House Sitting Winter Park
Find a loving house sitter to watch over your pets and your home.
Over 141 pet parents in Winter Park have booked house sitting
Winter Park, 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.
“Kenya did a great job watching my two cats for a week. She sent updates everyday with pictures. I felt at ease knowing my babies were in good hands.”
“Isabella was Great with our puppy! She made sure to send pictures everyday and update us throughout the day. She took amazing care of our dog and even went the extra mile for him! 10/10 would recommend her!”
“Thank you Peter for taking care of Malala and our home over the weekend. Sure did come home to a happy dog! We appreciate your timely update, clear communication and genuine respect for our space. We'll be sure to use your services again.”
“Autumn was absolutely phenomenal! She stayed at our house over the Thanksgiving holiday and took incredible care of our two dogs. She sent daily photos and videos, kept them active with walks, and gave them so much love and attention. On top of that, our home was spotless when we returned. We felt completely at ease knowing our pups were in such caring hands. We’ll 100% be using Autumn anytime we go out of town — and the dogs give her all the tail wags! 🐾”
“Dwight is extremely accommodating and friendly. He goes above and beyond to take care of our dog, Keaton. We know Keaton will be in amazing hands when Dwight is taking care of him. We hope to have Dwight care for Keaton for more vacations and long days of ours in the future!”
“Heather communicated very well, and I felt comfortable leaving my dogs with her watching them. She sent me pictures of my pups too. Overall, it was a nice experience and I really didn’t worry about anything while I was away on my trip. Thank you, Heather”
“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.”
“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.”
“Hailey took the best care of my senior dog. She watched Fiona for the weekend in my home. I was so nervous leaving her but she sent so many photos with little updates about what they were up to and how everything was going. Everything in the house was perfect when we got home and Fiona was so happy. Hailey is a true animal lover, compassionate, detail oriented and a great communicator. Your sweet little furry family member is in great hands with Hailey.”
“⭐️⭐️⭐️⭐️⭐️ Cedar was absolutely amazing! Extremely professional, communicative, and attentive throughout the entire stay. They kept me updated with pictures and detailed check-ins, ensuring I always knew how my dogs were doing. I couldn’t be happier with their service! My two dogs can be reactive and challenging at times, but they handled them with such patience and care. I highly recommend them to anyone looking for a reliable and skilled dog sitter. Will definitely be booking again!”
“Deborah did a fantastic job watching buddy. She kept us informed daily and even sent us photos. I would highly recommend her to anyone looking for a dog sitter. we will use her for sure going forward, thank you again Deborah”
About: I've grown up with pets my entire life and caring for animals has always been second nature to me. I have hands-on experience with senior dogs and understand the extra patience and care they need. Friends and family have trusted me for years to walk their dogs and provide reliable, loving pet sitting. I treat every pet like my own—whether that means long walks, belly rubs, or just keeping them company while you're away. I’m a college student on summer break, so I have a lot of free time and a super flexible schedule right now. Pet care fits in really easily for me—I’m available most days and happy to work with whatever routine your pet is used to! Whether I’m watching your pet at my place or yours, I make sure they’re safe, comfy, and happy. I follow your instructions and give them lots of love. I’ll treat your pet like one of my own and always be watching them with my full attention!
“Sara took amazing care of Prim. My dog had a vacation while I was away and it was very clear that she enjoyed herself. My dog is 14years old so she can't be easy at times but Sara had patience with her and took great care of her. Thank you.”
“Alicia took amazing care of my pets and home. She is very professional, a great communicator while away with multiple photos, and when I came home, everything was clean and neat with calm, happy babies! I highly recommend Alicia - she is the best pet sitter that I have met on Rover!”
About: I have utmost respect (and lots of love!) for all animals. I truly view them as real friends and equals. With experience, I have also learned how to set and maintain good (and firm - when necessary) boundaries. Dogs have been trusted members of my family since I was a child. I have cared for senior rescue dogs; I have socialized puppies; I have taught reserved dogs new tricks; and I have taught stubborn dogs to sit and wait. I have admittedly less history with cats, but just as much respect and care for them as any other animal. I do currently have one close cat companion (we used to be roommates, and have been best buds ever since). As with all animals, I find that the respect and love I give to the pets I interact with is reciprocated - and often multiplied! As a person who is both adventurous and empathetic, I am generally very well attuned to the health and wellbeing of those around me, and I really enjoy taking dogs for walks almost as much as they do! I also like to play, and I can handle all kinds of doggy games. Big dogs welcome! I am an early riser - morning walks are my favorite! From day to day, I am generally very flexible; I work part-time as an independent handyman (furniture assembly, TV mounting, etc). I can make almost anytime work, as long as we can agree in advance. All requests are welcome! I enjoy long walks (with lots of 30-second stand and sniff breaks). I am both energetic and patient I love to play Always send updates when leaving
“Hannah is amazing she was so good with my pups. She sent pictures daily which made me feel so much better about being away from home and I came home to a clean house. I will be using her anytime she is available. Thanks Hannah!”
