House Sitting in Windermere

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. Joshua Verified Enhanced Background Check

Educated Caretaker

Ocoee, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

"Joshua came through for us at the very last minute. His reply was prompt. He was on time and Cooper loved him. Definitely we will see him again. Excellent ex... (more)"

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2. Andrea Verified Background Check

Will provide lots of love

Orlando, FL, 32819

House Sitting, Drop-In Visits, Dog Walking

"I highly recommend Andrea. She sent me updates and pictures throughout the weekend. She left my house clean and neat. I will definitely use Andrea again. (more)"

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3. Brianna Verified Background Check

Pawsitively the best care

Windermere, FL, 32801

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

"Brianna was absolutely awesome for us. She literally saved the day when we realized, while staying in a rented RV at Disney’s Ft Wilderness, that our standar... (more)"

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4. Jasmine Verified Background Check

Fur mom to two beautiful cats

Winter garden, FL, 34787

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

"Jasmine is a wonderful human! She cared for my pets very lovingly. I will certainly use her again! ? (more)"

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5. Bonnie Verified Background CheckRover 101

Looking For A Reliable Sitter?

Metro West, orlando, FL, 32835

House Sitting, Drop-In Visits, Dog Walking

"Bonnie was beyond amazing! A last minute change of plan resulted in us having to visit Orlando with our dachshund in tow. Nervous to leave him alone at our... (more)"

Confirmed availability
Christmas and New Year
6. Kristi Verified Background CheckRover 101

TLC offered

Winter Garden, FL, 34787

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

"Kristi deserves 10 stars! She took excellent care of our 2 dogs and 2 cats while we were on a 10 day cruise. She kept us updated daily and went above and b... (more)"

Confirmed availability
Christmas and New Year
7. Sonya Verified Background Check

Reliable dog and cat lover!

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

"I couldn't have asked for a better sitter for my two pups, Bruno and Deuce. They just seem so happy with her. She sent me photos throughout the two days she ... (more)"

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8. Shelymar Verified Enhanced Background Check

🐶Dogs & Cats🐱 All sizes and ages

Metro West, Orlando, FL, 32835

House Sitting, Drop-In Visits, Dog Walking

"I had never left my babies With any one who was not a relative. God put shelymar on my way and I don't know how to Express how wonderful she is. She took car... (more)"

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9. 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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10. Rosana Verified Background Check

I love caring and training our love

Windermere, FL, 34786

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

"I don't even know how to start. I absolutely love Rosana, she was so kind with Scottie. Always came on time and as soon as he saw her, he ran towards to give... (more)"

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11. Lauren Verified Background Check

I like long walks on the beach!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Lauren is awesome. She's personable, flexible, helpful and was absolutely wonderful with my labradoodle, Mocha. Mocha is old, with diva-ish tendencies and ... (more)"

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12. Sara Verified Background Check

Hello, my name is Sara!

Windermere, FL, 34786

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

"Sara was fantastic with our baby boy. Bailey is not the easiest (hyper and needs exercise) and she bonded with him well. She communicated with us the whole... (more)"

Confirmed availability
This weekend
13. Vivianne Verified Enhanced Background Check

Hooray for Happy and Healthy Pets!

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

"Vivianne is such a great person! And my dog absolutely adores her!! She is loving, kind, gentle, and is always ready to play and cuddle with my little Pip. I... (more)"

14. 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)"

Confirmed availability
This weekend
15. 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)"

Confirmed availability
Christmas and New Year
16. Julia Verified Background Check

Julia Thorson

Metro West, Orlando, FL, 32835

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

About: I am 19 years old. I have a lot of energy and I'd love to use my energy to take care of animals that are in need of care. I have a huge heart when ... (more)

Confirmed availability
This weekend
17. Brooke Verified Background Check

You leave ‘em, I’ll love ‘em!

Orlando, FL, 32819

House Sitting, Drop-In Visits, Dog Walking

"Wonderful dog sitter! (more)"

Confirmed availability
This weekend
18. Livie Verified Background Check

Loving care when you’re not there!

Windemere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

"Livie is a wonderful dog and cat sitter! My pets always enjoy when she stays with them. Everything is taken care of well every time she has house sat and I f... (more)"

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19. June Verified Background CheckRoverGO

Love is a four legged word!

Orlando, FL, 32819

House Sitting, Drop-In Visits, Dog Walking

"I can not recommend June enough. We were on vacation for a little over a week and booked June to stay in our home with our three dogs. We had never done this... (more)"

20. Alyssa Verified Background Check

Doggo and Pupperino #1 Fan

Windermere, FL, 34786

Dog Boarding, House Sitting, Drop-In Visits

"I would recommend Alyssa with no reservations. She is honest, trustworthy and loves animals (dogs in particular) . She has taken care of my golden retriever... (more)"


Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog — and your home — turn to Rover for your Windermere house sitting needs. On Rover, it's easy to find a loving dog sitter in Windermere who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Windermere house sitters near you, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your dog's stay all through Rover — it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Windermere for your dog — people who'll treat him like family.