House Sitting Winter Park
Find a loving house sitter to watch over your pets and your home.
Over 151 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.
“Tori stepped in to help with my two dogs at such a crucial point for me. She completely lived up to all of her 5 star reviews. Communication in meeting the dogs, leading up to the stay and during the stay was excellent. She sent pictures and gave me the updates that were so important to me. I will always be grateful to her for helping me out this weekend. Thank you Tori!”
“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.”
“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!”
“Kenya was fantastic in every way, a wonderful dog sitter to our dogs and a wonderful communicator to us as well! She'd be the first choice to stay with our dogs any time we have to go away. They've never been so happy and content seeming after we came home before.”
“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.”
“Makenna dog sat for us for 4 nights and was great! She sent pictures daily and kept me in the loop. Dogs seemed happy as ever! She also was a great guest - stripped the bed before leaving and kept the house tidy. Will be rebooking. Thanks again!!!”
“This was my first experience using a house sitter with Penny. Bailey was great! I appreciated that I didn’t have to worry about Penny or my apartment at all, and loved getting pic updates of my girl. I would definitely rebook. Thanks, Bailey!”
“I can't sing praises enough for Michael. We typically make arrangements for dogsitting well in advance. This time, one of our sons was house/dogsitting. He had to be taken to the hospital, had emergency surgery, and is still hospitalized. Our other son and his family work full-time and couldn't stay at night. I made arrangements with Michael from a cruise ship in the Eastern Caribbean, which meant we couldn't do a meet and greet ahead of time. Our other son met up with Michael to introduce him to the dogs. Michael took great care of our dogs and our home while we were gone. He was very communicative. It's good to know we have an excellent option for care next time we're going away. Looking forward to actually meeting him in person next time. I highly recommend him if you're looking for someone to care for your furry family members. Thanks again, Michael.”
“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!”
“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.”
About: I've loved animals since childhood and I have a collection of my own! Including the basics, 3 cats, and.... geckos, snakes, and quails of cource all our non-venmous and completely hsrmless little ones! No matter what your pet is I would love to care for them and give them the best care possible! If boarding: you pet will be housed in a separate room from my 3 cats to make sure everyone is as comfortable as possible! I will spend as much time as needed with your furry, feathered or scaly pet as needed! No matter my schedule I always block off time to give your baby as much time as they require! I have a separate sectioned off area of my apartment where you pet will get all the enrichment they need without being disturbed by any of my babies.
“⭐️⭐️⭐️⭐️⭐️ 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!”
“I cannot recommend Logan highly enough. From our very first interaction, he was professional, communicative, and genuinely invested in making sure my dog felt comfortable and cared for. What impressed me most was the level of attention and care he provided. He was consistently reliable, arrived when expected, sent thoughtful updates, and clearly took the time to get to know my dog’s personality, needs, and routines. It gave me tremendous peace of mind knowing my dog was in such capable hands. My dog absolutely adores him, which says more than I ever could. It’s obvious that he genuinely loves animals and treats them as if they were his own. Every walk left my dog happy, exercised, and excited for the next visit. If you’re looking for someone who is trustworthy, dependable, kind, and truly exceptional with dogs, look no further. Finding someone you can confidently trust with your pet is rare, and Logan has earned my highest recommendation. I would not hesitate to book with him again and will continue to do so whenever I need help caring for my dog.”
“Mariia was great! She communicated well, spent a lot of time with our cats, and left my house spotless. I came home to calm, happy cats and we will be using Mariia again :)”
“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!”
“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.”
“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!”
“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.”
The median cost per night for house sitting in Winter Park is $45
Pet parents share their Rover experiences - Winter Park
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!
Christina was a huge hit with both of my pups from their first meeting. Having her housesit for us for a long weekend was fabulous- she was very communicative, sending lots of pictures, and made sure the pups were comfortable. We’ll definitely work with 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!
Wynn took excellent care of our pets! We have a big fur crew and I get nervous giving the responsibility to someone, but I had peace of mind on my trip which made a world of difference. She Did everything I asked her to do and sent me detailed updates and photos daily. Communication was great and our cats and dogs got plenty of attention. We have already booked her again. She is a 10 star sitter!!
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 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 for House Sitting in Winter Park on Rover is $44.4 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 3,176 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:
- 90% of sitters can help with special care needs
- 95% can help with giving oral medications or injections
- 95% 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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