House Sitting in Winter Park

Find a loving house sitter to watch over your pets and your home.

End
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Winter Park house sitters

1 / 1
Sitter Profile Image: Hailey P.
Verified Enhanced Background Check
Hailey P.
Star Sitter
from
$38
per night
5.0 out of 5 stars
414 reviews
108 repeat clients
10 years of experience
Lake Eola Heights, Orlando, FL, 32803

Hailey was great! This was our first time using a dog sitter as well as the first time having someone stay in our home that wasn’t a friend or family member to help out. She made us feel comfortable with both our dog and our home in her hands. Great communication and it was obvious our dog had a great experience as well. We are lucky to already have her booked for a future trip :) thank you Hailey!

Profile image
Silvana D.
Sitter Profile Image: Kenya C.
Verified Enhanced Background Check
Kenya C.
Star Sitter
from
$40
per night
5.0 out of 5 stars
172 reviews
34 repeat clients
5 years of experience
Park Lake-Highland, Orlando, FL, 32803

Kenya did a great job looking after our dog Stevie! She communicated and took photos throughout the day and it seemed like Stevie had a great time.

Profile image
Eric H.
Sitter Profile Image: Marin W.
Verified Enhanced Background Check
Marin W.
from
$45
per night
5.0 out of 5 stars
9 reviews
1 repeat client
6 years of experience
Baldwin Park, Orlando, FL, 32814

Marin was so amazing with our two girls. She was responsive and sent pictures daily. Our two golden-doodles are not old so no special care necessarily but they are very needy. When we got home the house looked perfect and most importantly our two girls were so happy. That tells me she did a good job because sometimes they will act a little mad at us for leaving them. We will def. ask her again if we need to leave Phoebe and Ellie. Thanks Marin you’re amazing!

Profile image
Maria E.
Sitter Profile Image: Lexus & Tiffany A.
Verified Enhanced Background Check
Lexus & Tiffany A.
Star Sitter
from
$55
per night
5.0 out of 5 stars
66 reviews
19 repeat clients
6 years of experience
Orlando, FL, 32817

Lexus went above and beyond to take great care of boy! I’m a bit of a helicopter dog mom and Lexus put my mind at ease. Winston had a great time with her and I am so grateful. 💕

Profile image
Ivy K.
Sitter Profile Image: Kiri R.
Verified Enhanced Background Check
Kiri R.
from
$55
per night
5.0 out of 5 stars
65 reviews
26 repeat clients
17 years of experience
Orlando, FL, 32803

We are beyond thrilled to find Kiri. This was our first opportunity to use her and we are thankful. The house was spotless, she sent lots of pictures, walked them regularly and gave them lots of love. I hope she made herself at home as we appreciate her so much. We are already looking to book our next stay. 5 star all the way.

Profile image
Kim L.
Sitter Profile Image: Michael D.
Verified Enhanced Background Check
Michael D.
Star Sitter
from
$60
per night
5.0 out of 5 stars
43 reviews
17 repeat clients
10 years of experience
North Orange, Orlando, FL, 32804

Michael took such great care of our home and pets! He was in regular contact including pictures of the dogs for our kids. Will definitely book again for future trips!

Profile image
Scott P.
Sitter Profile Image: Peter B.
Verified Enhanced Background Check
Peter B.
Star Sitter
from
$50
per night
5.0 out of 5 stars
107 reviews
56 repeat clients
3 years of experience
Casselberry, FL, 32707

Peter did a great job… he was very caring for our dog and house. He has been open to our comments that allow him to fully understand what we look for in a dog/house sitter.

Profile image
Mark L.
Sitter Profile Image: Deborah M.
Verified Enhanced Background Check
Deborah M.
from
$35
per night
5.0 out of 5 stars
5 reviews
10 years of experience
Winter Park, FL, 32789

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.

Profile image
Jonathan G.
Sitter Profile Image: Nathan R.
Verified Enhanced Background Check
Nathan R.
from
$30
per night
5.0 out of 5 stars
3 reviews
6 years of experience
Winter Park, FL, 32792

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.

Sitter Profile Image: Isabella O.
Verified Enhanced Background Check
Isabella O.
Star Sitter
from
$50
per night
4.9 out of 5 stars
32 reviews
9 repeat clients
7 years of experience
Ventura, Winter Park, FL, 32792

Isabella was amazing! I had no worries and she followed all my instructions exactly with plenty of updates and pictures. She went above and beyond helping me with my plants and package deliveries too. I was able to relax and enjoy my vacation knowing my babies were getting great care. We have already booked her again!

Profile image
Maria H.
Sitter Profile Image: Alayna N.
Verified Enhanced Background Check
Alayna N.
from
$27
per night
1 repeat client
3 years of experience
Casselberry, FL, 32707

About: I have experience caring for a diverse array of dogs, from Poodles to Bernese Mountain Dogs. While I was a student I was trusted by several families for recurring dog and child-sitting, and I also provided reliable house sitting services during their vacations. I have a flexible schedule that aligns perfectly with my remote work arrangement. I’m available for dog care and companionship on Mondays, Wednesdays, Fridays, and over weekends, ensuring that your furry friend receives constant attention and care. Your pet’s safety and well-being are my top priorities. I offer a secure and loving environment for dogs of all sizes. You can feel confident that your furry friend is in experienced and caring hands.

Sitter Profile Image: Heather C.
Verified Background Check
Heather C.
Star Sitter
from
$72
per night
5.0 out of 5 stars
89 reviews
22 repeat clients
17 years of experience
Winter Park, FL, 32789

Heather communicated very well, and I felt comfortable leaving my dogs with her watching them. She sent me pictures of my pups too. Overall, it was a nice experience and I really didn’t worry about anything while I was away on my trip. Thank you, Heather

Profile image
Debbie K.
Sitter Profile Image: Glacie D.
Verified Enhanced Background Check
Glacie D.
from
$50
per night
5.0 out of 5 stars
55 reviews
19 repeat clients
7 years of experience
Winter Park, FL, 32792

Glacie rocks!! She took Emmy for walks, followed the directions perfectly & kept our home clean. Glacie watched Emmy for 6 days and 5 nights and I had zero concern. We will 100% be using Glacie again in the future. Emmy is happy & tired out & that’s all we can ask for 🫶

Profile image
Libby W.
Sitter Profile Image: Alicia K.
Verified Enhanced Background Check
Alicia K.
Star Sitter
from
$86
per night
5.0 out of 5 stars
34 reviews
9 repeat clients
30 years of experience
Winter Park, FL, 32707

Great caring sitter. Everything was perfect. “Walking “Littleman in his stroller was so nice. He loves his “walks”. Everything was so clean and neat. Would use Alicia again and again. Thank you so much.

Profile image
Rebecca A.
Sitter Profile Image: Christina M.
Verified Enhanced Background Check
Christina M.
from
$70
per night
5.0 out of 5 stars
20 reviews
6 repeat clients
10 years of experience
Winter Park, FL, 32789

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.

Profile image
Mia T.
Sitter Profile Image: Rob & Wynn K.
Verified Enhanced Background Check
Rob & Wynn K.
Star Sitter
from
$65
per night
5.0 out of 5 stars
62 reviews
13 repeat clients
20 years of experience
Winter Park, FL, 32789

⭐️⭐️⭐️⭐️⭐️ 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!

Profile image
Santiago C.
Sitter Profile Image: Kailey D.
Verified Enhanced Background Check
Kailey D.
from
$40
per night
5.0 out of 5 stars
5 reviews
1 repeat client
10 years of experience
Winter park, FL, 32792

Kailey is awesome! She cared for my senior dog and cat while I was out of town. My animals loved her.

Profile image
John G.
Sitter Profile Image: Makenna W.
Verified Enhanced Background Check
Makenna W.
from
$55
per night
5.0 out of 5 stars
23 reviews
11 repeat clients
30 years of experience
Colonicaltown North, Orlando, FL, 32803

Makenna was amazing! Very communicative and sent lots of sweet photos during the stay. We could tell our pup loved her. Don’t hesitate to book with Makenna!

Profile image
Kristina H.
Sitter Profile Image: Bailey S.
Verified Background Check
Bailey S.
Star Sitter
from
$60
per night
5.0 out of 5 stars
14 reviews
2 repeat clients
15 years of experience
Winter Park, FL, 32792

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.

Profile image
Laura M.
Sitter Profile Image: John H.
Verified Enhanced Background Check
John H.
from
$65
per night
3 years of experience
Orlando, FL, 32803

About: Hi! My name is Jack :) I have spent the past several years working as a veterinary technician, caring for animals in a professional medical setting. I have experience with puppies, kittens, senior pets, and pets with medical needs. I love building trust with animals and helping them feel comfortable and secure. My goal is to provide the same level of care and attention that I would want for my own pets, so you can travel with confidence knowing they’re in good hands. 🐾 I strive to be flexible and accommodate your pet’s routine as closely as possible. Whether your pet needs morning, afternoon, evening, or overnight care, I will work with you to ensure their feeding, exercise, medication, and enrichment schedules are maintained. Consistency is important for both cats and dogs, and my goal is to keep their day-to-day routine familiar and stress-free while you’re away. I am happy to discuss your pet’s specific needs and create a care plan that works best for them. Your pet’s safety and well-being are my top priorities. As a veterinary technician with several years of experience, I am trained to recognize signs of illness, injury, or distress and respond appropriately. I provide a calm, patient, and low-stress environment tailored to each pet’s individual needs. Whether your pet is energetic, shy, senior, or requires medication, I will treat them with the same care and attention I give my own pets. You can expect reliable communication, regular updates, and peace of mind knowing your pet is being cared for by an experienced animal care professional.

