Drop-In Visits in Winter Garden

Book a pet sitter to stop by your home a few times a day to feed and play with your dog.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed Holiday Availability
1. 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)"

Available this weekend
2. Lauren

Norwegian & American husband & wife

Oakland, FL, 34760

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

"Lauren is an extremely diligent worker. One of her greatest strengths is the enthusiasm she pours into everything she does. She faces every task with energy ... (more)"

3. Lores

Caring devoted animal lover!

Ocoee, FL, 34761

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

83 repeat clients

About: I go above and beyond just merely loving your pets. As each day passes your pet and I will develop a genuine respect for each other which is a key.... (more)

4. Amanda

Experienced dog mom ready to work

Orlando, FL, 32818

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

"Amanda is a dedicated dog mom to her Cav, Rosie. She takes great care of her and loves her unconditionally. Whats more, Amanda is a sweet, good-natured perso... (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)

6. 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)

7. 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)

Confirmed Holiday Availability
8. 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)"

9. Sean

Ex Manager at PetSmart

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Sean loves dogs and dogs love Sean. When he worked at PetSmart he gave money directly out of his check towards the chip technology for pet owner's. Sean wi... (more)"

Confirmed Holiday Availability
10. Jeff and Gaby

Jeff & Gabys pet paradise

Ocoee, FL, 34761

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

22 repeat clients

"Thanks Jeff & Gaby for taking care of Jack while I was away...you did a great job!! (more)"

Confirmed Holiday Availability
11. 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)"

12. 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)"

13. Jessica

Animal lover, motherly, careing

Apopka, FL, 32703

House Sitting, Drop-In Visits, Dog Walking

About: I Have 5 animals! Yes you read that right ;) I rescued every single one of them my oldest is 10 years old and my youngest is 2. I have two dogs an... (more)

14. 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)"

15. 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)

16. Melodee

Caring, responsible, pet lover.

Winter Garden, FL, 34787

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

"Melodee did an exceptional job watching our dog Buddy. He was pampered and loved as if Buddy was family. He received multiple walks and lots of belly rubs. I... (more)"

Confirmed Holiday Availability
17. 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)

18. 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)

19. Shannon

Well-Trained Dog (and Cat) Lovers!

Winter Garden, FL, 34787

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

1 repeat client

"We used Shannon's and her son ANDREW's dog walking services for about 3 years and were very pleased! Shannon is dependable, honest and thorough in her busin... (more)"

20. Wesley

passionate, loving, and respectful

Ocoee , FL, 34761

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

"I have used Wesley many times over the last few years to watch my animals (Dog and Cat) He is great with both of my pets! He is always willing to help in any... (more)"

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Pet owners love Winter Garden pet sitters on Rover. 102 owners have reviewed sitters in Winter Garden, FL, giving them an average rating of 5.0/5.

Want to be added to this list of sitters in Winter Garden? Become a pet sitter or dog walker on Rover.

As pet lovers, we understand how difficult it can be to leave your pet when you have to head out of town. Luckily, you can find the perfect pet sitter in seconds on Rover.com. If you're looking for trusted pet sitters while you're away, whether it's for one night or a whole month, you can find a sitter who meets your - and your pet's - needs. We manually review and approve every profile on our site, and we offer tools to help you make the right decision for your pet - including background checks, sitter testimonials, community reviews. We also offer training and extra safety tools, such as the Protection Package. And we always recommend an in-person Meet & Greet so you can see that your sitter is the perfect fit for your dog. Rover is proud to be the nation's largest network of pet lovers for hire.