House Sitting Winter Garden
Find a loving house sitter to watch over your pets and your home.
Over 126 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.
“I couldn’t have asked for a better pet sitter! From start to finish, Jezabell’s communication was excellent, she kept me updated and gave me complete peace of mind while I was away. My fur-babies were clearly well cared for, happy, and comfortable when I returned, which says everything. She also treated my home with so much respect and left everything clean and in great condition. It’s such a relief to find someone who is not only reliable but truly cares. I would absolutely recommend Jezabell to anyone looking for a trustworthy, attentive, and compassionate pet sitter. I’ll definitely be booking with her again!”
“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.”
“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”
“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.”
“Alyson watched our two GSP’s for a quick trip to Naples. This was our first time entrusting the care of our girls and home to anyone else and she was great. Communication was great and she left the house spotless and out dogs happy and well cared for. So glad we decided to try out Rover because it’s going to make these quick trips more enjoyable knowing our dogs are being loved and cared for”
About: My first sitting job was at 14 for the neighbors across the street, during a month long trip. I have been sitting for friends on and off for the last 4 years, dogs and cats. I have a lot of experience with senior cats and cats who are on medication. I am currently an independent contractor, working as a performer. When in a show, weekends would be difficult, and at most a show run lasts 5 weeks. I also bartend at a theater, those shifts are only 4 hours, and are also only during the run of a show. My schedule always remains very flexible. Growing up I was the designated dog walker in the family, he was a very excitable and friendly dog so I have a lot of experience with dogs who pull on their leashes. I also was responsible for baths. I also have some experience with multiple dogs at a time, of all sorts of personalities. I have owned at least one cat since I was 6, I'm the girl who seeks out the cat at the party to hang out.
“First of all, I must say that Brenda and Dwain are great ambassadors for Dog setting. Prior to us going on vacation our dog Molly suffered two seizures in one day and we were about to go on vacation in a month and a half, having Brenda and Dwayne taking care of Molly and ensuring she got her medication while we were on a cruise in the Caribbean. There was a point during the vacation. Molly didn’t want to take her medication with the pill pockets. Dwayne and Brenda got some peanut butter and insured that Molly had her medication the entire time we were gone. I plan on using Dwayne and Brenda more often because of the care that they gave Molly, also they took pictures and gave us daily reports and how she was feeling while we were on the cruise. I would highly recommend if you have a pet that you love very much hire Brenda and Dwayne.. I want to thank both Brenda and Dwayne for taking care of our puppy. I highly recommend them. David & Denise. 🙏”
“Steffanie was great with Madelyn. Maddie was well cared for and she took steps to keep me informed while I was traveling. I really appreciate everything she did for us. I felt very comfortable with her caring and attentive manner. She is easy to talk to and cared for Maddie as I do. I will definitely ask her back when the time comes.”
“Sarah took care of Mora while we were in Puerto Rico for 6 days. She kept us up to date with how Mora was doing and sent us lots of pictures. We love that she was able to stay here at our home, so Mora did not have to deal with the stress of being in an unfamiliar place. ”
“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!”
“Thanya was a fantastic housesitter and we would be happy to have her back at any point in the future. Our large dog and two cats were well cared for and completely chilled out and happy when we got back home. Thanya kept us in the loop with plenty of updates and made sure to communicate with any questions/details we forgot in our initial meet and greet. I know our new kitten was a handful in particular so I really appreciate her patience and attention. Thanks so much Thanya!”
“Shelley was very communicative during her stay. After a rough start for not having the code to our door (completely my fault) things went very smoothly. Daisy and the house were well cared for.”
“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.”
“Alexis was amazing! She sent us pictures and kept us updated. The dogs looked so happy!! She stayed at our house, and we came back to a beautiful, clean home. We’d definitely use Alexis again!”
About: I’m patient with older dogs and pups just learning, as well as those missing their people and are scared. Grand mom to 4 sweet puppers. Lifetime pet family, we have guinea pigs, hamsters and every kind of dog and cat. I always helped neighbors when the needed pet care as well as years of volunteer work in shelters. Pets are family. I am a retired teacher due to injury and have a home based business so my hours are flexible. With enough notice I will do my best to accommodate care needed. I am unable to care for other pets in my home, we have 7 cats. I will follow all instructions given to lovingly care for your pets at your home
“Nick was an amazing sitter for my dog Leonard! The peace of mind was really something that was invaluable. Plenty of contact and accommodation for my travel schedule, really can't recommend him enough!”
“Kaitlyn was amazing with my dogs! She did an outstanding job house sitting and taking care of my two dogs for the weekend. She is a great communicator and sends updates as requested. I will definitely have Kaitlyn back to house sit and take care of my dogs in the future!”
The median cost per night for house sitting in Winter Garden is $45
Pet parents share their Rover experiences - Winter Garden
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.
How Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winter Garden sitters!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 $35.42 per night (as of July 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 July 2026, there are 3,113 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:
- 91% of sitters can help with special care needs
- 96% 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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