House Sitting Windward Trail
Find a loving house sitter to watch over your pets and your home.

Over 71 pet parents in Windward Trail have booked house sitting
Windward Trail, 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.
About: I’ve been caring for dogs for most of my life. At 13, I started a neighborhood dog-walking business for owners who were “too pooped to walk their dogs,” which quickly grew into in-home and overnight dog sitting. I got my first dog at age ten and trained her myself, and I’ve since attended multiple dog training classes because I genuinely enjoy working with dogs. Over the years, I’ve cared for labs, golden doodles, pit bulls, and more for families that I have worked with through high school and college. Now that I have my own home (next to a park) I’m excited to start again with plenty of space, structure, and love for every pup. Pet care fits naturally into my weekly routine. I’m an emergency nurse and work every Monday and Tuesday and every other weekend, which gives me most weekdays free and flexible for walks, drop-ins, and sitting. On my off days, I enjoy staying active with walking, running, and hiking, and I love including dogs in those activities for both exercise and enrichment. I plan my schedule carefully to ensure every pet receives consistent attention, timely care, and plenty of love. Safety and trust are my top priorities. As an emergency nurse, I have strong medical training and stay calm and attentive in all situations, including emergencies. I closely follow pet parents’ instructions and routines in both my home and theirs, ensuring a low-stress, loving environment. I provide supervised play, secure walks, and plenty of mental and physical stimulation. Living next to a park gives dogs safe space to explore, exercise, and enjoy structured outdoor time while always being carefully monitored.
About: I’ve taken care of my family and friends puppies often, whether they’re big or small. I can administer any medications, give extra snuggles, really anything needed! I’m currently a college student at Greenville Technical College. Monday-Thursday I have one class each day til 11am, otherwise I’m completely free to take care or your pets! I care for pets in clients' homes by following their routines, providing playtime, walks, and all the love they need. I ensure they feel safe, comfortable, and stress-free while sticking to their usual habits.
About: Growing up, my family always had at least two dogs at all times. Although I don’t have a dog of my own, I love taking care of and spending time with other people’s dogs. 🩷 I am a teacher by day (Aug-end of May) and dog sitter on the side! I love kids but dogs truly have my heart. The bigger, the better! I am a teacher, so I will be gone from 6:30am-3:30pm. I have watched dogs while I’ve been at school who are used to be alone for an extended amount of time but but I will walk them prior to leaving for work and then spend the evening with them once I get home. :) ***If your dog isn’t used to being alone while I would be at work, I do have someone who can check on your pet and also take them out midday while I’m at work! :) Although I do not have a fenced in yard, my neighborhood community has a fenced in dog park area to give your dog(s) the space and freedom to roam as needed. :)

About: I grew up on a farm, so I’ve had the opportunity to work with many different kinds of animals. Since that time, I’ve rescued a few cats and dogs with mental and physical issues. I’ve learned that each animal has their own personality and needs and am happy to provide what they need. I have a flexible schedule. I am able to give your pet the time they need. Whether it’s a potty break, playtime, or some cuddles. I am able to follow instructions. I understand how important it is to keep your pet on a routine, especially when you are not home.
About: I have always grown up with pets: 3 dogs, 1 cat, and a beared dragon. I have helped train a puppy, cared for a dying senior dog, and everything in between. I have experience with pets who have high energy, anxiety, dietary needs, and physical disabilities. Family, friends, and neighbors have trusted me to pet sit, drop in, provide over night care, and walk their dogs. I have worked at a dog groomer for over 2 years, which has given me experience with a wide variety of animals and their temperaments. I’m a full time student at Clemson University who has most afternoons/ evenings and weekend free to care for your pets! I am studying wildlife conservation so spending time with animals is one of my favorite things to do! Following instructions, I can care for your pet however you direct me to. I am comfortable taking your dog for walks/ hikes, playing indoors and outdoors, dosing medications, keeping up with training, and providing all the love and comfort your pet will need while you are away!
“She was amazing with our fur baby Milo! We can not recommend her enough! she went above and beyond in everything with him. She even took him to a place for him to play and now we have a new spot to take him that we didn’t know about. Our baby was happy and well taken care of with her! If we ever need someone again I know who our first call will be!”

