Pet Sitting & Drop In Visits in Winston, 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 Memorial day Availability
1. Sheyenne

I will treat your pup like family!

Florida Southern College, Lakeland, FL, 33801

Drop-In Visits, Dog Walking

2 repeat clients

"Wonderful! (more)"

2. Lori

Full Time home-Fenced Yard ❤️

Lakeland, FL, 33811

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

"Lori is one of the greatest dog lovers ever! As long as I have known her she has been an extraordinary person when it comes to pets. She has 2 Yorkies that... (more)"

3. Sandra

Animals are family members.

Lakeland, FL, 33809

House Sitting, Drop-In Visits, Dog Walking

10 repeat clients

"Very nice and took great pictures. Comfort to know my dog was in good hands. (more)"

4. Andria

I am a very loving pet owner.

Lakeland, FL, 33815

Drop-In Visits, Dog Walking

"Andria did a wonderful job of taking care of our two dogs. We will use her again the next time we go out of town. (more)"

Confirmed Memorial day Availability
5. Timothy

I will make your pets day!

Lakeland, FL, 33811

House Sitting, Drop-In Visits, Dog Walking

"I have used Timothy many times over the years when I go on vacation to house sit and take care of my pets. He loves animals and gives them plenty of attentio... (more)"

6. Alexis

I'll treat your friend like my own

lakeland, FL, 33803

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

1 repeat client

"Alexis was great with my Chow chows! (more)"

7. Brittany

Anismals are my passion

Lakeland, FL, 33803

Drop-In Visits, Doggy Day Care, Dog Walking

"She is a loving person with a big heart for animals. She would rather spoil her dogs then herself . She makes sure the dogs are fed, updated on shots and med... (more)"

8. Megan

Always available for some pup love!

Lake Hollingsworth, Lakeland, FL, 33813

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"I found out last minute that I was going to be out of town and booked Megan on Rover. She was so responsive and professional, and it was such a relief to kno... (more)"

9. Margaret

I'm gonna be your dog's new BFF

Southwest, Lakeland, FL, 33803

Drop-In Visits, Dog Walking

"Margaret is not only an amazing dog sitter, she is fantastic with all of our farm animals as well. Excellent communication with us while we’re away. Punctual... (more)"

10. Cierra

Nursing student & dog lover!

Raintree, Lakeland, FL, 33803

Drop-In Visits, Dog Walking

"Cierra has had a sincere love for dogs since ahe was a little tike. They take well to her and I've seen her play with them and love them with her whole hear... (more)"

11. Marcy

Dogs are our babies, too!

Southwest, Lakeland, FL, 33803

Dog Boarding, Drop-In Visits, Dog Walking

"Ive known marcy murray for several years now. One of the things i admire about her is her compassion for animals in fact any living thing is highly regarded ... (more)"

12. Sarah

I love dogs!!!

Edgewood, Lakeland, FL, 33803

House Sitting, Drop-In Visits, Dog Walking

"Sarah has watched my dogs, Panda (small dog) and Gracie (border collie) while I've been out of town. She is joyful, reliable and loves dogs. Her own dog, A... (more)"

13. Ashley

I've been doing this since age 13

Florida Southern College, Lakeland, FL, 33801

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Ashley is a very nurturing and experienced dog caregiver. She has had dogs of her own from the age of 4 and assisted with dog rescue and fostering with me s... (more)"

14. Brittany

Veterinary Technician

Lakeland, FL, 33803

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

About: Hey there! I am Brittany - A Vet Tech and pet sitter who just moved from North Carolina. Experience with dogs, cats, farm animals, and some exo... (more)

15. Dannyl

I'm home full time, & I enjoy walks

Westgate, Lakeland, FL, 33566

House Sitting, Drop-In Visits, Dog Walking

About: I have had little experience with pet care due to my dog's death; however, I was Nation's care taker for a year. He was a red nose pitt. I had to a... (more)

16. Ryan

Playing with my dog as I type this

Camphor, Lakeland, FL, 33803

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

About: My name is Ryan, I am a professional guitar instructor, and I also happen to love dogs! I currently have a pet Papillon named Brando but I also hav... (more)

17. Alexis

Cuddle care

Central Avenue, Lakeland, FL, 33815

House Sitting, Drop-In Visits, Dog Walking

"I have known Alexis for over 7 years. During that time I have known her to take care of her animals with the utmost care and love. I have entrusted her numer... (more)"

18. Kenneth

Love to play with dogs

Lakeland, FL, 33803

Drop-In Visits, Dog Walking

"Kenneth watched our dog Freckles while we went on vacation. I could tell from the moment that they met, that Kenneth loved and cared about animals. Freckles,... (more)"

19. Erica

I treat your fur baby as my own.

Kathleen, Lakeland, FL, 33805

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

"Erica would b a great person for this dog caregiver. She very loving an caring person. She is responsible.sgevhas taking very good care of my dog in the past... (more)"

20. Samantha

Sams Pawsitive Petcare

Lake Hunter Terrace, Lakeland, FL, 33815

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Samantha has been great with watching my two dogs! She sent me pictures anytime i requested or every other day while caring for my pets. She kept me informed... (more)"


Rover.com is the simple, savvy way to find and book Winston 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 Winston. 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.