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.
“She was excellent. I highly recommend her. We will be using her, again. Our dogs loved her. Even our timid dog snuggled her. Excellent communication. Left the house very clean and tidy.”
“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.”
“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. 🙏”
“Yelena was great, easy to reach and communicate with. Skai loved her and she even left her a new toy to play with! You can tell she is very experienced with dogs especially being that Skai can be very hyper but it did not seem to bother her at all. I would definitely book again, she made things very easy and smooth thank you :)”
“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.”
“Alyson has gone out of her way to make sure our girl is well taken care of! We appreciate all she has done and will continue to book with her knowing that Gracie is in good hands 💕”
“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!”
“Elizabeth was great with my three very different personality dogs. They are little with big personalities! She managed them all so well, no accidents in the house, and gave them love as if they were her own. I’m happy to have found someone reliable and patient to be with our pups when we go out of town:)”
“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.”
“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!”
“Tiffany was so great! She arrived as promised and even took our dog out one extra time for us since we were returning late. The dog was happy and well- cared for, left the house in great shape. Will definitely use Tiffany again and highly recommend!”
“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!”
“Karrie watched our two GSP’s for a long weekend we were away. We got some good pics of the girls to let us know all was well and it definitely made being away from them easier. Karrie is friendly, personable and the girls seemed to enjoy their time with her.”
“This was the longest stretch we have left our dogs and we came home to two healthy, happy pups and an immaculate home. We are eternally grateful we have found Sarah! She takes great care of them and is a great communicator. ”
“Nathan took such great care of our pup Winston! He communicated frequently with pictures and updates. Winston seemed very happy and at ease with him. I definitely recommend Nathan!”
“Nick was a life saver. We needed to travel last minute and was incredibly personable and attentive to our needs, even while planning over Thanksgiving weekend. He kept us updated with daily messages and pictures of pets, and felt more like a family friend helping us out rather than a stranger just hired on the app. I would highly recommend Nick for any pet care needs. Thanks Nick!!!!”
The median cost per night for house sitting in Winter Garden is $45
Pet parents share their Rover experiences - Winter Garden
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.
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 $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.
Connect anywhere with the Rover app
