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.

1. Tracy

dedicated to pets wellbeing

Windermere, FL, 34786

Dog Boarding, Drop-In Visits, Dog Walking

14 repeat clients

"We moved to Florida and a week later needed to go on a trip. Since we literally did not know anyone in town, I used Rover.com to locate a pet sitter. We ha... (more)"

2. Lores

Caring devoted animal lover!

Ocoee, FL, 34761

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

172 repeat clients

"Lores is amazing! Definitely helps make being away easy with all the pics of my pup having fun! Will use again and recommend to anyone in the area- Thank you... (more)"

3. Lynne

The perfect playmate.

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Lynne is one of the rare people who dogs are drawn to immediately! Dogs are a good judge of character. Lynne via exceptional with dogsEach is her own and the... (more)"

4. Lauren

Norwegian & American husband & wife

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

14 repeat clients

"Lauren is AMAZING! It is hard trusting someone with your dog (and also sometimes embarrassing to show someone how much of a crazy dog mom you are!) and she w... (more)"

5. 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)

6. Andrea

Flexible Schedule

Ocoee, FL, 34761

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Andrea was great ! Her and my shy pup had so much fun, she sent lots of pictures and kept me constantly updated. So great! (more)"

Confirmed Memorial day Availability
7. Maghen

100% in love with dogs

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)"

8. Emily

dogs are the best thing ever

Windermere, FL, 34786

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

"Emily is a wonderful, loving and responsible young adult. She is a true pet lover and I've watched her care for numerous pets over the last 18 years. Your p... (more)"

Confirmed Memorial day Availability
9. Morgan

Home full-time; love to play & run!

Winter Garden, FL, 34787

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

"Morgan. Is a reliable, honest person. She is a responsible, lover of animals. She has a gentle, soft spoken demeanor and plenty of common sense. I have tr... (more)"

10. 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)

11. Celina

Home full time, & a big dog lover!!

Winter garden, FL, 34787

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

2 repeat clients

"Celina is the best! We know when our four- legged girl is happy. And by the pictures she send daily it is clearly seen. We are 100% happy with Celina’s servi... (more)"

Confirmed Memorial day Availability
12. Jennifer

Dogs are my passion!

Winter Garden, FL, 34787

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

"I had the pleasure of working with Jennifer at Pet Alliance, a pet adoption shelter and low cost veterinary clinic. From the start, it was evident that she h... (more)"

13. Jessica

Former veterinary technician

Ocoee, FL, 34761

Drop-In Visits, Dog Walking

"I have known Jessica for nearly 20 years and throughout that time she has always worked with animals. Caring for animals is a passion for Jessica and it come... (more)"

14. Anthony

Happy Dog, Happy Life

Winter Garden, FL, 34787

Dog Boarding, Drop-In Visits, Dog Walking

"Anthony is a great dog sitter. Our dog loves him and I trust him fully to play and take care of her. I've referred him to a couple of friends and they love ... (more)"

15. Maggie

Dog trainer becomes dog walker!

Winter Garden, FL, 34787

Drop-In Visits, Dog Walking

1 repeat client

"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)"

16. Wendy

Home full-time, can medicate

Winter Garden, FL, 34787

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

11 repeat clients

"Wendy has taken care of our Siberian Husky Roxy when we have had to go away for a long day or overnight weekend. She walks her, plays with her, and feeds he... (more)"

Confirmed Memorial day Availability
17. Cason

I will exercise with your pup!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Our two furry family members love Cason. They get so excited when they see him because they know he is always up for taking them for a long walk in the park.... (more)"

18. Shannon

Well-Trained Dog (and Cat) Lovers!

Winter Garden, FL, 34787

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

5 repeat clients

"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)"

19. Angela

Southern Pecan Fur Babies Resort

Winter Garden, FL, 34787

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

About: I am a single Mom of two boys I am home during the day and evenings. I have two dogs a Chiweenie and a Pug but unfortunately no longer live with us... (more)

20. 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)"


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.