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.
“As always, Jackie was the perfect pet sitter. She gives our kitties lots of attention, cleans up their space, leaves everything immaculate, and sends us pictures and let’s us know how they are doing. They are very content when we get home.”
“Zana watched our two dogs and cat for a week and we are thrilled with our experience. Zana was extremely communicative and sent great pictures along with the updates. Our elder dog got sick and Zana was a champ handling some unexpected cleanup duty, leaving our house nice and clean. We sincerely hope we can rebook Zana the next time we leave town.”
“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!”
“Lois goes above and beyond. She genuinely cares about our dog PeeWee and it shows. It’s great to get pictures and videos of their time together. Our dog loves it when she watches him. We couldn’t be happier.”
“Amanda was wonderful with our pets while we were out of town. Our doggo is wary of new people, but Ananda has a magic touch and knew just how to make her feel safe. We came home to a very clean house and two happy, healthy pets.”
“Karenna is great! She always takes wonderful care of our girl and I love the photos she sends through the day. She has been amazing on short notice and with schedule changes.”
“Kelly watched our whole pack, 2 great Danes and our foster dog who needed meds and special attention. We are very happy with the care she provided and our house was well respected. We would definitely use her again!”
“We left our year old dog in the capable hands of Dan for nine days. He stayed in our house and took such a good care of our dog and our home. We will definitely book Dan for any future trips!”
“Viktorya was very communicative and patient from setting up the meet and greet and having our little Auggie meet her adorable Milo, to being open to taking Auggie out on an adventure (his favorite!) on a nice trail. Viktorya was attentive to our care instructions, and did a great job at tiring Auggie out. By time we got home, Auggie was a relaxed cuddle buddy after we, ourselves, had a long day out. She sent lots of photos and videos! Thank you for being such a caring person for our Auggie!”
“Damien is SUCH a fabulous human. The extraordinary care he gave towards my fur babies warmed my heart. He went out of his way to text me pictures and updates on how things were going. I absolutely plan on hiring him again! Thanks! Sarah”
About: Hi! I’m a dependable and caring dog lover with years of hands-on experience caring for pets. I’ve helped care for my family dog for the past 7 years, so I understand the daily responsibility, attention, and love that dogs need to feel happy and comfortable. In addition to caring for my own dog, I’ve also house-sat and watched dogs for others, including taking them on regular walks, sticking to feeding schedules and breakfast/dinner routines, giving them plenty of attention and playtime, and helping administer medications when needed. I know how important consistency and trust are when someone is caring for your pet, and I always do my best to make dogs feel safe, relaxed, and cared for while their owners are away. I genuinely love dogs and enjoy getting to know each dog’s personality and routine. Whether your dog is energetic and playful or more calm and cuddly, I’ll make sure they receive attentive, reliable care and lots of affection. I work a full-time 9–5 job during the week, but I’m available for dog walks, drop-in visits, and pet care in the evenings after work after 5:30. I’m also available for overnight stays during the week if needed, though I would be away during typical work hours (approximately 7:30 AM–5:30 PM). On weekends, I have much more flexibility and am available for walks, drop-ins, sitting, overnights, and extended care as needed. I’m happy to work with your pet’s routine and make sure they receive dependable, attentive care while you’re away. I’ve been caring for dogs for years through both personal experience and dog sitting for others, and I genuinely love spending time with animals. I do my best to create a safe, loving, and comfortable environment where pets feel relaxed and cared for while their owners are away. Whether a dog is playful and energetic or prefers calm cuddles and quiet time, I’m happy to match their personality and routine. I also understand how important consistency is for pets, so I take owners’ instructions seriously and always respect boundaries, routines, feeding schedules, walk preferences, medication needs, and any house rules. My goal is to make your pet feel as comfortable as possible and provide care that feels like a natural extension of their home environment.
“Seritta helped us with a last minute house sitting while we were at work. She was friendly, super responsive, prompt and accommodating. We received a bunch of great pictures of our puppy thoughout the day as well. Would highly recommend!”
About: I specialize with big dogs and elderly dogs. I'm a taller guy with a longer walking stride so larger dogs can get more for workout. My schedule is daily throughout the whole day. I normally like to plan 24 hours in advance but if my schedule is open I don't mind same day or last minute. Tuesday -Thursday from 11am-3pm I am not available I currently have no pets right now at my home I do have a rather large backyard. At the parents home, I do make sure that the pets are well fed and hydrated before leaving unless otherwise told. Disclaimer: If there issues at the home during my time at your residence and not disclosed before booking such as but not limited to: proper running water, working AC/HEAT, controlled pest infestation, power outage, violent pet(s), unsanitary conditions, health concerns without proper insurance you will liable for the vet bill and transportation cost or all day 24 hour care with a pet(s) that can not be alone for 3-4 hours than will incur with an extra inconvenience charge of $100 or more and/or cancellation with the help of Rovers support team.
“Breanna is a wonderful pet sitter! Both of my dogs immediately took to her, and even snuggled with her on the couch. She was timely, sent lots of photos of my pups, and communicated effectively. She even came by for a lengthy meet and greet before house sitting! I'd hire her again in a heartbeat.”
“Elvis is amazing! He stays at our house with our two big labs when we go away. He sends videos and pictures and ensures the boys are active and also loved! We can’t recommend him enough!”
About: Ive been around animals for as long as ive been alive . Having helped take care of a wide array of animals since a very young age. I’ve helped care for mice, hamster's, cats, rats, guinea pigs , small dogs and even dogs as bit as y mastiff’s .i have experience with nail cutting ,administering medicines ,feeding, giving water and playing with all types of animals.i have a undying love for animals and want nothing more then too help take care of yours whileyour gone! Im very very flexible in my schedule i can make any accommodations needed .im willing too stay over night and make any accommodations needed too help you take care of yours dog. I always made it a point too make sure my animals felt safe and secure.always paying attention too body language and there mood so i knew how too make them most comfy.i always made sure they were properly fed, watered and got enough exercise.
“Kalliope spent the holiday weekend taking care of my two dogs. She was communicative and share photo updates of the dogs over the weekend. When I came back my house was organized and cared for plus my dogs were happy. I will be booking kalliope again in the near future.”
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.
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 - Windemere
Select a filter and find qualifying sitters offering house sitting.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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