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.

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

Bring on the fur babies!

Safety Harbor , FL, 34695

Dog Boarding, Drop-In Visits, Dog Walking

"Candice is the most responsible and organized person I have ever worked with. She loves taking her dog out for walks and to the dog park. I know she will tre... (more)"

2. Kim

Animal lover with lots of patience

Clearwater, FL, 33758

House Sitting, Drop-In Visits, Dog Walking

4 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)"

Available this weekend
3. Kaitlyn

Dogs deserve the best in care

Largo, FL, 33771

House Sitting, Drop-In Visits, Dog Walking

About: I have dog sat my neighbors dogs for years. I recently moved to the area and am trying to make my love of dogs a career by caring for them and maki... (more)

Confirmed Christmas Availability
4. Angie

"Loving Care when you're not there"

Oldsmar, FL, 34677

Dog Boarding, House Sitting, Drop-In Visits

18 repeat clients

"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)"

Confirmed Holiday Availability
5. Jennifer

Animals are our family!

Palm Harbor, FL, 34683

Drop-In Visits, Dog Walking

"Jenny and her family simply ADORE all animals! They have experience with many different kinds of pets with varying needs. Visiting her home makes me smile f... (more)"

6. Savannah

Experienced Kennel Tech

Clearwater, FL, 33756

House Sitting, Drop-In Visits, Dog Walking

"Savannah is the only person that I trust with my pup in the entire Clearwater area, and one of the few people my dog approves of when it comes to petsitting!... (more)"

Confirmed Holiday Availability
7. 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

"David and Kara were awesome! They took great care of my girls and sent us pictures every day. Both dogs seemed really happy while we were gone and we appreci... (more)"

8. Stacey

Must love dogs

Palm harbor , FL, 34684

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"Stacey was great! She was very flexible with my last minute request. She sent me multiple pictures and I feel great knowing Maggie was cared for while I was ... (more)"

Confirmed Holiday Availability
9. Susan

Treating your dog like family

Palm Harbor, FL, 34684

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

2 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)"

Confirmed Holiday Availability
10. Simone

Experience with dogs small to large

Safety Harbor, FL, 34695

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

9 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)"

Confirmed Holiday Availability
11. Harry

Force-free complete canine care.

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

"Harry was fabulous w Karma. Harry genuinely cared for Karma's well being and happiness as well as mine. I highly remcommend Harry and his dog care service... (more)"

12. 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)

Confirmed Christmas Availability
13. Ashley

Your dogs Home away from Home

Clearwater, FL, 33763

Dog Boarding, Drop-In Visits, Doggy Day Care

8 repeat clients

"Ashley was awesome! She dropped in and cared for our kitties and gave them love while we were away. She also took the time each day to send us a quick text... (more)"

Confirmed Holiday Availability
14. Hannah

The "Crazy Dog Lady" you'll love!

Clearwater, FL, 33764

Drop-In Visits, Dog Walking

"There are very few people I trust to take care of my Gracie. She is a rescue, who has some anxiety and reactive issues with other dogs and Hannah is a pro at... (more)"

15. Erin

I will treat your babies as my own!

Clearwater, FL, 33763

House Sitting, Drop-In Visits, 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)"

16. 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)"

17. 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)"

Confirmed Holiday Availability
18. Melissa

Energetic Dog Loving Uni Student

Palm Harbor, FL, 34685

House Sitting, Drop-In Visits, Dog Walking

9 repeat clients

"The the meet and great went perfect, she was patient with our sometimes hectic pups, and after every visit sent a text and let us know all the details. Went ... (more)"

19. Emily

Fun dog walks at park or beach.

Safety Harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

"I'm always so happy to leave our Corgi, Foster, in Emily's very qualified care. He's happy when we pick him up and I know from all the daily photos she sends... (more)"

Confirmed New Years Availability
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: