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 dog.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
One Time
Repeat Weekly
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What size are your dogs (lbs)?

Search Results

Confirmed availability: Easter Weekend
Sitter Profile Image: Luna E.
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Sitter Profile Image: Luna E.
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1. Luna E.

Cat Lady that also loves Dogs
Fern Park, FL, 32730
3.4 mi. away
Drop-In Visits
5.0 out of 5 stars
69 reviews
26 repeat clients
from
$15
per visit

Short review: Outstanding care and communication. Longer review: I have a very anxious cat, and I was going out of town for 5 days. Luna not only checked on my cat, but she also went above and beyond. Her cat experience was great because she knew my orange tabby could/couldn’t have certain wet food due to his urinary problems. She actually switched to wet food, despite me not having any, so my cat would stay hydrated. It wasn’t just someone checking in on my cat, Luna was attentive to his eating and hydrating. She monitored it extremely closely and kept me updated. This was my first time using Rover, and the other reviews helped me pick Luna.

Confirmed availability: Easter Weekend
Sitter Profile Image: Kelley A.
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Sitter Profile Image: Kelley A.
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2. Kelley A.

Caring, Dependable and Trustworthy
Winter Park, FL, 32792
2.6 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
112 reviews
42 repeat clients
from
$18
per visit

Absolutely amazing. Kelly is prompt to respond when I had questions or concerns. She treated my animals with so much care and attention. It's the little details that matters the most. I will be contacting Kelly for my animal care for years to come.

Sitter Profile Image: Zannia F.
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Sitter Profile Image: Zannia F.
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3. Zannia F.

Care and respect for your babies.
Orlando, FL, 32825
5.2 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
64 reviews
16 repeat clients
from
$18
per visit

Zannia has given me peace of mind while away. I was provided with updates and photos of her visits. My dogs love her. I will definitely use her services soon.

Confirmed availability: Easter Weekend
Sitter Profile Image: Trinity G.
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Sitter Profile Image: Trinity G.
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4. Trinity G.

Pet Lover and Husky Momma
Winter Park, FL, 32792
3.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
15 reviews
6 repeat clients
from
$13
per visit

Trinity is amazing and genuinely cared for our cats! She kept us updated and made sure they were tell taken care of. We will definitely be asking trinity to watch our cats again!!

Confirmed availability: Easter Weekend
Sitter Profile Image: ASALIA C.
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Sitter Profile Image: ASALIA C.
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5. ASALIA C.

Flexible schedule, cats & dogs!
Central Business District, Orlando, FL, 32801
4.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
13 reviews
1 repeat client
from
$20
per visit

Asalia was wonderful and super flexible with our last minute request! Will 100% rebook.

Confirmed availability: Easter Weekend
Sitter Profile Image: Roxsanna P.
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Sitter Profile Image: Roxsanna P.
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6. Roxsanna P.

Your Pets New Best Friend
Winter Park, FL, 32789
1.0 mi. away
Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
3 reviews
4 repeat clients
from
$17
per visit

Roxanne was amazing. Definitely someone to keep when a dog sitter is needed. She’s calm and all of my dogs love her. She did great with my rescue who on the first meeting wouldn’t stop barking at her. She knew exactly what to do. In the end he approved. She sends the best pictures and is very communicative.

Confirmed availability: Easter Weekend
Sitter Profile Image: David S.
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Sitter Profile Image: David S.
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7. David S.

Rover 101
Your pooch’s best friend!
Orlando, FL, 32801
4.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
133 reviews
53 repeat clients
from
$20
per visit

David was amazing! He was super communicative and helpful. Even my super shy kitty came out for him which is saying a lot, I will definitely be reaching out to David for future cat-sitting :)

Confirmed availability: Easter Weekend
Sitter Profile Image: Jereny R.
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Sitter Profile Image: Jereny R.
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8. Jereny R.

Experienced K9 Handler and Athlete
Orlando, FL, 32803
2.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
18 reviews
10 repeat clients
from
$18
per visit

Jereny is incredible and super reliable. Our puppy is an escape artist and Jereny went early to keep the pup safe and found a good way to secure the crate for us in the first week. She has been flexible with the schedule when we randomly have a change. She has also work led on many training things with the pup and describes the techniques so we can repeat. Great service!

Confirmed availability: Easter Weekend
Sitter Profile Image: Alina G.
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Sitter Profile Image: Alina G.
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9. Alina G.

Dogs are a woman’s bestfriend!
Orlando, FL, 32814
2.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$17
per visit

Alina was great. Very responsive and sent me up dates with photos of Slash and Chili Thank You Alina!!

Confirmed availability: Easter Weekend
Sitter Profile Image: Julieane G.
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Sitter Profile Image: Julieane G.
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10. Julieane G.

From 1 pet owner/lover to another!
Baldwin Park, Orlando, FL, 32814
2.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
53 reviews
20 repeat clients
from
$15
per visit

Julieane helped me out last minute and was really great! She was very communicative and followed all the instructions i asked of her, and my dogs really liked her. I will definitely use her again in the future!

Confirmed availability: Easter Weekend
Sitter Profile Image: Anna Lilley S.
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Sitter Profile Image: Anna Lilley S.
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11. Anna Lilley S.

Dog Auntie for Hire
Winter Park, FL, 32789
2.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
70 reviews
21 repeat clients
from
$23
per visit

Anna took great care of my dog Flora while I went out of town. This was my second time using rover and I was very hesitant since my trip was last minute and have only used the same few people to watch my dog over the years. Anna did a great job in making me feel confident my dog was being left in good hands! We unfortunately were not able to do a greet and meet first before I left but she called me and was extremely thorough in going over what my needs and expectations were and asking detailed questions. My dog is a big girl, very strong, and bossy. I had a lot of anxiety since my dog is not "easy" but Anna took all the steps to ease my anxiety and allowed this to be an overall good experience where I was able to enjoy my trip away without having constant worry. I will definitely be booking with Anna again in the future :)

Confirmed availability: Easter Weekend
Sitter Profile Image: Caitlin E.
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Sitter Profile Image: Caitlin E.
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12. Caitlin E.

Your kitty’s next best friend :)
Orlando, FL, 32804
3.1 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
33 reviews
14 repeat clients
from
$20
per visit

Caitlin was AMAZING! Her communication with me was awesome and she took such great care of my fur baby. I highly recommend her services. She’s so professional and really caring and nice! 10/10 pet sitter! Will absolutely be booking her in the future.

Confirmed availability: Easter Weekend
Sitter Profile Image: Tayler M.
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Sitter Profile Image: Tayler M.
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13. Tayler M.

Orlando Walk, Watch and Sit Service
Winter Park, FL, 32789
1.4 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
15 reviews
5 repeat clients
from
$20
per visit

Tayler was great, very communicative, sent us pictures of our kitty and took care of her as expected. Our grumpy old cat doesn't really get along with strangers but Tayler even managed to pet her! Highly recommend, we will definitely be hiring her again.

Confirmed availability: Easter Weekend
Sitter Profile Image: Daniela D.
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Sitter Profile Image: Daniela D.
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14. Daniela D.

A Tail-Wagging Good Time!
Winter Park, FL, 32792
2.2 mi. away
House Sitting, Drop-In Visits, Dog Walking
10 years of experience
from
$11
per visit

About: As a pet sitter on Roover, what sets me apart is my genuine love and passion for animals, which is evident in the way I care for each and every pet under my watch. With many years of experience caring for newborns to full grown adults, I understand the unique needs and personalities of each pet, and I take great pride in providing personalized attention to ensure their comfort and happiness. But what really sets me apart is my willingness to go the extra mile for each and every pet in my care. Whether it's taking them on long, leisurely walks to help them stay active and healthy, or simply spending quality time with them to make sure they feel loved and valued, I am committed to providing the highest level of care and attention to each and every pet. So if you're looking for a pet sitter who truly cares about the well-being of your furry friend, look no further than me. Let's work together to ensure your pet receives the loving care they deserve while you're away, and who knows, your furry friend might just get to join me on my daily walks! I provide quality attention and care to pets while also accommodating my clients' schedules. With a low-maintenance and remote setup, I can work in between and still ensure that your furry friend receives the best possible care and attention. I tailor my schedule to meet each pet's unique needs and provide consistent care to ensure their comfort and happiness. You can rest easy knowing that your pet is in good hands with me. I offer both in-home pet sitting and pet sitting in my own home. I provide a safe and comfortable environment for pets to stay in while their owners are away. I have a big, fenced yard where pets can play and get exercise, and if needed, I can take them to the nearby dog park. Whether I care for pets in my own home or in their own home, I provide plenty of exercise, playtime, and affection to ensure their well-being, and I always follow established routines and schedules. I also maintain open communication with pet parents to ensure their peace of mind.

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Sitter Profile Image: Vanessa G.
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Sitter Profile Image: Vanessa G.
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15. Vanessa G.

15 yrs exp. They will be loved.
Maitland, FL, 32751
2.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
6 reviews
2 repeat clients
from
$14
per visit

Leaving my old girl can be tough, but with Vanessa, I know she's in the most loving and caring environment. Her genuine passion for animals shines through in everything she does. My older Aussie absolutely adores her, and I always receive daily updates and pictures that melt my heart. Vanessa goes above and beyond to truly makes a difference. If you're looking for someone who treats your dog like family, Vanessa is your answer.

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Sitter Profile Image: Joselin V.
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Sitter Profile Image: Joselin V.
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16. Joselin V.

A Genuine Love for the Pups!
Winter Park, FL, 32792
1.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
24 reviews
13 repeat clients
from
$15
per visit

As repeat customers, Joselin is our “go-to” sitter and hope she NEVER RETIRES lol! It’s always hard leaving our fur babies behind, but knowing Joselin is there always means they’ll be well taken care of! 5 out of 5 paws - would recommend :)

Sitter Profile Image: Kathleen D.
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Sitter Profile Image: Kathleen D.
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17. Kathleen D.

Rover 101
A Home Away from Home for Your Pet!
Winter Park, FL, 32792
1.7 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
46 reviews
13 repeat clients
from
$20
per visit

Kathleen bonded quickly with both of our pets. She is punctual, quick to respond and sent updates and pictures every day. She even brought in our mail and packages. Kathleen gives us total peace of mind when we’re out of town because we know our cats are getting great care. We are so grateful!

Confirmed availability: Easter Weekend
Sitter Profile Image: Lani E.
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Sitter Profile Image: Lani E.
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18. Lani E.

I treat your pets like family🤍🐾
Winter Park, FL, 32789
0.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
19 reviews
6 repeat clients
from
$15
per visit

Lani checked in on our 2 dogs while we were away and we appreciated her prompt communication and caring attitude. She sent pictures and provided updates on their status. I would highly recommend her

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Sitter Profile Image: Abby D.
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Sitter Profile Image: Abby D.
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19. Abby D.

Kind, caring, and loves dogs!!
Winter Park, FL, 32789
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$15
per visit

Abby has grown up with Labrador retrievers and loves dogs! She is a responsible pet owner and sitter. She not only takes care of the basics, but loves to play with furry friends!

Confirmed availability: Easter Weekend
Sitter Profile Image: Samantha R.
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Sitter Profile Image: Samantha R.
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20. Samantha R.

A friendly neighborhood pet sitter
Winter Park, FL, 32792
1.3 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
21 reviews
7 repeat clients
from
$16
per visit

Samantha is so kind and amazing when it comes to dogs. She definitely knows what she’s doing. She helped watch my dogs for my boyfriend and I, my American Bulldog is a crazy one and likes jumping on people but she never one told us she had a problem dealing with him or with our other dog who is way much more calm. Definitely recommend booking your dogs with Samantha!

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Winter Park Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Winter Park are rated on average 5 out of 5 stars based on 419 reviews.

Rover also offers Pet Sitting & Drop Ins in:

Rover also offers other services in Winter Park:

Never beg a friend to drop in on your pets while you're on vacation again. With Rover, you can find the perfect pet sitter in seconds. Rover sitters are pet lovers, who will be happy to sit dogs, cats, caged pets, and even horses while they take care of your home. By removing common pet care obstacles, Rover ensures pets nationwide are happy and well-cared for even when their human is away, and empowers pet lovers to live happy and fulfilling lives. Founded on the belief that everyone should have the opportunity to experience the unconditional love of a pet, Rover makes it easy for you to reach trusted pet sitters who can provide the care your pet needs, when they need it.

Drop-In Visits