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

“We had a fantastic experience with Andrea. She was incredibly communicative throughout her time with our pets, asking plenty of questions and providing frequent updates. We even returned home to a detailed daily schedule of how she spent her time with our animals. Additionally, she asked thoughtful questions about caring for our home and inquired about emergency procedures, which gave me extra peace of mind—especially since we live in an area with an increased fire risk. We came home to a clean house and happy pets. I would definitely recommend having her care for your home and animals!”

“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.”


About: I have had dogs and cats my entire life along with an assortment of other pets growing up. I was the go to puppy sitter in college before I got my own beautiful baby doodle and now as all proud puppy parents I’m obsessed. We go on walks every other day and visit parks when we can depending on schedules. I will give your family pet the love and care it deserves whether that means pets, toys, or belly rubs while you are out of town, orrr just a good old fashion walk around the park. Please let me know your dogs temperament and any dislikes or habits and I will accommodate for them as needed. I understand some pets have different needs and am happy to cater to make sure they have a great day in the absence of their momma or daddy.

“Jadyn did a great job with my little fur ball. She walked her multiple times and took many pictures. She was also flexible with her time when we ran into a traffic issue. Definitely will use her again.”


“Devon and Taylor did an amazing job taking care of our 3 furbabies. We loved it when they’d send us pictures and updates. They left the house spotless on top of it all which was really wonderful to come home to. Would definitely recommend Devon!”


“I'm so glad we found Keaton to watch our pups! He is kind, responsible, considerate and a great communicator. Plus our pups loved having him around. Our place was left in perfect condition. I would recommend him to anyone and we will definitely use him again in the future.”



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.

“So glad we found Cynthia! Since she is a vet tech, I really felt more at ease with trusting a stranger with our 3 dogs who can be a handful! The dogs instantly took a liking to her and she was so sweet to them. She was very responsive and also sent us updates & cute individual portraits of our dogs! Our house and pups were happy and well taken care! And she even took them time to write us a sweet note. We would not hesitate to ask Cynthia to watch our pups in the future! Thank you Cynthia!”

“Bella did a fantastic job of caring for our young blue heeler pup. She is a clear communicator and she handled a last minute change in care regime graciously (originally tasked with exercising an energetic pup to instead administering medicine and helping to nurse a sprained wrist). We would definitely ask her to pupper-sit again!”


About: I’ve been a dog owner for over 10 years and truly can’t imagine life without animals. Friends and family often rely on me to care for their pets, whether it’s daily walks, overnight stays, or just extra love and attention. Working from home gives me the flexibility to spend plenty of quality time with your pup—making sure they’re safe, happy, and well cared for while you’re away. I work full time from home, so I’m available 24/7 to give your pup attention, playtime, and care throughout the day. Whether weekdays or weekends, your dog will never be left alone for more than 2 hours. My home is pet-friendly with a fully fenced yard and one well-socialized dog to keep your pup company. I always prioritize safety—whether that means supervised playtime, separate spaces for shy dogs, or crating if preferred. You can trust that your pet will be cared for like family in a safe, loving environment with plenty of room to play and relax.

“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.”


“Molly did a good job with my high maintenance puppies! She was flexible and willing to meet up without a ton of notice. She sent pictures and updates throughout her stay which made me feel more comfortable about being away.”


“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 have taken care of my own families dogs, my neighbors pets, and even my family friends pets since I was about 11 years old I work a landscaping job and I have weekends off, including most fridays! I would love to fill those days with more things, such as watching over and taking care of your pets!! :) I cater to the pets needs, whether that’s needing food, exercise, or to go outside to the bathroom, I always make sure to be on top of what the pet needs. I am respectful in clients homes and make sure everything in the home is just how they left it, if not even better. I take care of everything like it is my own, I like to show my respect and appreciation! As well as help you out by watching over your fur babies!

“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!”


About: Ive taken care of dogs since I was in college and have always love giving my pets attention! I’m super active and enjoy scenic daily dog walks - the more the merrier! I’m a remote worker and my schedule can be flexible! I love early mornings and am happy to take dogs on longer walks in the afternoon and evening. I live in a small quiet area with a great dog walking loop. I have my own transportation and wouldn’t mind taking the pups on an outing!

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.
Loving house sitters in your neighborhood
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Ken S.

“Ken was great! Jasper was happy and the house was in great shape. We have already booked again with Ken. We would highly recommend him for house/pet sitting.”


Andrea B.
“We had a fantastic experience with Andrea. She was incredibly communicative throughout her time with our pets, asking plenty of questions and providing frequent updates. We even returned home to a detailed daily schedule of how she spent her time with our animals. Additionally, she asked thoughtful questions about caring for our home and inquired about emergency procedures, which gave me extra peace of mind—especially since we live in an area with an increased fire risk. We came home to a clean house and happy pets. I would definitely recommend having her care for your home and animals!”


Trisha B.

“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.”


Karlee R.
“Karlee is genuinely caring and always treats my dog as her own. She is very attentive to my dog and always seems to know what she needs to be happy.”


Jadyn L.

“Jadyn did a great job with my little fur ball. She walked her multiple times and took many pictures. She was also flexible with her time when we ran into a traffic issue. Definitely will use her again.”


Devon S.

“Devon and Taylor did an amazing job taking care of our 3 furbabies. We loved it when they’d send us pictures and updates. They left the house spotless on top of it all which was really wonderful to come home to. Would definitely recommend Devon!”


Keaton B.

“I'm so glad we found Keaton to watch our pups! He is kind, responsible, considerate and a great communicator. Plus our pups loved having him around. Our place was left in perfect condition. I would recommend him to anyone and we will definitely use him again in the future.”




Jan R.Star Sitter
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.


Melody W.

“Melody is absolutely wonderful! She brings a calming presence and my dogs love her. I feel so much more relaxed knowing she’s hanging with my pups. Highly recommend her!”


Cynthia A.
“So glad we found Cynthia! Since she is a vet tech, I really felt more at ease with trusting a stranger with our 3 dogs who can be a handful! The dogs instantly took a liking to her and she was so sweet to them. She was very responsive and also sent us updates & cute individual portraits of our dogs! Our house and pups were happy and well taken care! And she even took them time to write us a sweet note. We would not hesitate to ask Cynthia to watch our pups in the future! Thank you Cynthia!”


Bella F.

“Bella did a fantastic job of caring for our young blue heeler pup. She is a clear communicator and she handled a last minute change in care regime graciously (originally tasked with exercising an energetic pup to instead administering medicine and helping to nurse a sprained wrist). We would definitely ask her to pupper-sit again!”


William D.
“William is one of the kindest, most considerate and reliable people I know, especially when it comes to caring for doggies. I get anxious leaving my dog in the hands of others, but I always feel at ease when my dog is with William. 10/10 would recommend him to any pet parent!”




Tiffany W.

“Tiffany was great taking care of Stu. Thanks!”


Mae S.

“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.”


Molly W.

“Molly did a good job with my high maintenance puppies! She was flexible and willing to meet up without a ton of notice. She sent pictures and updates throughout her stay which made me feel more comfortable about being away.”


Patti B.

“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.”


Lucy M.
About: I have taken care of my own families dogs, my neighbors pets, and even my family friends pets since I was about 11 years old I work a landscaping job and I have weekends off, including most fridays! I would love to fill those days with more things, such as watching over and taking care of your pets!! :) I cater to the pets needs, whether that’s needing food, exercise, or to go outside to the bathroom, I always make sure to be on top of what the pet needs. I am respectful in clients homes and make sure everything in the home is just how they left it, if not even better. I take care of everything like it is my own, I like to show my respect and appreciation! As well as help you out by watching over your fur babies!


Lauren N.

“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!”


Sarah M.
About: Ive taken care of dogs since I was in college and have always love giving my pets attention! I’m super active and enjoy scenic daily dog walks - the more the merrier! I’m a remote worker and my schedule can be flexible! I love early mornings and am happy to take dogs on longer walks in the afternoon and evening. I live in a small quiet area with a great dog walking loop. I have my own transportation and wouldn’t mind taking the pups on an outing!


Christopher G.
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.
How Rover works
1. Search
Read verified reviews and choose a house sitter who’s a great match for you and your pets2. 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 away3. Book & Pay
All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!
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.
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 Aug 2025 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 Aug 2025, there are 162 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, 81% of Winter Park house sitters respond in under an hour.
House sitters in Winter Park have an average of 16 years of experience. House sitters with repeat customers have an average of 6 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.
