Pet Sitting & Drop In Visits in Oakland, FL

Book a pet sitter to stop by your home a few times a day to feed and play with your cat or dog.

Confirmed availability
President's Day
1. Jessica

Former veterinary technician

Ocoee, FL, 34761

Drop-In Visits, Dog Walking

"This was my first time using Rover.com while having to go out of town for a few short days, and I was extremely pleased. Jessica was very reliable and paid e... (more)"

2. Andrea

Flexible Schedule

Ocoee, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

"Andrea is great! This is the second time she has watched our pups when we had to go out of town for the day. I love that she gives a thorough update and tons... (more)"

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3. Katy

I will play with your dog.

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Katy has been a reliable sitter this week , keeping to her agreed schedule and posting pictures as she promised. This really set our minds a ease as we were ... (more)"

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4. Lindsay

Certified Vet Tech!

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

"Lindsay is great! She often watches my dogs (both large and full of energy) when I go out of town. She is so friendly and respectful when she updates me on t... (more)"

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5. Christie

Belly rub pro, fetch extraordinaire

Clermont, FL, 34711

House Sitting, Drop-In Visits, Dog Walking

"Christie did an excellent job! A puppy is a lot of work, and she went out if her way to play with Prairie. I loved the pics and the Rover updates. Highly rec... (more)"

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6. Kim

Compassionate dog walker & sitter

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Dog Walking

"Kim would be a great dog sitter! She has 3 dogs and treats them as a member of the family. I would highly recommend Kim as a trustworthy and responsible i... (more)"

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7. Elaina

Pets are family!

34787, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Elaina will love your dog as if it is her own. From the first day I met her I saw the passion she has for pets. She doesn’t think of them just as a dog or ca... (more)"

8. Lauren

Norwegian & American husband & wife

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

"Lauren does such a good job with Barkley! She not only spends time with him, she has been training him on basic commands during her time with him. (more)"

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9. Jeannine

Walks are better with a dog :)

clermont, FL, 34711

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

"She was soo awesome!!!! She even spent extra time to love on my pups! Which I really appreciate, since I had to stay out of town an extra day! Jeannine is wo... (more)"

10. Wendy

Home full-time, can medicate

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Dog Walking

"Wendy was great and thorough with talking through what my pup would need from her, which I was appreciative because it was the first time I have had someone ... (more)"

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11. Tatiana

Work from home mom and dog lover

Windermere, FL, 34787

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

"Great meet and greet! Looking forward to leaving our little guy with Tatiana for doggy daycare and out of town trips! (more)"

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12. Shelley

Exp. dog owner with flexible sch.

Clermont, FL, 34711

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

"I have known Shelley for about 16 years. She has always been great with her own pets, a very loving pet mom. I have been in a bind of my own recently and s... (more)"

13. Carissa

I will love your dog just like you

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Carissa has done a great job taking care of our dog! We are repeat customers and will continue to ask her for help! (more)"

14. Jennifer

I am your Dog Whisperer

CLERMONT, FL, 34711

House Sitting, Drop-In Visits, Dog Walking

"Jennifer has been an excellent caretaker of our dogs. She has on numerous occasions stayed at our house to watch our three dogs, sometimes for up to a week. ... (more)"

15. Katie

Reliable And Highly Flexible Sitter

Oakland, FL, 34760

House Sitting, Drop-In Visits, Dog Walking

"Katie was a pleasure to meet and attend to my dog's needs. She is extremely reliable and flexible, which I appreciated especially during the holiday season. ... (more)"

16. Celeste

Large yard to run like the wind

Winter Garden, FL, 34787

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

"OMG! is all I can say... I used Celeste to care for my Django (5 yr old terrier mix) while I was away for 3 days. It seemed like he is the one that was away ... (more)"

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17. Amanda

Your Fur Baby's Home Away From Home

Winter Garden, FL, 34787

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

"We were very nervous about leaving our babies while we were away. When I first met Amanda, I started feeling much better. She was very thorough, loved on a... (more)"

18. Siedah

Friendly Walker

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

About: Hello! As a current dog owner I love nothing more to extend that love to other pups. I have had dogs all my life and really value their company. I ... (more)

19. Kelly

Dogs touch our hearts and souls :)

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"I have known Kelly for many years. From the time he was very young he has been a lover of animals of all kinds. He has always supported causes to benefit t... (more)"

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20. Kristina

Compassionate, friendly, fun!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

About: I have many years of experience with dogs - I have 2 dogs of my own! I'm that girl that sees a dog and runs to go pet it. Haha! I can't help it...d... (more)


Rover.com is the simple, savvy way to find and book Oakland drop in pet sitting. It's easy to find the perfect pet sitter — many sitters have offered pet sitting on Rover for years, and 95% of reviewed stays have received a perfect five-star rating. You'll get daily photo updates, and every stay booked through Rover also includes premium pet insurance, 24/7 support, and a reservation guarantee. Pet sitters on Rover have the option to complete a background check, which you can see from their background check badge. Pet sitters are booked on Rover every minute of every day, and 92% of the population lives within a short drive of one of the more 60,000 sitters who've listed their services on Rover, so you're sure to find the perfect pet sitter in Oakland. When you book with one of our trusted pet sitters on Rover you get peace of mind that your home and pets are in loving hands.