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
“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.”
“Great communication and a sincere effort to make sure he took care of everything while I was gone.”
“Andrea was great! The house was left in prestige condition, she was very considerate of our home. She was very kind to our pets and took great care of them. Our dog had an accident and she took care of it completely and even did a store run to restock on some things our dog needed.”
“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!”
“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.”
“Taylor was great! Left the place in good shape and took good care of our kitties. We certainly plan on using her services again in the future.”
“Allison was wonderful and I highly recommend her. She is professional and communicative. She stayed with our pups for multiple nights- provided daily updates and photos, was flexible and left our home spotless. Can’t wait to use her again!”
“This is our first time using Keaton. He stayed at our apt with our two dog while we were gone for the holidays. He is an extremely nice guy and our dogs took to him right away. He sent us text throughout our trip as well as pics of the dogs so we knew how everything was going. A fire occurred close to our apt during this time, which he informed us about and told us he was ready to evacuate with the dogs setting our mind at ease. We highly recommend him.”
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 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!”
“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!”
“Josie was the absolute best. She was a very thoughtful communicator and truly went above and beyond - giving the pups a bath and leaving my house cleaner than she found it. I know they got lots of love and attention while I was out of town and I didn’t have to worry at all. ?”
“Tiffany was great taking care of Stu. Thanks!”
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!
“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.”
“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.”
“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: 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!
“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: 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.”
Liang Z.
“Great communication and a sincere effort to make sure he took care of everything while I was gone.”
Andrea B.
“Andrea was great! The house was left in prestige condition, she was very considerate of our home. She was very kind to our pets and took great care of them. Our dog had an accident and she took care of it completely and even did a store run to restock on some things our dog needed.”
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!”
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.”
Taylor M.
“Taylor was great! Left the place in good shape and took good care of our kitties. We certainly plan on using her services again in the future.”
Alison M.
“Allison was wonderful and I highly recommend her. She is professional and communicative. She stayed with our pups for multiple nights- provided daily updates and photos, was flexible and left our home spotless. Can’t wait to use her again!”
Keaton B.
“This is our first time using Keaton. He stayed at our apt with our two dog while we were gone for the holidays. He is an extremely nice guy and our dogs took to him right away. He sent us text throughout our trip as well as pics of the dogs so we knew how everything was going. A fire occurred close to our apt during this time, which he informed us about and told us he was ready to evacuate with the dogs setting our mind at ease. We highly recommend him.”
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!”
Josephine B.
“Josie was the absolute best. She was a very thoughtful communicator and truly went above and beyond - giving the pups a bath and leaving my house cleaner than she found it. I know they got lots of love and attention while I was out of town and I didn’t have to worry at all. ?”
Tiffany W.
“Tiffany was great taking care of Stu. Thanks!”
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!
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.”
AnnaLiese J.
“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.”
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.”
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!
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!”
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 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!
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.
Connect anywhere with the Rover app
