House Sitting Windward Trail
Find a loving house sitter to watch over your pets and your home.
Over 74 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.
“Julie was wonderful! She came prior to our getaway to meet us and our animals. She kept us updated on how they were doing while we were gone and with pictures! My dogs seemed very comfortable with her! Grateful to have found her and look forward to more getaways now that we have a sitter!”
“Jamie really liked Kimberly from our initial meet and great visit. He was well cared for, Kimberly worked during the day, which quite a distance from my home but still came back every day to spend her lunchtime with him, to get him out and play. Jamie wasn’t feeling well one day and immediately contacted me. She stayed with him and worked from home that day to be with him. Kimberly communicated and sent pictures every day. We found a winner, and I will definitely call upon her again whenever I have to leave my precious boy, who is my world.”
“Robin was outstanding! Always attentive, quick to reply. She kept my home in great shape, clean, and happy to come back to. Our plants seemed greener and I felt like our dogs have been better behaved after spending a few days with her. We will definitely seek Robin out in the future to help with our pets…and we highly recommend you do too!”
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 grew up with dogs and have been a caregiver on Wag! since 2022. At a doggy daycare, I managed large groups of dogs, ensuring safe, structured, and attentive care! I work full-time during the day, but pet care fits into my routine in the evenings and on weekends. I’m available for drop-ins, walks, and overnight care, and I make sure to plan my schedule so pets get consistent, reliable attention! I provide attentive, reliable care tailored to each pet’s needs in both my home and the client’s home. I follow their normal routine as closely as possible, including feeding schedules, walks, playtime, and comfort breaks. I prioritize safety, supervision, and communication, and I always provide updates and photos so owners feel at ease!
About: I have been on Rover for over a year now and have fallen in love with pet sitting! I have several repeat clients who I love. I have always had dogs in my house and I am currently raising my puppy Roy! I feel as though pets have more feelings than humans so I make sure to give them special attention! I am a full time student at Clemson University and work a part time job so when i’m away from those i always make sure to spend time playing with my dog and taking care of him. I love to be around and let him hangout with me anytime I can since he’s so sweet and funny! I typically find myself watching a few pets every month! I typically work a few days out of the week and 4-6 hour shifts! I always give pets as much attention as they will let me. I feel as though feedings schedules and daily walks and attention are necessary for animals. I also like to make sure they have clean food and water and plenty of it! I also make sure to pay special attention to their body language and can change my routines or anything they may need to make them more comfortable.
“Sketcher did great housesitting our anxious 2 yr old dog and 11 yr old indoor cat. She was good at communicating promptly during booking and during the stay. We came home to happy pets and everything was as expected.”
“Amber did a wonderful job with our two pups. They can be a handful but Amber was patient with them and made sure they were well loved! She also left our home just as we left it. We will be working with her again.”
About: I’ve been caring for dogs of all sizes, breeds, and temperaments for over 10 years. Friends, family, and neighbors trust me to feed, walk, play with, and look after their pets as if they were my own. I’m comfortable with puppies, senior dogs, and pets that need extra patience or attention. I pay close attention to routines, behavior, and safety, and I genuinely enjoy spending time with animals—not just watching them, but making sure they feel comfortable, cared for, and happy while you’re away. I currently work part-time, which gives me plenty of flexibility to provide consistent and attentive care for your pets. I’m available for boarding on weekends and most weekdays after 2 PM, with time set aside for walks, play, feeding, and check-ins. I make sure each pet gets dedicated attention and isn’t just “fit into” my schedule—they’re part of it. Your pet’s safety and comfort are my top priorities. I have a secure fenced yard and two friendly, well-socialized dogs who enjoy having company. I always introduce pets slowly to make sure everyone feels comfortable. I can crate your dog if needed and will follow any specific routines, feeding schedules, or care instructions you provide. Whether in my home or yours, I focus on creating a calm, safe, and stress-free environment where your pet feels at home.
About: I've been around dogs all of my life. Even as a baby my dad had dogs, and there hasn't been a time in my life I didn't have at least 1 in the house! I've dealt with all ages of dogs, from newborn puppies to seniors, I have the skills! I look forward to meeting your fur babies!! Currently, I'm working odd jobs here and there, so I'll be there whenever you need me if I have the availability!! I can stay as long as you need me to as long as I have a heads up If you ask me to do it, I'll do it!! Want me to crate your baby before I leave? You got it! Want me to put on their cartoons, done and done! I'll do any and every need for your animals, just be sure to tell me so I'll know!
“Ella was wonderful with my dog Charlotte. Took her on a walk, pampered her and made sure that she was fed on time and pampered. She also went the extra mile and helped me with my two outdoor cats. I will definitely use Ella again. She is a rare find!”
“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.”
“Michelle did an outstanding job taking care of not only my pet but my home. Would recommend and will be contacting her again to take care of my dog which I believe is the highest compliment. Thanks, Michelle!”
About: I don't have formal experience training puppies, but I have experience caring for an older dog and I understand patience, attention , and gental care that senior dogs need. Pet care fits well into my daily routine because i have a flexible schedule and can be available during the dat for feeding, walks ,and care. I do not offer pet care in my home. I provide care in the client's home, following their instructions to keep pets comfortable,safe,and on their normal routine
The median cost per night for house sitting in Windward Trail is $50
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?
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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
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Schedule a free in-person Meet & Greet to find the perfect fit
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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 for House Sitting in Windward Trail on Rover is $38.85 per night (as of August 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 August 2026, there are 849 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.
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 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 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 Windward Trail. On Rover:
- 95% of sitters can help with special care needs
- 100% can help with giving oral medications or injections
- 95% 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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