House Sitting Windermere Woods
Find a loving house sitter to watch over your pets and your home.
Over 12 pet parents in Windermere Woods have booked house sitting
Windermere Woods, 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.
“Ayshah stayed in our home to watch our two Frenchies. One was a puppy so he needed more care, time, patience and attention during our 3 night absence. She sent a daily picture.”
“Jasmine has taken care of our animals several times and has done a great job each time. I like having consistency when it comes to our animals caregiver and Jasmine is who we use exclusively.”
“Lanae was great! She was super friendly and our pup really liked her. She kept us updated and sent lots of pictures and videos. We will definitely book her again next time we need a sitter.”
“Our pets were well taken care of and we didn't have to worry about anything while we were away on vacation! We came home to happy pets and a clean well cared for home. Thank you so much Ariel!”
“This was our first time using a pet sitting service and it was absolutely amazing! Aniyah is so sweet and kind and she treated our Kingston like her own from the very first time of meeting him. Aniyah sent us pictures and updates throughout the whole stay which made us feel so relieved and comfortable knowing our boy was being well looked after. If you're looking for a dog sitter we highly recommend Aniyah, she was the best!!”
About: What sets me apart is the level of care, patience, and empathy I bring to every pet I look after. As a pet parent myself, I understand that pets are family—not just animals. Recently, I experienced the loss of my own beloved fur baby, which deepened my appreciation for the trust pet owners place in someone caring for their pets. That experience reinforced how important it is for pets to feel safe, loved, and comfortable when their owners are away. I pay close attention to each pet's personality, routine, and individual needs, whether that means extra playtime, a slower pace for a senior pet, or simply providing companionship and reassurance. I pride myself on being dependable, communicative, and detail-oriented. Pet parents can expect regular updates, photos, and the peace of mind that comes from knowing their pet is receiving genuine care and attention. My goal is not just to watch your pet—it's to make them feel cared for, understood, and loved while you're away. Pet care fits naturally into my daily routine. I work a structured schedule that allows me to plan dedicated time for walks, feeding, playtime, and companionship throughout the day. I enjoy being active and spending time with animals, so providing consistent care, attention, and updates to pet parents is something I genuinely look forward to. Whether it's maintaining a pet's regular routine, administering medications if needed, or simply providing extra affection and exercise, I make sure each pet receives personalized care and attention. I believe every pet is happiest when their routine is respected, so I take the time to learn each pet's feeding schedule, exercise needs, preferences, and any special instructions. In both my home and a client's home, I prioritize safety, comfort, and consistency. When caring for pets in a client's home, I strive to maintain their normal routine as closely as possible through regular walks, feeding, playtime, and plenty of affection. I also provide updates and photos so pet parents can feel confident and connected while they're away. When caring for pets in my home, I create a calm, pet-friendly environment where they receive plenty of attention, exercise, and supervision. I monitor pets closely, ensure they have access to fresh water, comfortable resting areas, and opportunities for play and enrichment throughout the day. My goal is always to make pets feel safe, loved, and well cared for while giving owners peace of mind knowing their furry family member is in good hands.
“Tiana was absolutely incredible. I definitely plan to book with her again and very soon. She took care of my dog and took care of my home while I was gone. I had no worries no concerns. She stayed in contact with me continuously throughout the time book with her if you have an opportunity to.”
“Sarah was perfect! It was a last minute booking and she was a godsend. She came to meet me and my dog Tegan before the trip, communicated and sent pictures and it was such a relief for me! She took amazing care of my dog, gave her her medicine and sent me updates. I will definitely use her again and again!”
“Sydney was great! She’s very personable and easy to interact with, which put me at ease since this was my first time using a pet sitter. Mimzy immediately felt comfortable with her and my shy cat warmed up to her, as well. Sydney was quick to respond to messages and sent daily picture updates. I’d recommend her to anyone and plan to use her again in the future.”
“Lois does a great job taking care of our home and our pup. We feel so much more comfortable traveling now that we know we have someone taking care of our dog and his separation anxiety.”
About: After spending my childhood years helping take care of dogs of many breeds and sizes, I naturally became a dog lover! I have been a dog owner for 15+ years to my pom-chi and I recently added a bichon-poo to my pack. They are treated like my babies as I have been nurturing them since they were puppies. Along side my mom's Chihuahua at times- the girls are very healthy, happy and playful. Outside of being a dog mom, I always have a love and connection to the animals and enjoy volunteering at the shelters and horseback ranch. I've administered oral and ear medication, post op care, given baths/grooming, brushing teeth, taken care of puppies... among other pet care needs. I signed up to provide these services as I enjoy the company of dogs. They're fun loving animals and a pleasure to take care of. I ensure to make your fur baby feel like they're at a home away from home. I currently live with 3 dogs and a cat of all different ages, while working from home full time. We have a routine of our own which other fur babies are welcome to join. I'm currently working from home full time and have time throughout the day to look after and care for your pets with plenty of play, rest, water and care. I have a fenced in back yard for the dogs to enjoy. My 2 other playful girls are there to join in on the fun while my senior dog can show off her favorite spots to lounge and sun bathe. I sometimes take the dogs for walks around my neighborhood so they're able to release energy and enjoy time outside the property. Although I am home, I do have crates available, if your dog prefers their own personal space. I've administered oral and ear medication, post op care, given baths/grooming, brushing teeth, taken care of puppies... among other pet care needs. In case of emergency, I'm 5 minutes away from a caring vet that I use as well as a 24 hour animal hospital.
