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

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Top rated Winter Garden house sitters
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“I am so glad that I found Diahann to pet/house sit while we were traveling internationally. She was great with our 2 pugs. She was extremely responsible and communicative, sending us daily updates about our girls. Our home was also in perfect condition when we returned. Being a veterinarian myself, I can be picky about who takes care of our dogs, but Diahann definitely passed with flying colors. As long as she is available, she will be my go to pet sitter from now on.”

“If I could give Nickolas 10 stars, I would! He was literally perfect. Very professional and an outstanding communicator. The whole time I was gone, he provided daily updates with pictures. I was anxious about leaving my Skye Sissy with anyone whom she didn't know, but she loved him from the minute he met her. I felt confident leaving, I did not worry because I know that she was in capable and loving hands. Bravo to Nickolas for simply being AWESOME!”

“Brittney was amazing with my fur baby!. She provided tons of updates each day and even a photoshoot! I would definitely recommend Brittney and would book with her again. I came home to a very happy and healthy puppy.”

“Such a great feeling to feel confident and at ease in leaving my precious baby with Emma. She is very sweet and took great care of my Pug and my home. She made sure to send me pictures and put my mind at ease. I will definitely be using her again.”

“Yelena was great, easy to reach and communicate with. Skai loved her and she even left her a new toy to play with! You can tell she is very experienced with dogs especially being that Skai can be very hyper but it did not seem to bother her at all. I would definitely book again, she made things very easy and smooth thank you :)”


“Thank you for caring for our boys... The pictures your sent and all the fun moments and experiences with them kept us calm and relaxed while away. We came home to happy Cats. You are wonderful 😊”

“My girl got into some meds while I was at work. Dwain was quick to try to contact me when he stopped by the house and quick to action. They couldn't be in better hands and I'm so grateful.”

“Kaitlyn took great care of my dog when I was away. She made sure she had plenty of walks and playtime. My dog seemed very happy when I came home to a clean house. Will be using her again!”

“Jezabell was great with Gabby and Romeo! This was our first time leaving them alone with someone outside our family since adopting them 7 months ago. Jezabell shared multiple photos a day with us and updates on how they were doing. We were concerned with Gabby eating as she can be picky and has not had her appetite when left before. Jezabell was very successful getting her to eat and kept to their routine. She has given us peace of mind when leaving town without them. Definitely found a great sitter to stay overnight with them and will definitely use her again!!!”


“Thanya was a fantastic housesitter and we would be happy to have her back at any point in the future. Our large dog and two cats were well cared for and completely chilled out and happy when we got back home. Thanya kept us in the loop with plenty of updates and made sure to communicate with any questions/details we forgot in our initial meet and greet. I know our new kitten was a handful in particular so I really appreciate her patience and attention. Thanks so much Thanya!”

“Alyson stayed at my home x 2 nights with my mischievous Great Dane pup and my 10 year old Doberman. She was prompt with communication and sent updates which allowed me to enjoy my first weekend away in a long time. My dogs were well cared for! I definitely recommend her and will book with her in the future!”

“Karrie went above and beyond her call of duty. I always call text and let er know when I am leaving and same when i get back. when she had not heard from me she text and did not get an answer. The air terrific in orland had been shut down and we were in a holding pattern due to the storm that was over Orlando. She went back to my home fed the babies, storming too bad to walk them at the time. Then she came back to walk them, and I had just gotten home. My babies were just as happy to see her as they were me. She loves my babies and treats them like they were her own. If you're looking for someone to trust and take care of your pets like you do, she is the one. I will not use anyone but her. I will reschedule my plans so that she takes care of my babies. I was very nervous at first, now no worries at all.”

“Imani did an outstanding job caring for our 4 dogs. She was communicative, professional and very sweet with our pups. They responded positively towards her right away. We are happy to have Imani for our pet sitting needs!”

“Zoe did a wonderful job taking care of my scared pup. He surprisingly opened up to her right away. She was very responsive and I'll certainly be booking again.”

About: My first sitting job was at 14 for the neighbors across the street, during a month long trip. I have been sitting for friends on and off for the last 4 years, dogs and cats. I have a lot of experience with senior cats and cats who are on medication. I am currently an independent contractor, working as a performer. When in a show, weekends would be difficult, and at most a show run lasts 5 weeks. I also bartend at a theater, those shifts are only 4 hours, and are also only during the run of a show. My schedule always remains very flexible. Growing up I was the designated dog walker in the family, he was a very excitable and friendly dog so I have a lot of experience with dogs who pull on their leashes. I also was responsible for baths. I also have some experience with multiple dogs at a time, of all sorts of personalities. I have owned at least one cat since I was 6, I'm the girl who seeks out the cat at the party to hang out.
“Sophia was excellent from our initial contact through until she left after completing the job. We received updates and photos throughout her time with Coleman. She was prompt, polite, and just the caregiver our boy needed for the night. Will not hesitate to call her again!”

“Aaliyah was very friendly and communicative with the dogs. She was very attentive and available and kept sending updates each day. Aaliyah was also very clean and left no messes behind after housesitting for us. We would definitely hire Aaliyah again.”

Over 722 pet parents in Winter Garden have booked house sitting
Winter Garden pet parents share their Rover experiences
I can’t say enough good things about Delanie. She went above and beyond in every way. From the moment we booked, communication was effortless, updates were thoughtful, and the level of care she gave Oliver and Sophie was exceptional. I came home to a happy, relaxed fur babies. Absolutely perfect, thank you Delanie for everything!
Emma was absolutely wonderful from start to finish. She was so kind, caring, and attentive, and I immediately felt comfortable leaving Cosmo in her care. Her communication throughout the stay was excellent, and she consistently kept me updated which gave me so much peace of mind. On top of that, she was incredibly adaptable and flexible when my AC unexpectedly went out. I felt terrible about the situation, but Emma remained so positive, understanding, and accommodating through it all. Because of her, I was able to stay with my family without worrying about Cosmo and knew he was being very well cared for. I’m beyond thankful for Emma and truly could not recommend her enough. Anyone would be lucky to have her care for their pets!
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 Garden is $45
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 Garden average 4 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 Garden on Rover as of Jun 2026 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 Jun 2026, there are 2,861 house sitters in Winter Garden. 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, 87% of Winter Garden house sitters respond in under an hour.
House sitters in Winter Garden have an average of 14 years of experience. House sitters with repeat customers have an average of 4 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 Garden.
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 Garden 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.








