Dog Sitting Winter Park
Book a Winter Park dog sitter to watch your dog in your sitter’s home or yours.

Over 705 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.
“Sarah was great with my dog. She went above and beyond to make sure Chloe was taken care of. And always communicated with me to keep me updated. We will def be using Sarah again to care for my dog.”

About: I’ve spent years dog and cat sitting for family, friends, and people from my church while they travel so I’ve basically already been doing this, just without the app. Boarding is where I’m strongest. Whatever you’re away for a weekend trip, a long workweek, a stretch out of town your pet gets a quiet, pet free home and someone who’s actually paying attention to them, not just checking a box. It’s just me and my roommate here, no kids, no chaos, no other pets running around unless we’re talking about yours LOL. But if boarding isn’t what you need, I also do drop in visits and walks. A midday or evening walk for your dog, or a quick morning/night stop to feed and check on your cat while you’re out. My schedule’s flexible (I work fulltime but it’s not a rigid 9-5), so I can usually make mornings, evenings, weekends, whenever your pet needs me. I’m not the type to drop them off with food and a bowl and disappear for the day. I want to actually know their personality by the time you pick them up. I’ve taken care of dogs and cats of pretty much every age and energy level, from the zoomies at 6am crowd to older pets who just want someone patient around and a quiet spot to nap. Routines matter to me too if your pet eats at a certain time, walks a certain route, or has a little quirk, I want to know about it and stick to it. I’ll keep you in the loop while I’m with them. Feeding on schedule, medication if they need it, litter box scooped, fresh water, the whole routine handled the way you’d do it yourself. Photo updates too, so you’re never left wondering how things are going. Can’t wait to meet you both and hear what your pet’s routine looks like. My schedule is flexible, so I’m available mornings, evenings, weekends, and throughout the week as needed. I take the time to learn your pet’s personality, preferences, and routine so they can feel as comfortable as possible. I know how hard it can be to leave your pet with someone else, so I do my best to make them feel safe, comfortable, and loved while you’re away. Whether they’re staying in my home or I’m stopping by yours, I follow their routine as closely as possible, including feeding schedules, potty breaks, walks, medications, and any special instructions you provide. I provide a calm, pet free home for boarding and make sure every pet gets plenty of attention and care. I also send photo updates throughout their stay because I’d want the same thing if it were my pet. My goal is for you to enjoy your time away knowing your pet is in good hands
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.

“Nyssa was wonderful and very communicative. I was out of the country for 3 weeks and she made sure all of sage’s needs were met. When Sage was running low on water or treats she would let me know ahead of time. I would book with her again! ⭐️⭐️⭐️⭐️⭐️”

“Wynn did an amazing job! She dropped in to feed Sprout, took him out for a potty break, and kept me updated with photos and messages. Sprout was so happy and well-cared-for. Highly recommend! Thank you so much!! 😊”

“Kaia took great care of my cat and home while I was away on business. She followed all my instructions, was always on time, and took great photos! Highly recommend.”

“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.”

About: Animals have been part of my life from day one. I grew up with two veterinary technicians as parents, so caring for pets wasn't just something we did, it was part of our family. At 15, I got my first job as a kennel technician, where I learned how to safely handle dogs of every size, age, and personality. Over the years, I've had the joy of owning dogs and cats of all kinds, including raising three Great Pyrenees through college and adulthood. Giant breeds taught me patience, consistency, and how to confidently handle even the strongest dogs. Whether your pup loves a leisurely "sniffari" with plenty of time to explore or prefers an energetic jog to burn off some zoomies, I'm happy to match their pace and personality. I have experience with puppies, seniors, large breeds, small breeds, and everything in between. I know your pets are family, and I'll care for them with the same attention, safety, and love I'd want for my own. I work from home with a flexible schedule, which allows me to accommodate walks, drop-in visits, and pet sitting throughout the day. I'm available mornings, afternoons, evenings, and weekends, and I can often accommodate last-minute requests. My flexible workday means your pets will receive reliable, attentive care and won't be left waiting for their visit. I understand that trusting someone with both your pets and your home is a big decision. I'll treat your home with the same care and respect I would my own, keeping it clean, secure, and exactly as you left it. Your pet's safety and comfort are always my top priorities, and I'll follow your routines and instructions carefully to help them feel relaxed while you're away. You can expect reliable communication, photo updates, and dependable care every step of the way.
“Rafaela is awesome. We she came to the house 3 times a day. We have one dog that is difficult to know and can nip. But my dog quickly loved Rafaela. We will be calling on Rafaela again soon.”

About: Pet parents love leaving their dogs in my care because they know they don’t have to worry. I take the time to learn your dog’s routine, send regular updates with quality photos, and provide a cozy home sanctuary where your pup will be loved and cared for like my own. I provide exclusive and personalized care by hosting dogs from only one family at a time, ensuring a true home-away-from-home experience. I’m an artist working out of my home studio, allowing plenty of flexibility throughout the week to offer hands-on care. I’m also available most weekends for boarding. Your dog will spend the day in a calm, loving home with a large, fully fenced yard — perfect for play, sunbathing, and safe exploration. Inside, pets enjoy a relaxed environment with cozy rest areas and plenty of attention. We will enjoy multiple walks per day in a quiet and safe neighborhood.

“Nina was wonderful! Kept me updated the whole time and sent great pictures. I could tell my cats were well taken care of by the way they greeted me at the door. Will be working with Nina again!!”

About: I have had and taken care of dogs since I was little and have always had a dog. I love to volunteer at shelters and help too! I’ve always had a special place in my heart for furry angels. I’ll also send cute pics! :) I work from home so I can take your pup outside before work, at lunch, and after work. Also the weekends if you go away I can take care of doggies! Since I work from home I can come by your place to walk the pups when needed. 😊 I will make sure all instructions are followed and reach out if I have questions and give proactive updates! :)
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.
The median cost per visit for dog sitting in Winter Park is $20
Dog 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.

Anna has been wonderful with our puppy! She’s kind, reliable, and always keeps us updated with photos and messages after her visits. We’re very grateful for her help and would highly recommend her to anyone looking for a caring and trustworthy pet sitter or dog walker.

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
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 for Dog 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 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 September 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.
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.
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 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 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:
- 91% 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.
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.
























