House Sitting Windermere
Find a loving house sitter to watch over your pets and your home.
Over 75 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 amazing! She was very attentive and a great communicator. She kept us informed about the pups regularly and provided photos. Our little pack welcomed her with open paws. She took great care of our fur babies and our home. We will definitely have her take care of our pups next time we are out of town.”
“Alyson stayed at our house with our spunky pup for 4 nights. She took good care of both our home and our dog, kept me updated, and we came home to a happy, well-cared-for pup.”
“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!”
“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.”
“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!”
“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 :)”
About: I’ve adored animals my entire life and have taken care of many different types of pets for the last 15 years ranging from my neighbors cats and dogs, to my friends reptiles, and my many pets over the years. Consisting of walking, playing, feeding, bathing, and occasionally overnight stays with their animals. I’ve owned many fish, hamsters, a bunny, duck, and 6 dogs over the course of my life. For the past 8 years I’ve been raising my two beautiful female Rottweilers who are giant teddy bears, full of energy and love. I’m currently working around my full-time job. If you’re looking for care outside of my availability, send me a message and I’ll do my best to accommodate you. Availability: Sunday after 7pm Monday after 5pm Tuesday before noon Wednesday ALL DAY Thursday after 5pm Friday after 3pm Saturday ALL DAY As of now, I offer both dog walking and day visits at your home, and will eventually be offering dog boarding services. I am physically fit to keep up with your dogs no matter their energy level and will give them plenty of exercise during walks throughout your neighborhood or a nearby park. I am well organized and a clean person who will treat your home like my own!
“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:)”
“Sarah took a last minute booking when plans to go out of town for the weekend popped up on our schedule. She was amazing with our babies and sent a few updated photos. She left our home clean with the dogs poop picked up. We will definitely book with her again in the future!!”
“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!”
“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!”
“Ariella did an amazing job! Our dog had a stomach issue while we were gone and Ariella took such great care of her, even offering to take her to the vet. She went above and beyond, washing blankets and sheets, handling a dog that threw up every night she was here. We are so grateful Ariella was with our dog when this happened.”
“Our doggy enjoyed having Liz watch him again! Liz is attentive to his needs, sends us cute pictures of him, and is very communicative. When we arrive home, our doggy is relaxed and happy. We are so happy to have found Liz!”
“Mason was great at taking care of our 10 years old pup, Bender, for a weekend at our home. She was willing to do meet and greet first and both I and Bender felt very comfortable with her right away. The house was clean when she left. I would ask her to care for Bender again.”
“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!”
About: Hands on experience caring for animals I provide dependable, compassionate care tailored to each pet’s unique needs. I’m comfortable with a wide variety of animals from large to small. I am retired and I do Uber on the side. I have very flexible hours and I’m available from dog walking, spending time with your animals to staying with them in your home to house sitting. What sets me apart is that I treat every pet as if they were my own. I understand that every animal is different, and I will take the time to learn their routines, preferences, and any special needs that they may have. Whether your pet needs lots of playtime, quiet, companionship, medication or extra patience, I provide loving a attentive care so you can have peace of mind while you’re away. My goal is for both you and your pets is to feel completely comfortable, knowing they’re in experienced, caring and trustworthy hands.
“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.”
The median cost per night for house sitting in Windermere is $45
Pet parents share their Rover experiences - Windermere
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!
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!
Elizabeth is incredible!! She is so caring and took amazing care of our dog and cat. She sent lots of pictures and updates and answered any questions we had very quickly. What I loved most was that you can tell our boys got lots of love and we came home to two happy pets!
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!
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 - 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 for House Sitting in Windermere on Rover is $55.5 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 3,090 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 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 Windermere. On Rover:
- 90% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 95% 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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