Dog Sitting in Winter Park

Book a Winter Park dog sitter to watch your dog in your sitter’s home or yours.

End Date
Search

Every sitter passes an enhanced background check. Learn about RoverProtect

Top rated Winter Park dog sitters

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

1 / 1
Sitter Profile Image: Carolina S.
Verified Enhanced Background Check
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!

Profile image
Erika W.
Sitter Profile Image: Christopher Q.
Verified Enhanced Background Check
Christopher Q.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
23 reviews
5 repeat clients
6 years of experience
Orlando, FL, 32817

Christopher was fantastic with my animals and took great care of them ! He was timely and sent plenty of photos

Profile image
Robert H.
Sitter Profile Image: Carolina P.
Verified Background Check
Carolina P.
from
$21
per visit
5.0 out of 5 stars
10 reviews
6 repeat clients
7 years of experience
Casselberry, FL, 32707

There is no better sitter than Carolina. Firstly she is one of the kindest people I have ever met. I met her daughter who was equally as sweet! She took amazing care of my kitty, sent lots of pictures and kept me worry-free on my trip. I also came home to a holiday toy for both my dog and cat! As hard as it is to leave your pets for a trip, it felt a lot better knowing they were in such great care. A+ experience with Carolina!!

Profile image
Clair S.
Sitter Profile Image: Emilee P.
Verified Enhanced Background Check
Emilee P.
from
$15
per visit
1 repeat client
8 years of experience
Orlando, FL, 32803

About: I’ve had all kinds of pets growing up through childhood, always had dogs and cats especially. Worked at a vet clinic for 2 years, loved it and miss it. Took courses on animal care and calming while working in the clinic. I’m currently working at Amazon as a flex employee, right now I’m only working 1-2 days a week there. I make my own schedule there and I plan to make my pet sitting schedule a priority. I won’t be able to bring any pets to my house for the time being, but going to houses I love playing with all the pets:) Always have had the biggest love for pets.

Sitter Profile Image: Jonathan A.
Verified Enhanced Background Check
Jonathan A.
from
$19
per visit
5.0 out of 5 stars
72 reviews
20 repeat clients
15 years of experience
Orlando, FL, 32810

Jonathan was great with the boys! I appreciated his time and effort to take care of the cats, and his reports were wonderfully detailed! Thank you so much!!!

Profile image
Meredith S.
Sitter Profile Image: Marin W.
Verified Enhanced Background Check
Marin W.
from
$14
per visit
5.0 out of 5 stars
9 reviews
1 repeat client
6 years of experience
Baldwin Park, Orlando, FL, 32814

About: When I was 12 years old, I created my own business, "Dog Walking Done Wright", where I would house sit/dog sit in my neighborhood. Once I turned 16 and was able to drive, I became an employee at KampK9, a local doggy day care, where I learned the ins/outs of pet care. I think that both having my own business and becoming a part of one has given me many skills that I use today to do it the WRIGHT way. I make sure that once given the opportunity to care for my clients' pets, I make them the priority of my days. No owner wants their dogs/cats to be forgotten, so I make sure that they become a fever important element of my day. For house sitting, I would stay in the house most of the day/night. For drop ins, I would stay 30-45 minutes. For dog walking, it would depend how long the owner would want the walk to be, plus some extra time with the dog after the walk.

Sitter Profile Image: John H.
Verified Enhanced Background Check
John H.
from
$14
per visit
3 years of experience
Orlando, FL, 32801

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.

Sitter Profile Image: Rob & Wynn K.
Verified Enhanced Background Check
Rob & Wynn K.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
62 reviews
13 repeat clients
20 years of experience
Winter Park, FL, 32789

Wynn did an amazing job! She dropped in to feed Sprout, took him out for a potty break, and kept me updated with photos and messages. Sprout was so happy and well-cared-for. Highly recommend! Thank you so much!! 😊

Profile image
Alissa H.
Sitter Profile Image: Tatiana M.
Verified Background Check
Tatiana M.
Star Sitter
from
$26
per visit
5.0 out of 5 stars
184 reviews
88 repeat clients
10 years of experience
Casselberry, FL, 32707

Tatiana was very kind and friendly. She did all the things I asked her to in caring for my dog. I felt very comfortable being away knowing that my dog would be cared for.

Profile image
Robin M.
Sitter Profile Image: Makenna W.
Verified Enhanced Background Check
Makenna W.
from
$25
per visit
5.0 out of 5 stars
23 reviews
11 repeat clients
30 years of experience
Colonicaltown North, Orlando, FL, 32803

Makenna is the best! We hired her for drop in visits to check on our house and elderly cat while we were away on vacation. She was quick to respond to requests, quick to communicate any concerns, flexible, friendly, and easy to work with. She also sent us beautiful pictures of our happy cat! We will definitely be booking her again.

Profile image
Mara T.
Sitter Profile Image: Amber P.
Verified Enhanced Background Check
Amber P.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
19 reviews
3 repeat clients
10 years of experience
Winter Park, FL, 32789

About: Pet parents love leaving their dogs in my care because they know they don’t have to worry. I take the time to learn your dog’s routine, send regular updates with quality photos, and provide a cozy home sanctuary where your pup will be loved and cared for like my own. I’m an artist working out of my home studio, allowing plenty of flexibility throughout the week to offer hands-on care. I’m also available most weekends for boarding. Your dog will spend the day in a calm, loving home with a large, fully fenced yard — perfect for play, sunbathing, and safe exploration. Inside, pets enjoy a relaxed environment with cozy rest areas and plenty of attention. We will enjoy multiple walks per day in a quiet and safe neighborhood.

Sitter Profile Image: Nina A.
Verified Enhanced Background Check
Nina A.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
91 reviews
16 repeat clients
10 years of experience
Baldwin Park, Orlando, FL, 32814

Nina was absolutely amazing and quick to respond! I usually don’t trust people without getting to meet them but Nina was truly amazing with my pups and will rebook again :)

Profile image
Elizabeth Y.
Sitter Profile Image: Katie H.
Verified Enhanced Background Check
Katie H.
from
$15
per visit
1 year of experience
winter park, FL, 32792

About: I am responsible, caring and trust worthy. I’ve been around animals especially dogs my whole life and have had my own dog now for almost a year. I am a full time teacher looking to walk dogs over the summer! Animals are my passion and I can’t wait to incorporate this love for mine into my schedule. I am a natural care giver at heart, humans and animals. I have one dog at home who is my best friend and I’d love to care for your furry friends like they are my own.

Sitter Profile Image: Kaia B.
Verified Enhanced Background Check
Kaia B.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
20 reviews
7 repeat clients
12 years of experience
Lake Davis-Greenwood, Orlando, FL, 32806

Kaia took great care of my cat and home while I was away on business. She followed all my instructions, was always on time, and took great photos! Highly recommend.

Profile image
Sean M.
Sitter Profile Image: Luisa E.
Verified Background Check
Luisa E.
from
$18
per visit
5.0 out of 5 stars
39 reviews
12 repeat clients
13 years of experience
Orlando, FL, 32804

Luisa is an excellent caregiver for all of my pets! She goes above and beyond in her communication and I always have peace of mind knowing she’s looking after my babies. I can’t recommend her enough!

Profile image
Jessica R.
Sitter Profile Image: Brittney R.
Verified Enhanced Background Check
Brittney R.
from
$17
per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
8 years of experience
Maitland, FL, 32751

Incredibly helpful and quick to assist in a pinch. Adapted to my dogs’ usual schedules for a few visits while we were out of town. We’ll definitely reach back out (with more of a heads up next time)!

Profile image
Adam L.
Sitter Profile Image: Danielle R.
Verified Enhanced Background Check
Danielle R.
from
$13
per visit
5.0 out of 5 stars
5 reviews
1 repeat client
16 years of experience
Orlando, FL, 32804

About: I have experience caring for both dogs and cats, including currently taking care of two kittens of my own. I truly see pets as family and always care for other people’s pets the same way I would care for my own. I’m very attentive to animals’ behaviors and needs, whether they’re bored, tired, dehydrated, stressed, sick, or just needing attention and playtime. I have experience watching multiple dogs at once and making sure every pet feels safe, comfortable, loved, and well cared for while their owners are away. I understand how important trust is when leaving your pets with someone, and I always do my best to provide a caring and reliable environment. I currently have a flexible schedule with a part time job, which allows me to spend plenty of time caring for and checking in on pets throughout the day. I make sure cats get attention, playtime, clean food and water, litter box care or walks, and a comfortable environment while their owners are away. I’m patient with shy or anxious pets and always try to follow their normal routine as closely as possible to help them feel safe and relaxed. I treat every pet as if they were my own and always prioritize their safety, comfort, and wellbeing. I pay close attention to cats’ behavior and can usually tell when they’re stressed, sick, dehydrated, tired, playful, or needing space. I keep a calm and clean environment and make sure pets have fresh water, food, attention, and a safe place to rest. I also have experience caring for kittens, senior cats, and cats needing extra patience or medication. I’m happy to provide updates and photos so owners feel comfortable while away. I live in a gated apartment complex community with a big fenced field right behind my patio and a lot of space to take your dogs on a walk or play with them.

Sitter Profile Image: Veronica S.
Verified Background Check
Veronica S.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
22 reviews
4 repeat clients
24 years of experience
Orlando, FL, 32804

Excellent pet care and service! Veronica was very detailed oriented and went above and beyond to take care of my sweet cat. I’m very thankful and will use her services again!

Profile image
David K.
Sitter Profile Image: Athena M.
Verified Background Check
Athena M.
from
$15
per visit
5.0 out of 5 stars
112 reviews
38 repeat clients
20 years of experience
Orlando, FL, 32803

Always appreciate Athena's clear communication and I know my kitties are in good hands. She is very reliable and I look forward to rebooking her again!

Profile image
Kathleen D.
Sitter Profile Image: Adriana H.
Verified Enhanced Background Check
Adriana H.
from
$15
per visit
4.7 out of 5 stars
9 reviews
16 years of experience
Maitland, FL, 32751

About: I’ve cared for my sister’s cat and my best friend’s husky for extended periods of time, helping with feeding, walks, playing, and cleaning up after them. I also had my own dog from ages 5–18, so I’ve been around animals my whole life and understand the patience, responsibility, and attention they need. I currently work part-time at a gym, take online summer classes through FAU, and work independently as a personal trainer, which gives me a very flexible schedule. I’m reliable, communicative, and genuinely love being around animals. I work part-time at a gym over the summer and take online summer classes for FAU, so I have a very flexible schedule throughout the week. I’m also a self-employed personal trainer, which allows me to adjust my hours easily. I’m reliable, good with communication, and always make sure pet owners stay updated and while I am taking care of their pets. I always make sure the pets feel safe, comfortable, and cared for when I am taking care of them. I pay close attention to their routines, feeding schedules, walks, and any instructions. I’m very patient, responsible, and good with communication.

1 / 1
View more sitters

Winter Park dog parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Natalie came into a crazy first time working with me and 7 of my pets. One of the ferrets had neglected to get in the cage at the appropriate time and so she had to corral her. All while trying to give the appropriate attention to the cats and the dogs. She did a phenomenal job! all the Pets and the house were good to go and ready for me when I got home. Definitely recommend and will rebook.

Profile image
Linda L.
Drop-In Visits
5.0 out of 5 stars

Natalie is fantastic with our furry crew. She is patient, confident, and communicative. Thanks Natalie!!

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

Thank you Rebecca! Stevie seems more compliant and not jumping as much. Thanks for working with her.

Profile image
John G.
Drop-In Visits
5.0 out of 5 stars

Nina was absolutely amazing and quick to respond! I usually don’t trust people without getting to meet them but Nina was truly amazing with my pups and will rebook again :)

Profile image
Elizabeth Y.
Drop-In Visits
5.0 out of 5 stars

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

Profile image
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.

Profile image
Deborah M.
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

Profile image
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!!!

Profile image
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!!

Profile image
Teeya B.
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!

Profile image
Wanda D.
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.

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

Jazzlyn was amazing and both of my fur babies fell in love with her the moment they met her. So much so that when I took them for a walk and returned home they both went looking for her in all the rooms hoping to find her. Jazzlyn is knowledgeable and gentle and I couldn’t be more happy knowing that when I am not home with my pups Jazzlyn is there taking care of them. I will definitely re-book with the amazing Jazzlyn.

Profile image
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!

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

Caitlin came over at the last minute over the atto take care of my dog. She was on time and communicating with her was easy. I totally recommend her services, asked all the important questions to make sure my baby was safe and happy.

Profile image
Kendel p.
Drop-In Visits
5.0 out of 5 stars

Kendall did twice-daily drop-in visits for my boys and was great! She was dependable, kind, and kept me updated. I came home to happy pups and couldn’t ask for more, will definitely book with her again!

Profile image
Elaine M.
Drop-In Visits
5.0 out of 5 stars

Reyna does an excellent job with Kira and is super responsive even for last minute requests which is so appreciated!

Profile image
Sarah B.
Drop-In Visits
5.0 out of 5 stars

I feel so lucky to have connected with Carolina on my first use of Rover! I have a senior French Bulldog who can't be alone all day. Carolina did a meet and greet with us and then two drop in visits while I was gone all day. My dog, who can be pretty grouchy and protective, has been won over! We will hire Carolina again.

Profile image
Sara D.
Drop-In Visits
5.0 out of 5 stars

Sam is amazing with my 10 week old puppy and has been a rock star helping me walk him mid morning while I'm at work, before I can take him out during my late afternoon lunch 😊😊 Benito loves him & he's been amazing!

Profile image
Lidyamar C.
Drop-In Visits
5.0 out of 5 stars

Victoria has been wonderful with Ellie. She is reliable, communicative, and clearly very caring. I always appreciate the updates and feel confident Ellie is in great hands. I would absolutely recommend her to anyone looking for a trustworthy sitter.

Profile image
Victoria C.
Drop-In Visits
5.0 out of 5 stars

Roxsanna was the absolute best! I felt very comfortable leaving my 2 dogs as soon as I met her. She has great communication which I really appreciated! She came 3 times a day and was always right on time and sent updates and pics of our pups which made me so happy to see them happy. When I got home my pups were very happy and my house looked cleaner than when I left it! I would be thrilled to hire Roxsanna again! Thank you!!

Profile image
JACKIE C.
Drop-In Visits
1 / 1
Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs 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!

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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

Dog Sitting FAQs

Frequently asked questions about Rover

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

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

Rover makes it easy to reach out to multiple dog sitters about your booking. Typically, dog sitters on Rover respond in under an hour.

Experience can vary widely from dog sitter to dog sitter, but you can view reviews, years of experience, and number of repeat clients when comparing dog sitters available in Winter Park.

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

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

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

Note: If your dog 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 dog sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your dog sitter’s cancellation policy.