House Sitting Winter Garden
Find a loving house sitter to watch over your pets and your home.
Over 120 pet parents in Winter Garden have booked house sitting
Winter Garden, Find top rated house sitting
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Yelena was absolutely wonderful! She responded quickly and was able to accommodate us last minute to watch our fur-babies, which we really appreciated. Throughout the day, she sent us pictures and updates, giving us peace of mind that they were happy and well cared for. She also treated our home with the utmost respect and was such a pleasure to have in our home. We couldn’t have asked for a better pet sitter and would definitely recommend Yelena to anyone looking for someone trustworthy, caring, and dependable. We will absolutely be using her again! 🐾❤️”
“Tiffany was awesome. She stayed with my two rambunctious Boston Terrier puppies for a long weekend. We recieved many pictures and updates during our time away giving us comfort that our babies were being well taken care of. Our babies are spoiled and sleep in bed with us. Tiffany didn't bat an eye in sharing the bed. Best yet the house was clean and dog poop all picked up. We definately would use her again. Highly recommended!”
“Karrie was so easy to work with and loved on our pups even giving extra patience to our pup who needs some warmup time. She communicated with us the whole time and just made us feel very comfortable. Thanks for everything!!”
“Kiara was amazing. She stayed with Coco the whole day. Coco met her once prior to sitting and when Kiara walked in the door Coco was excited. Dogs are a great judge of character I believe. She was very accommodating and I will definitely use her again.”
“Margarita was very good with my fur baby . Her attention to details for both the care of my dog, who is blind and her respect of our home was greatly appreciated . We have already booked our next need with her”
About: Hi, I'm Ken! With 8 years of pet care experience, I provide top-tier dog walking, pet sitting, and drop-in check-ins tailored to your pet's exact routine. Whether your dog needs an energetic walk to shake off the "ruff" days, or your cat needs some quiet cuddle time during a check-in, I’ve got you covered. Why Choose Me? -8+ Years Experience: Deep understanding of dog and cat behaviors and body language. -Flexible Services: Available for high-energy walks, overnight sitting, or quick potty breaks and feedings. -Safety First: Reliable, fully vetted, and dedicated to keeping your pets secure and happy. I treat every dog and cat like my own family. Book a service today, and let's give your pet the smooth, stress-free day they deserve! I work a steady evening schedule, my routine is perfectly tailored for pets who need dedicated overnight care, morning routines, or daytime attention on my days off. Here is exactly how my availability breaks down: • Mondays & Thursdays (Completely Free): These are my full days off! I am available all day and night for extended playtime, daytime drop-ins, mid-day walks, or a seamless start to an overnight stay. • Wednesday, Friday, Saturday, & Sunday (Evening Workdays With Tuesday as an Occasional Morning): • Mornings & Early Afternoons: Available for morning walks and early drop-in visits before I head out for the evening. • Nights & Overnights: Perfect for overnight House Sitting! I am available to arrive in the late evening to tuck your pets into bed, stay through the night, and provide a full morning routine with breakfast and a walk before leaving. I treat your home with the utmost respect and your pets like members of my own family. Because change can sometimes be 'ruff' for animals, my primary goal is to maintain their familiar habits, scents, and routines as closely as possible while you are away. Here is exactly what you can expect when I care for your pets in your home: • Consistency & Routines: I stick strictly to your established schedule for feeding, medication, crate time, and bathroom breaks. • Active Engagement: I provide active playtime, mental stimulation, and plenty of one-on-one affection. • Thorough Clean-up: I keep all pet areas tidy, including washing food bowls, scooping litter boxes daily, and cleaning up any accidental messes immediately. • Frequent, Detailed Updates: You will receive regular photo and/or video updates through Rover Cards or Messaging along with detailed summaries of how your pet is doing, so you never have to wonder. I also offer meet and greets, so schedule yours today!
“Sharon was so great with our pup, Davy! She helped us out with house sitting for a weekend while we were out of town, and she sent us updates with photos while we were away. She brought her own little pup over to spend time with Davy, and we loved hearing that they got along and had a companion for one another. Sharon left our house clean and tidy after her stay. Highly recommend and will definitely be reaching out for future help! Thank you, Sharon!!”
“Glory was great with the animals, my dog is very skittish of people and she took her time with him. WE had some issues with flights on our way back into the country and she was willing and ready to come back if need be”
About: Experienced dog sitter, trainer, and groomer. Fully sidwalked neighborhood for Pack walks, the dog park is only 2 miles away for excursions, round trip transportation to keep your car clean. looking forward to pampering your pooch. offer inexpensive dog bathing and full grooming can be requested so your dog always come home clean and we'll cared for. Full time stay at home avalible from 6am to 10pm dog park trips each morning are generally between 8-10am. Depending on weather I like to get the dogs well exercised early in the day so we are inside between 10am and 2pm to avoid the heat of the day Plenty of time for training, outback play, and socializing or pack walks If I have other out of the house apointments I keep my area of care to a 15/20 miles radius to do stop in care or walks so your dogs wont ever be alone for longer than a couple of hours tops I have a 8ft fenced in back yard multiple crates if needed as well as a 4 foot fenced partitioned side yard to seperate large and small dogs if needed. I own one female standard poodle excellently behaved so your dog will get socialized unless requested otherwise. Multiple food/water bowls are inside and outside. Bathing is optional but if your dog is a digger and gets particularly dirty i will to do a simple rinse and dry for free. We can arrange for full shaving/sanitary trims after shampooing, or de-shedding shampoo and brushing for double coats like huskies
About: Many have said that I am a dog whisperer. I enjoy walking dogs or just being a companion for cats and dogs. I also have senior care training to include giving meds. Right now this is my only job so I am available at all times of morning, mid day and evenings. I always accept positions that leave enough time in between sittings. I have a huge fenced in back yard. I do have a Staffy and he loves making new friends. H had a small dog for 6 of his years in our home and he was so good with him.
“Adriana did a great job with our pack. She arrived timely, spent most if not all of her days while we were gone at the house with them. It rained most of our time away so they were cooped up inside and we came home to a normal house so she found a way to keep them engaged and go out in the rain to potty. For at least one of them that isn't an easy task. She communicated daily with photos and updates and responded promptly to our messages. We came home to 3 healthy and happy dogs.”
About: I have always been the "go to" person to care for friend and family pets. Mostly dogs and cats but willing to learn if you need any other kind of pet watched :) I currently work from home. I am home all day with the pets and will be able to tend to anything they might need. :) I have a large living room and am able to keep an eye on all pets at all times along with provide the required amount of walks your pet might need
“Noelle was fantastic with our babies! We will definitely reach out to her again for our next weekend getaway! She was attentive to their needs, patient with our pug's disability, cognizant of their comfort throughout the weekend, and kept them on their schedule/routine. She checked in often and kept us informed of their activities, leaving us to a stress-free, mostly unplugged weekend. We are very happy to have found Noelle!”
About: What sets me apart is my genuine love for animals, patience, and dedication to making every pet feel safe, happy, and loved! 🐾💕 I understand that every pet has a unique personality and individual needs, whether they’re a playful puppy or a senior companion who needs extra love and gentle care. I also prioritize constant communication with pet parents because I know just how much their furry babies mean to them! I love sharing regular photo and video updates so you can feel connected, reassured, and part of every adorable moment, even when you’re away. My goal is to give your pets the same love and attention you would, while giving you complete peace of mind! 🐶🐱💗 Pet care fits naturally into my daily routine because I genuinely enjoy spending time with animals! 🐾💕 I prioritize staying organized and maintaining a flexible schedule to accommodate walks, feeding times, playtime, and each pet’s individual needs. I believe consistency, love, and attention are essential to keeping pets happy and comfortable. I also make time to send regular photos, videos, and updates to pet parents so they always feel connected to their furry babies! 🐶💗 I treat every pet as if they were my own, providing a safe, loving, and comfortable environment filled with attention and affection! 🐾💕 Whether caring for pets in my home or a client’s home, I prioritize maintaining their usual routines, including feeding schedules, walks, playtime, and plenty of cuddles. I carefully follow each pet parent’s instructions and respect their home and preferences. I also believe communication is key, so I provide regular photos, videos, and updates to give pet parents peace of mind while they’re away. My goal is to make every furry baby feel loved, secure, and happy! 🐶🐱💗
“Isabella did an amazing job, taking care of our house and our three dogs. She went above and beyond to make sure that we knew exactly what was going on while we were away. Photos were sent, extreme care was taken, instructions were followed perfectly. I highly recommend and look forward to booking her again!”
“Liz was wonderful with our doggy! Our senior dog liked her from the moment he met her and was at ease in her presence early on. Liz was especially attentive to taking frequent photos and sending updates daily. When we arrived home, our doggy was comfortable and calm. We are so glad to have found Liz and will be booking with her again very soon!”
About: My family always had pets. I took care of them since childhood - cats, Pomeranian, German Shepherd, Golden Retriever. Also I always help my friends and neighbors with their pets, cats and dogs when they went on vacation. I have experience in dog training. My German Shepherd and I passed a general training course for 98 points out of 100. I adhere to the principle of positive reinforcement. My work schedule is pretty flexible, so I can help you with your pets most of the time. I can walk and sitting with your pets all weekdays. I have a nice small backyard for small walk and the Orange Trail nearby for nice long walks. I have two kids (five and eight y.o.). They have always grown up surrounded by pets and know how to behave with them. So if your pet is kids-friendly 😊, then everything will be great 🤗
The median cost per night for house sitting in Winter Garden is $45
Pet parents share their Rover experiences - Winter Garden
Elizabeth was wonderful with Cosmo! She arrived promptly for our meet and greet, and Cosmo took to her right away. Her communication throughout the stay was excellent, and I really appreciated her evening updates. She is easygoing, positive, and professional, which made me feel completely comfortable leaving Cosmo in her care. I would absolutely recommend Elizabeth to anyone looking for a trustworthy and caring pet sitter. We would love to have her watch Cosmo again!
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 November 2026. Most bookings cost between $26 and $108 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 November 2026, there are 3,053 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 Rover Guarantee, 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 Rover's Trust & Safety page.
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 Meet & Greet.
sitters on Rover set their own cancellation policy, 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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