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.
“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.”
“Stephanie provides frequent updates while dog sitting. She sends pictures and sweet messages. Our dogs love spending time with her because she takes such great care to ensure they get long walks and plenty of snuggles!”
“This was our first time using Rover (or even a dog sitter that we didn’t know) and Caroline did not disappoint! Her communication throughout our 8 day trip was amazing - the almost daily pictures were so appreciated and she was quick to reply to our messages. Highly recommend!”
“Allison was by far the best sitter we have had on Rover thus far. She stayed in our home with our two dogs and was trustworthy, great with communication but most of all cared for our pets like they were her own. She sent daily updates with pictures and video. It was nice being on vacation and not having to worry. She went above and beyond and even left our house spotless. Book her now if you’re reading this! Thank you Allison.”
“Hailey is very kind and friendly. She did a good job with Ginger making sure felt comfortable for the overnight stay. Ginger warmed up to her and Hailey kept me updated with pictures and texts.”
“Sarah watched our 2.5yr old Golden Retriever, Blitz, over this last weekend and she was GREAT! She is very in tune with Blitz and we always feel comfortable going away knowing he is in good hands with Sarah. She has watched Blitz before and is always very good about giving us updates with lots of pictures and videos which we really appreciate. We highly recommend Sarah for your next dog sitter! Your loved one will be in the best of hands.”
About: Hands on experience caring for animals I provide dependable, compassionate care tailored to each pet’s unique needs. I’m comfortable with a wide variety of animals from large to small. I am retired and I do Uber on the side. I have very flexible hours and I’m available from dog walking, spending time with your animals to staying with them in your home to house sitting. What sets me apart is that I treat every pet as if they were my own. I understand that every animal is different, and I will take the time to learn their routines, preferences, and any special needs that they may have. Whether your pet needs lots of playtime, quiet, companionship, medication or extra patience, I provide loving a attentive care so you can have peace of mind while you’re away. My goal is for both you and your pets is to feel completely comfortable, knowing they’re in experienced, caring and trustworthy hands.
“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!”
“Alicia stayed at our home for the weekend and took care of our 2 small dogs. They can be barky but they seemed to relax around her pretty quickly. She sent several pix -our doxie was snuggling up to her the same night we left and our nervous chihuahua was in out in the yard wagging away the next day. The house was the same as we left it. We would definitely book Alicia again 😀”
“Tiffany was so great! She arrived as promised and even took our dog out one extra time for us since we were returning late. The dog was happy and well- cared for, left the house in great shape. Will definitely use Tiffany again and highly recommend!”
“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!”
“Jenna did an amazing job caring for our two pups while we were out of the country for two weeks. She sent lots of pics & videos and the doggies loved her. We highly recommend Jenna for your dog sitting needs.”
“Dana was absolutely amazing with our pets. Due to unforeseen circumstances, we were forced into our first experience with Rover. I feel so lucky that we were able to connect with Dana and that she had availability to watch our pups. Her communication was amazing. She was very easy to work with. She seemed very comfortable with both personalities of our dogs, which is something considering how different they are. The communication and pictures during our trip were outstanding. I couldn’t recommend Dana more. In fact, we have already sent her profile to some of our closest friends. Thank you so much for all the help!”
“David did an amazing job with our two labs. We appreciated him keeping us updated through pictures and videos. David was available at the last minute which meant a lot to us.”
“Sonal is always amazing with our pets. She really goes above and beyond your normal pet care. She's super responsive and gives plenty of updates so we're always up to date on how our pets are in her care. I would recommend her services to anyone looking for a super caring, loving pet sitter.”
About: I have had taken care of/lived with various dog breeds, and have walked and raised dogs since I can remember. I have volunteered at Alaqua walking and playing with dogs, and I have experience dog sitting and walking dogs via Rover and family connections. I have worked with puppies, middle aged dogs, older dogs, both big and small! I love dogs unconditionally and I will do everything in my power to ensure they stay spoiled and happy :). As of now, I am attending University of Central Florida, so I am willing to work around my classes and my work schedule once I find a stable job! I cannot care for pets at my own home, but I will ensure that when I come to your home, I will keep it looking good as new. I am a chronic dish washer if any dishes or slight cleaning needs to be made. I am also no stranger to accidents that dogs are prone to, as one of my past dogs had a sensitive stomach, especially when it came to my carpeted floors. I will do whatever your dog wants to do, but my favorite aspect of it all is to ensure that the dog is happy and to make a connection with them. I love being active and playing, but I can also just simply snuggle up with them.
“Maria was great! She took great care of my golden (Wally), sent lots of pics, and provided excellent communication throughout her stay with him. I would fully recommend her and would not hesitate to have her stay with Wally 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.”
The median cost per night for house sitting in Winter Park is $45
Pet parents share their Rover experiences - Winter Park
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!!
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.
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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