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.
“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!!”

“Ayshah is truly one of the best sitters I’ve found on rover. I believe she goes above and beyond for both you as a pet parent AND your dog. So impressive, highly highly recommend.”


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.”


About: I provide intentional, attentive care, treating every pet like my own. I don’t just “watch” pets; I engage with them, learn their routines, and make sure they feel safe, comfortable, and loved. I have hands-on experience with puppy training (basic commands, leash manners, crate and potty training), along with public access and service animal training. I’m patient, consistent, and focused on building strong habits. I’m also experienced in senior pet care, including gentle handling, medication support, and slower-paced walks tailored to their comfort and mobility. * For cat care, I respect each cat’s personality, whether they’re social or more independent. I’m attentive to litter box cleanliness, feeding routines, enrichment, and creating a calm, stress-free environment. Whether your pet is high-energy or needs extra care, you can count on dependable service, clear communication, and regular updates with photos. Pet care fits naturally into my day since I work from home, which allows me to be present, flexible, and attentive. I’m able to maintain consistent schedules for feeding, walks, potty breaks, and playtime without long gaps in supervision. Because I’m home throughout the day, pets get more than just check-ins. They get companionship, engagement, and close monitoring. I can easily adjust to their routine, whether that means midday walks, reinforcing training, or providing extra comfort for senior pets. My schedule allows me to give pets the time, structure, and attention they deserve while keeping owners updated with regular communication and photos. Your pet’s safety and comfort is my top priority. In my home, I provide a clean, calm, and pet-friendly environment with a secure fenced yard for safe outdoor breaks and play. Pets are always supervised, and I’m mindful of introductions, boundaries, and maintaining a low-stress atmosphere. When caring for pets in a client’s home, I respect your space and stick closely to your pet’s normal routine to keep things consistent. I double-check doors, gates, and leashes, and I’m attentive to any changes in behavior, appetite, or energy. Not only do I take the time to understand each pet’s needs, triggers, and preferences, and I’m experienced with puppies, seniors, and pets in training. Whether it’s reinforcing routines, administering basic medications, or providing a safe, structured environment, I aim to give you complete peace of mind with regular updates and photos.
“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.”

“Lanae took such wonderful care of my baby Ollie! Such great updates of him playing, cuddling, and eating his fave treats! We even were able to work through a small eating issue thanks to her communication skills! Would definitely rebook with Lanae in the future!”

“Ashley was so wonderful with our pup! She came when we needed a last minute dog sitter and sent the best photo updates while we were out! We would definitely call Ashley again—she’s great and will take good care of your pup!”

About: I’ve been taking care of dogs since I was 6 I take care of dogs bc I like animals. friends an family have relied on me taking care of there dogs an pets. I’m currently a pets owner right now I take care of my own dog for instance I feed him of course and take him for walks daily. I have a big back yard although i have no fence and i have a friendly dog for your fur baby to play with but mostly I have the dog in the house
“Sean was very communicative and left our house super clean! He took such good care of our senior dog and also checked in our chickens every day. I would definitely recommend Sean to anyone who needs someone they trust to take care of their animals and home!”

About: I am a 24 year-old full time worker trying to make some extra money on the side for life expenses. I am always ready for any lovely animal whether they are a bit scared, old, or even too friendly I would love to take care of your pets! Working with both dogs and cats I have experience giving care as well as very basic training when needed in a long term space. I have interned at an exotic animal care location and would love to get experience taking care for your pets as well! I take care of my own dogs at home and would love to add your pets to my schedule! I do currently work part-time nights on some days but as long as your needs fall on one of my free days or earlier in the day of my work day I would be glad to be of service to you! I care for 2 dogs at home currently that get along with everyone they meet and 1 cat that needs a little warming up to get to know you. They are feed 2 times a day as well as taken out before eating for ample play time. At random times they are given even more play time and trained if time permits it! I would love to care for your pets the same way I do to my own and would give nothing but love towards them the way you do so they feel just as safe and happy as if you were still there with them! I have been trusted with other family members pets and put pet safety at the upmost priority.

“This is a repeat booking. Sydney is a conscientious house sitter, they are great with the kitties, show up on time and even took care of taking out the trash and washing the bedding. 10/10 would recommend!”

