Pet Sitting & Drop In Visits in Oakland, VA

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

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1. Aliya

Love adventuring with your pets!

The Fan, Richmond, VA, 23220

Drop-In Visits, Dog Walking

"Aliya has been great with our dog - she's been sending us pictures and keeping us updated. These are always high points in my day at work! Also, she's famili... (more)"

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2. Chandler

Young, energetic, ready to go

Richmond, VA, 23224

House Sitting, Drop-In Visits, Dog Walking

"Chandler was great! We were apprehensive about letting someone into our home and nervous about leaving our new pup, but both were no stress with Chandler! He... (more)"

3. Schyller

Active, Trustworthy, and Flexible!!

Northrop, Richmond, VA, 23225

House Sitting, Drop-In Visits, Dog Walking

"Schyller is awesome! She comes regularly M-F to let my two Pugs out while I am at work. She is reliable, trustworthy, and responsive. I recently had a wor... (more)"

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4. Bree

Your pet's new BFF

Church Hill, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Fantastic as always! (more)"

5. Elizabeth

Dog Walking & Pet Sitting Pro

Shockoe Bottom, Richmond, VA, 23223

Drop-In Visits, Dog Walking

"Elizabeth took excellent care of my cats! Her check-ins were very thorough with picture updates and a writeup of exactly what the visit entailed. Also she wa... (more)"

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6. Emily

I’ll love your dog like it’s my own

Shockoe Bottom, Richmond, VA, 23223

Drop-In Visits, Dog Walking

"Clyde and Ella love Emily! She’s super flexible and just a pleasure to deal with. (more)"

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7. Annie

Life-Long Dog Pal - Let's Walk!

Jackson Ward, Richmond, VA, 23220

House Sitting, Drop-In Visits, Dog Walking

"Our experience with Annie is that she is very organized, responsible, and very loving toward all sorts of dogs. We regularly leave one or even both our dogs ... (more)"

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8. Jess

Looking for new furry friends!

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Jess is great - kind, conscientious, and clearly good with animals! We will definitely work with her again. (more)"

9. Mari

Self Employed, and loves dogs!

Old Town Manchester, Richmond, VA, 23224

Drop-In Visits, Dog Walking

"Mari was flexible, responsive and (most importantly) loves dogs!! I recommend her to anyone looking for a sitter (more)"

10. Emma

Teacher by day, dog mom by night

Union Hill, Richmond, VA, 23223

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

"Emma was a wonderful weekend cat-sitter! This was our first time having her check-in on our two kitties and we absolutely appreciate her responsiveness, flex... (more)"

Confirmed availability
This weekend
11. Ifeatu

Sick of high costs- hire me :)

Union Hill, Richmond, VA, 23223

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

About: I love dogs. Ever since I was able to have one I’ve always had a dog and it will always be that way. I’m not here to break the bank in dog sitting.... (more)

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12. Isaac

Teacher home full time this summer!

Shockoe Bottom, Richmond, VA, 23223

Drop-In Visits, Dog Walking

"Isaac is the person I would choose to care for my pets because he is responsible, punctual, and caring. He can be counted on to thoroughly complete any assig... (more)"

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13. Anna

Friendly dog walked next door!

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"We called upon Anna for the first time on very short notice to drop in and take care of our dog. We were so happy with her work. She came at the two times ... (more)"

14. Maddie

Help me explore RVA!

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I'm a New York via DC transplant to Richmond, and I'd love to get out of the house more and have a dog join me! I grew up in a house with ca... (more)

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15. Matty

Young, active graduate student!

Union Hill, Richmond, VA, 23223

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

"Matty watches my dog, Molly, every time I’ve out of town and he’s awesome! He is responsible with Molly and sends me updates and pictures throughout the stay... (more)"

Confirmed availability
This weekend
16. Ysenia

Energetic & Patient with Free Time!

Church Hill, Richmond, VA, 23220

Drop-In Visits, Dog Walking

About: I have grown up around dogs all my life, ranging to many types or breeds and sizes while also assisting in training, with this experience I am easi... (more)

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17. Natalie

Treat your dog as if it were mine!

Richmond, VA, 23224

Drop-In Visits, Dog Walking

About: Being a dog owner myself, I absolutely love each and every furry pooch! I think all pets deserve the best life possible; play time, exercise, and o... (more)

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18. Josephine

Jo's Dog Sitting!

Chimborazo, Richmond, VA, 23223

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

"Rover is lucky to have Jo join as a dog sitter! We have used her as our pet sitter throughout the past 4 years whether it be walking, overnight stays and/or ... (more)"

Confirmed availability
This weekend
19. Glencora

Excited to meet your best friend!

Chimborazo, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Cora has been outstanding in caring for our puppy. She has been responsible, on time, and has provided feedback during twice daily drop-in visits with texts ... (more)"

Confirmed availability
This weekend
20. London

Home full time/ goes on long walks

Old Town Manchester, Richmond, VA, 23224

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

About: I love all kinds of dogs! I've had dogs since I was a child - all different sizes. Currently I have a black lab who is 10 years old ~ 60 lbs. Exper... (more)


The next time you head out of town and need someone to take care of your pets — and check in on you home — turn to Rover. It's easy to find a loving Oakland pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Oakland, VA, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). 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 house and pet sitter all through Rover — it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Oakland pet sitters and avoid the kennel.