Pet Setting & 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.

1. Andrea

My fur children are beyond spoiled!

Clearwater, FL, 33764

House Sitting, Drop-In Visits, Dog Walking

"Andrea is my go-to gal when I need a trustworthy pet sitter for several reasons. She values your relationship with your pet because she is a dog mom who puts... (more)"

2. Meghan

Complete dog lover, fenced yard

Charter Oaks, Clearwater, FL, 33763

House Sitting, Drop-In Visits, Dog Walking

"Meghan is a the kind of person you can trust you pets and your home with. I have known Meghan for a VERY long time and she has watched my pups a few times an... (more)"

3. Kara and David

Responsible and loving sitters!

Palm Harbor, FL, 34684

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

46 repeat clients

"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)"

4. Stephanie

Full time fun and play

Clearwater, FL, 33759

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

About: I have always been a dog lover and treat them as my babies. I promise I will fulfill my promise of their every need and treat them like the kings o... (more)

Available this weekend
5. Helen

I love dogs, flexible schedule.

Safety harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

"Helen is a loving, caring and very responsible dog caregiver. You can feel confident knowing that Helen will care for your doggie and make them happy. She ... (more)"

6. Sandy

Vacation Home offered for your pet

Palm Harbor, FL, 34684

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

8 repeat clients

About: I have a passion for all types of dogs and cats. I have experience with both small and large dogs, and all ages as well. I will care for your dog o... (more)

7. Dianna

It's a dogs world

Bonaventure, Palm Harbor, FL, 34684

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

9 repeat clients

About: Hi there! My wife and I have a small American Cocker she loves to play with small like dogs. Our home is a Condo in the Countryside area, it is v... (more)

8. Angie

"Loving Care when you're not there"

Oldsmar, FL, 34677

Dog Boarding, Drop-In Visits

31 repeat clients

"Angie is wonderful! Our dog loved her, and she sent us. constant updates and cute pictures. She went above and beyond what we had asked for, and we couldn't ... (more)"

9. Bradley

Caring and trustworthy animal lover

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

"I am out of town on business quite often and recently created a Rover account in hopes of finding a suitable house/dog sitter for my Rottweiler, Oscar. At fi... (more)"

10. Erin

Experienced Petsitter

Clearwater, FL, 33761

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Erin was absolutely wonderful! My pups were so happy and I felt so much better being away knowing they were in great hands! I'm definitkely be rebooking! (more)"

11. Sarah

Lovable: Dog First Aid Certified

Clearwater, FL, 33759

House Sitting, Drop-In Visits, Dog Walking

8 repeat clients

"Sarah, thank you for taking care of our little Juanito. I can't express enough how professional and caring you were from begining to end. To all other pet ow... (more)"

12. Simone

Dogs Cats and Exotics OH MY!

Safety Harbor, FL, 34695

Drop-In Visits, Dog Walking

10 repeat clients

"Exceptional. Dedicated to knowing your pet, punctual, detailed, genuinely concerned for the well-being of your pet, and you while you travel. (more)"

13. Laura

Dogs love me. I love to train.

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Provided extra care and attention for my dogs during drop in visits! (more)"

14. Melissa

Energetic Dog Loving Uni Student

Palm Harbor, FL, 34685

House Sitting, Drop-In Visits, Dog Walking

13 repeat clients

"I thought Melissa did a wonderful job and kept me informed before, during and after the visit. I will definitely use her again. She was extremely reliable ... (more)"

15. Jacquelyn

Loving Care Pet Care Provider

Safety Harbor, FL, 34695

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

4 repeat clients

"Hi, I am Jacquelyn's sister, Linda. Jackie has been a lover of animals since childhood. Animals are comfortable around her and she is quite relaxed, loving ... (more)"

16. Eileen

Fenced yard and I love dogs !

Dunedin, FL, 34698

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

1 repeat client

"Eileen has watched my puppy mill rescue several times. My dog is afraid of everything but she loves Eileen! You can count on her to be kind and patient with ... (more)"

17. Maria Ined

Animal Lover

Clearwater, FL, 33765

Drop-In Visits, Doggy Day Care, Dog Walking

"Maria has watched my dog(Leo) many of times . He is always well taken care of, fed, given a bath if needed after taking him to the dog park. Leo has never sh... (more)"

18. Susan

Treating your dog like family

Palm Harbor, FL, 34684

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

3 repeat clients

"I could not feel any more sure that my dog Logan is in good hands than when she is in Susan's care. Logan was able to stay with Susan while I had to spend so... (more)"

19. Rachel

Excellent Animal Caretaker- UF grad

Clearwater, FL, 33759

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

About: I am 24 years old and have owned or cared for nearly every type of animal. I have a Bachelors degree from the University of Florida (Animal Science... (more)

20. Catrina

I am a christian who loves animals!

Dunedin, FL, 34698

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

4 repeat clients

"Catrina watched my dog Casey numerous times... He would often stay overnight 3-4 days per week while I was working out of town. She would send me text messa... (more)"

Experience exceptional service and a personalized match

From start to finish, we'll handle all the details for you.

Learn About Premier

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: