House Sitting Winter Park
Find a loving house sitter to watch over your pets and your home.
Over 6 pet parents in Winter Park have booked house sitting
Winter Park, Find top rated house sitting
Prices are estimates per night for 1 dog. Pricing may vary based on your search and includes a booking fee of 11%.
“Sarah did such an amazing job taking care of our two dogs during our wedding weekend! She was so communicative, provided updates and always made us feel comfortable and confident our dogs were in great hands! We also had her bring our lab Remi to several key wedding events throughout the weekend and she was always on time and always communicated with us making sure everything was perfect! For what can be such a busy stressful wedding weekend, sarah took all the stress and worry out of it for us and Remi was the star of the wedding! Thanks again for everything and we will definitely book you again next time we are up in WP!”
About: Animals have been a part of my entire life having grown up with 3 large dogs, a small flock of chickens and other little critters. Currently I have a wonderful German Shepard - staffie mix named Esther that I love with my whole heart. I currently work for Wintr Park resort ski and ride school. Since the resort is currently closed I have full availability until May 29. I’ve been spending my days going on walks or to the park with my dog Esther. I have lots of experience caring for all kinds of animals—from cats and chickens to big, energetic dogs. If you’re interested, take a look at my calendar to see when I’m available! I can host pets at my home, where I have a great yard space, and I’m always happy to take dogs on walks or out to open fields to run and play. I’ll make sure your pets get the care, attention, and exercise they need. I’d love to help take care of your furry family!
“We can’t express enough how great AmyJayne is! She not only watched our pups the night of our wedding, she picked them up from our wedding venue and took them back home to stay with them that evening. She then came back to watch them while we were on our honeymoon. Our pups love her and she spoils them like crazy with walks and snuggles! She is very quick with communication and sends daily picture updates. She also left our house super clean and tidy! 10/10 would recommend!”
About: My husband and I both work remotely from home so someone will be with your furry friend pretty much at all times. We’ve lived in Fraser since 2021 and love it here! Our little condo at Meadowridge has a huge unofficial “dog park meadow” where other friendly dog owners love to take their pets. I’m happy to take yours there for a play too! If your dog isn’t interested in other dogs though, I love walking around the neighborhood with them too! I do have one of my own. She is an older border collie mix of 12 years, always gets along with others. I work remotely from home so will be with your doggo at all times! We love taking ours out for walks around the neighborhood, so happy to have an extra one of yours! I live in a 2 bedroom condo. There is lots of room to roam around, nap, hang out. We back an unenclosed patio grass area where they can easily go out for a quick potty.
About: I’ve taken care of newborn puppies all the way up to senior dogs. I’ve had a soft spot for animals all my life! This platform seems like a perfect fit! I currently work part time doing videography and travel all over the country so I plan to care for dogs in each place I visit! We have a small farm but it’s not fenced in. Our dogs run and play all day long and then just hangout. Lots to do around here as me and the dogs love to go explore!
“AnnaLiese was great!!! We have never left our dog with a stranger before. Our dog loved her and she spent the day hiking with him and relaxing at her house while we went to a concert. I would definitely recommend AnnaLiese.”
“We left our two very active golden retrievers with Alec for the week. Along with plants to water and bird feeders to manage. He was professional, caring, and communicated well. My animals and home were tended as if it was his own ( or maybe his family home!) . I would never hesitate to have him come back and he certainly earned a 5 star rating. The house was clean on our return and although the dogs were excited to see us I could tell there was no stress evident from our absence.”
“Jake was awesome! He took great care of my 2 dogs and my house. He was very patient with my dogs and letting them get used to him. He took them on many walks and kept me well updated with texts and photos. I would highly recommend him and will definitely use him again!”
About: I have been taking care of a large variety of dogs for 20 years. From eight weeks old to 16 years old, from pugs to chows and pitbulls to 140 pound malamutes I have cared for them all. I can come by to walk and feed your best friends once a day or stay and cook them meals as per your request. I want to make sure you and your loved ones are as comfortable as possible while you are away. I do freelance work so I have pretty open availability. Making sure you're needs are met so you are comfortable is my top priority. If for some reason I can't meet all of your needs I will tell you before committing to something that doesn't fit my schedule or abilities. I am here for you. How I care for your pets and home is mostly dependent on your requests. I give medicine, food and exercise as requested. I can simply fill a food bowl, measure servings and even cook protein and veggies for your dogs if that is what you want. I am happy to keep you updated or send you pictures if you'd like. Walks are as far/long/plentiful as requested. I want to provide you with the comfort of knowing someone is there to care for your loved one as you would while you are away.
“Patti was great! very responsive and professional. She sent me lots of pictures and videos during her stay. Left me house in great condition and my dogs seems well taken care of! I would recommend her to others and would use her again!”
“Lucy did a great job with my pets. They were well cared for & my outdoor cameras showed her outside with them, throwing the ball & also taking walks with them. She also was there when she said that she would be. I will certainly use Lucy again!”
About: I have over 30 years experience raising, training, fostering, foster-failing and generally loving and caring for dogs. I work from home so will be with your pet most of the time and I love to go for long walks and runs with them. I am very active (walk, run, hike...) and have a large fenced in yard and a dog park nearby to keep your pup busy and well-exercised. Most of my clients are repeat customers as they find my services truly a "home away from home" for their fur-baby. Although I am new to Rover I have several references available outside of Rover - feel fee to request any you may like to see. I work from home so I am able to let dogs out every few hours in our fenced yard. Also walk at least an hour a day. Dogs in my home are treated as (and sometimes better 😉) than humans. Run of the house and the fenced yard. Lots of love and snuggles. Lots of walks/hikes/fetch/etc.
About: Animals have always been a big part of my life — from fostering dogs to managing a farm and raising multiple litters. I truly understand the patience, structure, and love that pets need to thrive. I enjoy grooming, hiking in the mountains with four-legged companions, and making sure every pet feels safe, happy, and cared for. Whether it’s daily walks, overnight care, or just extra cuddles, I treat every animal like my own. Working from home gives me the flexibility to give pets plenty of attention throughout the day — whether that’s walks, playtime, or snuggles between meetings. I’ve successfully fostered dogs, managed a farm, and raised multiple litters, so I understand the unique needs of animals at every stage of life. With an active lifestyle and love for the outdoors, your pup will enjoy safe adventures, fresh air, and plenty of exercise. Grooming and extra TLC come naturally — I’ll care for your pet like part of my family. ⸻ In My Home: Pets have a safe, calm, and pet-friendly environment with plenty of space to relax and play. I keep a consistent routine with feeding, walks, and bathroom breaks to make them feel secure. I never leave pets unsupervised for long periods, and I always ensure water, comfort, and a cozy place to rest are available. In Your Home: I respect your space and follow your pet’s established routine closely. From feeding schedules to walk preferences, I’ll maintain consistency so your pet feels comfortable and cared for while you’re away. I provide updates, photos, and check-ins so you always know your pet is safe and happy. Overall: Safety, trust, and comfort are my top priorities. With experience fostering dogs, raising litters, and caring for animals of all sizes, I understand how important it is to give your pets the same love and attention they’re used to at home.
“Mae took wonderful care of our home and dog! She provided daily updates and was very responsive. Our shy dog seemed to become comfortable with her quickly. We will definitely book with Mae again.”
About: I look forward to being able to help you with outdoor doggy adventures! My daycare/dog hike times are; pickup between 8-9am and half day drop off between 12-1pm ($60), full day drop off between 3-4pm ($120). These times are a bit flexible, talk to me about working outside these guidelines! I have loved dogs and animals in general since I was a boy. I have worked as a professional dog caregiver for the last 15 years. My clients have always relied on my love of their dogs, consistency of care, and my flexibility with their schedules. I will take your dog on half or full day adventures in the great outdoors! Examples of activities are; hiking, biking, trail running, cross country skiing, snowshoeing, etc. I am trained in E-collar use and have helped my clients learn basic skills such as; come, sit, stay, drop, etc. I have owned senior dogs and had to administer medications and IV bags. It is a full time job for me. I love working with dogs and will continue to make it my number one priority going forward I am in a condo with a dog door that leads to a deck. Dogs that visit are allowed on the couch, 4 or 5 dog beds available, or sleeping on my bed! I walk all clients dogs on leash in the neighborhood, on/off leash on my outdoor doggy adventures depending on dogs skill set and owners preference.
“Rebecca is a wonderful and extremely caring and diligent petsitter. I knew Marilyn was in great hands and Rebecca eased my mind every day with her level of care. I appreciate how well she looked after my old girl and would love to use her services again in the future!”
The median cost per night for house sitting in Winter Park is $60
Pet parents share their Rover experiences - Winter Park
Sarah did such an amazing job taking care of our two dogs during our wedding weekend! She was so communicative, provided updates and always made us feel comfortable and confident our dogs were in great hands! We also had her bring our lab Remi to several key wedding events throughout the weekend and she was always on time and always communicated with us making sure everything was perfect! For what can be such a busy stressful wedding weekend, sarah took all the stress and worry out of it for us and Remi was the star of the wedding! Thanks again for everything and we will definitely book you again next time we are up in WP!
Sarah took exceptional care of Max and Minnie, especially when Minnie became sick during her stay. She was attentive, compassionate, and proactive, keeping me updated every step of the way and making sure Minnie received the care and attention she needed. Knowing Sarah was looking after them gave me tremendous peace of mind. I highly recommend Sarah!
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 Rover works
1. Search
Browse profiles of sitters near you who offer house sitting2. Meet & Greet
Schedule a free in-person Meet & Greet to find the perfect fit3. Book & Pay
It's that easy! All payments are processed through Rover's secured platform
Popular requests near you
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 1,929 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:
- 95% of sitters can help with special care needs
- 98% can help with giving oral medications or injections
- 98% 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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