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.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Lauren

Norwegian & American husband & wife

Oakland, FL, 34760

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

"A kind and gentle, soft spoken walker. Our Pekingese, who's pretty picky had a super walk with Lauren. We're unable to walk her because of health issues so... (more)"

Confirmed Holiday Availability
2. Christina

Delivering Love and Care they need!

Clermont, FL, 34711

Drop-In Visits, Dog Walking

5 repeat clients

"Christina took amazing care of all three of my pups, and my house. The pups were happy and the house cleaner than I left it. Will recommend. Thanks Christina! (more)"

Confirmed Holiday Availability
3. Alisha

Loving Dog Sitters Near Disney

Winter Garden, FL, 34787

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

64 repeat clients

"Alisha was FANTASTIC with my dog Julep! She really went the extra mile and kept in constant communication while I was away from home! Loved all the pictures ... (more)"

4. Kimberly

I love walking & cuddling dogs!

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Dog Walking

About: I have been a dog parent for 14+ years but currently do not have a dog. I would love to spend time with, play with, walk and love on your pet! ... (more)

5. Frank

simple & caring pet sitter

Winter Garden, FL, 34787

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

1 repeat client

About: I've never actually thought you could make something of dog sitting. Who knew? I've had dogs, cats, and birds through my life. I'm the go to sit... (more)

Confirmed New Years Availability
6. Hannah

Patient, caring, and loving sitter

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Hannah did a great job. My cats seemed happy. The food/water dishes were clean and so were the litter boxes. (more)"

Confirmed Holiday Availability
7. Lauren

Your pets new favorite sitter (:

winter garden, FL, 34777

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

1 repeat client

"Let me say lauren is the best of the best. She is definitly one of chewys (My dog) favorite people). I was worried because he is normally shy but went straig... (more)"

Confirmed Holiday Availability
8. Sarah

Your Fur Family is always Welcome!

Clermont, FL, 34711

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

20 repeat clients

"Sarah did a great job; she was not only able to accommodate our schedule but the dogs loved her. They all were very happy when we came home from the attentio... (more)"

9. Suzanne

Stay at home mom with 1 dog!

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Doggy Day Care

About: Hey, I'm Suzanne! I'm a stay at home mom but my kids are off in school half the time now. I have a 1 year old Australian Shepherd who just wants to... (more)

10. 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)"

Confirmed Holiday Availability
11. Jeff and Gaby

Jeff & Gabys pet paradise

Ocoee, FL, 34761

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

22 repeat clients

About: We are a family of animal lovers. We actually met at PetSmart! Our home will be your pets home while on vacation. Jeff is a certified dog trainer a... (more)

Confirmed Holiday Availability
12. Ki

Delightful dog watching!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kiara is responsible and nurturing. She takes great care of my fur baby when I am away. She creates a loving and stress free environment and my dog loves i... (more)"

13. Torey

Dogs absolutely love me!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Torey has been dog sitting for my house for over 3 years now. He goes above and beyond when taking care of our dog. We always know that our dog is in good ha... (more)"

14. Menchie

Caring and loving dog sitter!

Clermont , FL, 34711

House Sitting, Drop-In Visits, Dog Walking

"Menchie has had pets all of her life. She treats every animal with such care and love that they become an extension of part of her family. She has worked wit... (more)"

15. Kelly

Dogs touch our hearts and souls :)

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"I have known Kelly for many years. From the time he was very young he has been a lover of animals of all kinds. He has always supported causes to benefit t... (more)"

16. Sara

My dog is my best friend!

Winter garden, FL, 34787

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

About: I have always loved dogs but more than anything my child is a 6 year old lab named drake! My husband and I can't have children. 6 years ago drake w... (more)

17. Melodee

Caring, responsible, pet lover.

Winter Garden, FL, 34787

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

"Melodee did a great job caring for our dog Maya! Maya was at easy and she received attentive care. We were relieved to know we had someone we could trust wat... (more)"

Confirmed Holiday Availability
18. Kristina

Compassionate, friendly, fun!

Winter Garden, FL, 34787

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

About: I have many years of experience with dogs - I have 2 dogs of my own! I'm that girl that sees a dog and runs to go pet it. Haha! I can't help it...d... (more)

19. Jessica

I am a lover of all fur babies

Winter Garden , FL, 34787

House Sitting, Drop-In Visits, Dog Walking

About: I have been a pet owner for my entire life, I have lived both with cats and dogs, I am also a former Equestrian. My love for animals has no boundar... (more)

20. Jeyde

The passion I put into everything!

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

About: I've had dogs all my life so I know exactly how to take care of one. I have had 6 dogs in my whole life and I loved each of my dogs. I love any kin... (more)

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Learn About Premier

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 free 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.