House Sitting in Winter Garden

Find a loving dog sitter to watch your dog overnight in your home.

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Heather B.
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Sitter Profile Image: Heather B.
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1.

Heather B.

Just a girl who loves animals
Apopka, FL, 32712
House Sitting, Drop-In Visits, Dog Walking
5.0
58 reviews
25 repeat clients
from
$30
per night

Heather was such a great puppy sitter for our two fur-babies. She was very polite and responsive. She sent us pictures and videos multiple times everyday and was so sweet and caring towards our kids. ? We will be booking with her again next time we have to leave town. I highly recommend her and would give her a 10 out of 10 star ⭐️ review!

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Sitter Profile Image: Caitlin & Jamie B.
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Sitter Profile Image: Caitlin & Jamie B.
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2.

Caitlin & Jamie B.

TWO background checked sitters!
Winter Garden, FL, 34787
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
30 reviews
6 repeat clients
from
$52
per night

Caitlin and Jamie did a great job with our pups. We had to book last minute and they were super accommodating, flexible, and responsive. They were great with both of our pups, who can be a handful! They left the place looking great and even washed the sheets (which a totally unnecessary surprise!). They left adorable polariods of our babies and sent photos and videos throughout their stay. Very highly recommended.

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Sitter Profile Image: MARK B.
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Sitter Profile Image: MARK B.
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3.

MARK B.

For great pet care, and Exercise
Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking
5.0
55 reviews
24 repeat clients
from
$45
per night

Mark took care of our pup for over a week while we were on vacation. She can be somewhat anxious, but she warmed up to Mark and we know he provided her comfort while we were away. We got lots of pictures of her getting good walks and outdoor time. I would recommend Mark to anyone looking for someone to watch their pet, and would definitely ask him to stay with our dog again when we are out of town.

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Sitter Profile Image: Jasmine C.
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Sitter Profile Image: Jasmine C.
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4.

Jasmine C.

Furtopia; Where fur babies vacation
Winter garden, FL, 34787
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
109 reviews
49 repeat clients
from
$45
per night

The second time we booked with Jasmine, this time as a house and cat sitter! Our cats love her, and she is a cat whisperer! Our normally aloof girl who is happy to say hi and do her own thing elsewhere loved Jasmine and followed her around! I’ve only ever seen her do that with me and I’m so happy to hear it and only a little jealous 😜. She is always respectful, kind, responsive, and sends pictures and updates. She checked the mail and had already even put away an unexpected frozen cat food order before I even asked her to. Will 100% book with Jasmine again and you should too! Thank you Jasmine!

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Sitter Profile Image: Marlene W.
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Sitter Profile Image: Marlene W.
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5.

Marlene W.

You dog's new buddy is here!
Clermont, FL, 34711
House Sitting, Drop-In Visits, Dog Walking
5.0
18 reviews
4 repeat clients
from
$28
per night

Very considerate to pet owners, regarding putting the owners at ease while they are away with video and pictures. My dog looks happy so I am happy.

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Sitter Profile Image: Susie M.
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Sitter Profile Image: Susie M.
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6.

Susie M.

Caring for your pets like my own
Orlando, FL, 32819
Boarding, House Sitting, Drop-In Visits
5.0
3 reviews
from
$35
per night

About: I have been pet sitting since childhood. I am the type of sitter who will take the time to love on your pet, play with them, and spend time with them while you are away. Whether I’m staying with them or I’m doing drop in visits, I will spend quality time with your pets. I’m experienced with and have personally owned cats, dogs, rodents, and snakes. I also have experience caring for birds. I work M-Th in the office from about 8-5, but have a flexible schedule and can work remotely if required. I’m off every Friday-Sunday. I am available to do boarding, house sitting or drop in care up to twice a day (I am not able to support 3 or more times a day unless it is a weekend only). I have a fenced back yard with a dog door that can be locked if not appropriate for your pet. I have a large shaded neighborhood to take your pet for walks in. I have two cats that can be separated from boarders if required. If your pet needs isolation, I have a guest room that can be a dedicated space for your pet.

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Sitter Profile Image: Elizabeth S.
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Sitter Profile Image: Elizabeth S.
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7.

Elizabeth S.

I just love dogs!
Orlando, FL, 32811
House Sitting
5.0
3 reviews
1 repeat client
from
$40
per night

Amazing experience from start to finish! Communication was wonderful and included pictures. Liz bonded with our girls quickly and they had a great time together. Great care was taken of our home and dogs. We will definitely book her again!

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Sitter Profile Image: Jerilyn B.
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Sitter Profile Image: Jerilyn B.
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8.

Jerilyn B.

I grew up with all kinds of pets!
Ocoee, FL, 32818
House Sitting, Drop-In Visits, Dog Walking
5.0
4 reviews
3 repeat clients
from
$40
per night

Jerilyn did a great job caring for my two cats and dog! They were very comfortable with her, even my shy cat! She left our home impeccable. I would recommend her services!

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Sitter Profile Image: Ava A.
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Sitter Profile Image: Ava A.
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9.

Ava A.

Sincere and honest care for pets!
winter garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking
5.0
31 reviews
10 repeat clients
from
$56
per night

Ava was absolutely amazing. She really loves pets. She always kept me updated and sent lots of amazing pictures. We will definitely book her again.

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Sitter Profile Image: Malik G.
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Sitter Profile Image: Malik G.
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10.

Malik G.

I love animals and their hearts.
Ocoee, FL, 34761
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
77 reviews
23 repeat clients
from
$30
per night

Malik is incredibly patient and considerate of Cedars needs and ours. We absolutely couldn’t have left him in safer hands. Our trip got caught short because of unfortunate circumstances but he was there to help out the entire way! Would absolutely recommend and look forward to using him again!

Sitter Profile Image: Grace R.
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Sitter Profile Image: Grace R.
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11.

Grace R.

I can’t wait to meet your fur baby
Clermont, FL, 34711
House Sitting, Drop-In Visits, Dog Walking
5.0
4 reviews
1 repeat client
from
$25
per night

Grace did in home sitting for my two pups during a holiday weekend. She is conscientious, dependable, resourceful and thorough in her care. My dogs will welcome Grace any time we need to leave them behind!

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Sitter Profile Image: Tim & Tess O.
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Sitter Profile Image: Tim & Tess O.
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12.

Tim & Tess O.

Walk/run or sleepover for your pup
Ocoee, FL, 34761
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
33 reviews
4 repeat clients
from
$55
per night

About: We have experience with special needs dogs. We are active so we are happy to tire your puppy. A tired dog is a better behaved dog for sure. We have had dogs all our lives and love every dog, even the tough ones. Your dog or dogs will be spoiled and loved. We are not new to Rover, nor watching visiting dogs. We believe your dog will benefit from us being it's friend. My wife works from home everyday so potty breaks are plentiful. We love dogs and can't imagine life without them. Your fur baby will be in great hands and get the spoil treatment. We look forward to spoiling your puppy. You will get pictures and information throughout the stay. We know you will miss your puppies so we will do our best to bridge that gap We spend the majority of our days focused and trying to tire out the puppies every single day. Our dogs are the most important thing in our world and will treat your dog(s) like our own. Our back yard is fenced in with secure fencing and has no soft spots or gaps for small dogs to get out of. We keep a close eye on all the dogs while in the back yard.

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Sitter Profile Image: Sydney W.
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Sitter Profile Image: Sydney W.
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13.

Sydney W.

I’d love to care for your pup! :)
Winter Garden, FL, 34787
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
35 reviews
13 repeat clients
from
$75
per night

Sydney was absolutely great with my pups! As someone who has a anxious / nervous dog that’s slow to warm up to people she was able to make sure he was fully comfortable! Definitely recommend!

Sitter Profile Image: James W.
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Sitter Profile Image: James W.
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14.

James W.

Hyper active dogs welcome
Ocoee, FL, 34761
House Sitting, Drop-In Visits, Dog Walking
5.0
22 reviews
7 repeat clients
from
$50
per night

Super honest and reliable

Sitter Profile Image: Katie S.
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Sitter Profile Image: Katie S.
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15.

Katie S.

Rover 101
Dependable and Flexible Pet Sitter!
Oakland, FL, 34760
House Sitting, Drop-In Visits, Dog Walking
5.0
12 reviews
6 repeat clients
from
$50
per night

Katie took outstanding care of our family's 2 dogs! Her daily text communications including updates & images (per our request) put us at ease while we were on vacation and warmed our hearts. Katie is flexible, professional and both our young & senior dog responded very positively towards her. She did a fantastic job, we will be rebooking with Katie in the future!

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Sitter Profile Image: Adriana D.
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Sitter Profile Image: Adriana D.
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16.

Adriana D.

Rover 101
Full-time pet lover!
Winter Garden, FL, 34787
Boarding, House Sitting
5.0
16 reviews
5 repeat clients
from
$35
per night

Adriana was fantastic! I have a big (Great Dane mix) 7.5 month old deaf puppy and she was so good with her and my cat. She took time to send me photos throughout her stay with both of them and kept me updated. (They looked so happy and content in all the pictures.:)) She was so good I already booked her to watch them again!

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Sitter Profile Image: Chris W.
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Sitter Profile Image: Chris W.
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17.

Chris W.

Compassionate and professional!
Winter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking
5.0
2 reviews
1 repeat client
from
$27
per night

Excellent care. Even notified us when our cat food got spilled and took care of it when he was watching the dog.

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Sitter Profile Image: Sabrina R.
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Sitter Profile Image: Sabrina R.
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18.

Sabrina R.

I have a warm heart for cold noses!
Winter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking
2 reviews
from
$27
per night

Sabrina has worked with guinea pigs, green anole, several cats and several dogs. She has cared for them and has a loving heart for all living things. She would take our Maincoon for walks, feed, wash, and care for him as he got older. Our dog loves to see her coming and will roll over for a good belly rub (she seems to give the best according to the way our dog behaves). She is a very reliable and trustworthy person.

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Sitter Profile Image: Sterling S.
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Sitter Profile Image: Sterling S.
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19.

Sterling S.

Rover 101
Experienced and Loving Pet Sitter
Winter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking
5.0
5 reviews
1 repeat client
from
$40
per night

Sterling obviously loves animals and they know it! He has been such a help with my two pups and cat. I know he has worked dog rescue in his past and really cares about their health and happiness. Always reliably shows up and is excited to see them. Good notes and observations. Very involved and responsible.

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Sitter Profile Image: Michele B.
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Sitter Profile Image: Michele B.
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20.

Michele B.

🐈 🐾 Dog’s Best Friend 🐾 🦜
Winter Garden, FL, 34787
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0
60 reviews
29 repeat clients
from
$60
per night

Michele was amazing! We have never used Rover before or ever had a sitter at the house for our 2 German Shepherds and she exceeded all expectations! We got updates daily and came home to the dogs exhausted - which is always a nice perk. We will definitely use her in the future!

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Winter Garden House Sitting ratings

Overall Rating:

House sitters in Winter Garden are rated on average 4.9 out of 5 stars based on 420 reviews.


As dog 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 house sitter in seconds on Rover.com. If you're looking for trusted house 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 pet. Rover is proud to be the nation's largest network of pet lovers for hire.

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