House Sitting in Winter Garden

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

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

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Nickolas J.
Best Home for Lazy DogsFlorida Center North, Orlando, FL, 32811
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Nick was fantastic! I was able to book him day of. He was very nice and flexible. He started getting to know my little Hazelnut right away and she took right to… (more)

from
$40
per night
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Kristi A.
2.
TLC offeredWinter Garden, FL, 34787
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Kristi did an awesome job! We have never used a service like this before and all of our concerns have been eased. She kept in full communication, sent pics and … (more)

from
$80
per night
Kristine C.
Wag on overWindermere, FL, 34786
Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

Kristine is fantastic! Her attention to detail and her compassion for animals was obvious from the first time we met her. She took great care of our little guy! (more)

from
$38
per night
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Skylar M.
4.
I love animalsWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Skylar provided frequent updates and photos of our dogs while we were out of town for a few days. She spent majority of the days at home with the pups, which is… (more)

from
$50
per night
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Gabrielle F.
Your pets, my passion!Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

Gabrielle did an outstanding job. Her communication with us was excellent. The dogs warmed up to her, right away. We will be using her, again. Thanks so much. (more)

from
$40
per night
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6.
For great pet care, and ExerciseWindermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

Mark was awesome! He sent pictures everyday, and kept us up-to-date on how they were doing together. He made sure she had her allergy medicine daily, taking gre… (more)

from
$27
per night
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Engineer | Love to Make Tails Wag!Windermere, FL, 34786
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

You will not be disappointed with Kevin and Gabriella! It was so wonderful being able to enjoy the holidays and not stress knowing that our dogs are being so we… (more)

from
$70
per night
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8.
Dog Mom to 5!! IN YOUR HOME CARE!!Winter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Roni is EXCELLENT!!!! If we could give more than 5 stars we would!!! We didn’t worry one bit when leaving our 2 dogs and 2 cats with her! She kept in touch, sen… (more)

from
$75
per night
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9.
Certified Prof. Pet Sitter w/ ALCOcoee, FL, 34761
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

We absolutely loved having Eboni care for our pets over the weekend. It’s difficult to find a trustworthy person to know only care for your pets, but also stay … (more)

from
$95
per night
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10.
Unlimited Walks, Playtime, & Love!Orlando, FL, 32818
House Sitting, Drop-In Visits, Dog Walking

Sarah is great. She’s very communicative, sends pictures and keeps us up-to-date. We’ve used her several times and will continue to do so! Thanks Sarah! (more)

from
$62
per night
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I can’t wait to meet my new friendsWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Whitney did a great job with taking care of our dogs! She communicated a few times each day and sent pictures while we were out out town. It gave us peace of mi… (more)

from
$40
per night
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12.
Great with any dog big or small!Winter garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Chloe did an amazing job making sure my pests were well taken care of! Would strongly recommend! (more)

from
$40
per night
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Who let the dogs out!Windermere, FL, 34786
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Christopher would make a caregiver as he currently has a boxer; therefore, he has experience with dogs. He is responsible and will ensure that the pets are well… (more)

from
$27
per night
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14.
You new fur baby new best buddyWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Jordan is the most loyal loving dog owner I have ever met. Over the past 5 years I have known her she has always put the well being of her animals above everyth… (more)

from
$27
per night
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15.
Walks, pets, & play....OH MY!Winter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Sabrina is absolutely great. She took care of our babies even when one was sick. On top of that she took care of our home too. Will be using her again. (more)

from
$40
per night
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16.
🐈 🐾 Dog’s Best Friend 🐾 🦜Winter Garden, FL, 34787
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Michele, was great with our girls. She stayed at our house while we were gone and when she left, our house was just as clean as it was when we left. She sent pe… (more)

from
$40
per night
While you’re away,let me sit & stayOcoee, FL, 34761
House Sitting, Drop-In Visits, Dog Walking

Kellie, was sweet, kind hearted, and caring. All you can ask for, when leaving your beloved pets at home. She reported in, and sent pics. for us look at. I was … (more)

from
$80
per night
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18.
Jim 
Verified Enhanced Background Check
Teacher looking for Summer Job.Winter Garden, FL, 34787
House Sitting
20 years of experience

About: I’ve had/taken care of dogs since I was 10. As a teacher, this is great opportunity for a break in my summer days. Hope I can help you out. Currentl… (more)

from
$40
per night
19.
animal loverWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Paige is a dependable and responsible dog sitter! Bear is a special dog that doesn’t do well with other animals, has anxiety issues, and is very picky about th… (more)

from
$30
per night
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20.
Dog loving mommaWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Lena is a true animal lover & whisperer! My 3 dogs and cat come running when they hear Lena walk in the house. Which is interesting because usually the cat hide… (more)

from
$30
per night

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.