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.
“Jezabell was absolutely wonderful! During our meet and greet, she took the time to really understand our dogs’ routine and asked thoughtful questions. Throughout her stay, she sent regular updates and photos that gave us so much peace of mind. It was such a relief knowing our pups were in caring, capable hands. We came home to happy dogs and a spotless house. We couldn’t have asked for a better experience. Highly recommend hiring Jezabell. She’s amazing!”
“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.”
“Alyson Stepped in quickly right before a storm and our previous house sitter leaving. She was able to follow directions even though we weren’t around and our cats were nervous due to a storm that was going to hit.”
“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.”
“Skylar was awesome. I needed a last minute dog sitter for a couple of hours and Skylar was kind enough to do a last minute meet and greet the day before I needed her. Would definitely recommend and will book again when I need help with my doggies again!”
“Diahann is amazing! My senior Miniature Schnauzer loves her. My Maltese suffered trauma while he was at a boarding facility that really shook him up. However, with Diahann, he’s so happy to see her and loves playing with her. She’s truly an answer to my prayers.”
“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”
“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!”
“Steffanie was wonderful with our dog and fussy cat. We got updates and pictures from her daily. She went above and beyond in everything she did. I would have her sit with our pets again in a heartbeat. Thanks Steffanie. 👏”
“Shelley was fantastic taking care of our animals while we were away. She went above and beyond our expectations and provided tons of updates. The pets were all very happy and well cared for, and the house was nice and tidy when we returned home. We will definitely be booking her again when we need a sitter!”
“Ella took great care of our puppies, house-sitting while we were out of town. She fed/walked the dogs as requested and even brought in our mail, shoveled the snow in the driveway and took the garbage out before leaving! Truly a gem ✨”
About: I’ve taken care of dogs my whole life! Since I was a kid, I’ve had real responsibilities caring for my four dogs. I also help neighbors with pet care while they were away, from feeding to walking. Last summer, I worked at pet paradise as a playtime coordinator. In this role I supervised play groups, read body language, and made sure every pet was safe and having fun. I’m a recent graduate from UF and my schedule is very flexible right now. I’m dedicating time to study for the LSAT, but that gives me a consistent routine at home, which makes me a reliable option for regular walks, drop ins, or longer sits. Your pets safety is my top priority, and I’ve take multiple online courses on this for my previous pet care job. I stay alert and know how to stop signs of discomfort or stress. I always follow specific care instructions from the parents. If anything unexpected comes up, I communicate right away, I treat every pet as if they’re my own!
“Sarah was great. We went away for two weeks and had to find a pet sitter last minute. Sarah communicated well, took good care of the pups, and left the house cleaner than when she arrived.”
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
“Madison was great with our 3 boys right from the beginning! We have a very anxious dog and she did so well with keeping him calm and giving him his medicine to keep him relaxed while neighbors were setting off fireworks. She took great care of our house and I look forward to having her stay with our boys in the future!”
About: Hi! I’m a true animal lover with a big heart for both dogs and cats. I understand that pets are family, and I treat every animal in my care with the same love, patience, and attention I would give my own. Whether your pup needs long walks and playtime or your cat prefers quiet companionship and gentle care, I’m happy to match their unique personality and routine. I currently work part-time and have a flexible schedule, which allows me to accommodate drop-in visits and pet sitting in your home. Whether your puppy needs patience, playtime, and consistency, or your senior dog needs a slower pace and extra TLC, I have experience providing attentive, compassionate care for both. I’m happy to follow your pet’s routine closely, provide regular updates and photos, and make sure they feel safe, comfortable, and loved while you’re away. My goal is to give you peace of mind and keep your furry family members happy in their own familiar environment.
The median cost per night for house sitting in Winter Garden is $45
Pet parents share their Rover experiences - Winter Garden
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.
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