Pet Sitting in Winter Park

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Winter Park pet sitters

Prices are estimates per visit. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Brooke A.
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Brooke A.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
252 reviews
76 repeat clients
4 years of experience
Winter Park, FL, 32789

Brooke is fantastic! She is super flexible, attentive to detail, and so sweet. I will definitely be using her again and would highly recommend her!

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Alli F.
Sitter Profile Image: Bailey S.
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Bailey S.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
13 reviews
2 repeat clients
15 years of experience
Winter Park, FL, 32792

Sage was very happy with his new paw friend 🐾 great communication and updates, Bailey did not skip a beat! Always on time! She’s everything you want and need as a pet sitter!

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Wanda D.
Sitter Profile Image: Susan H.
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Susan H.
Star Sitter
from
$22
per visit
5.0 out of 5 stars
14 reviews
3 repeat clients
40 years of experience
Maitland, FL, 32751

I was very nervous to leave Chiquita because she was injured but Susan took great care of her and sent lots of pictures! Very pleased and would book again

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cara h.
Sitter Profile Image: Jereny R.
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Jereny R.
from
$23
per visit
5.0 out of 5 stars
49 reviews
17 repeat clients
11 years of experience
Winter Park, FL, 32789

Jereny is a fantastic pet sitter. She takes care of my two cats, Harley and Ray quite often when I travel for work. They are always in a great mood when I get back home because she takes great care of them.

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Joe P.
Sitter Profile Image: Peter B.
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Peter B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
107 reviews
55 repeat clients
3 years of experience
Casselberry, FL, 32707

Peter was great with our two cats. He sent photos and was able to adapt to their prescription dietary needs. We also had a few packages delivered while we were gone and he brought them in! Would recommend.

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Lilly & Destry K.
Sitter Profile Image: Heather G.
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Heather G.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
36 reviews
8 repeat clients
10 years of experience
Winter Park, FL, 32792

Heather did a wonderful job caring for my cat, Benson, during my trip. She visited twice a day, made sure he was fed on schedule, and kept his litter box clean. Even though Benson decided to hide for all three days, Heather was patient, gentle, and consistent with her check‑ins. I really appreciated her reliability and the peace of mind knowing everything was taken care of. I would happily book her again.

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Anastasia O.
Sitter Profile Image: Natalie P.
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Natalie P.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
72 reviews
29 repeat clients
20 years of experience
Orlando, FL, 32804

natalie was the absolute best. so communicative, friendly, helpful, and amazing with my cat of course. my cat felt so comfortable with her and i was so much more at ease away knowing someone like natalie was watching over the kitty. she has extensive experience with animals, will truly treat your pet like one of her own and take her time during her visits with them! this is my first time using Rover and i could not recommend natalie more.

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Paige M.
Sitter Profile Image: Kellye B.
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Kellye B.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
25 reviews
4 repeat clients
10 years of experience
Casselberry, FL, 32707

Thank you, Kellye for servicing my cats. They mean a lot to me, and knowing that you were efficient and kind to them, makes me excited to rebook with you in the future.

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Heather B.
Sitter Profile Image: Hannah Z.
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Hannah Z.
from
$18
per visit
5.0 out of 5 stars
24 reviews
10 repeat clients
5 years of experience
College Park, Orlando, FL, 32804

Hannah was AMAZING! She went above & beyond to make our pets comfortable. We had some issues with our house while we were away and she helped us with that as well. She stayed in contact with us nonstop and our dogs adored her. She was always prompt and stayed the full length of time, and sometimes longer to help with our house situation. She also took the dogs on an unplanned walk, just to help get them out of the house for a bit. She truly was amazing. We recommend Hannah 1000% and hope to use her every time we go out of town!

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Tani S.
Sitter Profile Image: Isabella P.
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Isabella P.
Star Sitter
from
$16
per visit
5.0 out of 5 stars
11 reviews
4 repeat clients
6 years of experience
Altamonte, FL, 32701

She took great care of Nudy while I was away. I really appreciated the detailed updates, photos, and notes after each visit. Nudy looked happy, comfortable, and well cared for, and I could tell she gave him lots of attention. I would definitely book with her again!

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Charvaiy F.
Sitter Profile Image: Zoe P.
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Zoe P.
Star Sitter
from
$24
per visit
4.9 out of 5 stars
119 reviews
49 repeat clients
15 years of experience
Winter Park, FL, 32792

This was my first time using Rover and leaving my munchkin behind. Zoe showed my Nola so much love, took her out on walks so she could her energy out, made sure she had tv to watch while she was home alone, and sent lots of cute lil pics every day to show how good she’s doing. I have really bad trust issues when it comes to my dog and Zoe def made me feel like my fur baby was in good hands and was well taken care of. I’ll def book with her again and so should you, she’s amazing!!!

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J
Sitter Profile Image: Autumn M.
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Autumn M.
from
$14
per visit
4.8 out of 5 stars
25 reviews
7 repeat clients
2 years of experience
Winter Park, FL, 32792

Great dog walker. Helped me out at short notice was definitely book again. 😊

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Jim B.
Sitter Profile Image: Carolina S.
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Carolina S.
from
$30
per visit
5.0 out of 5 stars
34 reviews
19 repeat clients
25 years of experience
North Orange, Winter Park, FL, 32789

Carolina did a wonderful job with Levi for his drop in visit! She kept me well informed and made sure my little guy was feeling relaxed before leaving him, and overall exceeded expectations. Would highly recommend her!

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Erika W.
Sitter Profile Image: David W.
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David W.
Star Sitter
from
$28
per visit
5.0 out of 5 stars
98 reviews
40 repeat clients
17 years of experience
Winter Park, FL, 32789

David was more than willing to work with me and my partners extremely busy schedule. He was super patient with my socially defensive dog and calmed all of my nerves about them meeting and the intense instructions I have for my pup. Once my partner read his profile, he said "YUP! This is the guy!" and he was right. I'd highly recommend him to all of my friends and family if they are in need of a dog sitter/walker.

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Kacie R.
Sitter Profile Image: Sherry c.
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Sherry c.
Star Sitter
from
$14
per visit
5.0 out of 5 stars
5 reviews
2 repeat clients
40 years of experience
Winter Park, FL, 32792

Sherry went above and beyond!! I came home to two happy cats and tidy litter boxes. She even fixed the annoying automatic feeder with no complaints. She’s bright and cheerful, it was lovely! Thank you Sherry!

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Sherree L.
Sitter Profile Image: Mya R.
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Mya R.
from
$20
per visit
5.0 out of 5 stars
6 reviews
1 repeat client
3 years of experience
Winter Park, FL, 32789

About: What sets me apart is my hands-on experience with senior and special-needs dogs, shaped by caring for my own senior pup who requires dietary and lifestyle adjustments. I spent three years working in a veterinary office, giving me minor medical training and confidence with medications and health monitoring. I come from a lifelong family of animal lovers, work from home, and have a large, secure yard—so your pet receives knowledgeable, attentive, and loving care in a calm environment. Pet care fits seamlessly into my daily routine since I work from home and structure my days around the animals in my care. I’m able to provide consistent feeding, playtime, litter maintenance, medications if needed, and plenty of companionship throughout the day. Caring for pets isn’t something I squeeze in—it’s part of my everyday life. I care for pets by following their normal routine as closely as possible to keep them comfortable and stress-free. In my home, pets receive a calm environment, regular feeding, playtime, enrichment, and rest, along with supervision throughout the day since I work from home. In a client’s home, I focus on maintaining their familiar schedule, providing attentive care, administering medications if needed, and keeping their space clean and secure. I always prioritize safety, comfort, and individualized care based on each pet’s needs and personality.

Sitter Profile Image: Rebecca S.
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Rebecca S.
Star Sitter
from
$17
per visit
5.0 out of 5 stars
295 reviews
71 repeat clients
8 years of experience
Orlando, FL, 32804

Rebecca did a great job during her drop-in visits to care for my 2 cats over the Thanksgiving weekend. She communicated quickly, was extremely punctual for all visits, took care of all required activities and spent the agreed upon time with my cats. As a photographer myself, I also appreciated the high-quality photos that she sent after each visit. I wouldn’t hesitate to hire Rebecca again.

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Mark S.
Sitter Profile Image: Rebecca A.
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Rebecca A.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
132 reviews
43 repeat clients
15 years of experience
Maitland, FL, 32751

We were gone for two weeks, and not gonna lie, we missed Salem and Sabrina (I call them Satan and Sabby, Salem earned his nickname). Anyway, we were immediately comfortable with Rebecca and she did take such good care of them. There is no doubt that we will invite her back the next time we travel.

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Andrew N.
Sitter Profile Image: Altynai G.
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Altynai G.
from
$17
per visit
4.9 out of 5 stars
161 reviews
53 repeat clients
10 years of experience
Maitland, FL, 32751

Ali did an amazing job taking care of our two pups. She asked all the right questions and showed intention & care. We’ll definitely use her services again the future.

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Chelsea T.
Sitter Profile Image: Meghan W.
Verified Enhanced Background Check
Meghan W.
from
$20
per visit
5.0 out of 5 stars
17 reviews
7 repeat clients
25 years of experience
Winter Park, FL, 32792

Meghan was excellent! I get anxious leaving our babies, but made me feel confident that our doggos were in good hands. She sent lots of pics and updates.

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Melissa R.
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Over 955
pet parents in Winter Park have booked pet sitting

Winter Park pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Took great care of my dog while I was out of town. Very communicative throughout the entire process.

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Misa O.
Drop-In Visits
5.0 out of 5 stars

Anna has been wonderful with our puppy! She’s kind, reliable, and always keeps us updated with photos and messages after her visits. We’re very grateful for her help and would highly recommend her to anyone looking for a caring and trustworthy pet sitter or dog walker.

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Deborah M.
Drop-In Visits
5.0 out of 5 stars

Cali is amazing!!! Both my kittens were so well taken care of after having an international trip for 2 weeks. Anyone would be very lucky to get to work with her!

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Emmii
Drop-In Visits
5.0 out of 5 stars

Thanks Natalie! Wonderful working with you today! Professional, inquisitive, and a fabulous fit for our fuzzy crew!

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Jessica B.
Drop-In Visits
5.0 out of 5 stars

Laura did a wonderful job caring for my two cats. She was attentive, dependable, and kept me updated throughout my trip.

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Alexis M.
Drop-In Visits
5.0 out of 5 stars

I cannot recommend Zoe highly enough. From the moment I entrusted my three cats to her care, I knew they were in excellent hands. One of my cats, Hope, has special medical needs and requires nebulizer treatments. She handled those treatments with confidence, patience, and ease, which gave me tremendous peace of mind while I was away. It's not easy to find someone who is both capable and comfortable providing that level of care. Beyond meeting their physical needs, she genuinely spent quality time with all three of my cats. She played with them, gave them attention and affection, and treated them as if they were her own. It was clear from the photos and updates she sent that she truly cared about their well-being and happiness. She was consistently punctual, reliable, and professional. Every visit was communicated clearly, and I received thoughtful updates and pictures each time, which meant so much to me. As a pet parent, especially to a cat with medical needs, that level of communication is invaluable. What sets her apart is her empathy and genuine love for animals. She doesn't simply "check in" on pets, she cares for them. Knowing my cats were safe, loved, and receiving excellent care allowed me to relax and enjoy my time away without worry. If you're looking for someone trustworthy, compassionate, dependable, and exceptional with animals, I would recommend her without hesitation.

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Jessica C.
Drop-In Visits
5.0 out of 5 stars

Awesome! I’m very picky when it comes to my dogs and Sarah was absolutely amazing with them and they loved her visits!!! Highly recommended

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Russell H.
Drop-In Visits
5.0 out of 5 stars

Cheyenne is attentive, flexible and took great care of our boys. She even adjusted her schedule when a medical issue came up for one of our dogs during her visit. 12/10 recommend her!!!

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A&B M.
Drop-In Visits
5.0 out of 5 stars

Yesenia did a wonderful job dropping in on Cookie & Rajah over the weekend. She kept us updated on everything & sent pics everyday which was really nice. If we weren’t moving we’d book with her again, the girls loved her. Thank you so much Yesenia!!

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Teeya B.
Drop-In Visits
5.0 out of 5 stars

Another wonderful experience with Natalie! Excellent communication and engagement with my cats. I’ll absolutely be requesting her services again!

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Liam T.
Drop-In Visits
5.0 out of 5 stars

Sage was very happy with his new paw friend 🐾 great communication and updates, Bailey did not skip a beat! Always on time! She’s everything you want and need as a pet sitter!

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Wanda D.
Drop-In Visits
5.0 out of 5 stars

Jazzlyn is super communicative and responsive, and she took great care of my two kitties, including my high needs senior cat who needed medication twice daily. She fearlessly administered it for him, which is exactly what he needed. She even spent extra time with him so he wouldn’t feel so lonely. I highly recommend!

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Leanna A.
Drop-In Visits
5.0 out of 5 stars

Leah is an absolute darling and both my pups fell in love with her instantly. They felt so comfortable with her and she is incredibly knowledgeable and caring. I could focus on my work and meetings knowing Leah is there taking care of my fur babies. We are all thrilled (my pups and I) that we found Leah! I will definitely rebook very soon.

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Lorena W.
Drop-In Visits
5.0 out of 5 stars

Bluey was well taken care of by Susan while we were away. Nice to have the peace of mind knowing our girl was in good hands!

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Tiffany M.
Drop-In Visits
5.0 out of 5 stars

Caitlin was terrific. She followed all of my requests. She spent time and effort to play with my cat stimulate his mind. I'll be happy to book her again.

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Alan A.
Drop-In Visits
5.0 out of 5 stars

Amber did a great job checking in on my little one. She gives very detailed summaries of the visit and kept me up-to-date on everything she thought I might want or need to know. Little Kitty was well taken care of.

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Yolanda M.
Drop-In Visits
5.0 out of 5 stars

Hunter did an excellent job taking care of our cat, Theo, while we were away for the week. She gave detailed recaps of each visit and took plenty of cute pictures. We would absolutely recommend her!

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Patience Z.
Drop-In Visits
5.0 out of 5 stars

I’m typically one to worry about my girls while I’m gone but Altynai made sure that they were well taken care of so that I didn’t have to worry about them. Will definitely be using her again!

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Emily D.
Drop-In Visits
5.0 out of 5 stars

Harley does a great job and is very trustworthy! My cats love her and she has watched them twice now.

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Lexy K.
Drop-In Visits
5.0 out of 5 stars

Lilliana was incredibly sweet and both of our cats immediately liked her during the meet and greet which was great! She’s one of the few Rover sitters on here that isn’t dedicated to just dogs, and has provided care for a variety of different animals. She was able to provide oral liquid medication for my special needs boy, which I greatly appreciate! She sent cute pictures and updates during her visits. We will definitely be booking her again!

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Amy M.
Drop-In Visits
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a 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 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 pet sitting in Winter Park is $20

Why Choose Rover?

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  • Reservation protection

    It doesn’t happen often, but if your pet sitter has to cancel, we’ll work with you to find a new sitter.

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    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Winter Park average 6
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Winter Park on Rover as of Jun 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

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

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

As of Jun 2026, there are 1,326 pet sitters in Winter Park. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

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

Pet sitters in Winter Park have an average of 14 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Winter Park.

Rover makes it easy to find Winter Park pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 1,326 pet sitters in Winter Park on Rover, so you’re sure to find the perfect match for your pet! In Winter Park, 100% of pet sitters offer daily exercise, 98% offer medication administration, and 94% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet 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 pet 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 pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.