House Sitting Winter Garden
Find a loving house sitter to watch over your pets and your home.
Over 116 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.
“Sarah is wonderful! She took excellent care of Ellie and Theo, and excellent care of our home. She lived up to every promise she made. She handled everything that came up competently annd professionally, including a couple of unexpected problems. The dogs were healthy and happy when we got home and our house was very clean and in good order. We will have Sarah come and stay again, without hesitation.”
“Jezabell was fantastic with our gentle giant. Björn is not a fan of being home by himself and Jezabell was very mindful of that. Love all the communication during our trip. She always put my mind at ease with her texts, pictures and videos. I highly recommend Jezabell to care for your furry babies.”
“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.”
“Adriana was awesome! She stayed at our house with our 6 month old pup and was very communicative, sent pics and updates daily. Definitely recommend and will definitely use her again!”
“Steffanie is a wonderful sitter and I highly recommend her to watch your pets! She is very friendly, professional, self sufficient and a natural with animals. Steffanie stayed in our home for a week and took care of our 2 dogs and 1 cat, she kept us updated with texts and photos to let us know that all was well and gave our dogs extra love during the daily Florida storms. We returned home to a spotless house and happy pets!”
About: For over 15 years, I have provided comprehensive, high-quality care for both dogs and cats. My experience ranges from high-energy playtime to specialized senior care and positive reinforcement training. I pride myself on creating a safe, structured, and joyful environment for every pet. What I Offer- Medical & Senior Care: Confident in administering oral medications and skin topicals, as well as managing specialized routines for aging pets. Positive Training: Skilled in teaching basic manners, tricks, and reinforcing good behavior using force-free methods. Play & Enrichment: Expert at reading animal body language to deliver the perfect balance of physical exercise and mental stimulation. Feline Expertise: Experienced in managing cat behavior, specialized diets, and giving space to timid or anxious felines. Whether your pet needs basic puppy training, gentle elder care, or just a fun day of structured play, I adapt my approach to their unique personality. Because my work schedule varies week-to-week, I am highly adaptable and can often accommodate non-traditional times, last-minute requests, and mid-day visits that standard 9-to-5 sitters cannot. I manage my calendar tightly to ensure that when your pet is booked, they get my 100% undivided attention, medical care, and training focus. As a seasoned pet professional specializing in medical administration and behavioral training, I look at safety through a clinical and preventative lens. I do not just watch your pet; I actively monitor their health, behavior, and physical surroundings to prevent accidents before they happen. You can travel with total peace of mind knowing an expert is at the helm.
“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!”
“Under unexpected and difficult circumstances during her stay, Yelena cared for my dogs in an extraordinarily special manner…an effort I won’t forget and remain thankful for”
“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.”
“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!”
“So glad to have Fanny as a sitter! She took care of my dog and 2 cats like they were her own babies. I felt relaxed knowing my babies were safe and well cared for. We have a high energy kitten, a high energy adult dog, and a senior cat and she gave them each the individualized care they need with lots of love and cuddles. My house was also well cared for. Absolutely recommend hiring Fanny for your pet sitting needs!”
“Kiara was by far the best dog/house sitter we have ever had stay in our home & take care of our fur baby. She was very attentive to our dog & communicated with us on a regular basis. She was extremely respectful of our home. Highly recommend!”
“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.”
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
“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!”
The median cost per night for house sitting in Winter Garden is $45
Pet parents share their Rover experiences - Winter Garden
My girlfriend and I were worried about leaving our cats with someone for the week, but Francesca made us feel completely comfortable and we didn't worry even a little when we were gone. She sent us lots and lots of updates and photos and always asked questions if she wasn't sure of something. Thank you so much for taking such good care of our babies. We really appreciate it and we will definitely be reaching out again if we go away!!
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!
Hailey is the best! She came and house sat for us while watching our little Pomeranian for 4 nights while we took a little trip up to GA. She always communicated with us, sent us pictures, kept us updated, and went above and beyond. If you’re looking for someone to treat your fur baby like their own, Hailey is the one!
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!
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.
Meet local sitters who will treat your pets like family
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 for House Sitting in Winter Garden on Rover is $38.85 per night (as of September 2026). However, all sitters set their own rates based on experience, location, and availability.
Rover makes budgeting the cost of House Sitting easy. As long as your dates and pet profiles are correct, the price you see before you book is the same price you pay for House Sitting. For more information on service fees, click here .
As of September 2026, there are 3,089 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 short introductory meeting between you, your pet, and a sitter. It can take place in person or virtually, although we recommend in-person so that your pet can get to know your sitter 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. Most pet parents and sitters on Rover welcome Meet & Greets because the process can give confidence and peace of mind for service experiences, especially for longer stays or first-time bookings.
Sitters on Rover set their own cancellation policy, which you can find on their profile under their calendar availability.
Cancelling before a booking begins and before the sitter's cutoff time qualifies you for a full refund. Same-day cancellations for walks, day care, and drop-ins follow the full refund policy. Otherwise, for dog boarding and house sitting, you will receive a 50% refund for the first seven days of the booking and a 100% refund for the remaining days when you cancel the same day a booking should begin.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means our support team works 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:
- 90% of sitters can help with special care needs
- 95% 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.
Connect anywhere with the Rover app
