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.

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1. Connie

No pets of my own for the 1st time.

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)"

Confirmed availability
This weekend
2. Jessica

Full-time Pet Lover! Available Now!

Clearwater, FL, 33765

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

"Jessica was amazing!!! She did everything imaginable to make our boys first pet sitting experience the best ever! We appreciate her kindness and willingness ... (more)"

3. Rebecca

Dog loving college student

Palm Harbor, FL, 34685

House Sitting, Drop-In Visits, Dog Walking

"Rebecca is the best! She takes wonderful care of my two fur-kids. Lots of pets and love. I don’t worry about them at all. She also sends updates and pictures... (more)"

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4. Danielle

Caring Animal Lover

Dunedin, FL, 34698

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

"So grateful to find you to sit for our precious boy. He took to you so quickly and made us feel confident to leave him in your care. Your updates and photo... (more)"

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5. Dianna

It's a dogs world

Bonaventure, Palm Harbor, FL, 34684

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

"Dianna was fantastic with our senior dog. It was great to see pictures of him so happy. (more)"

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6. Angie

Angie's Furry Family Retreat

Oldsmar, FL, 34677

Dog Boarding, Drop-In Visits

"Angie did such a great job with my dog Aussie! Great union between the two and I knew my dog was in good hands! Very professional and personable; great qua... (more)"

7. Jacquelyn

Loving Care Pet Care Provider

Safety Harbor, FL, 34695

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

"I would give 10 stars if I could! Jackie was awesome with my dog Chancey. She came right in on the meet and greet and sat down on the floor with him. He i... (more)"

Confirmed availability
This weekend
8. Troy

Active and Available Dog Lover!

clearwater florida, FL, 33759

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

"For the first time in Max's life - 14 years - I needed to find an option for his care while I was out of town, which didn't include a family member. I was ... (more)"

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9. Melissa

Animals are my people and my life!

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

"Melissa is just AMAZING with our dogs! She plays with them, loves on them, and they ADORE her!! She is always on time and she goes the extra mile to wear o... (more)"

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10. Martha & Brett

Work from Home-Large Fenced in Yard

clearwater, FL, 33761

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

"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)"

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11. Janice

Hugs & Attention!

Clearwater, FL, 33761

House Sitting, Drop-In Visits

"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)"

Confirmed availability
This weekend
12. Cheryl

Full time + doggie ♥️ + fenced yard

Clearwater, FL, 33761

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

"Jennifer is one of the best pet sitters I have had. She really cares about her clients, both animal and humans. She takes the time to get to know you. She is... (more)"

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13. Alana

Sanchez Family Dog Boarding

North Bay Hills, Safety Harbor, FL, 34695

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

About: Hi my family and I look forward to watching your pups at our home away from your home!! I am a stay at home mom and will home all day to take care ... (more)

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14. Eileen

safe comfy fenced home

Dunedin, FL, 34698

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

"Eileen Breslin is a loving, caring, responsible, and trusting individual. I would leave Lucky with her many times over the years. Lucky would come running ... (more)"

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15. Juliette

Experienced animal caretaker

Clearwater, FL, 33763

House Sitting, Drop-In Visits, Dog Walking

About: My first job was in a veterinary clinic taking care of animals in our boarding facility. After that I went on to intern at a farm animal rescue to ... (more)

Confirmed availability
This weekend
16. Liz

Comfortable home with fenced yard.

Dunedin, FL, 34698

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

"Liz loves dogs and treated mine like a queen. She is flexible in her hours and very nice to deal with. My dog runs to her door because she is so excited to... (more)"

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17. Amanda

Part-time- large fenced yard :)

CLEARWATER, FL, 33759

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

About: Hello! My name is Amanda I'm 26 years old and I would love to take care of your fluffy best friend/s. I have been surrounded by animals my entire... (more)

Confirmed availability
This weekend
18. Candice

Bring on the fur babies!

Safety Harbor, FL, 34695

Dog Boarding, Drop-In Visits, Dog Walking

"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)"

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19. Hanna

Fun,experienced,reliable dog lover

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

"Hanna is fantastic with dogs! She is very responsible, trustworthy, and ALWAYS on time!!! She is also physically fit and can handle multiple dogs at one time... (more)"

20. Thomas

Your Dog will be in good hands! :)

Dunedin, FL, 34698

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

About: Grew up with a Beagle-Basset hound of my own (Miss you Hector!). Currently help take care of two rescue dogs (that live at my girlfriends house), 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: