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. Kim

Animal lover with lots of patience

Clearwater, FL, 33758

House Sitting, Drop-In Visits, Dog Walking

5 repeat clients

"Super impressed with Kim! Meet and greet planning and communication was excellent, she was prompt and my dogs immediately loved her. Having a special needs... (more)"

2. Hallie

Performer passionate about pets!

Tampa, FL, 33635

House Sitting, Drop-In Visits, Dog Walking

About: Growing up, my family has always been a two-dog family. I am a professional dancer for a cruise line who is currently in between contracts, looking... (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

33 repeat clients

"Kara and David were great! it's a good feeling to have when you're away that your pets are in good hands. I will for sure use them in the future! (more)"

Available this weekend
4. Jennifer

Animals are our family!

Palm Harbor, FL, 34683

Drop-In Visits, Dog Walking

1 repeat client

"Jennifer and her family are wonderful. They took great care of my girls Pandora and Nala. Lots of love and care as well as daily updates. I will definitely ... (more)"

5. Angie

"Loving Care when you're not there"

Oldsmar, FL, 34677

Dog Boarding, House Sitting, Drop-In Visits

21 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)"

6. Stacey

Must love dogs

Palm harbor , FL, 34684

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Stacey is wonderful! She took good care of our dog and sent great updates and pictures. Our dog was happy and well cared for, and I highly recommend Stacey:) (more)"

Available this weekend
7. Ashley

Your dogs Home away from Home

Clearwater, FL, 33763

Dog Boarding, Drop-In Visits, Doggy Day Care

10 repeat clients

About: I have an inviting home allowing your dogs to be comfortable while you are away. If you have a pup with energy my two kids will play all day! Do... (more)

8. Kristine

Friendly, Caring, & Responsible

Palm Harbor, FL, 34683

Drop-In Visits, Dog Walking

1 repeat client

About: We have had 4 dogs: Lady, Heber, Prince, and Louie, big and small, during our 20 year marriage. We have 3 boys who love dogs and are very good wit... (more)

9. 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)"

10. Erin

Experienced Petsitter

Clearwater, FL, 33761

House Sitting, Drop-In Visits, Dog Walking

5 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. Melissa

Energetic Dog Loving Uni Student

Palm Harbor, FL, 34685

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"Melissa did an excellent job with both of my dogs. They 12 & 10 yrs.old. The 12 yr old has bladder issues & is on a strict schedule to help maintain his di... (more)"

12. Janice

Hugs & Attention!

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

"Janice is awesome. Got a good vibe from her the first time I spoke to her on the phone. She took great care of our three cats while we were on vacation fo... (more)"

13. Simone

Experience with dogs small to large

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)"

14. Stephanie

Energetic, outgoing animal lover!

Clearwater, FL, 33765

Drop-In Visits, Dog Walking

2 repeat clients

"Stephanie is GREAT!! My kitties loved her and she is wonderful with them. I got pictures and videos. She paid attention to them and learned their personaliti... (more)"

15. Tara

LifeLong Dog Lover

Palm Harbor, FL, 34683

Drop-In Visits, Dog Walking

2 repeat clients

"Tara took great care of Reno! Im so happy to have found her! You can really tell she loves animals. (more)"

16. Candice

Bring on the fur babies!

Safety Harbor , FL, 34695

Dog Boarding, Drop-In Visits, Dog Walking

"Candice is wonderful! She is like a 2nd mommy to my little Loki. He is so excited and happy to see her. She is very loving and attentive to him. Besides ... (more)"

17. Brett

Dog sitting inTampa Bay area

clearwater, FL, 33761

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

"Brett and his family were so easy to work with. They sent us daily updates and I could tell they took good care of their pets. Our 2 labs had a great time a... (more)"

18. Erin

I will treat your babies as my own!

Clearwater, FL, 33763

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

"I love having someone as caring as Erin available to watch our dog and parrots when we go on a trip. I never worry about them because she takes great care an... (more)"

19. Emily

Fun dog walks at park or beach.

Safety Harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

"Over the years Emily had been my go to person for pet sitting. Whether it was just for the evening when I wanted my dog, Buddy, to be looked after and given ... (more)"

20. Bryan

THE Dog Person

Rainbow Farms North, Safety Harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Bryan has always been a very loving and affectionate person-animals and humans alike! He has a great understanding of animals and an interest in animal psych... (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: