Pet Sitting in Winter Garden

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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Search Results

Confirmed availability: Juneteenth
Sitter Profile Image: Sharon P.
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Sitter Profile Image: Sharon P.
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1. Sharon P.

I luv pet sitting! Work from home
Ocoee, FL, 34761
4.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
19 reviews
4 repeat clients
from
$15
per visit
Profile image

So great with both our dogs - even our younger dog who normally is distrustful of everyone. Reliable. Always on time and dogs love her so nothing much else to say. Highly recommend.

Confirmed availability: Juneteenth
Sitter Profile Image: Adriana R.
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Sitter Profile Image: Adriana R.
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2. Adriana R.

Never met a dog that I didn’t like!
Ocoee, FL, 34761
5.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
31 reviews
14 repeat clients
from
$13
per visit
Profile image

Adriana was great! She took such good care of our old sweet boy. She went above and beyond with communication, photos, and care. I would definitely use her again and recommend her to others! Thank you!!

Confirmed availability: Juneteenth
Sitter Profile Image: Tathyana  F.
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Sitter Profile Image: Tathyana  F.
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3. Tathyana F.

Pets Care Inn
Windermere, FL, 34786
5.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
60 reviews
19 repeat clients
from
$20
per visit
Profile image

Thank you for caring for Layla. This was our first time leaving Layla and you made us feel at ease. I really appreciated the photos and feedback.

Confirmed availability: Juneteenth
Sitter Profile Image: Poliana D.
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Sitter Profile Image: Poliana D.
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4. Poliana D.

Wholehearted animal lover
Windermere, FL, 34786
5.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
277 reviews
102 repeat clients
from
$25
per visit
Profile image

Poliana is dependable and professional. She takes excellent care of our cat. We’ve booked multiple times and will continue to do so, she’s excellent!

Confirmed availability: Juneteenth
Sitter Profile Image: Danielle H.
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Sitter Profile Image: Danielle H.
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5. Danielle H.

Pet parent ready to care for yours!
Ocoee, FL, 34761
3.6 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
27 reviews
12 repeat clients
from
$18
per visit
Profile image

She is a sweet person! And did exactly as I requested. She even got along with my black cat who really does not like ppl. She is very trustworthy as well! Definitely rebooking soon! She sent photos and communicated very well too.

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Sitter Profile Image: Imani Z.
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Sitter Profile Image: Imani Z.
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6. Imani Z.

I care for your pets like family
Winter Garden, FL, 34787
1.3 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
2 repeat clients
from
$13
per visit
Profile image

Imani was great caring for my cat when I was gone for over a month period. She was attentive to my instructions, communicative, left the space clean on my return, and most importantly interacted well with my cat.

Confirmed availability: Juneteenth
Sitter Profile Image: Caitlin & Jamie B.
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Sitter Profile Image: Caitlin & Jamie B.
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7. Caitlin & Jamie B.

TWO background checked sitters!
Winter Garden, FL, 34787
3.6 mi. away
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
47 reviews
11 repeat clients
from
$14
per visit
Profile image

Very professional, did everything exactly the way I asked. Looking forward to working with them again.

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Sitter Profile Image: Jackie C.
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Sitter Profile Image: Jackie C.
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8. Jackie C.

Rover 101
I ❤️ your dogs like you do! 🐶
Ocoee, FL, 34761
3.3 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
20 reviews
7 repeat clients
from
$20
per visit

There isn’t anyone I trust more with my dogs than Jackie! Not only is she a complete and total dog lover, she has been rescuing bulldogs for years! She is well versed in finicky breeds and can handle anything thrown her way. My dogs are my babies and Jackie is the only person I trust them with because I have complete trust and confidence that they will be loved and protected with her! Cannot recommend enough!

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Sitter Profile Image: Elizabeth D.
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Sitter Profile Image: Elizabeth D.
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9. Elizabeth D.

Fur-tastic Pet Sitter!
Windermere, FL, 34786
3.8 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
from
$12
per visit

Elizabeth has been such a saving grace. I'm a Registered Veterinary Technician and I am EXTREMELY picky when it comes to who cares for my babies especially since I have "special needs" pets. My 12 year old chinchilla, Rosko is really specific with people that he trusts and he really enjoys her company. She has helped me feel at ease leaving my favorite little guy with her. His cage is always so clean and he always looks so happy whenever I mention Elizabeth's name to him. He's on medication and when he sees Elizabeth, he's always excited to take anything from her. I also had a special needs dog (Rest in Peace Kahlua) that needed lots of extra care. My 15 year old arthritic pup needed to be let out often to pee and lots of medications to be given. She also needed to be fed in smaller batches. While I wouldn't subject anyone to the amount of care my old girl needed, I could fully trust that she was in great care whenever I had to leave Kahlua with her. I gave her all these instructions (because I'm THAT kind of dog mom) and she listened, asked questions and reassured me that she could do it. Right then, I knew my old girl would be loved, watched and taken care of. I got so many photos of them snuggling and even going out to the yard just to get some sun. I appreciated the photos and updates especially while I was away missing my pup. When my old girl finally passed, Elizabeth sent me photos of them together and was so kind to our family during one of the most difficult moments of my life. When you're looking for someone to care for your family member, why not choose someone who would love your babies like you do? Elizabeth is definitely that person.

Sitter Profile Image: Samantha F.
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Sitter Profile Image: Samantha F.
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10. Samantha F.

Happy and fun pet lover!
Ocoee, FL, 34761
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
70 reviews
30 repeat clients
from
$20
per visit
Profile image

Samantha was absolutely amazing with my female Persian! I will definitely book her services again... she was awesome! Thank you, Samantha for taking such wonderful care of my baby girl!

Confirmed availability: Juneteenth
Sitter Profile Image: Opal C.
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Sitter Profile Image: Opal C.
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11. Opal C.

Cuddles & Exercise
Winter Garden, FL, 34787
0.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
3 repeat clients
from
$18
per visit

Opal has been pet sitting for our jack russell, Kellz for 3 years. We met her at a dog park in Vegas. She has been so sweet to our little guy while we are at work. She is professional and always on time. She has become apart of our family.

Confirmed availability: Juneteenth
Sitter Profile Image: Claire G.
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Sitter Profile Image: Claire G.
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12. Claire G.

Near downtown Winter Garden!
Winter Garden, FL, 34787
2.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
8 reviews
2 repeat clients
from
$18
per visit
Profile image

Claire was super communicative through out the service and did an awesome job with our cats! Would highly recommend her!

Confirmed availability: Juneteenth
Sitter Profile Image: Michele B.
Sitter Profile Image: Michele B.

13. Michele B.

🐈 🐾 Pet’s Best Friend 🐾 🦜
Winter Garden, FL, 34787
0.1 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
63 reviews
29 repeat clients
from
$20
per visit
Profile image

Michele is awesome! So caring, so good with my pups! I am so glad I found her. Communication is great. You know your fur babies are in the best hands with her.

Confirmed availability: Juneteenth
Sitter Profile Image: chrys w.
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Sitter Profile Image: chrys w.
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14. chrys w.

Providing love to fur babies
Winter garden, FL, 34787
2.5 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$15
per visit
Profile image

Chrys is great with my dog, always on time and a pleasure to speak with.

Sitter Profile Image: Kellie-Lynn R.
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Sitter Profile Image: Kellie-Lynn R.
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15. Kellie-Lynn R.

While you’re away,let me sit & stay
Ocoee, FL, 34761
2.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
41 reviews
12 repeat clients
from
$25
per visit
Profile image

Kellie was amazing. She was very communicative and followed my directions clearly for my medically needy pups. I trusted her with my babies and didn’t disappoint. I will definitely use her again!

Confirmed availability: Juneteenth
Sitter Profile Image: Alexandria & Dan L.
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Sitter Profile Image: Alexandria & Dan L.
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16. Alexandria & Dan L.

Eva and Val’s Puppy Pals LLC
Ocoee, FL, 34761
2.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
83 reviews
30 repeat clients
from
$20
per visit
Profile image

Both pups were taken care of by Alexandria very well. It was nice to see the pictures and get updates while we were away. I forgot my password so was not able to get in to see them all but saw the ones in the email. Thanks for the excellent care, Jan Hearn

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Sitter Profile Image: Tiana M.
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Sitter Profile Image: Tiana M.
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17. Tiana M.

Experienced dog lover of all sizes
winter garden, FL, 34747
1.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 review
from
$15
per visit

Tiana has the biggest heart I know! She has always been a pet lover and her love for animals is boundless. She embodies the spirit of kindness and empathy towards all living beings. Tiana always treats any animal she sees with immense love and care. Her unconditional love for pets is a testament to her generous heart and nurturing soul. It is a privilege to know someone who makes such a big difference in the lives of animals and people around her.

Confirmed availability: Juneteenth
Sitter Profile Image: Lillix J.
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Sitter Profile Image: Lillix J.
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18. Lillix J.

Working with animals is my passion
Winter garden, FL, 34787
0.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5 years of experience
from
$15
per visit

About: I work with dogs for a living so I have learned a lot, such as how to read their body language, what they need, and how to care for them in their own way. I also have worked with all kinds of dogs, seniors, seizure prone, dog aggressive dogs, hyper, calm. You name it and I’ve probably worked with it. And I know how to give medication if needed. I work part time at a doggy daycare/ hotel so on my days off I would LOVE to continue to work with dogs. I have a lot of free time during the week and my schedule is always flexible. I know how to properly lockup when I leave so you never have to worry about if the alarm was set right or if I may have forgotten something.

Confirmed availability: Juneteenth
Sitter Profile Image: Remy S.
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Sitter Profile Image: Remy S.
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19. Remy S.

Here to make your life easier:)
Winter garden, FL, 34787
2.0 mi. away
Drop-In Visits, Dog Walking
5.0 out of 5 stars
40 reviews
12 repeat clients
from
$19
per visit
Profile image

Couldn’t ask for a better Dog Walker for my puppy! I had an emergency trip out of town and was able to book Remy for a drop in visit outside her daily walk with River and it saved the day.

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Sitter Profile Image: Sara L.
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Sitter Profile Image: Sara L.
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20. Sara L.

I’ve always had a love for animals!
Winter Garden, FL, 34787
1.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
5 reviews
2 repeat clients
from
$20
per visit
Profile image

Sara was thoughtful and caring about my cats, and even called when she was worried one of them was sick. I’m so grateful for her accommodations and quick responses!

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Winter Garden Pet Sitting & Drop Ins ratings

Overall Rating:
5.0 out of 5 stars

Pet sitters in Winter Garden are rated on average 5 out of 5 stars based on 509 reviews.

Rover also offers Pet Sitting & Drop Ins in:

Rover also offers other services in Winter Garden:


As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a sitter who meets your - and your pet's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet - including background checks, sitter testimonials, community reviews. We also offer training and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet lovers for hire.

Drop-In Visits