About: I have a 16 year old Maine coon named Marv. He has hypothyroidism and chronic kidney disease so I know what it takes to give your little buddy what they need! I had to give him daily medication and am comfortable doing the same for your pets. I have had dogs and cats in my household for almost my entire life. Your pets will love me. I've even convinced a pet turkey to love me! I am a full time student at Tri-County and am also taking classing during the Summer. I typically have full availability with the exception of my classes. My class schedule during the Fall 2026 Semester when I will be unavailable: Mon 2pm-4:30pm, Tues 8am-1pm, Wed no class, Thurs 9am-1pm, Fri no class. I also have a work-study job with flexible hours. I love to play with cats and dogs to keep them active. Walking dogs is a fantastic excuse for me to get some exercise and to hang out with a furry friend!

About: I have over 8 years of experience caring for both dogs and cats. As a pet owner myself, I’ve had multiple dogs and have provided pet sitting services for countless dogs and cats over the years. I have experience with puppies, senior pets, and animals that require medication or extra attention. The most I’ve cared for at one time is two dogs and two cats, so I’m comfortable managing multiple pets while ensuring each one receives the care and attention they deserve. I genuinely love animals and have the flexibility to provide reliable, attentive, and compassionate care for your pets while you’re away. Over the next few months, I’ll be out of school, which gives me a very flexible schedule. I’m available throughout the week and on weekends to accommodate your pet care needs, whether it’s drop-in visits, walks, or overnight care! Your pet’s safety and comfort are always my top priorities. I take the time to learn each pet’s routine, preferences, and any special care instructions so they feel as comfortable as possible while you’re away. I treat every home with respect, keep a clean environment, and make sure doors, gates, and other safety measures are always secure. I’ll also send regular updates and photos so you can have peace of mind knowing your pet is happy and well cared for.

About: I currently work at a doggy daycare and have been working there for nearly 6 years. I have a certificate in pet first aid and CPR, currently in medical school, and I’m a qualified dog-lover! Even before my employment, I have had years of experience dog-sitting for people in my neighborhood. (Since before I could drive.) But my job has allowed me to learn difficult medication schedules, puppy care, senior dog care, and how to work with dogs as little as yorkies to as large as great danes. If I’m not taking care of dogs at work, then I am at home with my own babies. I have a dog and two cats, and my entire world revolves around them! I work best off of routine, and I will admit that I get a little flabbergasted when I don’t have a good schedule. My dogs are house-trained and fed twice a day during breakfast and dinner. However, when dogsitting I have been given crazy schedules to work with— so don’t feel bad if you think have a lot! My dogs aren’t crates at night and typically prefer to sleep in bed with me, but I understand and value the importance of crating. I don’t mind going on walks, either! My german shepherd goes everywhere with me, so please let me know if your dog enjoys going out. (Downtown, hiking, or just a walk in the park.)
About: I am a compassionate warm hearted person. I have always adored animals and look forward to spending time with new ones. Animals are a huge part of my life and I would love to help others feel safe knowing that a true animal lover is watching over their pet. I have been away from my pet and understand the anxiety that comes from worrying about them. It brings me joy to allow you to enjoy your time away from home without worrying about that family member you left behind I have taken care of my own animals since I was a child. I have watched many of my friends animals. I will respect our arrangement, your home (if I'm taking care of your pet at your resident), and above all I will respect your pet. Why I love dog sitting I have always had a love for dogs. I do not currently have any animals, but they have always been such a huge part of my life. I always treat animals like they are my own family,and the same love will be given to your pet! My experience administering medication I am comfortable administering medication given the proper instructions. I work from home and I am available to be with your animal for the majority of the time they are in my care. I am also naturally a home body so your pet will rarely be alone! I will respect are agreement and will treat your animal with the same love and respect I would treat one of my own. You can feel at ease knowing the person caring for your animal actually cares.
“Riley is absolutely amazing and we are so lucky to have found her. We use her often, and every single time she takes such wonderful care of our dog, Mika. It’s clear how much Riley genuinely cares—Mika is always happy, comfortable, and well loved when we return. Her communication is great and she gives us total peace of mind knowing Mika is in the best hands. We couldn’t recommend Riley more highly and will continue to book her every time we need a sitter!”


About: I’ve been caring for animals for years and truly enjoy getting to know each pet’s unique personality. As a longtime equestrian, I gained valuable experience caring for horses, which taught me responsibility, patience, and confidence in handling animals with different temperaments. In addition to caring for horses, I’ve lived with and cared for two cats over the past two years and have experience looking after multiple dogs and puppies. Last year, I house sat for a family with a very energetic dog, making sure they got plenty of exercise, playtime, attention, and companionship while their owners were away. What sets me apart is that I treat every pet as if they were my own. I understand how important routines are, so I carefully follow feeding schedules, walking routines, medication instructions if needed, and any special requests to help your pet feel comfortable and secure. Whether your pet loves adventures, playtime, or quiet companionship, my goal is to provide dependable, loving care and give you complete peace of mind while you’re away. Caring for animals is something I genuinely enjoy and naturally make time for in my routine. I have a flexible schedule that allows me to provide reliable care, whether that’s walks, drop-in visits, feeding, playtime, or overnight stays. Since I already care for my own cats every day, pet care is a regular part of my life, and I love spending time with animals whenever I can. I’m committed to being dependable, attentive, and making sure every pet feels safe, comfortable, and well cared for while their family is away. When caring for pets in my client’s home, I focus on keeping their routine as consistent and comfortable as possible. I understand that pets feel most secure in familiar surroundings, so I make sure to follow their normal schedule for meals, walks, playtime, medication (if needed), and any specific instructions from their owners. I also provide plenty of attention, affection, and companionship while making sure their home is respected and cared for. If caring for pets in my own home, I provide a safe, clean, and welcoming environment where they can feel comfortable and relaxed. I always take the time to learn each pet’s personality, needs, and preferences so they receive personalized care. My goal is to make every pet feel loved and cared for while giving owners peace of mind that their furry family member is in good hands.
“Anna was the security and peace of mind I needed. New to the area, the anxiety I was experiencing to find someone who could care for my pup like the sitter he had in my hometown was tangible. 2# has older dog issues, meds (eyedrops which are tricky) and other quirks that require a little more attention to keep him not just happy but more importantly, safe. I met Anna and she immediately went to 2# to get to know him. She asked questions got to know me and my pup. Im not unlike many other ridiculous pet owners who have written a novella on how to care for their dog when gone for more than 2 hours, but she was happy to oblige and cared for 2#. I didnt worry about 2#. I was sent pictures and updates, my home was clean and 2#'s items were cleaned as well! I highly recommend. As someone who has interviewed many to stay with 2# and has a pup that has a lot of nuances, travel is no longer a worry now that I have found Anna to watch 2# when out of town. Thank you Anna!”
About: I have taken care of dogs for 12 plus years ranging from walks, potty breaks, in home services, I aim to provide love and support I have so much free time on my hands, I would love to help anyone. I aim to provide the top quality services. I want your fur babies to have a great day while your at work I have high experience with dogs and cats, I have strong understanding of what a dog or a cat needs. I take instructions very well. I aim to provide comfort and safe supervision for your pets
“Payton was so incredible with our pup! She sent lots of photos and updates, I could tell our dog was in great hands. She was super flexible and accommodating to his schedule. I would highly recommend her services, we’ll be using her again for sure!”


About: I’ve been caring for dogs and other pets for several years. Friends, family, and neighbors trust me to feed, walk, play with, and care for their pets while they’re away. I enjoy spending time with animals and make sure they feel safe, comfortable, and loved. I’m reliable, patient, and attentive to each pet’s unique needs and personality. Pet care is a natural part of my weekly routine. I enjoy spending time with animals and make time every day for walks, feeding, playtime, and providing attention and companionship. I’m flexible When caring for dogs in a client’s home, I follow their regular routine to help them feel comfortable and secure. This includes feeding, fresh water, walks, playtime, bathroom breaks, and plenty of attention and affection.

