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 6 pet parents in Winter Park have booked pet sitting
Winter Park, Find top rated pet sitting
Prices are estimates per visit for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Lauren did 4 drop in visits for our two cats over a weekend and was absolutely fantastic! She sent plenty of photos and thorough updates. Quick to respond and left the place in great shape. Would recommend!!”
About: I have a multifaceted knowledge of dogs and cats of many breeds. My first job was as a receptionist at a veterinary clinic, and I have had many pets in my family over the years. Including a massive German Rottweiler, two tiny sphinx cats, and two bulldogs (that doesn't include the guinea pigs or bunnies). I have a well rounded knowledge of needs and medical necessities of different breeds. I have fed, bathed, walked and played with animals all my life, it’s like second nature. I live with several animals at home I feed, play, walk, bath and love on animals every day and have for the last 17 years. I am used to all different breeds of dogs/cats. In a clients home I am very flexible when it comes the to the individual needs of the pet and the parent. I know how different animals react to different things and understand each one is their own little Individual! I especially love all pets different quirks and routines.
“Sarah has been a lifesaver as our puppy Carly gets adjusted to her second home in the mountains. Having Sarah come to walk and spend time with Carly allows us to spend more time skiing.”
About: I’ve been caring for dogs for many years, both my own and those of family, friends, and anyone who has needed a helping hand. I have experience breeding Labrador Retrievers, raising litters of puppies, and caring for dogs through every stage of life. As a dog owner myself, I know how important it is to find someone you can trust. My three dogs are part of my family, and I treat every dog in my care with the same love, patience, and attention I give my own. To me, dogs are so much more than pets—they’re family. My goal is to make every dog feel safe, loved, comfortable, and well cared for while you’re away, so you can have peace of mind knowing they’re in good hands. I have a very flexible schedule, which allows me to provide reliable and consistent care for your pets. I work from home with our family business, giving me the flexibility to accommodate morning, afternoon, evening, and weekend visits whenever possible. Whether your pet needs a walk or drop in visit, I’m committed to providing dependable, attentive care while keeping their routine as normal as possible. My goal is to be available when you need someone you can trust with your furry family member. I provide dependable, loving care for pets in the comfort of their own home through drop-in visits, walks, and pet sitting. I know pets thrive in their familiar environment, so my goal is to keep their routine as consistent as possible while you’re away. Whether it’s feeding, fresh water, potty breaks, walks, playtime, companionship, or simply giving them extra love and attention, I’ll care for your pet as if they were my own. I understand that every pet has unique needs and personalities, and I’m happy to follow your instructions to ensure they feel safe, comfortable, and well cared for. My priority is giving you peace of mind, knowing your pet is receiving reliable, compassionate care while you’re away.
About: I’ve owned dogs throughout my whole life. I currently have two cattle dogs that are great with other dogs. I have experience with all dog types including high energy and anxious dogs. I also have a lot of experience giving medications. I have a flexible work schedule and understand how hard it is to leave your dog home alone all day. I can accommodate most times. I can accommodate the dog’s needs whether that is playing fetch in the yard, or multiple walks a day. In our home they will have access to our large fenced in yard. They won’t be left unattended.
“Aleah was great, highly recommend. We reached out less than 24 hours before due to a lack of communication and interest from the original sitter we had set up. Aleah responded right away and even did a meet and greet the same night we reached out. She was great at communication and sen us pictures of her drop in visits with Axel. Thank you Aleah!!”
“Sarah was an amazing dog sitter for our dog and new puppy while we were staying in Winter Park on a family trip! After doing a meet and greet we could tell our pets were in excellent hands and would get lots of love. Sarah was also super flexible and accommodating when we had late changes in our plans. I would highly recommend booking with Sarah!”
“Sandy & Chase are great! Super quick to respond and are great communicators. They sent nice pics and updates of our dog during the visit and we really appreciated their care.”
About: I take care of dogs the way I hope someone would take care of mine. Reliable, calm, and present. Your dog gets real attention. We have two friendly labs at home who love having a buddy around. They are well socialized and help visiting dogs feel comfortable fast. I keep things relaxed and structured with plenty of play, potty breaks, and downtime. I only take a limited number of bookings so I can focus on the dogs in my care. Drop-ins and walks include refreshing water, feeding if needed, a full potty break, and a quick tidy before I go. I stay the full time and I send updates with photos so you know how your dog is doing and don’t have to wonder. If you are visiting the area, I work often with dogs staying in rentals and I help keep routines steady so you can enjoy your trip without stress. If you want someone who treats your dog like family and communicates clearly, I’d love to help. I work from home, which gives me the flexibility to fit in walks and visits throughout the day. When I’m not out adventuring with our dogs, I’m happy to be spending time with yours. I currently provide care walks, check-ins and day care in my home. If staying for day care I have 2 labs and will follow your routines for feeding, walks, and playtime, and give them the same love and attention I give my own.
About: I have loved dogs my whole life and have been taking care of dogs for about 10 years! I have lots of experience walking and caring for neighbor’s dogs as well as taking care of dogs of friends and family. I have a pet friendly apartment and would also be happy to go anywhere to take care of your dog, whether that be your house or the park! I would able to take care of your dog almost any day of the week! Just need to know I’m advance to make sure it works with my schedule! I have a good sized apartment and there is also a yard area for dogs to run around outside. I am happy to walk, feed, and take care of your dog in any way you might need!
About: I have taken care of my own families dogs, my neighbors pets, and even my family friends pets since I was about 11 years old I work for Neil’s Lunceford Landscaping in Tabernash, but live in Winter Park. I work Monday-Thursday from 8am-6pm and occasionally on Fridays until about 2pm. Even with my work schedule, I am flexible to take care of your pets throughout the week! I cater to the pets needs, whether that’s needing food, exercise, or to go outside to the bathroom, I always make sure to be on top of what the pet needs. I am respectful in clients homes and make sure everything in the home is just how they left it, if not even better. I take care of everything like it is my own, I like to show my respect and appreciation! As well as help you out by watching over your fur babies!
About: I’ve been taking care of pets since a very young age- 4 different cats, 3 different dogs at home- and have also been a pet sitter more times than I can count, for neighbors and friends etc. I have experience with both older dogs and puppies, and same thing with cats. I work nights full-time at a bar in Winter Park and coach skiing all day on Saturdays. I try to be as active as possible, so dog walking/exercise is just as beneficial for me as it is for the pup! Days are definitely better (excluding my coaching days). I would ensure that my actions are familiar to the dog and not something that would offset their comfort. In my home, I will give the dog plenty of outside time as I have a fenced in backyard and live very close to a dog park. My household is very much a pet-loving environment!
About: Five years and running in Summit County. My love of animals is noticeable and after having spent many a day and weekend taking care of my friends and neighbors furbabies (including running with their dogs), I've decided to make dog/cat sitting a more permanent side hobby. As a pet owner myself (both cats and dogs), I understand how important a cat/dog sitter is to the wellbeing of both the owner and their pet(s). Therefore, I'll do all that I can to make sure I provide a fun, safe and positive experience for everyone. I am a consultant so my hours are somewhat flexible during the week and weekends. Let me know how I can help. My schedule is flexible, which allows me to provide dependable care and accommodate a variety of pet care needs. I am available for drop in visits, feeding, playtime, companionship, and overnight stays depending on the location. My priority is creating a safe calm and comfortable environment where pets can maintain their routine and feel secure. In a clients home I respect the pets established schedule and the owners preferences, including feeding routines, medications, exercise, playtime and household guidelines. I pay close attention to behavior and well-being and provide regular updates and photos so owners can feel confident their pets are happy and cared for.
“Haley completed some drop in visits with my cat ghost over a week period. She did amazing, always making sure to spend time with my cat and still complete the feedings and little box cleanings. Pictures would always show her cuddling up with my cat or playing with him, which is always great to see when you’re away for a bit. Would definitely recommend her to others as she is super caring, thoughtful and responsive! Thank you again Haley!”
About: Not only did I grow up my entire life helping raise dogs and cats with my family, but since being independent from my parents I have assisted friends with training, exercising, and loving their pets as well. I am well-recognized by my friend's dogs as the one who always takes them on hikes, so generally they express the same excitement as me when we get to see eachother. I will be available every day to help friends, family, and new folks care for their pets. I have no other work to do during this time so I will be entirely dedicated to giving these pets attention, love, and exercise. I love being outdoors and exercising, whether it is hanging out at a park or going for a walk/run, I always make sure to exercise the pet to their own capabilities. Based on their physical condition, I ensure that they are enjoying their time with me and not being over exerted. Whether they are still learning, just starting training, or fully trained, I always make sure to align myself with the owner or my peer's standards, that way I do not confuse the animal and can help improve upon it's behavior.
About: Hello! I was in the service industry for over 25 years, and developed lots of allergies…so I am now the Barktender! I own my own business, offering cleaning, petsitting and other services my commUNITY may need. Very rewarding! Love my life! I am using Rover to fill in the few gaps I have, hopefully outside my home area, to travel more. The winters are getting too long for me, after being in the mountains for almost 20 years. I have been apprenticing under a dog trainer for several years and about to venture on my own! I have experience with some livestock and eager for more experience! I have a thirst for knowledge and learn quickly. I love animals and do my best to treat all the animals as my own. I own my own business and try to schedule jobs to accommodate to your pets needs. I do cleaning, yard work etc on the side and my schedule is very flexible. I can not have pets in my home. This is why I started the business. I love animals and hard to find pet friendly places in the mountains! Your pets are my priority!
The median cost per visit for pet sitting in Winter Park is $21
Dog parents share their Rover experiences - Winter Park
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
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Popular requests for pet sitting - Winter Park
Select a filter and find qualifying sitters offering pet sitting.Sitters in Winter Park average 7 repeat pet sitting clients
FAQs for Drop-In Visits - Winter Park
Frequently asked questions about Rover
The average cost for Pet Sitting in Winter Park on Rover is $55.5 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 2,778 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:
- 94% of sitters can help with special care needs
- 97% 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.
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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