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 was amazing! She sent plenty of pictures and we came back to happy dogs. She allowed us to feel super comfortable while we were on our cruise. Highly recommend.”
“Autumn is so punctual, caring, communicates really well and took such good care of my dogs! She sent me pictures and videos often and kept me updated and gave them so much love and care. She is really awesome!”
“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!”
“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”
“Peter was able to accommodate two last-minute bookings to watch my dog really early in the morning. I am extremely grateful! He was on time and communicative. I would have him watch my dogs again in the future.”
“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.”
“We always contact Lexus first to watch our boys. This past weekend we had plans to go in our honey moon and were scared to leave our dogs because one had spent the week ill, in and out of the vet, and on a bunch of new meds. But Lexus took on the challenge gracefully and we are grateful for her regular reports and photos!!”
“Christina was absolutely amazing with my boys. Very caring and considerate. Thank you for taking such good care of them. I'm so glad to have found such a trusting sitter for my dogs.”
“Our 2 Dachshund pups had a wonderful time and were well taken care of by Michael for 4 nights in our home. Thank you so much Michael!! We highly recommend Michael and will continue to hire him going forth!”
“Kiri is so amazing! She is super nice and flexible. Our dogs love her. She sends us pictures and is very communicative. We already have plans for Kiri to help us out on future trips!”
“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.”
“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.”
“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.”
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
“Hailey is beyond wonderful! She is SO communicative, so kind, and truly an animal lover. We were able to enjoy our vacation because we knew our dog was in wonderful hands when we were gone! We are so grateful for her and know Leo can’t wait to see her soon! Thank you, Hailey❤️”
“Logan was absolutely fantastic with our dogs! Leaving them behind is never easy, especially because they are highly active and each have their own unique personalities, but Logan made the entire experience stress-free. He gave them plenty of attention, kept up with their energy levels, and made sure they were well cared for while we were away. We loved receiving updates and could tell our pups were happy, comfortable, and in great hands. It’s clear that Logan genuinely cares about the animals he watches, and that peace of mind is priceless. We came home to happy dogs and a well-cared-for home. We highly recommend Logan to anyone looking for a reliable, trustworthy, and caring dog sitter. We would gladly have him watch our dogs again!”
About: I have been a huge animal lover and caretaker ever since I was a child. I have a multitude of experiences with animals from all walks of life through my own personal pets and volunteering experiences with local rescues. I am currently a foster for a local rescue (Husky Haven) and I have experience with dogs of all ages (from puppy to senior) and have worked on house-training, proper leash manners, crate-training, socializing, and loving the dogs to get them adopted into their forever home. As someone who owns two dogs, I know it can be stressful finding someone to take care of your furry family members. I will do everything I can to give your pets the best care and communicate with you/send loads of pictures so you have an ease of mind! I have a job where I always work evenings, so I am free every day of the week from the morning to the afternoon (6 am-3pm). I also have weekend availability! If you have a fenced-in yard, I will monitor your dog make sure your dog does not escape or get into anything that would harm them. If you do not have a fence, I will make sure the dog is in a secure environment at all times and be careful to harness and leash them before taking them out.
The median cost per night for house sitting in Winter Park is $45
Pet parents share their Rover experiences - Winter Park
Taylor was incredible! We recently traveled out of the country and we were really nervous about leaving our dog for the first time. From the moment we met Taylor all of our worries went away. She’s super sweet and made us feel really comfortable about leaving our little one. She sent us pictures and videos every day, and our dog loved her. We will definitely use her for all future travels, and would recommend her to anyone in need of a dog sitter. :)
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.
Izzi did a phenomenal job caring for our SIX cats and TWO dogs a puppy golden retriever and senior Shiba Inu ! And cats of all ages including senior kitties. We truly felt at ease and relaxed on vacation knowing our babies were in amazing hands. She spent a lot of time with them, followed instructions exactly, asked questions, was extremely communicative, and she took many photos and videos that helped us feel relaxed on vacation. We are very attached to our babies and protective and it has been a long time since we have been on vacation but Izzi made us feel comfortable to do more trips since we trust her with our babies fully. She is a true animal lover and we highly recommend her!
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!
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.
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 $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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