About: I grew up with a chocolate lab and took in two cats in high school. I’ve primarily had cats as pets recently (and have become a master at giving cats pills). I’ve dog sat and cat sat for several friends. I always have a great time watching their home while spending time with their fur babies. I work fully remote for my 9-5 as well so any home with good wifi I can be there the whole working day. I have good experience giving cats pills and liquid medicine. I work remotely so I can work from any home with good wifi. So if your pet gets lonely I can keep them company all day long. For things that require a routine or specific timing, such as medicine, I set alarms and calendar reminders. I love getting a clear list of expectations from the pet owner of how to treat their specific pet. Every pet is unique and I want to make sure I’m caring for your pet in the way best for them! I’ve watched cats that needed three pills in the morning and one at night. I’ve watched dogs with special dietary restrictions where I had to tear up boiled chicken for them. I’ve also watched kitties that just want cuddles all day long and dogs who want to play fetch all day long. I always try to accommodate best I can!
“Great communicator and trustworthy sitter. Vanessa was a pleasure to work with and did a great job watching my fur babies in my home for a long weekend. I would book her again!”
About: I’ve been around dogs my whole life and am a current dog mom. I have cared for dogs for 10+ years for friends and family! My friends are the reason I have decided to come on rover to help even more people with their dogs’ training, care, and play. Even though I'm a dog mom I’m available to care for cats as well! I work nights so I can keep your pets cared for during the day. My schedule is pretty flexible so I can adjust as need be Having 3 dogs in my home to care for currently, I am not stray to managing various needs at once. I am able to provide enrichment time with play or walks and ensure your pets are safe and happy!
“We are so grateful for Chrysantheum for taking care of our pups during our long journey away. She was so sweet with them and kept us in the loop throughout the stay. Will be looking for her again the next time we’re out of town!”
About: I’ve cared for dogs through every stage of life, from raising puppies to supporting senior dogs with medical needs. My last dog was with me for 15 years and eventually became blind-she was also epileptic, so I’m very comfortable with patience, medication routines, senior care, and providing calm, attentive support to anxious or aging pets. I currently have a well-socialized 2-year-old Mini Schnauzer that I raised from 8 weeks old, so I understand the importance of structure, consistency, exercise, and positive interaction. As a retired military veteran, I’m dependable, detail-oriented, and home full time, which means pets in my care receive a lot of attention, supervision, and companionship throughout the day. I genuinely enjoy creating a calm, safe environment where pets feel comfortable and loved while their owners are away. Pet care fits naturally into my daily routine because I’m retired and home full time. I have a very flexible schedule, which allows me to provide frequent potty breaks, walks, playtime, feeding, medication support if needed, and lots of supervision throughout the day. Because I don’t have children or a demanding work schedule, I’m able to give pets consistent attention and maintain a calm, low-stress environment. In my home, pets have access to a safe, calm environment with a fenced yard for supervised outdoor time, exercise, and potty breaks. I also have a friendly 2-year-old Mini Schnauzer who enjoys the company of other dogs. I follow each pet owner’s instructions closely regarding feeding schedules, walks, routines, medications, crate preferences, and exercise needs. I understand how important consistency is for pets, especially when they’re away from their owners. In a client’s home, I focus on keeping pets comfortable by maintaining their normal routine as closely as possible while also making sure they receive attention, affection, exercise, and attentive care.
“Inaya is the sweetest person. We feel good knowing our boys are in kind hands. Always responsive, always dependable, always a joy to speak to. Thank you, Inaya, for taking such great care of Tank, Taco, and Kage!”
About: Hey guys! I’m an Army Veteran with 20 years of dog care experience. I have two dogs myself and trained my Cane Corso puppy to be a Service Dog. I understand that our dogs are our family. I am very friendly and accommodating and I will do anything I can to take good care of your pets. I look forward to speaking with you about how I can provide excellent service to you and your pets! I am currently in school and have plenty of time to care for your pets. I can accommodate any schedule and facilitate whatever you or your pet needs. I am very dependable and trustworthy. Whether I have your pets in my home or yours, you will receive adequate communication and pictures so you can rest easy knowing that your pet is in good hands. Your pet will be treated as if they were my own.
The median cost per night for house sitting in Windermere Woods is $50
Pet parents share their Rover experiences - Windermere Woods
I had a great experience with my dog sitter Kerry . She was incredibly kind, patient, and attentive with my clingy Gerberian Shepsky, which gave me so much peace of mind while I was away. She maintained a calm presence and clearly understands how to work with dogs that need a little extra attention and reassurance. She followed all of my house rules, stuck to the feeding schedule, and made sure my dog got regular walks and care. It was such a relief knowing everything was being handled responsibly and with genuine care. I would absolutely trust her again and highly recommend her to anyone looking for a reliable and compassionate sitter.
Mellanese was wonderful! She was polite, punctual, so sweet and great with our two golden retrievers. They loved her! Mellanese took good care of them and she reached out to us with updates. She left our home just as she found it. We hope she is available the next time we need a pet sitter.
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
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Popular requests for house sitting - Windermere Woods
Select a filter and find qualifying sitters offering house sitting.Sitters in Windermere Woods average 4 repeat house sitting clients
FAQs for House Sitting - Windermere Woods
Frequently asked questions about Rover
The average cost for House Sitting in Windermere Woods on Rover is $39.96 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 4,040 sitters on Rover offering House Sitting across Windermere Woods. 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 Woods 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 Woods 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 Woods 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 Woods. On Rover:
- 93% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 98% 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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