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.
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.
“Glacie was great with my kitty. He needs lots of attention and I really appciate the time she spent with him. He got comfortable enough with her after one day to roll on his back and beg for belly pets. It was easy to take a vacation, know he’s not lonely and taken care of. Will definately use her services next time we plan a vacation.”
“Rebecca takes great care of my cats and fish. She's always prompt, remembers all the little details and has a terrific rapport with the cats. I'm glad to have found her and will be booking her again very 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.
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.
“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 was a great pet sitter! She was quick to respond and sent so many photos and videos, along with great, detailed reports each visit. I would highly recommend Kaia and will be using her again in the future!”
About: I have never lived a day without a dog, dogs are a huge importance to me and I care very deeply for them. I have a good deal of experience of caring for dogs with many issues such as cancer, amputation, collapsible trachea, patellar luxation and much more. I will care for yours with patience and love. I work a set schedule of Wednesday-Friday. I am available Saturday, Sunday, Monday, Tuesday. Flexible on time. I am willling to do multiple walks if needed I have a grassy area that only I have access to behind my apartment which makes potty breaks easy. I have a large crate on hand if needed.
“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! ⭐️⭐️⭐️⭐️⭐️”
“Erika watched our 3 babies twice a day for an entire week. She was truly incredible. She is very responsible, timely, and took multiple pictures of each pup. She was so very patient, experienced, and listened to all of our directions so well. Even when one of our pups was anxious she cleaned up after him and cared for him. Thank you Erika for being so caring and loving to our fur baby family!!”
“Luisa is absolutely wonderful with our puppy! He gets so excited when she comes to check on him and she takes great care of him. She also gets the best photos of him during their puppy play sessions! She always makes sure he uses a ton of energy so by the time she has to leave he’s all tuckered out and ready for a nap until we return for more play time. I would highly recommend and trust Luisa with any pet!”
“This was my first time using Rover and leaving my munchkin behind. Zoe showed my Nola so much love, took her out on walks so she could her energy out, made sure she had tv to watch while she was home alone, and sent lots of cute lil pics every day to show how good she’s doing. I have really bad trust issues when it comes to my dog and Zoe def made me feel like my fur baby was in good hands and was well taken care of. I’ll def book with her again and so should you, she’s amazing!!!”
About: My Name if Kimberley. Leaving your dog with someone else can feel like a BIG deal. You want to know they are safe, loved and with someone who can handle them in all aspects. That's exactly what I'm here for! I have cared for dogs for over 25 years. I especially love working with active, playful, and high energy dogs who need more than just a quick walk around the block. I'm comfortable handling big personalities, lots of energy, and dogs who need plenty of mental and physical stimulation. If you're looking for someone who will treat your dog like one of their own, I'd love to meet you both. I live in Downtown Orlando very close to Lake Eola. I will care for your pets as if they were my own and I always treat them like part of the family. I do not smoke or have kids so your dog will get the attention he or she deserves. I am open to all different ranges of dog breeds and ages. I also do cat drop in visits. I'm currently working part time with a lot of flexibility in my schedule. I am available most days and evenings with advanced notice for potty breaks and Drop In visits. I live in Downtown Orlando so I'm very close to Lake Eola and Delany Park. Plus I'm close to many dog parks if that is something your dog loves.
About: I’ve been actively caring for animals since childhood. I grew up with German Shepherds and was involved in their daily care from about age five, so I became comfortable with large dogs at a very young age. Over the years, I’ve cared for both dogs and cats and understand that every animal has its own personality, routine, energy level, and needs. I’m active and enjoy walking and being outdoors, so I’m happy to give dogs an engaging walk as well as plenty of attention and playtime. I’m comfortable with large dogs, while also understanding the importance of respecting an individual dog’s temperament and handling needs. I’m also a longtime cat owner with particular experience in feline behavior and enrichment, including positive-reinforcement clicker training. I’m patient with animals who need time to warm up and attentive to body language and changes in behavior. Most importantly, I understand the trust involved in allowing someone to care for your pet and enter your home. I’m dependable, detail-oriented, communicative, and will carefully follow your instructions and keep you updated while you’re away. My schedule is flexible, which allows me to provide drop-in visits and walks throughout the week, including mornings, afternoons and evenings. I’m also available for recurring weekly care. I keep my service area local so I can be dependable, punctual and give each pet the time and attention they deserve. I take caring for someone else’s pet and entering their home seriously. I carefully follow each owner’s instructions regarding feeding, medications, walks, routines, doors and gates, and any behavioral or safety considerations. I pay close attention to an animal’s body language and never force interaction with a pet who needs time or space. I’m comfortable with animals of all sizes, including large and giant breeds, and will communicate promptly if I notice anything unusual. You can also expect updates and photos during every visit.
About: Hi! My name is Bay, and I'm a dog lover by day, flight attendant by night! I have an amazingly flexible schedule and am willing to work with your needs. I have two low key dachshunds Remy and Chloe. The coonhound is no longer with us even tho it shows a picture of her. I love dogs of all ages, sizes, and temperaments. In addition to house sitting and giving lots of snuggles. I also have a lot of experience feeding multiple pups at a time. If your dog has dietary restrictions, such as raw or diet food, I'm happy to adhere to his/her needs! Each dog is unique, with their own awesome personality. I can't wait to meet your fur baby and get slobbered on. Thank you!
“Raquel wasn’t able to do a last minute drop in so she offered to do daycare at her house instead, we ended up doing that and it seems like he had a great time! He’s nice and calm which is a rare thing in the evenings. I appreciate her flexibility and responsiveness. She always does a great job with him and sends lots of pictures!”
The median cost per visit for dog sitting in Winter Park is $20
Dog parents share their Rover experiences - Winter Park
My boy, Charlie, is such a timid, anxious dog. It is hard for him to trust people, and seeing how Cheyenne came in and made him feel comfortable was beyond amazing! I never thought he’d let anyone else take him outside, yet he did!! She is genuinely the BEST!!
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 Drop-In Visits - 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.
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