House Sitting Winter Garden
Find a loving house sitter to watch over your pets and your home.
Over 117 pet parents in Winter Garden have booked house sitting
Winter Garden, Find top rated house sitting
“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!”
“Tiffany was able to help us out last minute when other pet sitting plans fell through and we’re so happy to have found her! She was great with our two pups and sent us pics throughout her stay. She was great at communicating with us before and during and we came home to a clean home and happy pups. We will definitely use her again! Thank you Tiffany for your professionalism and for taking such good care of our pups!”
“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.”
“Alyson stayed at our house with our spunky pup for 4 nights. She took good care of both our home and our dog, kept me updated, and we came home to a happy, well-cared-for pup.”
“Sharon has been such a reliable and communicative dog sitter for our pup, Davy. During her stay, she sent photos and updates to ensure we stayed informed while we were away. She gives us peace of mind as we’re traveling in knowing that Davy is in such great hands! She also leaves our home clean and tidy, and we truly appreciate it. Would recommend Sharon to anyone looking for a reliable, caring sitter for their pet!”
“Taylor took excellent care of our dog and cat! We have quite a few "special" requirements for our senior four-legged family members and Taylor was up for the task. She stayed in our home and fit in like a champ! In fact, we've booked Taylor for another (longer) visit. Thank you, Taylor!”
About: I’ve had dogs in my house my whole life! I love all kinds of animals and have even volunteered at an animal shelter in high school. My most recent experience is working at a vet and boarding center. I’ve learned so much more about pet care this past year as my best friend/roommate works at a cat cafe and has a degree in Animal Health. I’ve even started administering medicine! Being with animals is truly the best part of my day! I’m currently working remotely, so I have plenty of free time to take care of your pets throughout the day! I’m available most weekdays and weekends. :) My basic house-sitting service includes staying overnight with your pup so they have company & comfort in their own home, along with daytime care every 3-5 hours for potty breaks, meals, playtime, and cuddles. I currently live with 3 small cats, so I’m very well versed in taking care and providing entertainment for multiple animals throughout the day.
“Lia was great- Super friendly, great communication, and punctual. I think she took good care of Apollo and was engaging and playful. Will definitely contact again for future needs!”
“I booked JaRavia at the last minute, and she was incredibly flexible with scheduling a meet-and-greet. During the boarding, she was patient and understanding with my shy dog, Bear, who can be a bit distant. She checked in frequently, and by the end of the visit, Bear had started to trust her. I highly recommend JaRavia for her kindness and love of animals!”
About: You would never know but I used to be afraid of dogs as a child. After we added a golden retriever named Joe to our family, I've been obsessed with dogs ever since. He passed away 6 years ago now and has left me longing to care for pups. I spent the summer helping my sister with her dog sitting business up north and am looking to do occasional dog sitting in the Orlando area. I am a preschool teacher during the week so I would be available to dogsit on the weekends. Or during the week if the situation allows. I would show your pup lots of love and attention! I feel comfortable going on long walks, playing fetch and keeping the dog on his daily routine to manintain his comfort while his family are away.
About: *Disney area Hi, I’m Jordan!! I grew up in a home surrounded by dogs, cats, reptiles, birds, etc. I have also previously worked as a veterinary assistant, so I have plenty of experience with all different types of pets and their personalities!! Currently I have a 2 year old Italian Spinone and a 4 year old cat, so I’m equipped for it all! I am a true animal lover at heart and I can’t wait to take care of your fur babies! I am available all throughout the Windermere/Winter Garden/Disney area I work part-time and only have online classes, so I am available Sunday-Wednesday at any time of day! I have plenty of time to care for & play with your pets! I am here for whatever you need! However you want me to go about caring for your pet in your home I’m able. I understand how important your pets are to you and I am determined to keep them safe, happy, and healthy!
About: I have taken care of dogs for neighbors and family friends since i was 10. I really want my own but i don’t have much time for it. So I would love to help any families needed. I provide a clean environment and i am great with instructions. I am currently working at disney so my hours vary from week to week. however i tend to work later in the day and can easily add a dog or cat into my schedule I don’t have a fenced in backyard however i do have space to walk your dog on a leash plenty. I do provide a clean house and would hope clients provide the same.
“Natalie took great care of Lily for 4 drop in visits! She sent me videos and pics and everything was just how I left it when I got home! Will be re booking her in the future….thank you Natalie!”
About: From fitness to a casual stroll,I adjust to your fur babies needs. I am a Central Florida Native so the heat and humidity is "home" for me and walking dogs is my zen space. I am fluid because of my private yoga classes. So I am free most mornings and evenings as well as weekends. I worked in the Theme Parks for over 27 years so I no longer have those hours. I can come to your location, I have experience with delivery services from Amazon and Ups, as well as in home yoga services so I provide the best home care with attention to your family's needs.
About: After 7+ years of pet sitting, I know that leaving your furry family member isn't easy. I began sitting after losing my own beloved dog a few years ago—and while my heart still misses him, caring for other pets has been incredibly healing. I treat every dog like they are my own, offering the same snuggles, playtime, and patience I gave him. Your pup won't just be 'watched'; they will be loved on while you're away. Home full-time while I prep for the LSAT, so your dog gets nonstop company 7 days a week. I live at home with my Mom and Dad whom are in their 60s. I weave walks and playtime into my study breaks—so while I'm hitting the books, your pup is getting all the belly rubs and fetch sessions they want. 7+ years of pet sitting experience, and I genuinely miss having a fluffy companion around since losing my own dog. Let me spoil yours while you're away! While I'm home full-time studying for the LSAT (available Sunday–Saturday), your dog will have the run of the place—literally. I have a large, fully fenced backyard for unlimited fetch, zoomies, and sunbathing, plus ample indoor space for cozy naps and supervised play when we come inside. With 7+ years of pet sitting experience and a heart still missing my own dog who passed a few years ago, I know how important it is to find a safe, roomy, and loving environment. Your pup will get daily walks, constant company, and all the space they need to feel right at home.
“Absolutely loved Shannon! She watched our fur babies while we went on a lil vacay. She asked plenty of questions before we left to make sure she knew our animals routine. Our pom absolutely loved her! And so did our cats, judging from the pics she sent. She communicated with us each day and sent us pics. 100% recommend and will be booking with her again!”
The median cost per night for house sitting in Winter Garden is $45
Pet parents share their Rover experiences - Winter Garden
Remy was so amazing with our baby girl! This was our first time leaving our 3 month old puppy and I felt no hesitation at all leaving her in Remy’s capable hands. We’ve already decided that we’d love to have her pet sit for us again in the future. She sent us adorable pictures of our baby girl and our puppy was so relaxed and comfortable that she fell asleep in her arms.
Elizabeth stayed with our girls, Nelly & Stella, at our home over Labor Day weekend. It was a somewhat last minute booking which she accommodated after a meet & greet at our home. She provided photos of our girls throughout her stay which helped us feel connected to our girls while we're traveling. We are very pleased with the experience!
Ava is fantastic, we've had her watch our home and fur babies multiple times now and can't say enough good things about her services. Kind, respectful, friendly are just a few of the words that come to mind . . . we feel at ease on holiday knowing she's in our home!
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!
Sherry was incredible with our pups! They were so happy we were home and then so sad that she wasn't there still! She sent exactly the right amount of pictures and updates for us. We know they can be a handful and we had a rushed exit for our trip, so we appreciated how flexible she was with our short-notice booking. Thank you Sherry!
Book with peace of mind
- Screened pet sitters have passed a third-party background check and show verified reviews from other pet parents, like you.
- Every booking is backed by the Rover Guarantee, which includes up to $25,000 reimbursement for eligible vet care. Learn more
- 24/7 support from the Rover team–here to help if you ever need someone to talk to.
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 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.
How to book house sitting
1. Search
Browse profiles of sitters near you who offer house sitting.
2. Meet In Person
Schedule a free in-person Meet & Greet to find the perfect fit.
3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform.
Popular requests for house sitting - Winter Garden
Select a filter and find qualifying sitters offering house sitting.Sitters in Winter Garden average 4 repeat house sitting clients
FAQs for House Sitting - Winter Garden
Frequently asked questions about Rover
The average cost of House Sitting in Winter Garden is $39 per night as of October 2026. Most bookings cost between $26 and $102 per night. On Rover, sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 3,064 sitters on Rover offering House Sitting across Winter Garden. Enter your ZIP code to see which available sitters are closest to your home.
Beyond belly rubs and feeding schedules, a house sitter’s presence may provide an additional layer of security for your home. However, you will need to arrange overnight stays and other household tasks with your sitter when reaching out to them. Not all sitters offer the same services. Common household tasks you can negotiate include:
- Mail & deliveries: Collecting letters and packages so they don't pile up.
- Plant care: Keeping your indoor or outdoor garden hydrated.
- Trash & recycling: Taking trash cans to the curb on scheduled pickup days.
- Home security: Sitters can stay overnight to keep your home occupied.
The best way to align on expectations is during your free Meet & Greet. Use this time to provide a "home cheat sheet" that includes your preferred Winter Garden walking routes, the location of your favorite pet store, and any specific quirks about your home’s security or appliances.
It’s helpful to think of house sitting as a "home base" service. Most sitters in Winter Garden maintain their normal daily routines, like running errands or heading to the office, meaning your pet should be comfortable being alone for a few hours at a time. If your pet needs a little extra company, here is how to find the perfect match:
- Look for "WFH" sitters: Many sitters mention "Work from Home" on their profile to indicate they’ll be present for the majority of the day.
- Update your pet’s profile: Write down how long your pet can comfortably be left alone. This helps sitters quickly determine if their schedule aligns with your needs.
- Communicate 24/7 needs: Standard house sitting usually doesn't include constant supervision. If your pet requires round-the-clock care, be sure to discuss this upfront.
Tip: Use the Meet & Greet to confirm a sitter's typical "away" windows. Transparency ensures your pet stays happy and your sitter can plan their day effectively!
Key handling is entirely up to you and your sitter to agree on during the Meet & Greet or in the Rover app. Most pet parents in Winter Garden choose to hand over a spare key or digital fob in person, while others arrange a lockbox or unique access code. Don't forget to discuss key returns as well!
The Rover Guarantee is Rover’s commitment to your peace of mind every time you book. It includes 24/7 customer support, sitter access to advice from qualified veterinary professionals for diagnostic issues, and a reimbursement program for eligible veterinary care in the rare event something goes wrong.
All bookings are backed by the , which provides up to $25,000 in eligible veterinary care reimbursement.
Every sitter on Rover is required to pass a background check before listing their services. This process confirms their identity and indicates they are not on the Department of Justice’s National Sex Offender Public Website or have any disqualifying offenses.
Beyond ID checks, you can review each sitter's star rating, read verified reviews from other pet parents, and see how many repeat clients they have. Every booking is backed by the Rover Guarantee, which includes up to $25,000 in eligible veterinary care. For more details, visit .
If a health concern arises during a stay, your sitter is instructed to contact you and our Trust & Safety team immediately and, if needed, take your pet to the closest veterinarian. Through our Trust & Safety support team, sitters can ask for diagnostic advice from a qualified veterinary professional if your pet is showing signs of possible illness.
For extra peace of mind, you can also prepare an authorization form for your regular vet. An authorization form outlines your preferred method of care and allows your sitter to bring your pet into their regular clinic.
Every qualified booking made on Rover is backed by the Rover Guarantee, which includes reimbursement for eligible emergency vet care.
A Meet & Greet is a casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet or the new environment.
During the Meet & Greet, you will have a chance to walk through your pet's routine, medical needs, and unique quirks. Take the time to ask your sitter questions about their skills and expertise, and make sure the fit feels right for everyone. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Winter Garden. On Rover:
- 89% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 96% can help with daily exercise
You can also find pet sitters on Rover who accept only one pet at a time, which is ideal for anxious puppies, kittens, or senior pets who move at a gentler pace. Some sitters will also list availability for 24/7 care, also known as constant care, in their profiles.
Use the search filters to narrow down sitters whose specific experience or environment meets your pet's needs. When reaching out to your sitter, outline your pet's care routine and use the Meet & Greet to walk your sitter through your expectations.
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