About: I have been around animals my entire life and have always had pets in my household. At one point, I lived in a home with 12 dogs and 2 cats, so I am very comfortable caring for multiple pets, different personalities, and different breeds. I currently have a 2-year-old Standard Poodle of my own who is very loved and well cared for. I am also a mom of three, a nursing student, and a business owner, so I am responsible, organized, dependable, and used to managing a busy schedule. I understand that pets are part of the family, and I will treat your pet with the same patience, attention, and care that I give my own. I make my own work schedule, which gives me plenty of flexibility to fit pet walks, drop-ins, and sittings into my routine. I’m also currently in nursing school, so I only work part-time. This allows me to plan my schedule around both school and pet care, making sure your pet gets the time, attention, and care they deserve. For the Safety, Trust & Environment section, you could put: I always make sure pets are in a safe, comfortable, and loving environment. I follow each owner’s instructions closely, including feeding schedules, walks, medications, and routines. I’m very attentive and will treat your pet like one of my own. When caring for pets in a client’s home, I’m also respectful of their space and make sure everything is secure before I leave.
The median cost per night for house sitting in Windward Trail is $50
Pet parents share their Rover experiences - Windward Trail
Mary was great house sitting and watching my two high energy dogs (Aussies)! She did daily walks as well as playing in the back yard + was able to accommodate their special needs (prescription food for one and chewable meds for the other). I would absolutely recommend her as a dog walker or sitter as she loved my dogs a whole lot.

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 to book house sitting

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 - Windward Trail
Select a filter and find qualifying sitters offering house sitting.Sitters in Windward Trail average 3 repeat house sitting clients
FAQs for House Sitting - Windward Trail
Frequently asked questions about Rover
The average cost of House Sitting in Windward Trail on Rover is $39 per night as of October 2026. Most bookings cost between $27 and $72 per night. sitters set their own rates based on factors such as their experience, the length of care, the number of pets, and your pet’s specific needs. As long as your booking dates and pet profiles are accurate, the price shown before you confirm is the total, including any booking fee.
As of October 2026, there are 827 sitters on Rover offering House Sitting across Windward Trail. 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 Windward Trail 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 Windward Trail 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.
<b>Tip:</b> 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 Windward Trail 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 , 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 .
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 casual meeting to vet potential sitters and communicate care needs for peace of mind before a booking begins. Only sitters who have never booked with you before can schedule a Meet & Greet on Rover; however, you are welcome to coordinate one in Rover messages with sitters you have previously booked. This can be helpful if you have a new pet or routine you want to go over with your sitter.
Meet & Greets can take place in person or virtually. If you are booking with a sitter for the first time, we recommend in-person Meet & Greets to get a clearer sense of how your sitter interacts with your pet 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. Meet & Greets are a great way to prepare your pet and sitter for longer stays or first-time bookings. Read our tips for your first .
sitters on Rover set their own , which you can find on their profile under their contact information. Sitters may set a same-day, one-, three-, or seven-day cancellation policy. Cancelling within your sitter’s cancellation policy qualifies you for a full refund.
Same-day cancellations for recurring services, which include walks, drop-ins, and day care, follow the full refund policy. Otherwise, for pet boarding and house sitting, if you cancel after 12 pm on the applicable cancellation deadline, you’ll receive a 50% refund for the first seven days of the booking and a 100% refund for any remaining days.
If your sitter needs to cancel within seven days of the booking's start date, then our reservation protection will kick in. This means you will get a full refund and our support team will work with you to find a replacement sitter.
Yes, you can find sitters who have experience with handling special pet needs in Windward Trail. On Rover:
- 91% of sitters can help with special care needs
- 97% can help with giving oral medications or injections
- 97% 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.







