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.
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1. Madison Verified Background Check

Love & care for your fur-babies!

Oakland, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Madison was outstanding with our 2 Golden Retrievers! They loved her and she was very responsible! She sent us pictures of the dogs and made us feel at ease ... (more)"

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2. Joshua Verified Enhanced Background Check

Educated Caretaker

Ocoee, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

"This was my first time leaving my little ones with anyone so I was extremely nervous. However, Joshua was a true professional and had a calming energy to him... (more)"

3. Grace Verified Background Check

Kindness and Care with Gracie

Wintergarden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Grace was absolutely wonderful!!!! She sent us pics of my dog every day and sent me texts to keep me Posted on how my dog was doing. I will Definitely use... (more)"

Confirmed availability
This weekend
4. Katy Verified Background Check

I will play with your dog.

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Katy stayed in my home over the Christmas holidays and took excellent care of my dog with separation anxiety. She even went above and beyond and stayed until... (more)"

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5. Linda & Christine Verified Enhanced Background CheckRoverGO

ALL YOU NEED IS LOVE LOVE

Winter Garden, FL, 34787

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Linda is such a wonderful caretaker for our pup Milton. She is so attentive and treats him as if he were her own. I wouldn’t trust him with anyone else but L... (more)"

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6. Tracy Verified Enhanced Background CheckRover 101

dedicated to pets wellbeing

Windermere, FL, 34786

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Tracy was amazing, we went on vacation and knew that our fur baby was going to be well taken care of. Tracy was very professional, prompt, kind and most imp... (more)"

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7. Kimberly Verified Enhanced Background Check

I' good with pets of all sizes&ages

Winter garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Kim is a very responsible cast member who takes pride in doing her best at all times. She is responsible and takes ownership of any task assigned to her. (more)"

8. Chelsea Verified Background Check

certified veterinarian technician

Oakland, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Chelsea’s passion for animals, especially dogs is unmatched in my opinion. She is a certified veterinarian technician and has dedicated her professional lif... (more)"

9. Jenn Verified Background Check

I love 4 legged friends!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Jenn has been taking care of our fur babies for over two years now. She has a natural love of animals, and they recognize that and love her right back. Our 3... (more)"

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10. Carissa Verified Background CheckRover 101

I will love your dog just like you

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Carissa was wonderful while staying overnight with my dogs. She took very good care of them and kept me updated as to how they were doing. I would definite... (more)"

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11. Danielle Verified Background Check

Pet parent ready to care for yours!

Ocoee, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

"Danielle is a huge animal lover filled with compassion for helping those in need for any reason. She has fostered kittens in our apartment, has grown up with... (more)"

Confirmed availability
This weekend
12. Jennifer Verified Background Check

The best care for your best friend!

OCOEE, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

"Jennifer was great! She took good care of our house and even better care of our pup! She made sure to send updates, pictures, and everything. We would defini... (more)"

13. Forrest Verified Background Check

Energizing Walks, Cozy & Safe Home

Oakland, FL, 34760

Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

"Forrest is an excellent dog sitter and will provide lots of attention to your furry companion. I can honestly say I trust him with my fur babies! (more)"

14. Kendall Verified Background Check

Walks, cuddles, & love for your pup

Oakland, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Kendall is a true animal lover and is extremely responsible. Beyond that, Kendall is one of the most positive people I have ever met. She is a wonderful hu... (more)"

Confirmed availability
Christmas and New Year
15. Hailee Verified Background Check

Nurturing and loving pet caretaker

ocoee, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

About: I have a geniune love and passion for all animals. I grew up with animals my whole life including; various dog breeds, birds, cats, and even squi... (more)

16. Ann Marie Verified Enhanced Background Check

“Let’s go to the dog park!”

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Ann Marie took great care of our little ones and kept us updated on how they were doing during our trip. We highly recommended her (more)"

17. Annalette Verified Enhanced Background Check

I'll play, run, & care for your dog

ocoee, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

"Annalette is very caring and passionate with animals. She’s always been loving with dogs. She volunteers at the Orlando animal shelter for about 7 months now... (more)"

Confirmed availability
Christmas and New Year
18. Christine Verified Background Check

Let’s play together

Winter garden, FL, 34787

Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

"Christine has the most loving nature when it comes to her babies. If long walks, short runs, and lots of ball throwing is what your looking for then she is ... (more)"

19. Betty Verified Enhanced Background Check

Loving Pet Sitter

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

About: My friends and family would always ask for me to dog set when they went out of town. I would make sure they had their food and water bowls full. T... (more)

20. Kelly Verified Background Check

Dogs touch our hearts and souls :)

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Kelly is one of the most dependable people I know. You'll never have to worry about your pets if he is taking care of them. His friendly and easy going man... (more)"


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.