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
Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Excellent pup care. Loved the daily updates and photos. I am confident my dogs had excellent care and one of my dogs is senior and takes medication and I had no worries!”
“Alyson was fantastic with our dogs. She stayed at the house and watched them. She kept us informed on how they were doing and sent pictures and videos. Normally, my dogs don’t eat well when we aren’t home, but they did well for Alyson. She went above and beyond by dealing with a power outage in our garage. She also checked our mailbox and brought our trash out on the trash days. We would highly recommended using Alyson. We definitely plan to reach out next time we need care for our dogs.”
“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.”
About: I’ve been pet sitting since 2015 and have loved every moment. I have a big heart for animals and the people who adore them. Pets bring so much joy to our lives, and they deserve the same love and care in return. When you’re away, you can feel at ease knowing your pets are safe, happy, and treated like family. I am in pet grooming school Monday through Friday from 9-3pm. I am fully available on weekends. If there are any other questions you may have about my schedule feel free to contact me! I do not have any pets (except a turtle), and my parents are animal lovers like me so they always give lots of extra love. We do not have a fence but we do have a good yard.
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
“Nathan is a great sitter. He sent me photos of my senior dog and younger dog while I was away/traveling for work. It’s a huge relief to find someone who can handle giving my senior dog arthritis medicine which I really appreciate. Thanks Nathan.”
“Kiara was exceptional. Her attention to detail and communication enabled us to relax knowing that our beloved cats, chickens, and ducks were all receiving excellent care. We would highly recommend her and will request her again.”
“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!”
“We had a family emergency and I needed a pet sitter last minute. My usual sitters were already booked up so I reached out to Anastasiia. She came within a few hours, we told her what she needed to know and I was on my way. I received regular updates and Anastasiia made my emergency situation a lot less stressful. I highly recommend her, you’ll come home to a house cleaner than how you left it.”
“Danielle was amazing with Skai and very communicative. She sent me pictures throughout the stay and I felt very secured. She took amazing care of Skai and I would definitely book again!”
“The best!!! Trust him completely! I felt very comfortable having my dogs with Nick and they were comfortable too, which is something! He's very flexible and super helpful, recommend him highly.”
“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!”
“Danielle was available to help us out last minute when our Sitter cancelled. She was fabulous. Very professional from the initial booking interaction to the excellent care provided for our pups. Nate and Oki loved their day with her and we could not have been happier with Dani’s Service. Thanks!!!… you helped to really make our day a fantastic one.”
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.
“Jennifer, was amazing. She would send me a lot of updates with lots of pictures. all of the pictures she sent my dog looked so happy. She was very respectful of the house and everything looked just as I left it when I got back. She took Marley for his usual walks, gave him his vitamins and was very loving with Marley. I felt at ease on my 12 day vacation and felt I left him in good hands. I would definitely book her next time. I was very blessed 😇 to have find her as she was a great dog sitter.”
“Mackenna is an actual godsend of a baby sitter. She goes way, way above and beyond for our fur kids (3 dogs + 2 cats). She keeps them busy through the day and they’re noticeably exhausted (in the best way) every time we come home. If I could give her 18 stars and keep her all to ourselves, I would!! Best sitter on this app by far!”
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
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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