Dog Boarding in Winding Wood, Clearwater, FL

Find a loving dog sitter to watch your dog overnight at your sitter's home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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Confirmed Holiday Availability
1. 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)"

Confirmed Holiday Availability
2. Susan

Treating your dog like family

Palm Harbor, FL, 34684

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

2 repeat clients

"Using Rover for the first time, I was VERY nervous leaving my precious fur babies with anyone; however, Susan isn't just 'anyone'. She took care of Coco and... (more)"

3. Angie

"Loving Care when you're not there"

Oldsmar, FL, 34677

Dog Boarding, House Sitting, Drop-In Visits

18 repeat clients

"My three dogs were with Angie for about a week. They returned home exhausted which showed me that they were exercise. And she was great about sending picture... (more)"

4. Alison

Peace, love, & muddy paws

Dunedin, FL, 34698

Dog Boarding, House Sitting, Dog Walking

"Very pleased with sitter. Nice home and secure yard. Dogs adjusted well to new environment and unfamiliar supervision. Would not hesitate to use this sitt... (more)"

Confirmed Christmas Availability
5. Ashley

Your dogs Home away from Home

Clearwater, FL, 33763

Dog Boarding, Drop-In Visits, Doggy Day Care

8 repeat clients

"Ashley and her family treated my dogs like part of their family. I could not be happier with the care they received. She sent me pictures regularly and updat... (more)"

6. Kara and David

Responsible and loving sitters!

Palm Harbor, FL, 34684

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

31 repeat clients

"Kara and David are exceptional, and take great care of my two pups whether on walks or when I'm out of town. The pictures they send show me that the girls a... (more)"

7. Peggy

Happiest with My Dogs

Clearwater, FL, 33755

Dog Boarding, Drop-In Visits, Doggy Day Care

7 repeat clients

"I came from out of state and so had no time for a meet a greet but at drop off, I felt very comfortable leaving my aging schnauzer with Peggy and her pugs. M... (more)"

Confirmed Holiday Availability
8. Lori

Experienced & Loving Pet Sitter

Dunedin, FL, 34698

Dog Boarding, Doggy Day Care, Dog Walking

38 repeat clients

"So far Lori and her son seem great ! Brutus spent the night with them last weekend and will be with again this saturday! She was great about sending photos a... (more)"

9. Debbie

Happy Hounds when you're not around

Palm Harbor, FL, 34683

Dog Boarding

7 repeat clients

"Debbie and her family are the best...truly dog people. I know Winston will be thrilled when he gets to stay there again. Thank you Debbie and family for taki... (more)"

10. Sharon

Trust your Beloved Pet with Me!

Safety Harbor, FL, 34695

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

1 repeat client

"Sharon is just the best! Wouldn't leave Charlie with anyone else and he just loves staying with Sharon and being spoiled ? So happy we found someone we trust... (more)"

Confirmed Christmas Availability
11. Danielle

Caring Animal Lover

Dunedin, FL, 34698

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

2 repeat clients

"Danielle was great! Buster loved having a yard to run around in. A wonderful experience for all of us! (more)"

12. Leslie

Spacious home with fenced yard & friendly family!

Dunedin, FL, 34698

Dog Boarding, Doggy Day Care

21 repeat clients

"Leslie and Garath were very caring and professional. Our dog enjoyed his stay and after a meet and greet, we felt very comfortable leaving him in their care. (more)"

13. Savannah

I love my pup snuggles!

Palm Harbor, FL, 34684

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

"Savannah is a very professional, courteous, and genuinely kind person. Her love of dogs and animals of all shapes and sizes is astounding. I wouldn't want ... (more)"

Available this weekend
14. Dawn

Lifelong dog mom!

Clearwater, FL, 33755

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

About: I have always had dogs in my life. I love them, and I would love yours as if he or she were one of my own family! I currently have two doggie kid... (more)

15. Dave

They're not dogs, they're family

Dunedin, FL, 34698

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

"Good dog-owner/sitter with three resident English Bulldogs in a good home/yard environment. Through no fault of the sitter, my Beagle (Zoe) escaped through ... (more)"

16. Sarah

Yard with a pool

CLEARWATER, FL, 33765

Dog Boarding, Doggy Day Care

1 repeat client

"Italy loves to see Sarah (more)"

Confirmed Holiday Availability
17. Andy

Love all animals

Clearwater, FL, 33761

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

About: Have had dogs, cats, rabbits and pocket pets for my whole life. Love all animals. We have several dogs currently in the house and have fostered and... (more)

18. Lindsey

Fun, loving and caring dog sitter!

Oldsmar, FL, 34677

Dog Boarding, House Sitting, Dog Walking

"We contacted Lindsey when we needed a place for our dog to stay while we were on a mandatory evacuation due to Hurricane Matthew. She got right back to me an... (more)"

19. Lisa

My fur babies are my world love em

oldsmar, FL, 34677

Dog Boarding, Doggy Day Care, Dog Walking

"Lisa has always loved all animals, she is great with dogs very caring and treats them with love and great care as of they were hers. She would make a wond... (more)"

20. Anne

Caring provider for your family pet

Clearwater, FL, 33761

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

About: I got my first dog when I was four years old and she was my best friend! I would love to care for pet as if they were my own! I have not gotten ano... (more)

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Learn About Premier

When it comes to dog boarding, dog owners in Winding Wood, Clearwater, FL love Rover.com. Over 5,453 owners have reviewed sitters in the Clearwater, FL metro area, giving them an average rating of 5.0/5. The cost of dog boarding in Winding Wood may surprise you - in a good way. That's because there's a dog sitter on Rover for nearly every price range and lifestyle. Curious about how much it you can expect to pay for dog boarding on Rover? Check out our average dog boarding rates to get an idea before you start a conversation with a sitter.

Rover.com offers the perfect alternative to dog kennels and traditional dog sitting. The next time you head out of town and need someone to take care of your dog, turn to Rover for your dog boarding needs. It's easy to find a loving Winding Wood dog sitter on Rover who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at their sitter's home. Search from hundreds of dog sitters in Winding Wood, Clearwater, FL, read sitter profiles, and reach out to sitters who seem like a good fit for you and your dog. 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. With Rover, pet boarding is guilt-free, cashless, and convenient. That way, you can hit the road happy knowing your dog's in loving hands while you're away.

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: