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

“Kiara was a great sitter for my little fur baby. He was a little scared at first but soon warmed up to her. I feel very happy to have found someone my baby feels comfortable with.”


“Therese did an amazing job with our boys! Our dogs typically bark at new people but during the meet and greet they went up to her no problem. She sent us daily updates and took great care of everything!”


“Margarita took excellent care of Java while I was away. She was reliable, loving, and kept me updated with photos and messages. It’s clear she truly cares for animals. I highly recommend her and will definitely book her again!”


“Sarah did an absolutely excellent job dog sitting our mini dachshunds! She is very responsible & truly cares for your pets. I felt very comfortable leaving my pups under her care. She asked great questions & truly wanted to provide the best care possible. I would HIGHLY recommend Sarah & will absolutely use her services again. Thank you so much!!!”


“Absolutely amazing again. Nick is so thoughtful in his daily updates with great information and pictures. We couldn't be happier knowing Molly is safe with him!”


“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.”


“Christina is awesome. She watched our dog overnight in our home, was prompt and sent us regular updates. Would highly recommend her services.”


“This is my first time using Rover.Com and Karrie and the experience was awesome! Easy to find the best qualified sitter by the photos/reviews, easy payment and follow up. Karrie was perfect for my pups! We chatted beforehand about my expectations, gave her background on my Doxies who both had IVDD surgery this past year, their unique personalities and explore Karrie’s qualifications. Perfect match! She stayed with my 2 Doxies 8 hours in our hotel suite while we attended a football game. She arrived on time, followed my instructions and my pups were safe & happy upon our return. Would definitely use her and Rover.Com again!”



“We have requested Sarah for dog walking and pet sitting a number of times now, and each time she has been fantastic. She has been flexible/accommodating, reliable, and considerate. She will be our first choice for pet sitting and dog walking in the future!”


“Skylar was awesome. I needed a last minute dog sitter for a couple of hours and Skylar was kind enough to do a last minute meet and greet the day before I needed her. Would definitely recommend and will book again when I need help with my doggies again!”

“Nova is a typical Shiba and they’re not the easiest dogs or for those with little dog experience. Alyson did a great job watching Nova and my home for a week while I was gone. There were definitely challenges and she found ways to overcome them. She provided daily updates and photos of Nova which gave us a sense of peace while we were gone. The home was clean when I got back and Nova was happy.”


“Chelsea did an amazing job watching our dog while we were gone for the week. We received an update of the day and a picture. We were able to really enjoy our time away knowing that our dog was in such great hands.”


About: I’ve taken care of Dogs & Cats since age 14. Started off as a Kennel Tech then moved up to a Vet Tech. After the Vet world, I have cared for pets that belonged to neighbors, coworkers, friends & family. I am currently unemployed. I was recently laid-off from my full-time job. My goal is to fill my week & weekends with dog & cat pet sitting. I have a very large fenced in yard with a friendly fur baby to help your fur baby feel comfortable. I can crate your fur baby as well, if needed. My house has multiple dog beds, couches, people beds that all fur babies are welcome to nap on. I have multiple water dishes outdoors & indoors that are cleaned/refilled 2x a day.

“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!”


“Sarah was amazing! Great communication super nice and also punctual. She will send you the cutest pictures while taking care of your pup. Thank you so much for everything Sarah and for taking care of Milo so last minute. He loved you!”


“She took excellent care of my babies while I was away. I will continue to use her any time I go on vacation so I can have a stress free time.”


“Nathan was AWESOME!! He came to our home to care for my 3 pups while we were on family vacation. He had his hands full with 2 young boxers & my older senior shih”


About: Dogs have been a part of my life for as long as I can remember, and my caretaking days started at a young age! From ensuring they get their daily vitamins, allergy medicine, or prescriptions, to preparing special diet foods and even orchestrating separate meal times when needed, I've done it all. I've also worked on basic obedience skills with several furbabies. Of course, there's been endless fun playtime, invigorating walks, and diligent poop-scooping to maintain cleanliness and hygiene. It's been a lifetime of love and dedication to our furry family members! Feel free to book me, I'm happy to help ☺️! I'm a 2nd Grade teacher, so Summers are primarily open! During the academic school year, I have free time after 4pm Monday to Friday. Weekends are open for discussion too! When I care for your beloved cat or dog in your home, their comfort and well-being are my absolute top priorities. My goal is for all Fur Friends to feel secure and happy in their own familiar environment, minimizing any stress while you're away. This includes maintaining their regular feeding schedule and dietary needs (please let me know all the specifics!), ensuring plenty of fun playtime, and diligently managing potty breaks. Potty Time: for our well-trained canine friends, I take them outside every 3-4 hours, while young puppies or those still learning house manners will be taken out every 2 hours. To ensure I'm not a stranger to your fur baby, I always recommend a **meet-and-greet** beforehand. This way, we can all get acquainted, and your pet can feel comfortable and safe with me from day one. I have a 2 year old Yorkie Terrior to keep your fur baby company. He's quiet & sleeps in his crate at night but if you're not comfortable with another doggo in your home, I can make arrangements for him 😊. Thank you!

“Alexis took great care of our two senior cats while housesitting — including caring for my houseplants. Our cats are very affectionate and can be very needy, so we were happy to receive regular updates with photos showing them being loved on. I highly recommend her services and we will be happy to book her again for our future travel.”

Loving house sitters in your neighborhood
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Kiara S.
Star Sitter


“Kiara was a great sitter for my little fur baby. He was a little scared at first but soon warmed up to her. I feel very happy to have found someone my baby feels comfortable with.”


Therese F.Star Sitter

“Therese did an amazing job with our boys! Our dogs typically bark at new people but during the meet and greet they went up to her no problem. She sent us daily updates and took great care of everything!”


Margarita N.Star Sitter

“Margarita took excellent care of Java while I was away. She was reliable, loving, and kept me updated with photos and messages. It’s clear she truly cares for animals. I highly recommend her and will definitely book her again!”


Sarah P.Star Sitter

“Sarah did an absolutely excellent job dog sitting our mini dachshunds! She is very responsible & truly cares for your pets. I felt very comfortable leaving my pups under her care. She asked great questions & truly wanted to provide the best care possible. I would HIGHLY recommend Sarah & will absolutely use her services again. Thank you so much!!!”


Nickolas J.Star Sitter

“Absolutely amazing again. Nick is so thoughtful in his daily updates with great information and pictures. We couldn't be happier knowing Molly is safe with him!”


Diahann B.Star Sitter

“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.”


Christina W.Star Sitter

“Christina is awesome. She watched our dog overnight in our home, was prompt and sent us regular updates. Would highly recommend her services.”


Karrie M.Star Sitter

“This is my first time using Rover.Com and Karrie and the experience was awesome! Easy to find the best qualified sitter by the photos/reviews, easy payment and follow up. Karrie was perfect for my pups! We chatted beforehand about my expectations, gave her background on my Doxies who both had IVDD surgery this past year, their unique personalities and explore Karrie’s qualifications. Perfect match! She stayed with my 2 Doxies 8 hours in our hotel suite while we attended a football game. She arrived on time, followed my instructions and my pups were safe & happy upon our return. Would definitely use her and Rover.Com again!”




Sarah H.
Star Sitter


“We have requested Sarah for dog walking and pet sitting a number of times now, and each time she has been fantastic. She has been flexible/accommodating, reliable, and considerate. She will be our first choice for pet sitting and dog walking in the future!”


Skylar D.
“Skylar was awesome. I needed a last minute dog sitter for a couple of hours and Skylar was kind enough to do a last minute meet and greet the day before I needed her. Would definitely recommend and will book again when I need help with my doggies again!”


Alyson F.Star Sitter

“Nova is a typical Shiba and they’re not the easiest dogs or for those with little dog experience. Alyson did a great job watching Nova and my home for a week while I was gone. There were definitely challenges and she found ways to overcome them. She provided daily updates and photos of Nova which gave us a sense of peace while we were gone. The home was clean when I got back and Nova was happy.”


Chelsea D.Star Sitter

“Chelsea did an amazing job watching our dog while we were gone for the week. We received an update of the day and a picture. We were able to really enjoy our time away knowing that our dog was in such great hands.”


Christina M.
“Christina takes amazing care of my dog! She keeps me updated with great communication, and I know gives the one-on-one attention my Nala demands. I never worry when she cares for my dog and highly recommend Christina!”


Imani Z.

“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!”


Sarah C.Star Sitter

“Sarah was amazing! Great communication super nice and also punctual. She will send you the cutest pictures while taking care of your pup. Thank you so much for everything Sarah and for taking care of Milo so last minute. He loved you!”


Ryeleigh N.

“She took excellent care of my babies while I was away. I will continue to use her any time I go on vacation so I can have a stress free time.”


Nathan B.
Star Sitter


“Nathan was AWESOME!! He came to our home to care for my 3 pups while we were on family vacation. He had his hands full with 2 young boxers & my older senior shih”


Brittney C.
“I should start saying KUDOS to a job well done every time Brittney, takes care of my cats. She’s very professional, loves and truly care for my cats. I knew her for 7 years now and I trust her to come into my home and take care of my cats. Her loving care is outstanding and gave me and my husband a peace of mind while on an extended trip. Excellent communication skills, sharing about food, photos and update! Brittney is very reliable, trustworthy and the best pet sitter! I highly recommend her…. Five star plus!!!! Go ahead and book Brittney!!!”


Alexis T.

“Alexis took great care of our two senior cats while housesitting — including caring for my houseplants. Our cats are very affectionate and can be very needy, so we were happy to receive regular updates with photos showing them being loved on. I highly recommend her services and we will be happy to book her again for our future travel.”


Hannah R.

“Hannah did a great job! She came in and sat with bruiser right away to make sure he was comfortable with her. Would highly recommend Hannah!”
Over 662 pet parents in Winter Garden have booked house sitting
Winter Garden pet parents share their Rover experiences
Chelsea took wonderful care of our 3 senior pups! She was extremely communicative and professional, thank you Chelsea! Appreciate you!

Alexis took great care of our two senior cats while housesitting — including caring for my houseplants. Our cats are very affectionate and can be very needy, so we were happy to receive regular updates with photos showing them being loved on. I highly recommend her services and we will be happy to book her again for our future travel.

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.

I so appreciated all Carlye did for my little dog, cat and house. She stayed in touch when the electricity went out and the cat ran out of food (my fault). We came home to a clean house with sheets in the washing machine and she even gave our dog a bath. Carlye is a very resourceful, sweet gal!

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!
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 3 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 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 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 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 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.