About: Beginning in childhood, I’ve had several dog breeds (over 20!) that I’ve been tasked to take care of, play with, keep healthy and whose needs I’ve grown to pay attention to and understand. I adore animals and I approach them gently and mindfully, always considering what support will help prolong their lifespan and keep them happy, yet trained and behaved. My friends and family often call on me to either keep their pets company, train or housesit them, and I’m always more than happy to spend time with their animals. I firmly believe pets are not toys, and much more like our own kids, deserving of care, compassion, joy and attention. I have 17+ years experience taking care of and loving French bulldogs and pugs, who notoriously require extra responsibility, attention and instruction, as they can be stubborn and prone to health and breathing issues (often brought on by heat). I have cared for senior dogs who deserve nothing but love towards the end of their lives, and also puppies who need time spent on training and feeling safe, and lots of play and activity to stimulate their growing minds. I am a graduate student, with flexible availability between Saturday to Tuesday, during my off days, when I’ll be studying from home, often lounging and relaxing in my space. Having a pet to look after, feed and care for would not only be a very welcomed time commitment, but would make my space feel even more homely and bring me joy. I have enough time to play with dogs, pay attention to their unique needs and keep them active and joyful, or to simply accompany them while they rest and rejuvenate. I have a spacious apartment and a shaded dog park within my apartment community, as well as a dog wash corner next to the park - helpful during hot days in Florida. I am extremely mindful towards any pet staying with me, and provide them with a comfortable, safe and cooled space, in which I am committed to staying aware of their habits, likes and dislikes, and learning to understand their groove. There are several areas for them to use the bathroom outside, take a walk within the apartment community, as well as designated pee pads inside the apartment. I am happy to be in touch with the clients as often as needed, to help them feel at ease about letting their little one stay with someone new. I care about building trust with a dog, and taking the time to grow our bond, so they can be at ease in their surroundings and reduce any anxiety from a new environment.
“Bailey takes such good care of our pups, she is responsive, ensures all needs are met and we have never had any problems after multiple sits. We will definitely continue to have her sit in the future.”
The median cost per night for house sitting in Winter Park is $45
Pet parents share their Rover experiences - Winter Park
I'm so grateful for Isabella taking care of Prim! She took on the job last minute and took such great care of her. When I got home Prim didn't seem to even notice I left. I could tell she was taken great care of her. My dog is a senior 14 year old dog and I know she can't always be the easiest. Isabella also stayed in communication with me which was absolutely appreciated! I highly recommend her.
Glacie is the absolute best. She has watched our girls three times (including 2 of which have been with a brand new puppy!). She is so attentive, responsive, and takes great care of them. It is so amazing to be able to be away from the house knowing my girls are in good hands. She’s the best!
It was my first time using rover and honestly the first time leaving my dog with anyone that wasn’t family and I am so glad that it was Izzy that I got to work with. She totally made me feel at ease and offered to come meet the dogs before hand (was watching mine and my sisters dog at the same time) she left our home spotless and all the pictures of the dogs when we were gone we could totally tell they adored her, will definitely be booking again with Izzy!
The clearest review I can give is the fact that we will be using Kaya each and every time that she is available. She was prompt, responsive, professional, and treated our house and our dog as if they were her own. I can highly recommend her, and as I indicated, we will be using her again in the future.
We could not have been happier with our decision to use Rebecca. She took amazing care of our senior pug, Tater. Her responses were always timely and she was awesome about sharing pictures throughout our time away. This was a great first experience with Rover and we cannot recommend Rebecca enough.
Bailey was great! Highly recommend. Super comfortable with dogs and followed all instructions left. Sent tons of photos everyday and always communicated. Very professional and friendly. She stayed in our home while we were away for 3 nights. Could not have asked for a better experience.
We were apprehensive at first basically getting a stranger to come stay in the house with our fur babies, but autumn was an absolute blessing. She kept us updated. The house was tidy my puppies look so happy and took to her very well. I love the open line of communication she provided and she was totally amazing. Looking forward for my next trip so she can come over and stay with our for babies again. I highly recommend her services and anyone will be lucky to choose her.
Elizabeth was very pleasant and professional with the meet and greet, this was the first time I did house sitting and she answered all of my questions gave me reassurance of the whole procedure. She met with Scarlett, and I showed all the quirky stuff I have setup with my dog. Elizabeth has great communication via text messaging, she let me know when she was going to arrive, she sent me pictures throughout the time she stayed with my dog for constant updates, putting my mind at ease since I never left my dog this long. She also updated me when she was leaving ,affirming that Scarlett was all set awaiting for me. Thank you Elizabeth for a great job.
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 Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
Select a filter and find qualifying Winter Park sitters!Sitters in Winter Park average 4 repeat house sitting clients
FAQs for House Sitting - Winter Park
Frequently asked questions about Rover
The average cost for House Sitting in Winter Park on Rover is $43.29 per night (as of July 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 July 2026, there are 3,201 sitters on Rover offering House Sitting across Winter Park. 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 Park 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 Park 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 Park 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 Park. On Rover:
- 91% of sitters can help with special care needs
- 96% 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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