knowledgeable, capable hands. I treat every dog as if they were my own. That means plenty of playtime, cuddles, enrichment, and one-on-one attention—not just the basics. I also love capturing adorable and funny moments, so you’ll receive photo updates that let you see exactly how much fun your pet is having while you’re away. My goal is simple: to make your pet feel loved, safe, and happy, and to give you complete peace of mind knowing they’re receiving the same care I’d want for my own furry family. Pet care is already a big part of my everyday life. I help care for my two Shibas, so my days naturally revolve around walks, playtime, feeding, enrichment, and making sure they’re happy and healthy. Working in a veterinary hospital since 2020 has also made caring for animals second nature. Spending time with pets isn’t something I squeeze into my schedule—it’s something I genuinely love and look forward to every day. When caring for pets in their own home, I do my best to keep their routine as normal as possible. I provide plenty of love, playtime, walks, enrichment, and one-on-one attention, while making sure they’re comfortable and feel safe in their familiar environment. I also send regular photo updates, so you can see your pet happy and enjoying their time while you’re away.
About: I have a 8 month old weenie mix named Ballpark. I also love volunteering at the animal shelters and taking pups on hikes with me! I’m available daily on weekdays and weekends! I want to spend more time supporting dogs in the community and loving on pups while their families are away <3 I love to be active and loving with the pups. I have experience with gentle and cozy seniors as well as young, energetic, fun puppies.
About: I've grown up with pets my entire life and caring for animals has always been second nature to me. I have hands-on experience with senior dogs and understand the extra patience and care they need. Friends and family have trusted me for years to walk their dogs and provide reliable, loving pet sitting. I treat every pet like my own—whether that means long walks, belly rubs, or just keeping them company while you're away. I’m a college student on summer break, so I have a lot of free time and a super flexible schedule right now. Pet care fits in really easily for me—I’m available most days and happy to work with whatever routine your pet is used to! Whether I’m watching your pet at my place or yours, I make sure they’re safe, comfy, and happy. I follow your instructions and give them lots of love. I’ll treat your pet like one of my own and always be watching them with my full attention!
About: I have had chocolate labs my whole life. From crazy puppies to gray seniors, so I am very comfortable with all the stages of a dog's life, including puppy energy and older dogs who need a gentler pace. One of my labs was 100+ lbs, so I am confident handling bigger, stronger dogs too, not just small or medium breeds. I also had a cat for 10+ years, so I am comfortable around other pets and know how to help dogs and cats coexist peacefully if needed. Beyond my own pets, I dog sit for family friends, so caring for animals outside my own home is second nature to me. Whatever size or stage your dog is in, I will treat them with the same patience and love I give my own. I recently graduated from college, so I have a very flexible schedule and plenty of time to dedicate to pet care. I am home most days, which means I can give dogs lots of attention, playtime, walks, and companionship instead of leaving them alone for long periods. I also have my own dog, so caring for pets is already part of my daily routine—from feeding and potty breaks to making sure they get plenty of love and exercise. I am happy to work around your pet's schedule and provide the care they need, whether that's early mornings, evenings, or throughout the day. Your pet's safety and comfort will always be my top priority. At my home, I have a fenced backyard where dogs can safely play and get some fresh air while always being supervised. If I am caring for your pet in your home, I will do my best to keep them on their normal routine with consistent feeding times, potty breaks, walks, playtime, and lots of attention. I know every pet is different, so I am happy to follow any instructions you leave to make sure they feel comfortable and well cared for. I also will not leave pets alone for long periods because they deserve companionship and quality care while you are away. If your dog needs to be watched inside my home, it is important to know that have chocolate lab. He is 8 years old and he is super friendly and gets along well with other dogs.
About: With 6 years of dedicated experience caring for dogs of all life stages from energetic puppies to gentle seniors I provide deeply reliable, attentive pet care. Living steps from a popular Orlando park, I specialize in active, scenic outdoor walks. Because I lived with and consistently pet sat my sister's dog for years, I treat every cat and dog with true, family style devotion. My availability is perfectly tailored for before 6AM walks, after 5 PM weekday check ins and open, flexible weekend boarding, giving busy local owners total peace of mind. As a professional engineer with a structured 8 AM to 4 PM office schedule, my daily routine is highly predictable and reliable. I kick off my mornings with early bird energy, meaning I am fully available for brisk morning walks or drop in visits anytime before 6 AM to get your pet ready for the day.After sitting at a desk all day, getting home to active exercise is exactly what I need. My evening hours after 5PM are completely wide open, making me highly available for long park walks, dinner feedings, and playtime. Weekends are even more flexible for extended care. Because I cannot have a dog of my own right now, your cats and dogs get 100% of my focus, affection, and energy! Safety and comfort are my top priorities. I maintain a highly secure, pet-friendly apartment equipped with a smart home system, allowing me to remotely verify locked doors and manage optimal lighting for your pets. I have dedicated cameras monitoring both the exterior entryway and the indoor living area, ensuring I can constantly check in on your pet visually even when I step out. Before any stay, I require a meet-and-greet to ensure a great fit. Because I do not own a dog of my own, your pet enjoys a stress-free environment as the exclusive center of attention. For cleanups, I keep a bissel green machine on hand to handle any accidental messes instantly, keeping the space pristine. As well as, living steps from a popular local dog park, I utilize secure, double clip leashes for all outdoor walks to guarantee zero risk of escape. I closely monitor the Florida heat and pavement temperatures, ensuring walks are safe, shaded, and well hydrated. During in home check ins, I strictly follow your specific entry, feeding, and locking instructions, and I will always send you photo updates and a detailed report card after every single visit.
The median cost per visit for pet sitting in Winter Park is $20
Pet parents share their Rover experiences - Winter Park
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.
Camryn was amazing!! Camryn was communicative throughout my entire trip and I felt extremely comfortable leaving my girls alone. She took daily pictures and kept me updated as necessary. The entire process from start to finish went smoothly. She took great care of my girls and would love to have her again! I’m so grateful for her and all she did for us. I would absolutely recommend Camryn for your pet needs. Thank you, Camyrn! :)
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 pets like family
1. Search
Browse profiles of sitters near you who offer pet 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 pet sitting - Winter Park
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winter Park average 6 repeat pet sitting clients
FAQs for Pet Sitting - Winter Park
Frequently asked questions about Rover
The average cost for Pet Sitting in Winter Park on Rover is $19.98 per visit (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of Pet 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 Pet Sitting. For more information on service fees, click here .
As of September 2026, there are 5,519 sitters on Rover offering Pet Sitting across Winter Park. 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 Park 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.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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.
Yes, you can find sitters who have experience with handling special pet needs in Winter Park. On Rover:
- 90% of sitters can help with special care needs
- 96% can help with giving oral medications or injections
- 98% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
A Meet & Greet is a short introductory meeting between you, your pet, 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.
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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