House Sitting Winter Springs
Find a loving house sitter to watch over your pets and your home.
Over 81 pet parents in Winter Springs have booked house sitting
Winter Springs, 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.
“Peter did a fantastic job watching our pets while we were out of town. He was quick to communicate and kept us updated on how they were doing. Our dogs warmed up to him super quickly too, so we know that they felt very comfortable with him. We would definitely recommend him for anyone looking for a kind, caring sitter for your pets!”
About: I have 9 years of dog sitting experience. I’ve taken care of small dogs and big dogs. I take the time to learn their unique personalities and make it the best time possible. Im am currently available from Monday-Friday, and selected weekends. I am currently working from home, so I have flexibility in my schedule. I am also flexible on holidays. I’ve had experience taking out dogs for potty breaks, feeding time, walks and play time. Always being mindful and having them leashed on the streets for safety precautions. At home I always ask of any particular routines, where do they potty, sleep and eat. Also of any behaviors I should be aware for the pets safety and mine. I do ask to be informed about any medications or food they are not allowed to have. All of this to assure the best care for your pet.
“Zack was great - we’re so glad we found him! We usually board our pup when we’re away but decided it was time for a change due to her age and some health issues. He does a great job communicating and sent lots of pictures and videos. He was also very capable of handling her health issues. It was relieving to know our pup was in such good hands while we were gone!”
“Kailey was amazing! She took wonderful care of Diesel and gave me such peace of mind while I was away. She kept me updated with photos, communicated quickly anytime I had a question, and was incredibly responsible throughout the entire stay. I also came home to a very clean and tidy house, which I really appreciated. I felt completely comfortable knowing Diesel and my home were in good hands. I would absolutely book Kailey again and highly recommend her to anyone looking for a reliable, caring, and trustworthy sitter!”
About: I’ve taken care of animals specifically dogs since i was little. My friends and family have trusted me to watch there animals over night. I bathed fed and took the animals on walks. I am currently a stay at home mom, but i do have time to walk or watch your little ones! I am available for walking and drop by visits any-day any time in the afternoons Monday- Saturday. For overnight or boarding I am available on the weekends. I live in a fenced yard. I have two little dogs one is a poodle mix and the other is a bulldog and pug mix. I can easily cage them to make you feel more comfortable if needed.
“Lexus was great with our dog, a Boston with a lot of personality. She was very present, sent lots of photos, and even left behind a little custom dog art. Very respectful of house and property as well.”
About: I’ve taken care of animals since I could remember! Growing up with dogs, cats, and birds, I have always loved animals and looking after them! I have taken care of my family/friends fur babies for years now and used to work at petco (5years) and would dog/cat sit for some of the regular clients that I got to know throughout my time there. I’m energetic and love being outside and love spending time playing with animals! My schedule is very flexible and open, I can be available any day of the week and most times as long as I don’t have another commitment. I make sure the animals are well fed and hydrated. I stay aware of my surroundings when on walks or inside, making sure I’m keeping an eye out for other animals nearby or that the door is properly secured..etc I pay attention to the animals body language as well to make sure if I’m playing with them or interacting in anyway, that they seem comfortable and open to that interaction.
“Isis was great. She took the time to do a meet and greet before my trip, to get the lay of the land and meet the pups. Throughout the tip got regular updates about how the pups were getting on, and very responsive to messages sent throughout the trip.”
“This was our first time using Kaylee and she was beyond fantastic! She regularly texted us and had pictures too. You can tell she really loves what she does. We will definitely be using her in the future!”
“Maria was great! She took great care of my golden (Wally), sent lots of pics, and provided excellent communication throughout her stay with him. I would fully recommend her and would not hesitate to have her stay with Wally again.”
“Cristina was wonderful with our three challenging dogs! She was on time, followed instructions, and kept me updated with frequent texts and photos. She went above any beyond to try to get one of our shy dogs to try to eat for her, and she cleaned up some vomit spots for us as well. She left the house looking spotless. I'd use her again to dog sit.”
“Lia was great- Super friendly, great communication, and punctual. I think she took good care of Apollo and was engaging and playful. Will definitely contact again for future needs!”
About: Hi! 🐾 I’m Anna, a caring, responsible, and animal-loving pet sitter who will treat your pets like my own. I understand how important it is to feel confident that your furry babies are safe, happy, and well cared for while you’re away. I’m attentive to their routines, personalities, and individual needs, and I’ll make sure they receive plenty of love, playtime, and attention. ❤️ Your pet’s comfort and happiness are my top priority! I have a very flexible schedule and can accommodate most pet-care needs with just 1–2 days’ notice. Whether your pet needs pickup or drop-off, overnight care, or a comfortable place to stay while you’re away, I’m happy to work with you and your pet’s routine. My home also has a large, securely fenced backyard where dogs can safely roam and enjoy plenty of outdoor time. For cats, I have a cat door that can provide supervised or limited free access depending on their comfort level and your preferences. My goal is to make your pet feel safe, comfortable, and at home while you’re away! 🐾 Your pet’s safety, comfort, and happiness are my top priorities! My home has a large, securely fenced backyard, a screened-in back patio, and a cat/dog door that can easily be closed or restricted whenever needed. I also have extra rooms available, so if your dog prefers or needs their own private space, they are welcome to have a room of their own. For my feline guests, the home has cat towers and jungle gyms throughout, giving them plenty of places to climb, play, explore, or retreat when they want some quiet time. I want every pet to feel safe, comfortable, and at home while they’re in my care. ❤️
“Sydney was great with our two pups while we were out of town. Our Malinois got sick just before we left and I let her know we gave him rice and he should be ok. She responded that even if he was still sick, she would take care of it. She let them out frequently and took great care of them! Will be utilizing Sydney again. Thank you! 😊”
“Valery is AWESOME!!! She has done drop in visits for our 5 1/2 month old puppy as well as has taken care of her for a weekend in her own home. We would definitely hire Valery again. She's reliable and takes amazing care of our baby!”