About: I’ve always had a special love for animals, especially dogs. I truly believe pets are family, and they deserve patience, love, attention, and someone who genuinely enjoys spending time with them. I love getting to know each pet’s personality, whether they’re playful and full of energy, shy and needing extra time to warm up, or just looking for some extra cuddles and companionship. I understand how important it is to feel comfortable leaving your pet with someone you trust. I’m experienced with caring for dogs through my own love and connection with animals, as well as spending time with pets belonging to friends, neighbors, and family. I’m comfortable with small to medium sized dogs and enjoy providing walks, playtime, potty breaks, feeding, and lots of love and attention. My goal is for your pet to feel safe, happy, and cared for while you’re away and for you to have peace of mind knowing they’re in good hands. I have a flexible schedule that allows me to give pets the time and attention they deserve. I enjoy spending time with animals and would love to make pet care a part of my routine. I’m someone who loves creating a calm and comfortable environment, and I enjoy taking the time to make pets feel safe and cared for. I’m happy to follow your pet’s normal routine, whether that includes walks, playtime, feeding, or simply keeping them company. I know every pet is different so I always take the time to learn what makes your furry friend feel comfortable and happy. Your pet’s safety and comfort will always come first. I know how much trust it takes to leave someone with your furry family member, so I take that responsibility seriously. I carefully follow your instructions, respect your home, and make sure your pet feels comfortable and cared for. I pay attention to details like their behavior, routine, and any changes they may show. I’m especially mindful with smaller and calmer dogs, making sure walks are safe, playtime is enjoyable, and your pet gets plenty of love and attention. I’ll also keep you updated with pictures and messages so you can relax knowing your pet is happy and being cared for.
About: Love taking care of my furry friends. They will brighten your day in a heart beat. Let me help take care of your furry friend Pet care is a natural part of my daily routine at Scoop & Stay. I structure my day to include morning walks, mid-day play sessions, and evening wind-downs to ensure each pet gets the attention and care they need. Whether it’s a quick potty break or extended playtime, I make space in my schedule to prioritize the well-being of every furry guest. At Scoop & Stay, I prioritize a clean, loving, and secure environment for every pet in my care—whether in my home or yours. I follow detailed routines for feeding, potty breaks, and playtime, and maintain sanitized spaces to prevent the spread of germs. I ensure all pets feel safe, respected, and loved, treating them as if they were my own. Regular updates and check-ins are provided to give pet parents peace of mind.

About: I started caring for pets in school by looking after classmates pets and later helping neighbors. I’ve been around animals my whole life and currently have four French Bulldogs who are like my sons. I love treating pets as family, celebrating their lives, and including them in my daily routine whenever possible. I have experience with both puppies and senior pets. I am patient, reliable, and attentive, and I always make sure pets feel safe, loved, and well cared for while their owners are away. I am currently on vacation, which allows me to have a flexible schedule to play with, walk, and fully care for your pet. I am available from 10:00 AM to 9:00 PM, both weekdays and weekends. I provide reliable and attentive care in the client’s home. I always follow instructions carefully, respect the home, and ensure pets are safe, comfortable, and well cared for. I give them exercise, attention, and affection to keep them happy and relaxed.
“Christian was absolutely one of the best sitters we’ve ever had! Our regular sitter was unavailable, and Christian may have just taken the top spot. He was incredibly responsive for a last-minute booking, and it was obvious from the start that he genuinely loves dogs. Our boys were very well cared for, and we felt completely at ease knowing they were with him. We would book with Christian again without hesitation!”

About: My name is kevin bell I am a Biology major at Stillman college working towards my veterinarian career. By letting me care to your little pup you’re giving me the opportunity to expand my knowledge on everything it takes to care for our furry loved ones. I have experience with all level energy dogs I’ve spent my younger years around many animals. your in good hands, but I’m not all-state Lol. This is my full time til my return to school so I have A LOT of availability so you can always book me regularly and you and your pup will be satisfied. I have a fenced in backyard and 2 pups to keep your dog company and we have multiple crates that they can comfortably be in if they need be.
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
It's that easy! All payments are processed through Rover's secured platform
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 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 3,990 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:
- 94% 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.





