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.
“Best dog sitter EVER! My dog was so comfortable with Karen. She went above and beyond watching my dog. She played with her in the backyard, walked her a couple times a day, let her snuggle with her at night and Sunny didn't care that I came back.”
“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!”
“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 love dogs, I can talk about my own baby dog for days. I’m bilingual (Spanish and English), I love walking and I love pets. Mix them together and I’m there. I’m probably available when you need me so you can trust that I will take good care of your pets when you are not able :) I am a freelance photographer, so I work from home and manage my own schedule. I am available mornings, afternoons and evenings as needed :) I can walk pets, come and feed them or play with them or I can pet sit in your home. Unfortunately not available to bring pets to my own home
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.
“Ava did an excellent job caring for our 2 dogs! Her calm approach was perfect and we appreciated her flexibility. I would highly recommend Ava, she’s a natural with animals. Thank you Ava!”
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.
“Mark has dogsit for me on many occasions and does a great job. He’s very diligent, provides great updates, and most importantly provides excellent care for my dogs. They are older and sometimes have health issues requiring medications, so it is great to have someone I can trust them with.”
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.
“I booked JaRavia at the last minute, and she was incredibly flexible with scheduling a meet-and-greet. During the boarding, she was patient and understanding with my shy dog, Bear, who can be a bit distant. She checked in frequently, and by the end of the visit, Bear had started to trust her. I highly recommend JaRavia for her kindness and love of animals!”
“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!”
“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!”
About: I’ve been caring for animals for as long as I can remember and have been a trusted Rover sitter for over 4 years. I have three dogs of my own - a bichon frise, greyhound, and a pitbull. I also have a cat and a 🐢! I’ll care for yours as I would want someone else to do for mine. I can’t wait to meet you and your pet/pets! Pet care is my full time job and am available for drop in visits and house sittings when needed. I’m also happy to accommodate last-minute requests! Every pet is unique, and I take the time to learn their routine, personality, and individual needs so they feel safe, comfortable, and loved while you’re away.
“Mackenna is an actual godsend of a baby sitter. She goes way, way above and beyond for our fur kids (3 dogs + 2 cats). She keeps them busy through the day and they’re noticeably exhausted (in the best way) every time we come home. If I could give her 18 stars and keep her all to ourselves, I would!! Best sitter on this app by far!”
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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