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 great! She kept us informed and sent us lots of photos! The pups seemed like they had a good time and well taken care of! Would for sure have Kenya take care of our pups again!”
“Autumn was Fabulous!! She is friendly, a great communicater, and sent me pictures throughout her time in my house. I have 3 goldendoodles and they gave her a 5 out of 5 review. Just watching my girls interact with her gave me such peace. The pictures captured their personalities and their smiles. I highly recommend Autumn for your pets needs.”
“Kiri is the absolute best dog/house sitter we have ever had! I loved her, my pups loved her, and she was in constant communication with me the entire time we were gone. The absolute best!!!”
“Dwight did a great job taking care of my two corgis! It was super last minute at a hotel, I was going to be busy with other stuff. He came in clutch. He followed direction perfectly and updated me on everything ! Gave them lots of attention and walks too. Will definitely use him again if need be and I’m in the Orlando area.”
“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!!”
“Peter was the best! He took perfect care of my pup and went above and beyond. My pup felt safe and happy and he left my home in perfect condition. Would definitely use again.”
“Finding a sitter for your pets can be nerve wracking. Trusting a stranger with your home, let alone your pets is a difficult decision to make. Rob and Wynn put us at ease during our first meet and greet and they clearly have great energy as our pets (including an anxious dog) warmed right up to them. They house sat for us for a few days, with daily updates, strict adherence to the instructions we'd requested, and our pets (2 dogs and cat) loved them. They were respectful of our home and very kind with our pets. We will absolutely use them in the future without a doubt and would encourage anyone on the fence to select them as well. Wynn was punctual, attentive, and professional as was Rob. Thank you for helping make a difficult decision so easy!”
“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'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!
“We always receive exceptional service from Hailey! Daily photos and updates - it makes traveling so much better knowing that someone is caring for our babies.”
“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.”
“Let me start off by saying that I highly recommend Heather for any of your pet related needs! We had a trip planned prior to knowing we'd have a little pup in our lives. Given that he was only 11 weeks old I was undecided as to whether to cancel the trip or find a sitter to stay in my condo with him while we were gone for the weekend. We found Heather on Rover and after an day of exchanging messages I felt comfortable enough to book and meet Heather the day prior to our departure. She took care of Linkin as if he was her own. She was 100% responsive to all of my texts and sent lots and lots of pictures of my little man having fun in the condo, while he was out for walks and even when he was exhausted from playing and fell asleep. If it's a friendly, reliable pet sitter you're looking for...look no further, Heather is great and I've personally found my go to sitter for Linkin from here out.”
“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.”
About: I have 3 cats. I love them all. One is a senior with the energy of a teen. One is reserved but playful. The last one is very selective with how she likes to receive attention and she gets all the love as such. They all get my attention and care in their unique ways, and I would be doing the same with your pets. I may be a cat person, but I love dogs too. Your dogs will be getting some extra attention and loving from me. Aside from just walking your dogs, we could go for a quick run, play some tug of war, whatever toys you have available. Now cats, I love playing with cats, snuggling with cats, and just occupying the same room as cats. Whatever your cats need, I'm just there to make sure they are okay and that they don't get too lonely while you're gone. I will be taking pictures of your pets and sending them to you so you know they are being taken care of or just to remind you how cute they are. Can also watch over cats colonies while you're gone. At the moment, I am very flexible. I am free most of the week for most of the day. I limit any visits between 10 am and 8 pm. I will be starting with soon, and I'll have to limit myself to evenings. For dogs, if you have any toys they like to play with, I will play with them using those toys. I will go on walks with them to make sure their business gets done. If they have been naughty and made a mess, I will tidy things back up for you with your permission. For cats, I bring my own toys if needed to play cats. Cats I've watched over loved the rainbow string wand and the mini plush soccer balls I bought for my own cats. I like to brush cats and help them de-shed. I regularly clean out the litter box and use a deodorizer on both the remaining litter and litter dumped if left in the trash bag. Essentially how I treat my cats, I would treat yours with the understanding that I am a stranger in their home.
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
“Michael was wonderful! He took such great care of our Dog Branch! Excellent communication and he sent sweet pictures everyday of Branch with an update. It gave us peace of mind knowing our pup was being taken care of and loved! He stayed in our home and took excellent care of Branch and the house was immaculate when we arrived home! Thank you Michael for such great care of our dog Branch! We will be happy to have him watch and care for him 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.”
“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!”
The median cost per night for house sitting in Winter Park is $45
Pet parents share their Rover experiences - Winter Park
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.
Autumn was Fabulous!! She is friendly, a great communicater, and sent me pictures throughout her time in my house. I have 3 goldendoodles and they gave her a 5 out of 5 review. Just watching my girls interact with her gave me such peace. The pictures captured their personalities and their smiles. I highly recommend Autumn for your pets needs.
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.
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.
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
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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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