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
“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! ❤️”
“Jenna is absolutely amazing! We had a small hiccup with the house key early on but we got it worked out quick and easy. Jenna took a ton of photos of my kiddo and was super communicative the entire time. Thank you so much for everything, I would absolutely rebook on my next trip! ❤️”
“Rebecca kept me up to date on when she was going to see River and took great care of him! She went above and beyond what I asked of her and even sent pictures of him! I will definitely be asking her to watch him in the future!”
“I had a great experience and will definitely rebook in the future! I hate leaving my babies when I travel but it gave me peace of mind knowing they were well taken care of. She even brought my package in that was delivered while I was away which is very much appreciated. Thank you so much!☺️☺️”
“Carolina did a wonderful job with Levi for his drop in visit! She kept me well informed and made sure my little guy was feeling relaxed before leaving him, and overall exceeded expectations. Would highly recommend her!”
“Cheyenne is attentive, flexible and took great care of our boys. She even adjusted her schedule when a medical issue came up for one of our dogs during her visit. 12/10 recommend her!!!”
“Nina saved me with a last minute request when LuLu and I arrived after a long day of travel from Denver to Orlando. She came to our hotel and got LuLu some much needed exercise and vitamin D. I sent her a lot of instructions and everything seemed to go smoothly and puppy was happy when I got home!”
“Sage was very happy with his new paw friend 🐾 great communication and updates, Bailey did not skip a beat! Always on time! She’s everything you want and need as a pet sitter!”
“Brooke has done such a great job of taking care of my cat, Latte. She has been so dependable and left wonderful pictures of their time together. I highly recommend Brooke to care for your pet.”
“Aly was fantastic! I have a senior blind dog, and she was so patient, accommodating and sweet to him. I was gone for an extended period, and I was nervous to leave my dog but she made me feel super comfortable and confident that my dog was not just safe but cared for too. She was very communicative and took wonderful care of my senior dog. Would highly recommend and will absolutely be booking with her again!”
“Peter was great with our pup and cats! They all took so well to him and loved Peter! He took great pictures and was very responsive and respectful. We loved Peter’s calm demeanor. We will definitely be requesting his services again in the future.”
“Tori is the wonderful pet sitter who takes excellent care of my odin. Right off the bat when we first met her we got an excellent first impression. She kept me in the loop about everything going on. I would wholeheartedly recommend tori😍”
“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.”
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!
“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.”
The median cost per visit for pet sitting in Winter Park is CA$20
Pet 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.
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! :)
Tess did such a great job. The communication was fantastic we were out of the country and did not have reception or internet most of the time but Tess made sure to keeps us in the loops so when we did get service we could read all the messages and see all the photos. We would book her again!
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 Drop-In Visits - 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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