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.

Confirmed Christmas Availability
1. Shannon

One On One Care For Your Dog

Clearwater, FL, 33759

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

4 repeat clients

"Shannon was amazing! My pup has never been away from me before so I hired Shannon to come visit a couple times during the day for our daytrip. My pup made a ... (more)"

Confirmed Christmas Availability
2. Ashley

Teacher, World Traveler, Pet Lover!

Landmark-Countryside, Clearwater, FL, 33761

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

1 repeat client

"Ashley was amazing! I had a last minute event and she stepped up to help with my lovable Berner. She was able to help me day-of without hesitation. Thank you... (more)"

Available this weekend
3. Candice

Bring on the fur babies!

Safety Harbor, FL, 34695

Dog Boarding, Drop-In Visits, Dog Walking

1 repeat client

"Candice was fantastic! Both me and my dogs just loved her and her lovely kids, who came by to give em some love, much to my furbabies' delight! She was great! (more)"

4. Melanie

Trust, Peace of Mind & Tons of Love

Dunedin, FL, 34698

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

"I am extremely happy with the time Melanie spent watching my cat. I felt completely up to date the whole week and I felt extremely comfortable that if anythi... (more)"

Confirmed Holiday Availability
5. Kara and David

Responsible and loving sitters!

Palm Harbor, FL, 34684

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

53 repeat clients

"Kara and David are wonderful! This was the first time we had ever used pet sitters and are just thrilled with Kara and David. I knew at the meet and greet ... (more)"

Confirmed Holiday Availability
6. Jamie

Professional Pet Care

Wilshire Estates, Dunedin, FL, 34698

Drop-In Visits, Dog Walking

"Jamie and her family are major dog lovers and treat their dogs as if they were their kids. They are well taken care of; ever medical or emotional need is me... (more)"

7. Dianna

It's a dogs world

Bonaventure, Palm Harbor, FL, 34684

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

12 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. Eileen

Fenced yard and I love dogs !

Dunedin, FL, 34698

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

5 repeat clients

"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)"

9. Rodd

Friendly Beard Walk'n & Board'n

Dunedin, FL, 34698

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

"Rodd was a great host! Our pupps were very well taken care of and the cost was very reasonable. We received photos of them on an almost daily basis and tha... (more)"

10. Danielle

Energetic animal lover and trainer!

On Top Of The World, Clearwater, FL, 33763

House Sitting, Drop-In Visits, Dog Walking

"I asked Danielle just a couple hours before I needed her if she would drop in to visit my pups a couple times, and she was more than happy to! This was our f... (more)"

Confirmed Holiday Availability
11. Traci

Dog lover whom you can trust!

Dunedin, FL, 34698

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

"Traci was extremely responsible and reliable. I loved the communication and the pictures of my pups. River.com really makes finding the perfect Dogsitter easy. (more)"

Available this weekend
12. Angie

"Loving Care when you're not there"

Oldsmar, FL, 34677

Dog Boarding, Drop-In Visits

41 repeat clients

"My 4 kitties & 2 bunnies loved Angie the moment she came for our meet & greet! 2 of my kitties are very leary of new people, but they were out & rubbing all... (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. Simone

Dogs Cats and Exotics OH MY!

Safety Harbor, FL, 34695

Drop-In Visits, Dog Walking

11 repeat clients

"I am very happy to find Simone. She is professional and detail oriented. I feel at ease to be away and not worrying about my cats. Thank you Simone and I ... (more)"

15. Stacy

Caring Dependable Pet-Sitter/Walker

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Took very good care of my babies! (more)"

16. Faith

Can't wait to love on your pup!!

Safety Harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

"Faith is amazing with my dog Brewster. She would spend time playing and interacting with him during the times she would watch him! Huge heart and very respon... (more)"

Confirmed Holiday Availability
17. Martha & Brett

Work from Home-Large Fenced in Yard

clearwater, FL, 33761

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

10 repeat clients

"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:... (more)"

Available this weekend
18. Kendall

All puppies wanted!

Clearwater, FL, 33759

House Sitting, Drop-In Visits, Dog Walking

"I’ve known Kendall for many years. She’s responsible, passionate and caring. She will take awesome care of your pet and love them like her own. I highly reco... (more)"

19. Kacey

Your dog's needs always come first!

Clearwater, FL, 33759

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kacey is one of the most trustworthy, responsible young woman I've ever known. Whenever we go out of town we only want her to watch out fur babies! She treat... (more)"

Confirmed Christmas Availability
20. Keri

Pampering your Pet

Countryside Woods, Clearwater, FL, 33761

Drop-In Visits, Dog Walking

"Keri loves animals, large and small, and especially dogs. She is responsible, dependable and prompt, and she will treat a dog as well as any member of her fa... (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: