House Sitting Winter Park
Find a loving house sitter to watch over your pets and your home.
Over 158 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.
“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!”
“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!”
“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.”
“Wonderful house sitter & took terrific care of our cat Oscar. Deborah leapt in to help us on short notice when another Rover sitter bailed the night before she was due to start. My wife and I highly recommend Deborah and would be happy to use her again.”
“Brenda and Dwain were INCREDIBLE! We left for a week long trip and I was so nervous about making sure our babies were okay. From the start Brenda and Dwain were very present and attentive to the animals and wanted to make sure they followed their routine to a T. Our dogs eat homemade food and they stayed active with making their food through the week, as well as stayed consistent with their daily walks. One of our dogs was having a hot spot issue when we left, but they stayed on top of treating it with the medicine we left and when we got home his hot spot was almost completely gone! They sent updates and pictures multiple times a day which made me feel so much better! They even took the time to write little “stories” about the day which were so fun to read! We didn’t have to worry at all on our trip because we knew they were all well taken care of. When we got home, our house was clean and virtually untouched and all the animals were happy and healthy! I couldn’t recommend Brenda and Dwain enough! If you want a family that will treat your animals and your home like their own while you are away, book them!! Thank you guys so much!”
“Anneke was a literal dream! This is the first time I've ever had a non-family member watch Rocco and she was so communicative and understanding. She was so good with Rocco and I felt so comfortable with her there. 10/10 all around. We will definitely be booking her again and again!”
“Makenna is the bomb! She not only made our two k-9 girls fall in love with her, she also changed the bed, cleaned the house and left us a wonderful unexpected surprise!!! She is also a classy dresser and a delightful person! Thank you Makenna, we will definitely ask you to stay again. Kathy and Michael”
“As always had another great experience with Lexus dog sitting our senior dog. Can’t say enough positive things about her professionalism and attention to detail.”
“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!”
“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.”
“Glacie was wonderful! She communicated very well, sent pictures of Duke often, and when we got home we can tell he was very well taken care of. She also left the house nice and neat!”
“Jessica was fantastic! Met us prior to their stay, asked excellent question, kept us updated when we checked in, and had no issues throughout their stay. Our dogs got along really well! Highly recommend Jessica if you ever need someone to take extra-good care of your fur babies!”
“Mariia was absolutely amazing with lotus and coco. Thanks to her I was finally able to enjoy a vacation worry and stress free. I’ve used Rover once in the past and had an awful experience with two different people canceling on me a day and two days before my trip and then the sitter that finally agreed to watch them, canceling on me after I left for my trip. My dogs can be super crazy at first and need some time getting used to someone new. Mariia came over once to meet them for a bit and then came over early the day I was leaving to spend some time with them before I left and that really helped my dogs get comfortable with her. I definitely over worry any time I’m away from my dogs and stress about whether they’re being good, but she stayed in contact with me every day sending messages and photos and it really helped me to enjoy my vacation and not worry about my dogs. I’m so happy I’ve finally found someone that I can rely on to watch them when I go on vacation. I can’t recommend her enough.”
“This was my first time using Rover for my 4 dogs and Colleen was amazing! She had great communication through the entire stay and I felt like my dogs were in great hands. I was not worried for a minute while they were in her care. I will definitely be rebooking Colleen in the future.”
“Caedmon did a wonderful job with our senior dog! He made sure she was comfortable from start to finish and spent so much time with her, which put us at ease for a last minute family emergency. We couldn’t be more thankful that he stayed with our Chloe girl!”
“Thank you Rachel for taking care of our Doberman Max. We were in an Airbnb located in Orlando and she was able to take care of my boy. Also, we arrange an extra time and was late night and she was fine with it. Do not hesitate to contact her to take care of your four legged friends. :)”
The median cost per night for house sitting in Winter Park is $46
Pet parents share their Rover experiences - Winter Park
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! :)
Jin was great! Very good communication, sent photos/updates, left home in great shape, and most importantly took care of Duke well even with all his health issues! She was also so kind to be flexible with the schedule due to my son coming home earlier than expected. Appreciate it!
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 October 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 October 2026, there are 3,154 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.
<b>Tip:</b> 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 , 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 Park. 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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