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

Every sitter passes an enhanced background check. Learn about RoverProtect
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%.
“Amy Jayne was great! This was our first time using Rover / also the first time leaving our dogs with someone other than family. She made this experience so easy, and made us feel comfortable the entire time we were away. We never had to wonder what was going on since she kept us updated throughout our trip. Truly, a great person to have with your pets!”

“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: 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.

About: I’ve taken care of newborn puppies all the way up to senior dogs. I’ve had a soft spot for animals all my life! This platform seems like a perfect fit! I currently work part time doing videography and travel all over the country so I plan to care for dogs in each place I visit! We have a small farm but it’s not fenced in. Our dogs run and play all day long and then just hangout. Lots to do around here as me and the dogs love to go explore!
“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!”

“We left our two very active golden retrievers with Alec for the week. Along with plants to water and bird feeders to manage. He was professional, caring, and communicated well. My animals and home were tended as if it was his own ( or maybe his family home!) . I would never hesitate to have him come back and he certainly earned a 5 star rating. The house was clean on our return and although the dogs were excited to see us I could tell there was no stress evident from our absence.”

“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!”

“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!”


About: Animals have been a part of my entire life having grown up with 3 large dogs, a small flock of chickens and other little critters. Currently I have a wonderful German Shepard - staffie mix named Esther that I love with my whole heart. I currently work for Wintr Park resort ski and ride school. Since the resort is currently closed I have full availability until May 29. I’ve been spending my days going on walks or to the park with my dog Esther. I have lots of experience caring for all kinds of animals—from cats and chickens to big, energetic dogs. If you’re interested, take a look at my calendar to see when I’m available! I can host pets at my home, where I have a great yard space, and I’m always happy to take dogs on walks or out to open fields to run and play. I’ll make sure your pets get the care, attention, and exercise they need. I’d love to help take care of your furry family!
About: I have been taking care of a large variety of dogs for 20 years. From eight weeks old to 16 years old, from pugs to chows and pitbulls to 140 pound malamutes I have cared for them all. I can come by to walk and feed your best friends once a day or stay and cook them meals as per your request. I want to make sure you and your loved ones are as comfortable as possible while you are away. I do freelance work so I have pretty open availability. Making sure you're needs are met so you are comfortable is my top priority. If for some reason I can't meet all of your needs I will tell you before committing to something that doesn't fit my schedule or abilities. I am here for you. How I care for your pets and home is mostly dependent on your requests. I give medicine, food and exercise as requested. I can simply fill a food bowl, measure servings and even cook protein and veggies for your dogs if that is what you want. I am happy to keep you updated or send you pictures if you'd like. Walks are as far/long/plentiful as requested. I want to provide you with the comfort of knowing someone is there to care for your loved one as you would while you are away.
About: Animals have always been a big part of my life — from fostering dogs to managing a farm and raising multiple litters. I truly understand the patience, structure, and love that pets need to thrive. I enjoy grooming, hiking in the mountains with four-legged companions, and making sure every pet feels safe, happy, and cared for. Whether it’s daily walks, overnight care, or just extra cuddles, I treat every animal like my own. Working from home gives me the flexibility to give pets plenty of attention throughout the day — whether that’s walks, playtime, or snuggles between meetings. I’ve successfully fostered dogs, managed a farm, and raised multiple litters, so I understand the unique needs of animals at every stage of life. With an active lifestyle and love for the outdoors, your pup will enjoy safe adventures, fresh air, and plenty of exercise. Grooming and extra TLC come naturally — I’ll care for your pet like part of my family. ⸻ In My Home: Pets have a safe, calm, and pet-friendly environment with plenty of space to relax and play. I keep a consistent routine with feeding, walks, and bathroom breaks to make them feel secure. I never leave pets unsupervised for long periods, and I always ensure water, comfort, and a cozy place to rest are available. In Your Home: I respect your space and follow your pet’s established routine closely. From feeding schedules to walk preferences, I’ll maintain consistency so your pet feels comfortable and cared for while you’re away. I provide updates, photos, and check-ins so you always know your pet is safe and happy. Overall: Safety, trust, and comfort are my top priorities. With experience fostering dogs, raising litters, and caring for animals of all sizes, I understand how important it is to give your pets the same love and attention they’re used to at home.
“Patti is the best! This was her second time taking care of our boxers and we could not be more happy with the attention and love she provides to them. Extremely reliable and we would have her stay with them over and over again.”

About: I look forward to being able to help you with outdoor doggy adventures! My daycare/dog hike times are; pickup between 8-9am and half day drop off between 12-1pm ($60), full day drop off between 3-4pm ($120). These times are a bit flexible, talk to me about working outside these guidelines! I have loved dogs and animals in general since I was a boy. I have worked as a professional dog caregiver for the last 15 years. My clients have always relied on my love of their dogs, consistency of care, and my flexibility with their schedules. I will take your dog on half or full day adventures in the great outdoors! Examples of activities are; hiking, biking, trail running, cross country skiing, snowshoeing, etc. I am trained in E-collar use and have helped my clients learn basic skills such as; come, sit, stay, drop, etc. I have owned senior dogs and had to administer medications and IV bags. It is a full time job for me. I love working with dogs and will continue to make it my number one priority going forward I am in a condo with a dog door that leads to a deck. Dogs that visit are allowed on the couch, 4 or 5 dog beds available, or sleeping on my bed! I walk all clients dogs on leash in the neighborhood, on/off leash on my outdoor doggy adventures depending on dogs skill set and owners preference.
“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 have loved dogs my whole life and have been taking care of dogs for about 10 years! I have lots of experience walking and caring for neighbor’s dogs as well as taking care of dogs of friends and family. I have a pet friendly apartment and would also be happy to go anywhere to take care of your dog, whether that be your house or the park! I would able to take care of your dog almost any day of the week! Just need to know I’m advance to make sure it works with my schedule! I have a good sized apartment and there is also a yard area for dogs to run around outside. I am happy to walk, feed, and take care of your dog in any way you might need!
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.
“Jake was awesome! He took great care of my 2 dogs and my house. He was very patient with my dogs and letting them get used to him. He took them on many walks and kept me well updated with texts and photos. I would highly recommend him and will definitely use him again!”

Over 20 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 Jun 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 Jun 2026, there are 167 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, 91% 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.




