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
Labor Day
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)"

Confirmed availability
Labor Day
2. Tracy

dedicated to pets wellbeing

Windermere, FL, 34786

Dog Boarding, Drop-In Visits, Dog Walking

"We recently reached out to Tracy for support in coverage for our puppy. Tracy reached out right away and schedule a meet and greet the same day! Tracy's genu... (more)"

Confirmed availability
Labor Day
3. 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)"

Confirmed availability
Labor Day
4. Jessica

Former veterinary technician

Ocoee, FL, 34761

Drop-In Visits, Dog Walking

"Jessica was great! She did a drop in visit for us when our normal house sitter canceled last minute. She took great care of our dogs and we would definitel... (more)"

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5. Lauren

Norwegian & American husband & wife

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

"Lauren took great care of my kids. She also gave me great reports to keep me updated while I was gone. She was very attentive and responsible! (more)"

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6. 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)"

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7. 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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8. 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)"

Calendar Recently Updated
9. Karina

Like Family

Winter Garden, FL, 34787

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

About: We love dogs, and will treat yours like our own. We have a moderate sized, fenced back yard for outside play when the weather is nice. Most of the ... (more)

10. Brooke

Adoring every dog!!!

winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

About: I am the absolute biggest dog lover you would probably find. Dogs seem to get along with me extremely well. I have been the biggest dog lover since... (more)

11. Maggie

Dog trainer becomes dog walker!

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

"I believe Maggie is a responsible and loving dog caregiver because she always goes above and beyond for her own dogs and loves them more than I have ever see... (more)"

Calendar Recently Updated
12. Mike

Ms. Belle's Pet Care LLC

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

About: I love animals, and giving them the good life they deserve. I take care of your furry (or feathery) friend, as if they were my own, which is as if ... (more)

Confirmed availability
Labor Day
13. Jeannine

Walks are better with a dog :)

clermont, FL, 34711

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

"Wonderful companion to our fur babies (more)"

Confirmed availability
Labor Day
14. Austin

I love walking and playing with dog

Winter Garden, FL, 34787

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

"Austin has taken care of our terrier (who can be a terror) on numerous occasions. From stopping by to take her on walks when we were unavailable to multiple ... (more)"

Confirmed availability
Labor Day
15. 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)"

Confirmed availability
Labor Day
16. Maghen

I prefer kids that are 4-legged (;

Winter Garden, FL, 34787

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

"Maghen is such a cool person. She loves her dog more than anything. She’s always outside walking or playing with dogs from the her neighborhood. Everyone I t... (more)"

Confirmed availability
Labor Day
17. Daniela

Retired Vet Tech of 10 years

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

"Great communication and flexibility! My go-to Rover-er! My pups love her :) (more)"

Confirmed availability
Labor Day
18. Jonathan

Home full-time, fenced yard

Winter Garden, FL, 34787

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

About: Hi there fur baby owner!, My name is Jonathan and I currently work for Walt Disney world one day a week as a bartender. I’m just looking for a gre... (more)

Confirmed availability
Labor Day
19. Wendy

Home full-time, can medicate

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Dog Walking

"Wendy is great! Very conscientious and caring. (more)"

Confirmed availability
Labor Day
20. Celina

Great with dogs, a big dog lover!!

Winter garden, FL, 34787

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

"Thanks Celina for great service and attentiveness. Princess seems so comfortable with her, which makes us very happy. She looks forward to seeing her while w... (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.