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.

Confirmed availability
Christmas and New Year
1. Aliya

Love adventuring with your pets!

The Museum District, Richmond, VA, 23220

Drop-In Visits, Dog Walking

"Aliya is wonderful! Our French Bulldog has back and knee problems and needs some special care, and Aliya was always incredibly accommodating and gave him ext... (more)"

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2. Sarah Jean

The Wonderful Wizard of Paws! :)

Church Hill North, Richmond, VA, 23223

Drop-In Visits, Doggy Day Care, Dog Walking

"Sarah Jean is wonderful! She is extremely accommodating, reliable, and I SO feel much better having her care for my babies when I have to travel and they can... (more)"

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3. Jess

Available for last minute requests!

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Jess was great!! She saved me big time when I had to go home for a medical emergency by being very responsive and helpful. She was great with my cat and sent... (more)"

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4. 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)"

Confirmed availability
This weekend
5. Christine

Work-from-home sitter/walker/runner

Richmond, VA, 23224

Drop-In Visits, Doggy Day Care, Dog Walking

"Christine is our top choice for a dog walker / sitter, we have used her services on several occasions. My mind is at ease when I know she is coming by. I c... (more)"

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6. Bree

Your pet's new BFF

Church Hill, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Fantastic as always! (more)"

Confirmed availability
Christmas and New Year
7. Andrea

Twelve year experience in pet care

Shockoe Bottom, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Andrea is great! I am a new puppy mom and she really made me feel comfortable leaving our puppy in her care. She also sends rover cards and pictures after d... (more)"

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8. Schyller

Active, Trustworthy, and Flexible!!

Northrop, Richmond, VA, 23225

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)"

Confirmed availability
Christmas and New Year
9. Kadeja

I’ll treat your dog as my own. love

Hickory Hill, Richmond, VA, 23234

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

"Kadeja is a happy, energetic person. She has a great spirit and is an outgoing person. Her best friend is Lexii, her fur pal. She demonstrates so much love ... (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)"

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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. Trenton

Nature Lover, Runner, Dog Owner

Central Office, Richmond, VA, 23219

House Sitting, Drop-In Visits, Dog Walking

"Trenton was amazing with my 2 dogs. They are very energetic and require a lot attention, and Trenton was able to care for them with no problems! I also recei... (more)"

13. Sophie

Can’t wait to meet you and your pup

Church Hill, Richmond, VA, 23223

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

"Punctual, friendly and active with the pups. She wrangled our three like a champ. It’s nice to come home to a poop-free house with tired pups because she t... (more)"

Confirmed availability
This weekend
14. Anna

Friendly dog walked next door!

Shockoe Bottom, Richmond, VA, 23223

Dog Boarding, Drop-In Visits, Dog Walking

"It was wonderful to meet Anna! She clearly knew much more about dogs that me and my partner did and was so great with our little puppy. I'll definitely be as... (more)"

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15. Sheila

Compassionate care for your canine!

Upper Shockoe Valley, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Sheila is an incredibly caring and loving person who I have known for many years. Whether it is volunteering her time at animal shelters, dog sitting for her... (more)"

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16. Allie

Happy to run and play with dogs

Upper Shockoe Valley, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

"Allie is an awesome doggie sitter! She truly loves dog and will give your dog lots of cuddles and special attention. She spoiled my Brantley Bear with love... (more)"

17. Stephanie

Flexible- Fenced in yard

Oak Grove, Richmond, VA, 23224

House Sitting, Drop-In Visits, Dog Walking

About: I am absolutely in love with all animals especially dogs. I am especially fond of big dogs, but they all have my heart. I am very active and love t... (more)

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18. Megan

Active, Friendly, Flexible

Chimborazo, Richmond, VA, 23223

House Sitting, Drop-In Visits, Dog Walking

About: Hi! My name is Meg, and I'd be happy to take care of your furry friend. I've had dogs my whole life, and I know how important care is while you're ... (more)

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19. Sara

Teacher home for the holidays!

Old Town Manchester, Richmond, VA, 23224

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

About: I am an RPS middle school science teacher, looking to care for my second passion- dogs!! I have a German Shepherd that loves to play, so your dog w... (more)

20. Henry

I will be your dog's best friend

Fulton, Richmond, VA, 23231

House Sitting, Drop-In Visits, Dog Walking

"Henry really loves dogs. He gets really excited to be around them when he sees one. Can't get wait to get near dogs to pet them and hug them. He has owned... (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.