1 / 1
View more sitters

Over 1,026
pet parents in Winter Park have booked house sitting

Winter Park pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Bailey was lovely to work with, great communication! She asked questions when things weren’t clear and gave my pets (including my VERY old cat) lots of snuggles! Will definitely ask her to sit for us again in the future!

Profile image
Alexandra S.
House Sitting
5.0 out of 5 stars

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.

Profile image
Robert H.
House Sitting
5.0 out of 5 stars

Isabella did a great job with my two fur babies. She kept me informed and followed their care instructions well.

Profile image
Crystal M.
House Sitting
5.0 out of 5 stars

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.

Profile image
Lindsey K.
House Sitting
5.0 out of 5 stars

Deborah was very responsive to text and calls. She did a great job with my spicy cat and left my home in immaculate condition

Profile image
Roshni G.
House Sitting
5.0 out of 5 stars

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.

Profile image
Laura M.
House Sitting
5.0 out of 5 stars

This was our second time booking with Glacie, and she was just as wonderful as the first time! Some of our pet care instructions had changed since our last booking, but she handled everything seamlessly without needing any additional guidance. We especially appreciate the updates and photos she sends—it always gives us peace of mind and helps us feel connected to our fur babies while we're away. She also took great care of our home, which we truly value. We can't recommend Glacie highly enough and will absolutely continue booking with her in the future! ⭐️⭐️⭐️⭐️⭐️

Profile image
Aranya B.
House Sitting
5.0 out of 5 stars

Kendall was great! Very caring with Cooper, sending thoughtful updates to us. She was also very responsible staying in our house—even washing and folding the bedsheets she used so we wouldn’t come home to laundry. I definitely recommend her to others!

Profile image
Joshua M.
House Sitting
5.0 out of 5 stars

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.

Profile image
Julia R.
House Sitting
5.0 out of 5 stars

Richard took great care of our three annoying dogs and saltwater fish. He was on time and left the house clean. I highly recommend him for your dog sitting needs.

Profile image
Danielle M.
House Sitting
5.0 out of 5 stars

Kailey is awesome! She cared for my senior dog and cat while I was out of town. My animals loved her.

Profile image
John G.
House Sitting
5.0 out of 5 stars

We were apprehensive at first basically getting a stranger to come stay in the house with our fur babies, but autumn was an absolute blessing. She kept us updated. The house was tidy my puppies look so happy and took to her very well. I love the open line of communication she provided and she was totally amazing. Looking forward for my next trip so she can come over and stay with our for babies again. I highly recommend her services and anyone will be lucky to choose her.

Profile image
Rob V.
House Sitting
5.0 out of 5 stars

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.

Profile image
Anthony M.
House Sitting
5.0 out of 5 stars

Heather is fantastic! She took such great care of our dogs, and I’m so grateful. She was very communicative, sent silly dog pictures, and they absolutely loved her. We will definitely work with her again! 💜🐾

Profile image
Maria M.
House Sitting
5.0 out of 5 stars

Repeat client. Kenya is great as always, my dog immediately takes to her and is so happy to see her.

Profile image
Veronica G.
House Sitting
5.0 out of 5 stars

Eran was great taking care of my fur baby while my family was gone for a week. She gave him all the love we would while we were away.

Profile image
Tracy W.
House Sitting
5.0 out of 5 stars

Dom did a great job sitting at my home with my two pups! She made sure they were happy and followed their routine. She communicated well and sent me updates daily.

Profile image
Justin D.
House Sitting
5.0 out of 5 stars

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!!!

Profile image
Mary Grace S.
House Sitting
5.0 out of 5 stars

Laura is our go to pet sitter. She is the best of the best. We had an international trip and she did a wonderful job taking care of our pups, as always. Thank you Laura!

Profile image
Neddie C.
House Sitting
5.0 out of 5 stars

Wynn took incredible care of our boys and our home while we were away!!! Knowing they were comfortable in their own home being loved and cared for made our time away much more enjoyable and stress-free. So glad we found such amazing pet sitters 😁

Profile image
Marissa
House Sitting
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Winter Park is $45

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 house 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.

Sitters in Winter Park average 4
repeat house sitting clients

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Winter Park on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

If you’re searching for a Winter Park house sitter for the first time, visit the house sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a house sitter before, learn more about how to do this in the Rover app or on your computer.

As of Jun 2026, there are 2,903 house sitters in Winter Park. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Winter Park house sitters respond in under an hour.

House sitters in Winter Park have an average of 14 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Winter Park.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Winter Park house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your house sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.