About: I’ll take time to learn your pet’s routine, personality, and any special needs before caring for them. I’ll follow your instructions for meals, walks, and medication, keep your pet’s surroundings secure, and send photos and updates so you know how they’re doing! I’m available Wednesdays and Friday through Sunday for pet care. On those days, I can plan walks, visits, and quality time around your pet’s needs and usual routine! I’ll follow your pet’s usual routine and care instructions to help them feel comfortable while you’re away as well as loving them with them and making them feel happy ! I’ll keep dogs leashed on walks, check that doors are secure, and make sure fresh water is always available. I’ll also respect your home and send photos and updates so you can feel at ease :)
“Lucia was awesome with my two dogs and my kitty! She sent me pictures gave me details on how they were doing. Tried everything to get my finicky eater to eat. And she did the dogs loved her and kitty too. I would definitely recommend her!”
About: I have always had animals in my life and can't imagine a life without them. I have cared for my friends pets and even my adult children's furbabies. I am comfortable given medications if the need arises. Part of my cat care, would of course include daily cleaning of litter boxes. I enjoy being outside playing catch & return with dogs. I am currently working part-time as a nail technician, so there are days I have plenty of time to do drop-in pet care, because I an independent contractor & manage my own schedule. I would comply to the pet parent's instructions based on each pet's individual requirement. I am very flexible in regards to a pet's needs.
“We had an excellent experience and would highly recommend this service. Our sitter was professional, communicative, and took outstanding care of our dogs while we were away. We received updates throughout our trip, and it was obvious our dogs were happy, comfortable, and well cared for. As an added bonus, our home was left clean and organized when we returned, which was greatly appreciated. It’s not easy leaving your pets behind, but this experience gave us complete peace of mind. We would gladly use this service again and look forward to booking in the future.”
The median cost per night for house sitting in Winter Springs is $48
Pet parents share their Rover experiences - Winter Springs
I can’t say enough good things about Eva! I had to book a sitter on very short notice for a trip out of town to attend a funeral. With my hectic schedule, I wasn’t sure I’d be able to make the trip until just a few days beforehand, so everything was a bit chaotic. I even managed to miss our scheduled meet and greet, but Eva was incredibly understanding, flexible, and accommodating throughout the entire process. She took wonderful care of Astro, and I’m pretty sure they became best friends! She also took great care of my home, sent lots of pictures and updates, and communicated really well. Having someone so reliable and caring made an already stressful week so much easier. I’m incredibly grateful for Eva and would absolutely book with her again. Highly recommend!
I had a last minute need for a pet sitter and Jackson made it so easy to book with him! The day before my trip he accommodated my schedule to come meet my dogs and me. Throughout the stay he sent pictures and gave status updates, never making me wonder or ask how things were going. I would absolutely book with Jackson again.
This was our first time having Brent stay with our pets and house sitting - and couldn’t have asked for a better experience. Brent sent plenty of updates and photos, took good care of the house, and left it spotless when we returned. Highly recommend him and will definitely be rebooking him in the future. Thanks for making our vacation less stressful by taking such good care of the girls.
It is always nerve wrecking to find a new pet sitter to stay in my home with my pooches- as they really are my babies. But Ashland was fantastic with them! I really appreciated all of the updates and amazing pictures she sent throughout her stay. She also went above and beyond to be extra caring with my senior doggies, providing them with some extra tlc which meant alot to me. The house was kept tidy and she followed instructions. I would highly recommend Ashland and would book her again for future stays. Thank you again from me and the Pom pack! 😊 🐾 🐾 🐾 🐾 🐾 ❤️
Stephanie was AMAZING! It is so hard to leave them, but she made me so comfortable in knowing my pups were okay. She sent photos and updates daily. And I came home to a clean house which was a fantastic surprise and super nice after being on a business trip! I hope she can take care off f my babes for all of my trips! Thank you Stephanie (and Husband!)
Kelsey came through as a last minute booking and saved the day. We reached out for a meet and greet 2 nights before we needed her and she responded almost immediately and was here an hour later to meet with myself and my giant pups. She was extremely professional and you can tell that she has a passion for dogs. She then came back to sit for them 2 days later, sent pictures and updated as I saw appropriate (not too much or too little). We will definitely use her again in the future😊
You can tell Kat has a real love for animals! She was punctual, reliable, and so loving with our fur babies. It was our first time leaving them in the hands of someone other than family and she made the process easy! She sent us photos, kept us updated, and was very responsive. She went above and beyond for our pets and we will definitely be working with her again in the future :)
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 - Winter Springs
Select a filter and find qualifying sitters offering house sitting.Sitters in Winter Springs average 4 repeat house sitting clients
FAQs for House Sitting - Winter Springs
Frequently asked questions about Rover
The average cost of House Sitting in Winter Springs is $40 per night as of October 2026. Most bookings cost between $33 and $67 per night. On Rover, 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 2,937 sitters on Rover offering House Sitting across Winter Springs. 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 Winter Springs 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 Winter Springs 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 Winter Springs 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 Winter Springs. On Rover:
- 89% of sitters can help with special care needs
- 94% can help with giving oral medications or injections
- 96% 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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