House Sitting in Winter Park
Find a loving house sitter to watch over your pets and your home.

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Top rated Winter Park house sitters
“Hailey was great! This was our first time using a dog sitter as well as the first time having someone stay in our home that wasn’t a friend or family member to help out. She made us feel comfortable with both our dog and our home in her hands. Great communication and it was obvious our dog had a great experience as well. We are lucky to already have her booked for a future trip :) thank you Hailey!”

“Marin was so amazing with our two girls. She was responsive and sent pictures daily. Our two golden-doodles are not old so no special care necessarily but they are very needy. When we got home the house looked perfect and most importantly our two girls were so happy. That tells me she did a good job because sometimes they will act a little mad at us for leaving them. We will def. ask her again if we need to leave Phoebe and Ellie. Thanks Marin you’re amazing!”


“Lexus went above and beyond to take great care of boy! I’m a bit of a helicopter dog mom and Lexus put my mind at ease. Winston had a great time with her and I am so grateful. 💕”

“We are beyond thrilled to find Kiri. This was our first opportunity to use her and we are thankful. The house was spotless, she sent lots of pictures, walked them regularly and gave them lots of love. I hope she made herself at home as we appreciate her so much. We are already looking to book our next stay. 5 star all the way.”

“Michael took such great care of our home and pets! He was in regular contact including pictures of the dogs for our kids. Will definitely book again for future trips!”

“Peter did a great job… he was very caring for our dog and house. He has been open to our comments that allow him to fully understand what we look for in a dog/house sitter.”

“Wonderful house sitter & took terrific care of our cat Oscar. Deborah leapt in to help us on short notice when another Rover sitter bailed the night before she was due to start. My wife and I highly recommend Deborah and would be happy to use her again.”

About: I have 3 cats. I love them all. One is a senior with the energy of a teen. One is reserved but playful. The last one is very selective with how she likes to receive attention and she gets all the love as such. They all get my attention and care in their unique ways, and I would be doing the same with your pets. I may be a cat person, but I love dogs too. Your dogs will be getting some extra attention and loving from me. Aside from just walking your dogs, we could go for a quick run, play some tug of war, whatever toys you have available. Now cats, I love playing with cats, snuggling with cats, and just occupying the same room as cats. Whatever your cats need, I'm just there to make sure they are okay and that they don't get too lonely while you're gone. I will be taking pictures of your pets and sending them to you so you know they are being taken care of or just to remind you how cute they are. Can also watch over cats colonies while you're gone. At the moment, I am very flexible. I am free most of the week for most of the day. I limit any visits between 10 am and 8 pm. I will be starting with soon, and I'll have to limit myself to evenings. For dogs, if you have any toys they like to play with, I will play with them using those toys. I will go on walks with them to make sure their business gets done. If they have been naughty and made a mess, I will tidy things back up for you with your permission. For cats, I bring my own toys if needed to play cats. Cats I've watched over loved the rainbow string wand and the mini plush soccer balls I bought for my own cats. I like to brush cats and help them de-shed. I regularly clean out the litter box and use a deodorizer on both the remaining litter and litter dumped if left in the trash bag. Essentially how I treat my cats, I would treat yours with the understanding that I am a stranger in their home.
“Isabella was amazing! I had no worries and she followed all my instructions exactly with plenty of updates and pictures. She went above and beyond helping me with my plants and package deliveries too. I was able to relax and enjoy my vacation knowing my babies were getting great care. We have already booked her again!”

About: I have experience caring for a diverse array of dogs, from Poodles to Bernese Mountain Dogs. While I was a student I was trusted by several families for recurring dog and child-sitting, and I also provided reliable house sitting services during their vacations. I have a flexible schedule that aligns perfectly with my remote work arrangement. I’m available for dog care and companionship on Mondays, Wednesdays, Fridays, and over weekends, ensuring that your furry friend receives constant attention and care. Your pet’s safety and well-being are my top priorities. I offer a secure and loving environment for dogs of all sizes. You can feel confident that your furry friend is in experienced and caring hands.
“Heather communicated very well, and I felt comfortable leaving my dogs with her watching them. She sent me pictures of my pups too. Overall, it was a nice experience and I really didn’t worry about anything while I was away on my trip. Thank you, Heather”

“Glacie rocks!! She took Emmy for walks, followed the directions perfectly & kept our home clean. Glacie watched Emmy for 6 days and 5 nights and I had zero concern. We will 100% be using Glacie again in the future. Emmy is happy & tired out & that’s all we can ask for 🫶”

“Great caring sitter. Everything was perfect. “Walking “Littleman in his stroller was so nice. He loves his “walks”. Everything was so clean and neat. Would use Alicia again and again. Thank you so much.”

“Christina was great & took the time to get to know our puppy Coco before we went on vacation. She sent us regular photos, videos & updates (she should be a photographer 📷). She took Coco for walks & played with her. We highly recommend Christina for taking care of and loving on your pet. We will definitely have her watch Coco again.”

