Pet Sitting Windward Trail
Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

Windward Trail, Find top rated pet sitting
Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.
“Colleen took care of our three cats while we were away for a week and she did a phenomenal job. Colleen provided daily updates with pictures which meant a lot to us. Will rebook if Colleen is available whenever we travel again.”

“Robin was fantastic! Her attention to detail and her communication is top notch. She did a fabulous job looking after our two Australian shepherds during a drop in visit. She played frisbee with them until their hearts were content and she even made sure to refill their water bowl while she was here. Thank you Robin!”

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’ve been caring for dogs since I was 7 years old. I have a natural bond and understanding with dogs that make caring for them easy. I would love to turn this into a full time business for myself due to my love and empathy for animals. My dogs are my world and this type of income would provide more time with them as well as other animals. I will be sure to listen to your directions and precautions for your pets! I like to stick to whatever routine you already have so that your dogs mind is at ease.
About: Growing up we had 7 cats, 3 dogs, 2 fish and 2 dwarf frogs. I loved caring for all the animals and knew I would always have animals in my life. Since, I have raised several cats and dogs over the years. I comfortably cared for our one dog through her battle with bladder cancer. I also raised a German Shepherd to the age of 16. I have also cared for family members and friends animals during vacations or illness. Today, I have 2 dogs and 2 cats. We strongly believe that the right food, exercise and lots of love help keep them safe and healthy. We treat our animals like kids by talking to them, playing with them and letting them sleep and cuddle on the bed.
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 pugs, 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 three days a week (every other weekend). This 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 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.

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.
“Madison helped us out with only a couple of hours notice. She was responsive, polite, and our dogs were well cared for and appropriately tired when we got home. I highly recommend Madison.”

About: Hi! My name is Kaitlyn and I love all things animals and the outdoors. If you’re wanting someone trustworthy to watch your dog(s) for the day, taking them on walks, or even stopping by to give them a good time I’m the person! I am genuinely happy to care for dogs, love on them, and can assure they will have a great time! Im very flexible and here for any questions you may have- have a blessed day! I daily take my own dogs to their favorite park or even on long walks, which they love. I like to throw balls and play fetch with dogs and make sure they are getting their energy out! I make sure they are getting fed the correct amount for whatever works for each one. I make sure each dog/ cat is satisfied in their space and accommodate whatever is needed for their daily routine. I am 100% able to listen and to the pet owners requests and I am making sure everything is fitting for you and your pet(s)!

About: CJ and I have owned and cared for dogs our whole lives! Between the two of us, we have over 20 years of dog care experience and we have worked at multiple dog daycares and boarding facilities as well as veterinary practices. We both still currently work and train at local facilities! We have such a passion for what we do we want to bring work home with us; WELCOME TO CAMP RECALL! We have a pack of our own, and our pups love to make new friends and play all day. We have experience with almost all breeds and we have experience with dogs of all sizes and energy levels. We are the perfect mix of a canine facility and a home environment! If your pup needs more individualized care, structure, and enrichment than large scale daycares can provide, we are the perfect fit for you. We will send updates and pictures of your dog having a great time as often as you would like. We can also train your pup while you are away, whether that be just for the day or for a longer term stay! Your dogs will be loved and cared for as part of our family and they will love to spend time at Camp! Dogs are our passion! We also have our own pack so dog care is in every aspect of our day to day lives. Between our varying schedules, someone is almost always home to be loving on the dogs! Your pup will have plenty of friends to play with. We have a fenced in yard that is spacious and secure. Pups in our care receive structured and safe, supervised play with other fur-iends as well as one on one time, enrichment, structure, and plenty of snuggles! We send pictures of your pup having the best time and can also offer training for an additional fee.

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.
About: I have approached every single dog owner I have ever seen in order to ask them to pet their dog. My friends and family have always called me a dog whisperer because I’m usually able to even pet the shyest of dogs. I am looking to work part time. I am about to go back to college, but I am free every day except Sunday mornings (church) and Monday night (small groups). I have two Australian shepherds whom I have helped to train. I take them on at least one walk a day and we have a fenced in yard which they can go out into multiple times a day. I help to feed them and take care of them on a daily basis.
About: Before I moved to College of Charleston I pet sat around my neighborhood for around 2 years. I also have 4 dogs at home including a foster dog currently and would love to meet y'all's furry friends because I don’t have an animal in my dorm currently! I can walk your doggies pretty much any time except for Wednesday's and Sunday's! typically on weekdays it’s after 12pm, and on Saturdays it’s all day! I take care of my animals with love. sticking to their schedule while involving the upmost playfulness and kindness. I will clean up after them, and like i would with my own dogs and cats put their safety and health first. If there was ever something to happen, immediately calling their owner and sticking by their 4 legged side!

“It was such a pleasure meeting Stacie, and getting to know her a little, along with hearing about her own love of animals! I so appreciated the photos she sent since my two cats are new to each other and she was totally thorough in caring for them!”


“Jacob was fantastic. Not only was he polite, he was attentive and responsive, and took great care of our Labrador retriever. We will definitely use Rover and hopefully have an opportunity to use Jacob again!”

Pet parents share their Rover experiences - Windward Trail
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 pet sitting

1. Search
Browse profiles of sitters near you who offer pet 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 pet sitting - Windward Trail
Select a filter and find qualifying sitters offering pet sitting.FAQs for Pet Sitting - Windward Trail
Frequently asked questions about Rover
Rover is the largest marketplace for local pet care. Whether you're looking for pet sitters, dog walkers, or house sitters who specialize in pet sitting, you can narrow your search by entering your ZIP code to find sitters within walking distance in your neighborhood.
You and your sitter can agree on a care schedule that fits your pet’s routine and the sitter’s availability. Pet Sitting can be booked as a one-time or recurring drop-in visit. If you need overnight care or dog walks, you may also be able to book House Sitting or Dog Walking through Rover with the same sitter, provided they offer those services.
Before booking, confirm:
- the timing, length, and frequency of visits;
- the care instructions the sitter should follow;
- which parts of your pet’s usual routine should be prioritized;
- how often you would like to receive messages, photos, or other updates.
Not every sitter offers the same services, availability, or booking options. Review their profile and discuss the care you need through Rover before booking each service.
If you would like updates while you’re away, you can discuss with your sitter how many or how frequent you’d like those updates to be. The Rover app allows sitters to send photos, videos, and messages about your pet, including how many pee or poop breaks occurred. You can message your sitter at any time through the app and our support team is available 24/7 by email or chat if you have concerns.
The personalized, in-home nature of pet care through Rover can mean more individual attention for your pet.
Many pet parents provide a spare key or arrange a lockbox. You can also exchange keys during the Meet & Greet and show your walker how to use digital fobs or personalized codes. It helps to arrange access to your home, from spare keys to concierge introductions, before pet care begins.
If you live in an apartment or condo, don’t forget to discuss details like buzzer access, codes, or elevator etiquette. These details can help a pet sitter feel more comfortable going in and out of your building.
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 .
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.
Yes, you can find sitters who have experience administering medication or managing dietary requirements. You can also find pet sitters who accept only one pet at a time, which is ideal for anxious puppies 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 request a Meet & Greet to walk your sitter through your expectations.
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.









