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
Thanksgiving
1. Christie

Belly rub pro, fetch extraordinaire

Clermont, FL, 34711

House Sitting, Drop-In Visits, Dog Walking

"Christie was excellent for our two Cocker Spaniels. One of our dog does not do well being boarded and due to an emergency trip I was looking for other optio... (more)"

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2. Andrea

Flexible Schedule

Ocoee, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

"Andrea is just the best. She always has us laughing with the pics and stories from her visits and our picky pooch just loves her!!! During her most recent vi... (more)"

3. Tracy

dedicated to pets wellbeing

Windermere, FL, 34786

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

"Our puppies love Tracy and we love her and how she cares for our two puppies. She goes above and beyond, making sure they are well cared for in all aspects. ... (more)"

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4. 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)"

Confirmed availability
Thanksgiving
5. 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)"

6. Lauren

Norwegian & American husband & wife

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

"Lauren did an amazing job of caring for our dog and making sure she was given plenty attention and love while we were on vacation. Highly recommended! (more)"

7. Rebekah

Experienced with special needs dogs

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Rebekah was absolutely awesome with our pup!! She was very attentive, took notes on my instructions, and quick with her responses. I felt comfortable and kne... (more)"

Confirmed availability
Thanksgiving
8. Tatiana

Work from home mom and dog lover

Windermere, FL, 34787

Dog Boarding, 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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9. 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)"

Confirmed availability
This weekend
10. Rachel

Animal Hospital Attendant Dog Lover

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Rachel is a great reliable resource to have for any of your pets needs! I have a dog that's a little shy and can be picky with who he likes but he loves her.... (more)"

11. 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)"

Confirmed availability
Thanksgiving
12. Katy

I will play with your dog.

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Katy has taken care of our dogs and cats for several years. She follows directions well and is devoted to all pets. She comes to our house and greets our pet... (more)"

13. Austin

I love walking & playing with dogs

Winter Garden, FL, 34787

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

"He cares for the three dogs we own. He loves playing with them and cuddling with them. He makes sure they all are cared for and get attention. (more)"

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14. Mike

Ms. Belle's Pet Care LLC

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

About: None (more)

15. 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)"

Confirmed availability
Thanksgiving
16. 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)"

17. Karina

Like Family

Winter Garden, FL, 34787

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

About: None (more)

18. Maggie

Attentive and active dog sittier!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Maggie was great! She responded promptly and was able to drop in to see my dog on rather short notice. My dog can be a bit shy, but she was great and hung ou... (more)"

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19. Celina

Great with dogs, a big dog lover!!

Winter garden, FL, 34787

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

"This was one of the longest drop in visits that Celina offered her services to. We got pictures everyday which we looked forward to. There were specific thin... (more)"

Confirmed availability
Thanksgiving
20. Katie

Reliable And Highly Flexible Sitter

Oakland, FL, 34760

House Sitting, Drop-In Visits, Dog Walking

About: None (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.