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

“Came back from my trip and our Shiba seemed actually sad (in his way) that Kenya was leaving. We were noting how much he’s grown accustomed to having Kenya around. They definitely have a bond.”


“Austin was great with Obi, even though Obi is definitely not the easiest to deal with! Austin was patient and caring, and kept me updated the whole time. I could tell he really made an effort to make him feel comfortable. Definitely recommend! Thank you Austin for everything!”


“Lexus is the best! She was absolutely amazing with my dog and home. You should definitely book her for your animal care needs. She spent a lot of time with my dog and kept me updated, I never had to worry about him. I also had a last minute issue with my home and she was able to very helpful to make sure it was taken care of! Highly recommend!”


“Maria was absolutely incredible with our two dogs, Finn and Chai! She went above and beyond—giving them tons of love, exercise, attention, and even handling medications with care. We came home to two very happy pups and a tidy space. She kept us updated the whole time and truly treated them like her own. We can’t recommend her enough and are so grateful to have found someone we trust completely!”


“Let me start off by saying that I highly recommend Heather for any of your pet related needs! We had a trip planned prior to knowing we'd have a little pup in our lives. Given that he was only 11 weeks old I was undecided as to whether to cancel the trip or find a sitter to stay in my condo with him while we were gone for the weekend. We found Heather on Rover and after an day of exchanging messages I felt comfortable enough to book and meet Heather the day prior to our departure. She took care of Linkin as if he was her own. She was 100% responsive to all of my texts and sent lots and lots of pictures of my little man having fun in the condo, while he was out for walks and even when he was exhausted from playing and fell asleep. If it's a friendly, reliable pet sitter you're looking for...look no further, Heather is great and I've personally found my go to sitter for Linkin from here out.”


“Sally is amazing! She was always on time and she was so gentle with my cat he loved her. He would flop to the side for her to give him all the scratches!! I will 100% trust her again with my cat, great person!”


“I would highly recommend Rob and Wynn to anyone who needed a dog sitter, these are people who genuinely love dogs and they take care of them as if they were their own. I was impressed by the amount of pictures they sent, constantly letting me know how things were going and how my pup was doing. I’ll definitely be using them again.”


“Kiri took great care of my pup, was very responsive and accommodating. I’d recommend her without reservations to anyone needing pet care. Thanks again Kiri!”


“Alicia took amazing care of my pets and home. She is very professional, a great communicator while away with multiple photos, and when I came home, everything was clean and neat with calm, happy babies! I highly recommend Alicia - she is the best pet sitter that I have met on Rover!”


“Destiny was an amazing sitter and house guest! Our old boy, Blue, loved her from the moment he met her. She stayed in our home for 16 days and not only took incredible care of Blue, sending regular updates and pics/videos, but she went above and beyond by bringing in our mail, watering plants and even cleaned the house before she left, leaving us a sweet note. She was communicative, professional, and has a high level of attention to detail. We will 100% be using her services again!”


“Highly recommend Ashlee. She is very good to my dogs and they love her too. Ashlee is very communicative and always lets me know when she’s coming and going and how the dogs are doing while I’m gone. I appreciate her taking care of my dogs and my home.”



“Vixana took such good care of my pets while I was overseas. She was responsive and kept in contact with me with regular updates and pictures. Both Poppy and Salem loved her and I didn’t feel bad leaving them I would recommend her in a heartbeat. Thank you.”


About: I’ve always have loved animals since and have taken care of my own dogs and cats since a child. I now have two cats which stops me from getting a dog but I still want to hang out with pups which is how I ended up here:) I currently work at a Bartender and part time fitness instructor. I love being out doors and going on walks already so for me it’s not much a change from my daily life I have my two cats at home, Noodle and Nugget. I originally was only going to get one but his sister couldn’t find a home. I didn’t want them to be split up so I did what I had to do and got both! They are the sweetest babies I could have ever asked for!

“Laura was amazing with my 2 month old puppy girl Ginger. She sent me daily updates with pictures and videos that would melt my heart. I felt confident she was taking good care of her. I highly recommend Laura she’s caring, thorough and kind. I will be using her again in the future.”


“Layla is a gem! She was very attentive to my pet and kept me updated during my vacation. She made sure the house was better than she found it and she paid attention to small details about my pup. I would highly recommend her to anyone who is going away for a short or long vacation. Thank you Layla for easing my mind with your updates. I hope to see you again. Best of luck.”


“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!”


“Kayla is the best. We needed last minute overnight care for our 6 month old puppy when our planned care fell through. Kayla’s communication, flexibility, and transparency make her a wonderful person and a fantastic dog sitter. Arugula loves her and we do too!”


“Maddie was a wonderful sitter for my pup. She was attentive to the special requests, kept my pup on a schedule, and cared for the home as her own. I received regular updates from her throughout my trip which eased my mind while away. I would highly recommend her and hope to use her in the future!”

About: Animals have always been a big part of my life. I’ve cared for dogs and cats of all ages, sizes, and personalities. I’m comfortable with everything from energetic puppies who need structure and playtime to sweet senior pets who require extra patience and gentle attention. I tailor my care to match each pet’s individual needs. My calm, intuitive energy and strong attention to detail allow me to connect thoughtfully with animals. I’m experienced with medication schedules, consistent feeding routines, and creating enrichment through long walks, play, or light training sessions. Every pet I care for is treated with love, safety, and respect. Your pet’s comfort and happiness always come first, and I care for them like they’re my own. I’m an early riser, so I’m up and ready to take care of pets first thing. Working remotely, allows me to stay available throughout the day. Whether it’s walks, check-ins, or just being a calm presence in the house, I have the flexibility to give pets the attention they need without rushing or distractions. Whether I’m walking your dog or staying in your home, your pet’s safety and comfort are always my top priorities. I follow your routines closely, keep a calm and consistent energy, and always treat your space and your pet with care and respect. On walks, I stay alert to the environment, avoid unsafe or crowded areas, and never walk pets off-leash unless in a fully enclosed space with your permission. I pay close attention to your dog’s body language and energy level to make sure they feel relaxed and happy throughout our time together. During house sitting, I maintain a peaceful, pet-focused environment. I make sure your pet sticks to their usual routine—whether it’s feeding times, medications, or favorite spots to nap and play. I keep your home clean and secure, and always keep you updated with photos and check-ins so you know your pet is safe, loved, and never alone. Building trust with you and your pet matters to me. I keep things calm, consistent, and always tuned into what your pet needs. Whether I’m in your home or out on a walk, I make sure they feel safe, cared for, and totally comfortable.

About: I have years of hands-on experience caring for my own pets—3 cats and a dog—and have looked after a variety of dogs in the past. I’m comfortable with pets of all ages and temperaments, and I treat every animal like family. Pet care fits easily into my routine since I’m available on both weekdays and weekends. I’m used to managing daily care for my own pets, so adding visits or check-ins throughout the week is no problem. I’m flexible and reliable, making it easy to fit your pet’s needs into my schedule. When caring for pets in a client’s home, I focus on making them feel safe and comfortable in their familiar space. I follow their usual routines for feeding, playtime, and walks, and I always keep things clean—especially litter boxes or food areas. I give each pet plenty of attention and affection, and I’m respectful of the home, treating it with care and professionalism.
Loving house sitters in your neighborhood
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Kenya C.Star Sitter

“Came back from my trip and our Shiba seemed actually sad (in his way) that Kenya was leaving. We were noting how much he’s grown accustomed to having Kenya around. They definitely have a bond.”


Austin D.Star Sitter

“Austin was great with Obi, even though Obi is definitely not the easiest to deal with! Austin was patient and caring, and kept me updated the whole time. I could tell he really made an effort to make him feel comfortable. Definitely recommend! Thank you Austin for everything!”


Lexus A.Star Sitter

“Lexus is the best! She was absolutely amazing with my dog and home. You should definitely book her for your animal care needs. She spent a lot of time with my dog and kept me updated, I never had to worry about him. I also had a last minute issue with my home and she was able to very helpful to make sure it was taken care of! Highly recommend!”


maria C.Star Sitter

“Maria was absolutely incredible with our two dogs, Finn and Chai! She went above and beyond—giving them tons of love, exercise, attention, and even handling medications with care. We came home to two very happy pups and a tidy space. She kept us updated the whole time and truly treated them like her own. We can’t recommend her enough and are so grateful to have found someone we trust completely!”


Heather C.
Star Sitter


“Let me start off by saying that I highly recommend Heather for any of your pet related needs! We had a trip planned prior to knowing we'd have a little pup in our lives. Given that he was only 11 weeks old I was undecided as to whether to cancel the trip or find a sitter to stay in my condo with him while we were gone for the weekend. We found Heather on Rover and after an day of exchanging messages I felt comfortable enough to book and meet Heather the day prior to our departure. She took care of Linkin as if he was her own. She was 100% responsive to all of my texts and sent lots and lots of pictures of my little man having fun in the condo, while he was out for walks and even when he was exhausted from playing and fell asleep. If it's a friendly, reliable pet sitter you're looking for...look no further, Heather is great and I've personally found my go to sitter for Linkin from here out.”


Sally O.


“Sally is amazing! She was always on time and she was so gentle with my cat he loved her. He would flop to the side for her to give him all the scratches!! I will 100% trust her again with my cat, great person!”


Rob & Wynn K.Star Sitter

“I would highly recommend Rob and Wynn to anyone who needed a dog sitter, these are people who genuinely love dogs and they take care of them as if they were their own. I was impressed by the amount of pictures they sent, constantly letting me know how things were going and how my pup was doing. I’ll definitely be using them again.”


Kiri R.Star Sitter

“Kiri took great care of my pup, was very responsive and accommodating. I’d recommend her without reservations to anyone needing pet care. Thanks again Kiri!”


Alicia K.

“Alicia took amazing care of my pets and home. She is very professional, a great communicator while away with multiple photos, and when I came home, everything was clean and neat with calm, happy babies! I highly recommend Alicia - she is the best pet sitter that I have met on Rover!”


Destiny P.Star Sitter

“Destiny was an amazing sitter and house guest! Our old boy, Blue, loved her from the moment he met her. She stayed in our home for 16 days and not only took incredible care of Blue, sending regular updates and pics/videos, but she went above and beyond by bringing in our mail, watering plants and even cleaned the house before she left, leaving us a sweet note. She was communicative, professional, and has a high level of attention to detail. We will 100% be using her services again!”


Ashlee B.Star Sitter

“Highly recommend Ashlee. She is very good to my dogs and they love her too. Ashlee is very communicative and always lets me know when she’s coming and going and how the dogs are doing while I’m gone. I appreciate her taking care of my dogs and my home.”




Vixana F.

“Vixana took such good care of my pets while I was overseas. She was responsive and kept in contact with me with regular updates and pictures. Both Poppy and Salem loved her and I didn’t feel bad leaving them I would recommend her in a heartbeat. Thank you.”


Daniela S.
“She takes such great care of my dog when I’m at work or out of town. He’s usually shy, but he warmed up to her right away. Daniela is super dependable, sends cute updates, and clearly loves what she does. Total peace of mind knowing she’s with him.”


Laura C.
Star Sitter


“Laura was amazing with my 2 month old puppy girl Ginger. She sent me daily updates with pictures and videos that would melt my heart. I felt confident she was taking good care of her. I highly recommend Laura she’s caring, thorough and kind. I will be using her again in the future.”


Layla F.

“Layla is a gem! She was very attentive to my pet and kept me updated during my vacation. She made sure the house was better than she found it and she paid attention to small details about my pup. I would highly recommend her to anyone who is going away for a short or long vacation. Thank you Layla for easing my mind with your updates. I hope to see you again. Best of luck.”


Michael D.Star Sitter

“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!”


Kayla R.Star Sitter

“Kayla is the best. We needed last minute overnight care for our 6 month old puppy when our planned care fell through. Kayla’s communication, flexibility, and transparency make her a wonderful person and a fantastic dog sitter. Arugula loves her and we do too!”


Madison C.Star Sitter
“Maddie was a wonderful sitter for my pup. She was attentive to the special requests, kept my pup on a schedule, and cared for the home as her own. I received regular updates from her throughout my trip which eased my mind while away. I would highly recommend her and hope to use her in the future!”


Kya W.
“I hired Kya W to watch my cat for a week. I am an overprotective cat dad so it’s always hard to part with my cat. I gave Kya a list of things to do and she did every single one of them! She was very diligent and attentive. She kept updated throughout the whole week on how my cat was doing. Even when I went to pick her up my cat had a hard time leaving! I would recommend Kya to anyone as she is a wonderful young lady!”


Maya C.
“Reliable, Loving, and Truly Exceptional! I couldn’t have asked for a better pet sitting experience! Our sitter went above and beyond in caring for both our playful pup and our shy little cat. From the start, communication was clear, friendly, and reassuring. Each day we received updates, adorable photos, and little notes about their behavior and routines. It was obvious our pets were not just being looked after — they were being genuinely cared for like family. We came home to two very happy animals and a tidy, peaceful home. Knowing our pets were in such loving hands made our time away stress-free. I wholeheartedly recommend this sitter to anyone who wants their pets treated with real compassion and attention!”
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 $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 Aug 2025, there are 2,679 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, 86% 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 3 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.