“⭐️⭐️⭐️⭐️⭐️ Cedar was absolutely amazing! Extremely professional, communicative, and attentive throughout the entire stay. They kept me updated with pictures and detailed check-ins, ensuring I always knew how my dogs were doing. I couldn’t be happier with their service! My two dogs can be reactive and challenging at times, but they handled them with such patience and care. I highly recommend them to anyone looking for a reliable and skilled dog sitter. Will definitely be booking again!”

“Makenna was amazing! Very communicative and sent lots of sweet photos during the stay. We could tell our pup loved her. Don’t hesitate to book with Makenna!”

“Bailey was great! Highly recommend. Super comfortable with dogs and followed all instructions left. Sent tons of photos everyday and always communicated. Very professional and friendly. She stayed in our home while we were away for 3 nights. Could not have asked for a better experience.”


About: Hi! My name is Jack :) I have spent the past several years working as a veterinary technician, caring for animals in a professional medical setting. I have experience with puppies, kittens, senior pets, and pets with medical needs. I love building trust with animals and helping them feel comfortable and secure. My goal is to provide the same level of care and attention that I would want for my own pets, so you can travel with confidence knowing they’re in good hands. 🐾 I strive to be flexible and accommodate your pet’s routine as closely as possible. Whether your pet needs morning, afternoon, evening, or overnight care, I will work with you to ensure their feeding, exercise, medication, and enrichment schedules are maintained. Consistency is important for both cats and dogs, and my goal is to keep their day-to-day routine familiar and stress-free while you’re away. I am happy to discuss your pet’s specific needs and create a care plan that works best for them. Your pet’s safety and well-being are my top priorities. As a veterinary technician with several years of experience, I am trained to recognize signs of illness, injury, or distress and respond appropriately. I provide a calm, patient, and low-stress environment tailored to each pet’s individual needs. Whether your pet is energetic, shy, senior, or requires medication, I will treat them with the same care and attention I give my own pets. You can expect reliable communication, regular updates, and peace of mind knowing your pet is being cared for by an experienced animal care professional.
Over 1,026 pet parents in Winter Park have booked house sitting
Winter Park pet parents share their Rover experiences
The clearest review I can give is the fact that we will be using Kaya each and every time that she is available. She was prompt, responsive, professional, and treated our house and our dog as if they were her own. I can highly recommend her, and as I indicated, we will be using her again in the future.

We could not have been happier with our decision to use Rebecca. She took amazing care of our senior pug, Tater. Her responses were always timely and she was awesome about sharing pictures throughout our time away. This was a great first experience with Rover and we cannot recommend Rebecca enough.

Bailey was great! Highly recommend. Super comfortable with dogs and followed all instructions left. Sent tons of photos everyday and always communicated. Very professional and friendly. She stayed in our home while we were away for 3 nights. Could not have asked for a better experience.

This was our second time booking with Glacie, and she was just as wonderful as the first time! Some of our pet care instructions had changed since our last booking, but she handled everything seamlessly without needing any additional guidance. We especially appreciate the updates and photos she sends—it always gives us peace of mind and helps us feel connected to our fur babies while we're away. She also took great care of our home, which we truly value. We can't recommend Glacie highly enough and will absolutely continue booking with her in the future! ⭐️⭐️⭐️⭐️⭐️

We were apprehensive at first basically getting a stranger to come stay in the house with our fur babies, but autumn was an absolute blessing. She kept us updated. The house was tidy my puppies look so happy and took to her very well. I love the open line of communication she provided and she was totally amazing. Looking forward for my next trip so she can come over and stay with our for babies again. I highly recommend her services and anyone will be lucky to choose her.
Elizabeth was very pleasant and professional with the meet and greet, this was the first time I did house sitting and she answered all of my questions gave me reassurance of the whole procedure. She met with Scarlett, and I showed all the quirky stuff I have setup with my dog. Elizabeth has great communication via text messaging, she let me know when she was going to arrive, she sent me pictures throughout the time she stayed with my dog for constant updates, putting my mind at ease since I never left my dog this long. She also updated me when she was leaving ,affirming that Scarlett was all set awaiting for me. Thank you Elizabeth for a great job.

How Rover works

1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets
2. Meet & Greet
Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
The median cost per night for house sitting in Winter Park is $45
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 house 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.
Sitters in Winter Park average 4 repeat house sitting clients
House Sitting FAQs
Frequently asked questions about Rover
House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winter Park on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.
As of Jun 2026, there are 2,903 house sitters in Winter Park. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.
Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Winter Park house sitters respond in under an hour.
House sitters in Winter Park have an average of 14 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winter Park.
Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winter Park house sitters are great for:
- Dogs who’d prefer to stay on their home turf
- Cats and caged pets
- Pet parents on a tight schedule
- Keeping an eye on your home and plants while you’re away
Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.
Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.
We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.














