House Sitting Windemere
Find a loving house sitter to watch over your pets and your home.
Over 7 pet parents in Windemere have booked house sitting
Windemere, 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.
“Kelly was amazing! Right on time to allow me to get to work even with first introductions, very kind, and sends updated pictures throughout the day to keep you as the owner comfortable that your pets are in safe hands! My pets took to her immediately and were very comfortable with her here. Will use again.”
“Zana was awesome! Our dogsitter caught Covid a few days before our weeklong vacation, so we really appreciated that Zana was available last-minute, did a meet and greet, and took great care of our senior pup and energetic 3-year old pup. She sent us lots of pictures so we wouldn't miss them so much. We highly recommend and would book Zana again!”
“Jackie is the best! Keeps me updated a few times a day. And my anxiety is much better about leaving Jasper b/c I know Jackie is here. She even strips the bed, washes, & dries the sheets. A dream cat & house sitter💛”
“Kaitlin was amazing! Will definitely rebook. My animals were so loved and well taken care of. She did a great job at communicating and sending updates. Left my house very clean and I returned to happy pets!”
“Raimey took wonderful care of my two kitties! It’s always stressful leaving behind pets when you go vacation but she made us feel very comfortable and reassured throughout the entire process. I got regular updates on their meals, playing and sleeping schedules. She’s very reliable and I will definitely be booking her again :)”
About: I’m currently training to be a therapist so I have a keen sense for emotions… pets included! I’ve dog sat for family numerous times and am hoping to branch out. I love being around animals, am a very easy guest, and will happily send you any pictures of your pets! I have class 1-9pm on Monday and Wednesday but am mostly free otherwise! I get up early to swim twice a week (Fri and Sat), but can go straight back if needed. I don’t do much, so I’m pretty open! I’m willing to do whatever I can to help the pet feel safe and welcomed. Whether they want to play, rest, eat, or walk, I’m happy to help them out!
“Our dogs had another amazing stay with Amanda! Amanda is so communicative and leaves our house is such perfect, clean condition. Most importantly our dogs love her and are always such well taken care of with her :)”
“Connie provided excellent care for our two dogs and two cats while housesitting. She sent daily updates and photos and everyone always looked so happy and content. She went above and beyond to tidy up and provide plenty of exercise for our two pups. She is professional, communicative, and a true animal whisperer!”
“Jeff was great. Very responsive, and he sent regular updates on my dog and cat. They were well taken care of, and my house was clean and tidy when I got home. Thank you, Jeff!”
“We couldn't be happier with Breana's care for our home and cat while we were away. She was a fantastic communicator from the start and we never had to wonder how things were going because Breana sent regular photos and updates that gave us total peace of mind. We returned to a spotless house — everything exactly as we left it. It was clear that Breana treated our home with real care and respect. Most importantly, our cat was happy, relaxed, and clearly well looked after. We'd trust Breana again without hesitation and highly recommend her to anyone looking for a responsible, communicative, and genuinely caring house and pet sitter!”
“Josephine was reliable and responsive. She very clearly adores animals and this was like a vacation for my dog to walk and hang out with her overnight. Would definitely book again.”
“Samm is amazing with our 4 (yes, FOUR) dogs! All members of our furry family are adopted and come from varying backgrounds. Samm is SO patient with each and every one of them, to include our big (115 lb) baby Scooby, who always needs a few minutes to get close to people. Scooby can take a lot of patience when he's getting to know someone and has taken MONTHS to warm up to people in the past (some people he will NEVER get near) - but not Samm! In just a few minutes, Samm had Scooby snuggling with her and even letter her walk him. Totally unheard of! We are so glad to have found Samm to take amazing care of all of the dogs when we're out of town and we know we can trust her to make sure everyone gets lots of time to play and exercise. Plus, knowing that we worry that Scooby might give people trouble, Samm thoughtfully sends us regular updates to reassure us that everything is going great! We cannot ask for more! :)”
“Kate was so wonderful to work with. Provided regular updates, and was super sweet to our girl when she was having some tummy issues. Went above and beyond to address it and was so wonderful. It really took the stress out of going away on a trip, and she took great great care of our place. Highly recommend Kate!”
About: Animals have always been an important part of my life, and I genuinely enjoy helping them feel safe, cared for, and loved while their people are away. I’ve cared for animals throughout my life, from family pets growing up to paid pet and house sitting for friends and private clients. I’m a longtime yoga teacher, so creating a calm, grounded environment comes naturally to me. Friends, clients, and neighbors have trusted me to care for their dogs, cats, and homes, and I understand how important consistency, communication, and reliability are. Whether your pet loves long walks, quiet companionship, or playful interaction, I’ll care for them with the same attention and respect I’d want for my own family. I’m a part-time yoga teacher with a flexible schedule, which allows me to provide attentive care for your pets. I carefully plan my schedule around the animals in my care and will always discuss my teaching times with you in advance. My priority is making sure your pets are safe, comfortable, and well cared for while you’re away. I understand that inviting someone into your home or entrusting them with your beloved pet requires a great deal of trust. I treat every home with respect and every animal with patience, kindness, and attentive care. I follow your pet’s routine as closely as possible, communicate regularly with updates and photos, and will always reach out if I have any questions or concerns. My goal is for you to return home to a happy pet and a well-cared-for home. If boarding is needed, I provide a quiet, calm, smoke free home and accept only one family’s pets at a time so I can give them my full attention. I carefully follow each pet’s established routine and will communicate regularly with updates and photos. My goal is for your pet to feel safe, comfortable, and loved while you’re away.
The median cost per night for house sitting in Windemere is $50
Pet parents share their Rover experiences - Windemere
Brooke was amazing! She went above and beyond to make sure my dog was well cared for and she communicated with me everyday. I got lots of pictures and updates on my dogs medication and food and walks. I had never left my dog with someone I didn’t know before, and Brooke made me feel so comfortable. I couldn’t be happier! She also stayed at my home while I was away and left everything super nice and neat, and took great care of everything while I was away. Truly 10/10!!!
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 Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Windemere sitters!Sitters in Windemere average 4 repeat house sitting clients
FAQs for House Sitting - Windemere
Frequently asked questions about Rover
The average cost for House Sitting in Windemere on Rover is $61.05 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 3,110 sitters on Rover offering House Sitting across Windemere. 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 Windemere 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 Windemere 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 Windemere 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 Windemere. On Rover:
- 92% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 94% 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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