House Sitting Winter Springs
Find a loving house sitter to watch over your pets and your home.
Over 78 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.
“Stephanie provides frequent updates while dog sitting. She sends pictures and sweet messages. Our dogs love spending time with her because she takes such great care to ensure they get long walks and plenty of snuggles!”
“Jackalyn was so wonderful! She was thorough and kind. I walked her through everything and she asked great questions when I missed something! I would highly recommend her for anyone’s fur babies!”
“Maria did an outstanding job taking care of our Rita for the weekend. She spent time playing and giving her lots of love, attention, and treats. We really appreciated the videos and picture updates while we were away. She even took extra care during the thunderstorms to make sure Rita was safe. Our house was kept cleaned and overall would definitely recommend Maria for any dogsitting needs!”
“Christina was great & took the time to get to know our puppy Coco before we went on vacation. She sent us regular photos, videos & updates (she should be a photographer 📷). She took Coco for walks & played with her. We highly recommend Christina for taking care of and loving on your pet. We will definitely have her watch Coco again.”
“Sonal is always amazing with our pets. She really goes above and beyond your normal pet care. She's super responsive and gives plenty of updates so we're always up to date on how our pets are in her care. I would recommend her services to anyone looking for a super caring, loving pet sitter.”
“Sarah was absolutely wonderful with our animals, she sent many detailed updates and some really cute photos! Our house looked wonderful when we returned. We will definitely be using her for our next vacation!”
“Jenna was everything and more we could have hoped for!! Our dog is nervous around new people, and she was SO patient with him, I am beyond grateful. We weren't sure if we would ever be able to take a vacation again, but Jenna has made it possible! She is truly a lifesaver! Highly recommend!”
“Alicia took very good care of our 2 boxers and sent pictures of them to me. She was great at communicating with me and responded quickly to my texts. This was our 1st experience with Rover and we were very pleased. Our house was immaculate when we returned home and she had even washed & dried any linens used & remade the bed.”
“Our second time having Peter take care of my boys was just as good as the first. He truly cares and took such amazing care of the dogs and house. Can’t recommend him enough!”
“Tiffany was so great! She arrived as promised and even took our dog out one extra time for us since we were returning late. The dog was happy and well- cared for, left the house in great shape. Will definitely use Tiffany again and highly recommend!”
“Rachel was AMAZING with my very nervous/anxious dog! She was so attentive to his needs and made me feel 100% at ease leaving my dog with her. This was my first time hiring a dog sitter and I would absolutely hire Rachel again with no hesitation!”
“Kaylee was great watching over our two boys. The dogs were very well taken care of and nurtured. She took care of the house and was communicative throughout the stay. Very much appreciated, we would recommend!”
“Brianne was amazing with our chaotic, nutty furry bunch! We left her with our trio of cats and the dynamic duo of dogs, for a total of five. The first thing we noticed was how all of our furry ones were drawn to her. Animals just know if a person is good. Being away is hard, but it feels better when you have someone you can trust to love you while you're gone. My wife and I had complete peace of mind with her caring for our babies. Brianne is the BEST!”
“Rachel took care of our senior cat & Great Dane for about two days. She was so communicative and sent us updates on how they were doing. We are so grateful & would recommend her to anyone who is interested in her taking care of their babies!”
“I booked JaRavia at the last minute, and she was incredibly flexible with scheduling a meet-and-greet. During the boarding, she was patient and understanding with my shy dog, Bear, who can be a bit distant. She checked in frequently, and by the end of the visit, Bear had started to trust her. I highly recommend JaRavia for her kindness and love of animals!”
“Thank you Isabella for your wonderful care from a repeat customer. I really appreciate you doing exactly what I ask and going above and beyond on things I didn't even think of. My crew is looking forward to seeing you again soon.”
“This was my first time using Rover and Katie did a wonderful job! Not only was she flexible and on time, she was absolutely great and patient with my ultra difficult chihuahua. Most people would have walked out but Katie assured me that he will be okay and he did fine! I would definitely have her house sit my dog in the future! Thank you Katie!!”
“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!”
The median cost per night for house sitting in Winter Springs is $45
Pet parents share their Rover experiences - Winter Springs
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!)
Our dogs really seemed to love her, and we came home to happy, well-cared-for pets and a house that was in great shape. Ashland took care of our dogs, cat, fish, and plants while we were away, and even did some thoughtful extras like taking out our trash and recycling. We really appreciated knowing our pets and home were well taken care of while we traveled. First time using Rover or non-family member since we all traveled together. Overall, we’re happy and will rebook in the future.
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😊
Here’s a smoother and more polished version that keeps your warmth and sincerity: I want to thank Brandee for taking such great care of Burton during his time with her! She was easy to communicate with, attentive to every detail I asked for, and made me feel completely comfortable leaving him in her care. Burton absolutely loved her, and he can be very selective about people. This was the longest time I’ve ever been away from him, and all of the pictures and check-ins gave me such a sense of peace while I was gone. I’m so grateful for the care and attention she gave him!
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 - 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 for House Sitting in Winter Springs on Rover is $39.96 per night (as of September 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 September 2026, there are 2,956 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 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 Winter Springs. On Rover:
- 91% of sitters can help with special care needs
- 95% 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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