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. Jessica

Full-time Pet Lover! Available Now!

Clearwater, FL, 33765

House Sitting, Drop-In Visits, Dog Walking

"We are glad we found Jessica. She was so patient with our little shy puppy. She took some extra time to meet her so my dog would feel comfortable with her. I... (more)"

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2. 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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3. Dianna

It's a dogs world

Bonaventure, Palm Harbor, FL, 34684

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

"Dianna is amazing. She came at the last minute when the sitter I booked cancelled the day before Thanksgiving as I was getting ready to leave for an extended... (more)"

Confirmed availability
Christmas and New Year
4. Sarah

Absolute doggy lover!

Palm Harbor, FL, 34684

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

"Sarah has loved and cared for animals for years. She is very kind, patient, professional, and responsible. I feel that she will do a great job dog walking an... (more)"

Confirmed availability
This weekend
5. Danielle

Caring Animal Lover

Dunedin, FL, 34698

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

"Danielle could not have been nicer, I enjoyed meeting her. she took great care with my boys Leo and Spence! Will be repeat clients for sure! (more)"

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6. Vicky

Home full-time

Palm Harbor, FL, 34684

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

"Vicky loved my furballs in my absence! GREAT job! (more)"

Confirmed availability
Christmas and New Year
7. Stephanie

Pet Walker/ Sitter - Available Xmas

OLDSMAR, FL, 34677

Dog Boarding, Drop-In Visits, Dog Walking

"Stephanie was so great with Casper and Bella. They get excited when she comes to walk them and then she will play with them after the walks. My dogs were so ... (more)"

8. Kara and David

Responsible and loving sitters!

Palm Harbor, FL, 34684

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

"Kara and David were awesome right from the start. They were quick to respond, had sweet outgoing personalities and our dogs took to them right away. We lov... (more)"

Confirmed availability
Christmas and New Year
9. 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)"

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10. Angie

Angie's Furry Family Retreat

Oldsmar, FL, 34677

Dog Boarding, Drop-In Visits

"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)"

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11. Alana

Sanchez Family Dog Boarding

North Bay Hills, Safety Harbor, FL, 34695

Dog Boarding, Drop-In Visits, Doggy Day Care

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)

Confirmed availability
Christmas and New Year
12. Liz

Comfortable home with fenced yard.

Dunedin, FL, 34698

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

"Liz is an awesome pet sitter! I trusted her 100% with my Westie when we were away for a week. She looked after him like she was her own. I’m extremely fussy ... (more)"

Confirmed availability
Christmas and New Year
13. Rebecca

Long walks, tennis balls, & treats!

Palm Harbor, FL, 34684

Drop-In Visits, Dog Walking

"It’s rare that you come across a person like Rebecca. She puts her heart into everything she does. Surely you can rest assured your pup would be in great hands. (more)"

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14. Candice

Bring on the fur babies!

Safety Harbor, FL, 34695

Drop-In Visits, Dog Walking

"Candice and her sweet daughter were amazing with Finn! I have never had so much peace of mind as I did with Candice. She provided very detailed notes from ea... (more)"

Confirmed availability
Christmas and New Year
15. Martha & Brett

Work from Home-Large Fenced in Yard

clearwater, FL, 33761

Dog Boarding, House Sitting, Drop-In Visits

"Brett and Martha are wonderful with both my dogs and cats. It’s nice to be able to go away for work and not have to worry about anything. They’re so consci... (more)"

Confirmed availability
Christmas and New Year
16. Janice

Hugs & Attention!

Clearwater, FL, 33761

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)"

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17. Eileen

safe comfy fenced home

Dunedin, FL, 34698

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

"I can personally guarantee that you will feel very lucky to have Eileen watch your dog or help you in any way. She has high integrity, a beautiful heart and... (more)"

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18. Ashley

Exp. Pet Groomer w. yard & dog door

Clearwater, FL, 33761

Dog Boarding, Drop-In Visits

"Ashley is great with any animal! My cats took an instant liking to her and she makes every animal feel comfortable and happy! She is very knowledgeable when ... (more)"

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19. Loren

Large Breed Specialty-Odd Hrs Avail

Winding Wood, Clearwater, FL, 33761

Dog Boarding, House Sitting, Drop-In Visits

"I cannot recommend Loren enough! She is an EXCEPTIONAL dog lover and has YEARS of owning and caring for a multitude of dogs of different breeds. I don’t trus... (more)"

Confirmed availability
Christmas and New Year
20. Christine

Walk and wag dog services

Clearwater, FL, 33765

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

About: I have loved animals since I was a child and have always had a passion for being around them any chance I can. I have done some dog walking and pet... (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: