House Sitting Windermere
Find a loving house sitter to watch over your pets and your home.
Over 80 pet parents in Windermere have booked house sitting
Windermere, 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.
“Karen was fantastic. I think Sophie did not want me to come back from my trip because she got along with Karen so much. Karen was extremely responsible. She walked and played with Sophie all the time. She also took great care of my house!”
“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!”
“Brittney was amazing with my fur baby!. She provided tons of updates each day and even a photoshoot! I would definitely recommend Brittney and would book with her again. I came home to a very happy and healthy puppy.”
“Nick was the absolute perfect sitter for our pup. This was our first time using Rover and we were a little worried about the process and he put our mind at ease. Now that we are home, our pup keeps going into our guest room to look for Nick, so our pup must have had a great time! Will definitely use again for our next trip!”
About: You would never know but I used to be afraid of dogs as a child. After we added a golden retriever named Joe to our family, I've been obsessed with dogs ever since. He passed away 6 years ago now and has left me longing to care for pups. I spent the summer helping my sister with her dog sitting business up north and am looking to do occasional dog sitting in the Orlando area. I am a preschool teacher during the week so I would be available to dogsit on the weekends. Or during the week if the situation allows. I would show your pup lots of love and attention! I feel comfortable going on long walks, playing fetch and keeping the dog on his daily routine to manintain his comfort while his family are away.
“Jonathan did an incredible job again! He has become our “go-to” sitter for our cat and dog. Our animals are so excited to see him and I suspect a little let down when they see us return. Lol. Jonathan provides such wonderful care and attention, sends updates and pics regularly, and it makes taking a family trip so much more relaxing knowing our fur babies are in great care. Can’t recommend him enough!”
“Taylor was tremendous for us during our vacation! She took great care of our dog and cat and took care of our house too! She was super caring and considerate of our pets and their senior status. While away, we did not worry one bit, which was such a wonderful relief! Taylor is tops!”
About: I’ve had dogs in my house my whole life! I love all kinds of animals and have even volunteered at an animal shelter in high school. My most recent experience is working at a vet and boarding center. I’ve learned so much more about pet care this past year as my best friend/roommate works at a cat cafe and has a degree in Animal Health. I’ve even started administering medicine! Being with animals is truly the best part of my day! I’m currently working remotely, so I have plenty of free time to take care of your pets throughout the day! I’m available most weekdays and weekends. :) My basic house-sitting service includes staying overnight with your pup so they have company & comfort in their own home, along with daytime care every 3-5 hours for potty breaks, meals, playtime, and cuddles. I currently live with 3 small cats, so I’m very well versed in taking care and providing entertainment for multiple animals throughout the day.
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.
About: I started working with animals at a dog kennel when I was 13 on top of always having multiple family pets. I started working with a veterinarian when I was 17 and was a veterinarian technician for 30 years. I have been house/pet sitting in clients home for around 25 years now stretching anywhere between Missouri Illinois Tennessee Florida South and North Carolina and Virginia. This is what I love to do. I have many many references to back up the excellent care I will provide for your fur babies and you. With in your home care I can also provide you with the security that your home will not be left un occupied as to ward off any potential problems.
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
About: I’m Brittney, married, no kids or pets of my own (apartment life). Previously worked in general practice and emergency room vet medicine. I love dogs and cats alike. Looking to love all over your fur baby and steal a few kisses! Central FL resident, Disney lover. Bed cuddles and couch snuggles are always welcome. I look forward to working with you and your fur baby. I appreciate open lines of communication and making both you and your pet feeling safe and cared for. Thanks for your time and consideration! Im working part time right now, with a lot of flexibility to care for your fur babies! I offer daily walks, home check ins, and in home boarding/house watching. I’m happy to come stay for any duration at your home with your pets to keep them feeling safe and in their routine. If you prefer I don’t spend the night, that is fine too! I have general and ER vet experience, I have an associates in annual science back when I thought I’d always work in vet med. I appreciate a good walk, just as much as any pup! Cats and fun toys are my favorite pastime.
About: I started dog-sitting while I was in high school. I am currently a medical student who would love to help take care of your animal (s). Being a medical student has strengthened my sense of responsibility, attention to detail, and compassion. I will carefully schedule my study blocks so I can provide dependable, attentive care. Time with pets is something I genuinely look forward to each week. I live in a pet-friendly apartment with plenty of safe outdoor space nearby for walks and fresh air. Inside, pets have a calm, clean, and comfortable environment where they can relax and feel at home.
“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!”
About: I grew up with plenty of pets and am well experienced on what it takes to care for animals. I’ve worked as a pet sitter and dog walker on the past. I also have my own Goldendoodle named Luna, she keeps me well trained 😂 I work from home and can work anywhere with WiFi/cell reception. My schedule is very flexible, So I can easily work pet care into my schedule without issue. I have a friendly, well acclimated Goldendoodle for play dates, I am experienced with animals that are both crate trained and non crate pets, so happy to follow clients preferences.
“Favianna did an amazing job watching our boys. She provided timely updates and lots of pictures which allowed peace of mind knowing our boys were in good hands. Will definitely be using her again!”
The median cost per night for house sitting in Windermere is $45
Pet parents share their Rover experiences - Windermere
My dog Penny is diabetic and I get worried leaving her any time I go on a trip , but Sarah was so kind , professional , and incredibly attentive to Penny. She warmed up to Sarah really quickly and I received the cutest updates / photos during my entire trip. Couldn't recommend her enough!
This was our first time to leave our two senior pups. We were so nervous, but Mason made it super simple to enjoy our vacation, knowing that she was taking care of them. She sent us pictures and updates while we were away, putting us at complete ease. Mason was a dream, and we’re so glad she took care of our babies.
Elizabeth was amazing!!! She was a great communicator, providing frequent updates and photos of our pets while we were away. She was equally attentive and loving to our dog and our cats. I never worried one bit about their well being because I knew they were in great hands! We will be rebooking!
Michelle was Amazing. So great with our little pup. She was flexible and so accommodating. We were able to do the parks thanks to her accepting a last minute request! She sent us adorable updates. It is clear she loves animals and is so good with both the parents and the furbabies. Thank you, Michelle for helping us have a great vacation!
Thanya went beyond expectations staying at our home and caring for our dog Bogy! She sent many photos, tried many options to get Bogy to take his Meds, my house was well kept! It look just as I left it !!! What a pleasure to come home to ! I highly recommend Thanya and plan on booking with her again!
Yanran cared for my four cats and one dog and we were very pleased with her care. I got photos and updates daily, the pets were all happy when we returned, she let the dog sleep in bed with her as he was obviously missing his family, and the house was clean when we returned. We greatly appreciated her care and will be booking her again soon!
Our doggy enjoyed another wonderful booking with Liz! We always feel confident that we are leaving our dog in the very best care when we leave him with Liz. She is quick to respond, sends updates and pics, and is missed by our doggy when she leaves. We have already booked her again for next month and will continue to do so! Thank you, Liz!
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 - Windermere
Select a filter and find qualifying sitters offering house sitting.Sitters in Windermere average 4 repeat house sitting clients
FAQs for House Sitting - Windermere
Frequently asked questions about Rover
The average cost of House Sitting in Windermere is $56 per night as of October 2026. Most bookings cost between $30 and $83 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 3,067 sitters on Rover offering House Sitting across Windermere. 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 Windermere 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 Windermere 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 Windermere 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 Windermere. 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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