House Sitting Winter Park
Find a loving house sitter to watch over your pets and your home.
Over 146 pet parents in Winter Park have booked house sitting
Winter Park, Find top rated house sitting
“Nathan took excellent care of our dog and cat, making sure to clarify instructions for medications, etc. When our flight was cancelled last minute, he was kind enough to stay another night at very short notice, which we greatly appreciated! He left the house very clean and tidy. We will certainly book him again.”
“Kenya was absolutely amazing! The daily updates and photos were incredible and the house was well taken care of. Our two dogs looked very happy the entire 12 day trip and were well taken care of. I highly recommend Kenya for any of your pet sitting needs. Thank you, Kenya!”
“Christina is the absolute best! She took amazing care of my two big dogs. She shared a ton of updates and went above and beyond to ensure they stayed safe. I cannot recommend her enough!”
“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”
“My girl got into some meds while I was at work. Dwain was quick to try to contact me when he stopped by the house and quick to action. They couldn't be in better hands and I'm so grateful.”
“My first experience with Rover is with Cristina, Cristina is fabulous with our puppy, Dash. Cristina played with Dash, brought him to the dog park and took him on various walks. Cristina is very pleasant, happy, and passes on her confident personality which makes a first-time Rover-user like me, feel confident when leaving their puppy with the caretaker for the day!! And Dash could sense immediately the pleasant character of Cristina, so he showed readiness in leaving his Mama, which came as a surprise to me!! When we come back to Central Florida, we will give you a shout! Thank you Cristina!”
“I would highly recommend Rob and Wynn to anyone who needed a dog sitter, these are people who genuinely love dogs and they take care of them as if they were their own. I was impressed by the amount of pictures they sent, constantly letting me know how things were going and how my pup was doing. I’ll definitely be using them again.”
“Raechel was great! This was my first time using the app and I was in a bit of a time crunch and this was also the first time I needed a house sitter for my animals. I have 2 dogs and 2 cats so the job was large and Raechel did not blink an eye to it! Her communication is fabulous as I was sent multiple pictures each day of the crew. Even my most reclusive cat seemed to love her new sitter which totally surprised me! Overall the dogs and cats seemed to love their new friend for the week and I felt completely confident in Raechel while I was gone.”
“Fantastically reassuring to my Havanese puppy who doesn’t like me to leave him. At all. With Barb he relaxed and was very calm when I got home. Would definitely have her again.”
About: I've taken care of pets since I was 8. I love all animals and would be happy to care for your fur baby any time!! I have a mini schnauzer named Apple who lives with me- she is the sweetest dog I have ever met (I know everyone says this but I swear it’s true😂)! I’m currently in school and will not be free from 7-3 Tuesday-Friday; I am available after 3 any of these days and all day Saturday-Monday! When in doubt just send a request and I can let you know if I can accommodate! I love going on walks so walking with your pet will be fun for both of us! Send me a message if you have any questions :) I will watch after your fur babies and treat them like my own! Just let me know your care preferences and I will accommodate them!
“Sonal was absolutely amazing! She was incredibly thorough and detailed, and warm & attentive to our babies. She kept us updated with photos and reports, and kept us at ease during our vacation. 10/10 will try to book again. :)”
“Trinity was absolutely fantastic with my 2 dogs. I have a Belgian malinois and a Staffordshire, 11 and 5 respectively, and both felt very comfortable around trinity. In the past my dogs would have nervous stomach problems with other sitters, but trinity made them feel loved and comfortable, and when we came back from our trip they were happy and loved. Trinity kept us in the loop the entire trip and respected our home and dogs like her own. Will definitely be hiring trinity again in the future.”
“Chris was an awesome dog sitter for our two pups while we were out of town. He kept us updated throughout the day and showed exceptional care for them both and asked questions when needed. He went the extra mile and took them out to play, go on car rides, and walk in the park. Great experience; we will definitely be contacting Chris for future care.”
“Natalie took great care of Lily for 4 drop in visits! She sent me videos and pics and everything was just how I left it when I got home! Will be re booking her in the future….thank you Natalie!”
About: I’ve taken care of dogs/cats all my life, my dream job since I was 5 was to be a veterinarian/zoologist currently what I am in school for. I seem to have a gift of an amazing heart every animal can sense, you could have the most aggressive animal and once they get around me they are very loving and cuddly. I would love to gain your trust to help take care of your furry animals for your needs. I have 4 little babies of my own, 2 dogs border collie and yorkie and 2 cats one tabby and a maine coon. They’re the sweetest animals ever, house trained, has have all their shots and gets along with every animal they meet. I work from home full time Monday-Friday and I have a schedule that allows me to watch your animals from the comfort of my home. I’ll be able to walk, feed, play and cuddle with your fur babies with no problem. If you need quick walks or would love for me to check on your animals for you I would love to make sure they are taken care of when you are not able to. My border collie is trained to walk her self while standing by me, she is my service dog. I take her to Baldwin Dog Park every weekend, every day when I take her out we go for our usual runs, she loves to sleep in the room with me, huge cuddle buddy. My yorkie is a house dog she goes outside for a few minutes goes right to the bathroom and goes right back to the door, she loves to just lay in her bed all day or up in the bed with me or my aunt. My cats are a cuddle buddies all they do is sleep and relax on my screened patio all day.
“Amanda took on our last minute booking and really saved us. She made an effort to bond with our pups and let them warm up to her. She was communicative while we were away and took great care of our home and pups.”
The median cost per night for house sitting in Winter Park is $45
Pet parents share their Rover experiences - Winter Park
Michael took excellent care of Branch! He communicated with us great and sent adorable pictures and updates on Branch that made us feel better about the long time away from our sweet pup and brought lots of joy to our day seeing his cute face! We feel great knowing Branch was so well loved by Michael! He also took excellent care of our home, when we arrived home all was clean and tidy and very well cared for. Thank you so much Michael for spending time and taking care of and loving Branch while we were away!
Thank you so much, Nathan, for taking such wonderful care of our doggies and our home! It was such a relief to know they were in good hands while we were away. The doggies were happy when we returned, and our house was clean and tidy. We truly appreciate your kindness, care, and thoughtfulness. We will definitely reach out to you again whenever we need help with our doggies and home. Thank you again for everything!
Nina was great with my pug, Daisy Mae. She made friends with her instantly! Nina not only took care of Daisy, but took her to a neighborhood coffee gathering so Daisy could play with her doggie friends. I appreciate Nina coming at such an early hour on a Saturday to pet sit. I would definitely recommend her to others.
Amy was absolutely amazing with Lotus and Coco. I over stress when leaving my dogs with someone new because they can be very crazy at first and take some time to get used to someone. She had so much patience with them and because of her I was able to relax and enjoy my vacation. She gave my dogs lots of love and snuggles, sent many updates and photos too. I will absolutely rebook with Amy next time I’m out of town.
The best pet sitter we've ever had. Hands down. We felt totally comfortable leaving our fur babies in her care. She kept in regular communication with us, shared photos of our babies enjoying their time, which allowed us to relax, and enjoy our vacation worry-free. Would hire her again in a heartbeat.
Kailey was communicative and amazing with my pets! She sent photos daily. My pets were really happy and loved. They went on walks, played fetch, and snuggled. We had a delayed flight home and she made sure they were taken care of. Highly recommended her to anyone in need of a pet sitter! 😊
Deborah is wonderful! I was really nervous about going to NYC for 7 days and leaving my kitty Chloe alone….who has never been left alone before. My aunt and a friend were available during the day to check on her, but I really wanted someone to stay overnight for a min of 2 nights. I discovered Rover and was very impressed with the app, reviews and pet sitter screenings. As soon as I met Deborah the day before my departure, she put my mind at ease and I knew that my little Chloe was in good hands and would be given some affection. When Deborah spent the night, she touched base with me via text and provided updates and photos of her interactions with Chloe. I highly recommend Deborah and will definitely hire her again!
We are thankful for the care Marin provided for both of our pups while we were away. We hired her for the weekend to house sit and take care of the dogs, and she did a great job! She kept us updated with photos and texts and even handled some unexpected, last minute medication needs for our older pup. We would highly recommend her and would definitely have her sit for us again!
Isabella was AMAZING with our cat, Finn! She made sure he was taken care of and gave him lots of cuddles while we were away overnight for my birthday trip. She’s very attentive and always asked what our preferences were while she stayed at our home. We will definitely be booking her again! :)
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 Park
Select a filter and find qualifying sitters offering house sitting.Sitters in Winter Park average 4 repeat house sitting clients
FAQs for House Sitting - Winter Park
Frequently asked questions about Rover
The average cost of House Sitting in Winter Park is $43 per night as of November 2026. Most bookings cost between $30 and $83 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 November 2026, there are 3,151 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 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 Meet & Greet.
sitters on Rover set their own cancellation policy, 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 Park. On Rover:
- 90% 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.
Connect anywhere with the Rover app
