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
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Edmond looked after my anxious pup while I was out of town for a wedding and made the process very easy! He got him out for exercise and sent me lots of photos. I felt very at ease and knew he was in good hands.”


About: My husband and I both work remotely from home so someone will be with your furry friend pretty much at all times. We’ve lived in Fraser since 2021 and love it here! Our little condo at Meadowridge has a huge unofficial “dog park meadow” where other friendly dog owners love to take their pets. I’m happy to take yours there for a play too! If your dog isn’t interested in other dogs though, I love walking around the neighborhood with them too! I do have one of my own. She is an older border collie mix of 12 years, always gets along with others. I work remotely from home so will be with your doggo at all times! We love taking ours out for walks around the neighborhood, so happy to have an extra one of yours! I live in a 2 bedroom condo. There is lots of room to roam around, nap, hang out. We back an unenclosed patio grass area where they can easily go out for a quick potty.
“Molly was amazing! She came and visited the animals before watching them! She went above and beyond taking care of our babies and the pictures she sent were so comforting! We would gladly have Molly watch our animals again!”


“AnnaLiese was great!!! We have never left our dog with a stranger before. Our dog loved her and she spent the day hiking with him and relaxing at her house while we went to a concert. I would definitely recommend AnnaLiese.”

About: I’ve owned dogs throughout my whole life. I currently have my own dogs but they’ll stay home for my pop-in visits/overnight stays. I have experience with all dog types including high energy and anxious dogs. I have a lot of experience giving medications to dogs. 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 dogs weather there is a yard or not. I’m happy to play with dogs in the yard or take them for a walk or run depending on the dog’s needs.
“Lauren took great care of our cat and our home while house sitting. Our house was clean and tidy when we got home and our cat was in good spirits. We would definitely trust Lauren with our pets again!”

“Anthony stepped in a pinch and flew all the way from California to make it happen. He took fantastic care of our two dogs and elderly cat that needed a diaper change and multiple medications a day. He's also super communicative and going to get you all the pictures you can possibly want.”

“Mae took wonderful care of our home and dog! She provided daily updates and was very responsive. Our shy dog seemed to become comfortable with her quickly. We will definitely book with Mae again.”

About: I’ve take care of my family pet for years. I have experience pet walking/ watching. Excited to see how I can make your pet happy. I work full time as a project estimator at an HVAC company. I am available Mon-Friday after 4:30. Saturday & Sunday I am available all day. I live near a dog park, enjoy physical exercise, I am a caring individual who will treat your pet like my own. I am excited to start.
“Trisha was great with our dogs. She is intuitive about what the dogs need and how to manage them. She was also good with communication and super flexible on working with us to accommodate logistics. Would definitely rebook.”

“Javier was great with my 2 big dogs and cat. While the cat box didn’t get cleaned, everyone was happy when I got home, which is all a pet mama can ask! He left the house in great shape as well, even stripping the bed he slept in. I’d absolutely rehire Javier; he’s a wonderful soul that animals respond to. They’re in good hands with him.”

“Brittany was a great sitter for our pup Cora! We were visiting the area for a wedding and Brittany kept my mind at ease while we attended the event, knowing that Cora wasn’t alone for a long period of time. Brittany was easy to communicate with, kept us updated and arrived early! I highly recommend her to care for your pet :)”

About: I have over 30 years experience raising, training, fostering, foster-failing and generally loving and caring for dogs. I work from home so will be with your pet most of the time and I love to go for long walks and runs with them. I am very active (walk, run, hike...) and have a large fenced in yard and a dog park nearby to keep your pup busy and well-exercised. Most of my clients are repeat customers as they find my services truly a "home away from home" for their fur-baby. Although I am new to Rover I have several references available outside of Rover - feel fee to request any you may like to see. I work from home so I am able to let dogs out every few hours in our fenced yard. Also walk at least an hour a day. Dogs in my home are treated as (and sometimes better 😉) than humans. Run of the house and the fenced yard. Lots of love and snuggles. Lots of walks/hikes/fetch/etc.
“Lucy did a great job with my pets. They were well cared for & my outdoor cameras showed her outside with them, throwing the ball & also taking walks with them. She also was there when she said that she would be. I will certainly use Lucy again!”

“Karlee was wonderful!! She was patient with & very comforting for my foster dog 🥰 my kitty got lots of attention too :-) Karlee sent me updates & photos. She asked about Waldo’s rules & clearly communicated her plans/ideas for activities, car rides, etc. I highly recommend her & will definitely use her pet services again!”

About: As a trainer I have a strong understanding of dog behaviors and body language. If you’re unsure about leaving your pups in the care of a random dog walker, i’m your gal! I’ve worked with hundreds of dogs, and have experience with anxiousness, aggression, special needs, and special breeds! I run a dog training business and have been doing pet care full time for years. It is not a side job or a fun hobby, it’s my livelihood! I can follow instructions, give meds, and never take any risks. I have secure kennels in my car to transport in case of emergency, and I am pet first-aid certified!
Over 18 pet parents in Winter Park have booked house sitting
Winter Park pet parents share their Rover experiences
Sarah did such an amazing job taking care of our two dogs during our wedding weekend! She was so communicative, provided updates and always made us feel comfortable and confident our dogs were in great hands! We also had her bring our lab Remi to several key wedding events throughout the weekend and she was always on time and always communicated with us making sure everything was perfect! For what can be such a busy stressful wedding weekend, sarah took all the stress and worry out of it for us and Remi was the star of the wedding! Thanks again for everything and we will definitely book you again next time we are up in WP!

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 $70
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 5 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 Jan 2026 was about $70 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 Jan 2026, there are 158 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, 88% of Winter Park house sitters respond in under an hour.
House sitters in Winter Park have an average of 15 years of experience. House sitters with repeat customers have an average of 5 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.



