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.

1. Lauren

Norwegian & American husband & wife

Oakland, FL, 34760

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

13 repeat clients

"This was our first experience using Rover and trusting a "stranger" with our "baby" and I can honestly say, it could not have gone better. Lauren and her hus... (more)"

Confirmed Holiday Availability
2. Jennifer

Large Yard to Play!

Clermont, FL, 34711

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

4 repeat clients

"First time visit went great! My larger dogs can be a handful and Jennifer was so friendly and attentive. Would definitely recommend and have already booked a... (more)"

3. Nicholas

Team Dan & Nicholas's Dog Services

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

6 repeat clients

"Nicholas was AWESOME. He went above and beyond helping mecwith my handicapped pug who can't walk, pee or poop in her own. He spoon fed her til she started ... (more)"

4. Dan

Team Dan & Nicholas's Dog Services

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

12 repeat clients

"I'm so thankful I found Dan. Not only does he love my little guy but on short notice he was there for me and Hercules when we needed him! my first time using... (more)"

5. Tracy

dedicated to pets wellbeing

Windermere, FL, 34786

Dog Boarding, Drop-In Visits

11 repeat clients

"Tracy was amazing with my nervous poodle, Vinny. Will definitely be using her in the future for drop-ins and maybe overnight boarding if needed! When my apar... (more)"

6. Wendy

Home full-time, can medicate

Winter Garden, FL, 34787

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

4 repeat clients

"Wendy is wonderful with animals. She is especially attentive and loving due to her passion, understanding, and knowledge of so many species and breeds. Asid... (more)"

7. Carol

1 acre fenced yard for running/play

Clermont, FL, 34711

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

4 repeat clients

"Took wonderful care of my babies - thank you ! ? (more)"

8. Aeriel

Full Time Dog Sitter!

Montverde, FL, 34756

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

7 repeat clients

"Aeriel did a great job communicating throughout her drop visits and her updates were spot on. The previous night we had a good meet and greet and everything ... (more)"

Confirmed Holiday Availability
9. Celina

Home full time, & a big dog lover!!

Winter garden, FL, 34787

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

1 repeat client

"Celina is great with Princess. She pays lots of attention to her. She comes within the time frame we suggested. Most of all I love receiving all the pictures... (more)"

Confirmed New Years Availability
10. Michelle

Dogs love hanging out with us!

Oakland, FL, 34787

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

12 repeat clients

"Michelle does such a great job with my dogs! I feel confident that she can handle them and they loved her as soon as she walked in through the door. She make... (more)"

Confirmed Holiday Availability
11. Regina

Loving grandma eager to help.

Clermont, FL, 34711

House Sitting, Drop-In Visits

1 repeat client

"Regina was excellent with our Sugar Bear! She played with and fed Sugar while we were away. I will definitely use her again. (more)"

Confirmed New Years Availability
12. 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)"

Confirmed Holiday Availability
13. Tiffany

Dog Lover! Professional Experience!

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

"Tiffany - Thank you for taking the time to repetitively love and take care of Thor! He really loves his visits with you and Sadie. I can't thank you enough... (more)"

14. Nicole

I'll Treat Your Dogs Like Family

Winter Garden, FL, 34787

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

1 repeat client

"Nicole is Awesome!! My dogs had such a good time with her that my dogs didn't even want to come back home with me lol! Thanks a bunch (more)"

Confirmed Holiday Availability
15. Megan

Dog lover w/ flexible day schedule!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

About: From the mitten to the sunshine state-- I adopted my "high maintenance" bully breed over 6 years ago, and she is my world! An animal lover-advocate... (more)

16. Sean

Ex Manager at PetSmart

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Sean is fantastic with my little dog, Maggie! Sean has been wonderful with his own dogs. I rarely trust anyone with my little girl, but Sean has dog-sat for ... (more)"

17. Alba

Will Talk To Your Pet

Winter Garten, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"I have known Alba for 16 years and she is the most caring person I know. She always puts others first. Recently one of my small dogs was bit by another one o... (more)"

18. Jazmin

Loving Mommy with a fenced yard

Clermont, FL, 34711

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

"Jazmin has such a passion for dogs! Your dog is in excellent hands with her many years for experience. No need to worry while you are away! (more)"

19. Kelly

Dogs touch our hearts and souls :)

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Kelly is one of the most dependable people I know. You'll never have to worry about your pets if he is taking care of them. His friendly and easy going man... (more)"

Confirmed Holiday Availability
20. Asia

Home Full Time, Flexible Hours

Oakland, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Asia watched my two dogs for three days over Christmas break last year while I was on vacation. I left detailed instructions on how they like their food, wha... (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.