Pet Sitting & Drop Ins in Winding Wood, Clearwater, FL

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

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1. Nicole Verified Background Check

1/1 Personalized Pet Care! <3

Tampa, FL, 33635

House Sitting, Drop-In Visits, Dog Walking

"Nicole is AMAZING!! My dogs are not easy and she was so patient ! She goes above and beyond!! This is my first time using Rover and I have already recommended … (more)"

2. Connie Verified Enhanced Background Check

No pets of my own let me love yours

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

"Chickee and I Love Connie! I have scheduled her to sit for Chickee again on Saint patties day weekend 3/16-20 Chickee can't wait for some extra Loven. (more)"

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3. Avary Verified Background Check

Avary Pop-ins😊🧡

Countryside Northridge, Clearwater, FL, 33761

House Sitting, Drop-In Visits, Dog Walking

"This was my first time using Rover and I was very hesitant with the entire idea, but had no other options. Avary really made my entire experience great! From … (more)"

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4. Brianna Verified Enhanced Background Check

Ready to meet and love your baby!!!

Clearwater, FL, 33759

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

"I recently moved to Tampa and I met Brianna through mutual friends. She told me about Rover and now watches my Shiba, Kya when I go out of town and shes usuall… (more)"

5. Kara and David Verified Background CheckRover 101

Responsible and loving sitters!

Palm Harbor, FL, 34684

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

"We felt at ease knowing our cats were in safe hands over the holidays. We enjoyed the daily pictures and came home to happy pets and a clean house. (more)"

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6. Valarie Verified Background Check

Second Mom for your Fur Babies

CLEARWATER, FL, 33763

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

"Valarie is a fantastic pet sitter. My furry babies are shy and they both fell in love with her right away. She spends time to snuggle with them and sends me up… (more)"

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7. Casey Verified Enhanced Background Check

Love dogs & cats of all sizes!

Palm Harbor, FL, 34684

Drop-In Visits, Dog Walking

"Casey is a loving and responsible pet sitter. She has cared for my dog Butters, a 6-year-old 125lb. Golden Retriever, many times - for stays long and short. Sh… (more)"

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8. Sarah Verified Enhanced Background CheckRover 101

Absolute doggy and cat lover!

Palm Harbor, FL, 34684

Dog Boarding, Drop-In Visits, Doggy Day Care

"Sarah has been such a blessing to me and my dog during our time here in Florida! She is flexible, dependable, punctual, professional, kind, clean, and very lov… (more)"

9. Lauren Verified Enhanced Background Check

Pet Lover - making your life easier

Clearwater, FL, 33763

Drop-In Visits, Dog Walking

"Lauren is very kind and thorough! Will definitely book again! (more)"

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10. Regina Verified Enhanced Background Check

Keeping Pets Happy & Safe!

Oldsmar, FL, 34677

House Sitting, Drop-In Visits, Dog Walking

"Regina is absolutely amazing with Bella. Regina loves Bella and is helping her mommy and daddy try to make her lose a bit of weight. (more)"

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11. Martha & Brett Verified Background CheckRover 101

Work from Home-Large Fenced in Yard

clearwater, FL, 33761

Dog Boarding, House Sitting, Drop-In Visits

"I️ am absolutely thrilled how well taken care my Dog was while I️ was away I️ received multiple texts and pictures assuring me that Henry was walked and fed: I… (more)"

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12. Jennyfer Verified Background Check

Your pup will be happy and safe.

Clearwater, FL, 33763

House Sitting, Drop-In Visits, Dog Walking

"Jennyfer has been a loving and responsible dog owner for the decade that I have known her. Not only does she take amazing care of her dog but also volunteers … (more)"

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13. Jessica Verified Enhanced Background CheckRover 101

Full-time Pet Lover! Available Now!

Clearwater, FL, 33765

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

"Jessica was fabulous!!! She bonded with my very shy chihuahua during her drop in visits and really took the time to get to know her and gain her trust. Jessica… (more)"

14. Tristan Verified Enhanced Background Check

Animal Lover, Loved by the Animals

Northwood Estates, Clearwater, FL, 33759

House Sitting, Drop-In Visits, Dog Walking

"I have two female mixed-breed dogs that are 10 and 6. Tristan has watched them numerous times for my family for the past five years anywhere from a few hours t… (more)"

15. Tracey Verified Background Check

Best Buddy Breaks

Clearwater, FL, 33759

Drop-In Visits, Dog Walking

"This was my first time using Rover and Tracey was amazing! She stopped by before to introduce herself, gave a great overview of the drop-in, and was on time. T… (more)"

16. Eileen Verified Background Check

safe comfy fenced home

Dunedin, FL, 34698

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

"Eileen was excellent. I just moved to Dunedin and needed a cat sitter. From the moment I met her I felt comfortable with her. She took great care of my two cat… (more)"

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17. Lisa Verified Enhanced Background Check

Loving Pet Caregiver

Safety Harbor, FL, 34695

Drop-In Visits, Dog Walking

About: Guaranteed to provide exceptional care for your fur babies, as if they were my own. I will provide a safe loving space for your loved ones. I said go… (more)

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18. Chloe Verified Enhanced Background Check

Animals > People, Right?

Safety Harbor, FL, 34695

Drop-In Visits, Dog Walking

"Chloe is a pet whisperer! Dogs and cats LOVE her. She is patient, loving and conscientious of each pet's temperament and needs. She works well with older mo… (more)"

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19. Mia Verified Background Check

Work from home - available all day!

Weatherstone, Safety Harbor, FL, 34695

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

"Mia was a lifesaver! She took great care of my girls and played with them during her drop-in. I highly recommend her. (more)"

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20. Yara Verified Background Check

Dependable, friendly & experienced!

Clearwater, FL, 33761

House Sitting, Drop-In Visits, Dog Walking

"Yara was wonderful with our puppy, Rudy. She is very warm and caring, and Rudy had a lot of fun during her house stay! We look forward to working with Yara a… (more)"

Pet parents turn to sitters on Rover.com when they're looking for pet-sitting. 5,453 owners have reviewed sitters in Winding Wood, Clearwater, FL, giving them an average rating of 5.0/5. Since 92% of pet owners live within a short drive of a sitter on Rover, it's easy to find the perfect pet sitter near you. 95% of reviewed stays have received a perfect 5-star rating. Wondering how much you can expect to pay on Rover.com? Check out our average pet sitting rates to get an idea before you start a conversation with a pet sitter. Exchange messages from your sitter's profile, ask to schedule a free in-person Meet & Greet, and book and pay on Rover. You'll receive adorable photo updates, premium insurance, and world-class support.

The next time you head out of town and need someone to take care of your pets and check in on you home, turn to Rover. It's easy to find a loving Winding Wood pet sitter on Rover who'll give your pet one-on-one attention while you're away, and take care of your home. Search from hundreds of trusted pet sitters in Winding Wood, Clearwater, read sitter profiles, and reach out to sitters who seem like a good fit for you and your pet(s). We know it can be tough to leave your pet, which is why we encourage every pet parent and sitter to have a Meet & Greet before booking the stay. Then, when you're ready, book and pay for your house and pet sitter all through Rover: it's easy, safe, and cashless. You'll have the peace of mind knowing that your sitter has free premium insurance, a team of safety experts available 24/7, and will send you cute photo updates throughout the stay. Rover is the easiest way to find trustworthy Winding Wood pet sitters and avoid the kennel.

A Daily Treat: A Blog by Rover

Rover's got you covered, even when you don't need a pet sitter or dog walker. Check out our blog for pictures of adorable dogs, help on your biggest dog-related questions, and more:

Book a Stay, Donate to a Cause

Sit a Dog, Save a Life lets you raise money for local dogs-in-need by doing something you do already: asking your neighbors to watch your dog instead of leaving them in a kennel. Many Rover sitters in Winding Wood, Clearwater donate a percentage of their earnings to nonprofits through Sit a Dog, Save a Life. When you book with a sitter who has the Rover Donation Badge on their profile, you're helping dogs in need, right here in Clearwater.

We're proud to support over 200 organizations across the nation, including: