House Sitting in Winding Wood, Clearwater, FL

Find a loving dog sitter to watch your dog overnight in your home.

To ensure accurate availability & pricing, please add your drop-off and pick-up dates.
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1. Emily

I'll be your pets bestfriend!

Oldsmar, FL, 34677

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

"Emily did a fantastic job taking care of our dog and cats. She kept us updated with lots of pictures throughout her stay. We will definitely call Emily again. (more)"

Confirmed New Years Availability
2. Melissa

Energetic Dog Loving Uni Student

Palm Harbor, FL, 34685

House Sitting, Drop-In Visits, Dog Walking

21 repeat clients

"Melissa was a pleasure to meet and my dog enjoyed having her company for the weekend. Melissa came prepared to our meet and greet with questions to ask, so I... (more)"

Available this weekend
3. Joanna

I will love on your dog

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

"I have used Joanna many times for my best friend, Pepper. She has house sat and watched her and has walked her numerous times. Joanna is sweet and caring a... (more)"

4. Madison

Home full-time!

Clearwater, FL, 33761

House Sitting, Drop-In Visits, Dog Walking

"Madison took loving care of our family dog (and other pets including a gecko, fish and birds) as well as our home while we were away. It can be challenging f... (more)"

Available this weekend
5. Rebecca

Looking for walking & play buddies

Safety Harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

"We cannot say enough great things about Rebecca and CiCi! Our pup looked like she was having a great time with them while we were away. Rebecca took our dog ... (more)"

Confirmed Holiday Availability
6. 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 fantastic sitters. I was updated with pictures and videos throughout my time away. Daisy really enjoyed her stay. We will definitely... (more)"

Available this weekend
7. Demi

All dogs are my favorite dogs.

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

"Knowing the loving passionate way in which Demi regards all animals of the world, I would highly recommend her to care for my pets with Love, attention to ... (more)"

Confirmed New Years Availability
8. Barbara

I'm an "avid" furbaby lover !!

Dunedin, FL, 34698

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

"Barbara has taken great care of my dog, Millie, on several occasions. Millie was a hard-to-walk dog, always pulling. Barbara changed that behavior and she ... (more)"

9. 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 fantastic. I had a very last minute trip come up, and she stepped in to save me, without having time to even meet me or my pup prior to taking the... (more)"

10. Alanna

5+ Years Experienced Pet Sitter

Dunedin, FL, 34698

House Sitting, Drop-In Visits

6 repeat clients

"Alanna is fantastic. We adopted a special needs dog and were cautious to leave her alone at home her first week with us. Alanna adapted to her routine and ha... (more)"

Confirmed New Years Availability
11. Troy

Active and Available Dog Lover!

clearwater florida, FL, 33759

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

"Troy has always been me and my fiancé go to guy to watch our dogs when we are out of town. Our dogs are always excited to see “Uncle Troy” So I would recomme... (more)"

Confirmed Holiday Availability
12. Bradley

Caring and trustworthy animal lover

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Bradley did an excellent job caring for my high energy dog, Zoe. I was looking for someone who was willing to keep up with Zoe's level of exercise while I wa... (more)"

13. Malia

Flexible hours, fenced, walk/run

Dunedin, FL, 34698

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

3 repeat clients

About: Hi! My name is Malia. We are a sweet , caring family who loves animals. We are happy to board your baby(babies). We only board for one family at a... (more)

14. Faith

Can't wait to love on your pup!!

Safety Harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

"I have known Faith for 6 years. She has taken care of our pets on multiple occasions, even a few times at last minute request by me. She has a key to our hom... (more)"

15. Janice

Hugs & Attention!

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

4 repeat clients

"My dog was happy with Janice and that's the most important thing. He was able to stay at home with her care. All his needs were met and Janice is a lovely ... (more)"

16. Regina

Walking is guaranteed!

Mission Hills, Clearwater, FL, 33759

House Sitting

"Regina is wonderful. My crazy, high-maintenance, older dog was well looked after. He was given his daily meds, walks, and lots of love. Regina even survived ... (more)"

Confirmed Holiday Availability
17. Jacquelyn

Loving Care Pet Care Provider

Safety Harbor, FL, 34695

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

13 repeat clients

"Jacquelyn house sat my dog and cat while I was on vacation, out of country for a week. This was the first time I had ever used a house sitter for my pets, ... (more)"

Confirmed Holiday Availability
18. Kendall

Available during the holidays!

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 was wonderful! I knew from the the first meet-and-greet that she would be a great fit for our dog. Kacey provided regular updates on our dog throughout... (more)"

Confirmed Holiday Availability
20. 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

"Martha and family were amazing with my babies. They kept me up to date with texts and pictires throughout my trip. I was able to enjoy my weekend away with... (more)"

When it comes to pet care and house sitting, pet owners in Winding Wood, Clearwater, FL trust their pets with sitters on Rover.com. Over 5,453 pet owners have reviewed house sitters in the Clearwater, FL metro area, giving them an average rating of 5.0/5. House sitting doesn't have to be expensive. In fact, it's probably a lot more affordable than you think. You'll quickly find that there's a house sitter on Rover for just about every price range and lifestyle. Wondering how much you might expect to pay for a house sitter and pet care on Rover? Check out our average house sitting rates to get an idea before you begin a conversation with a sitter who seems like a great match.

Rover offers the perfect alternative to dog kennels. The next time you head out of town and need someone to take care of your dog and your home, turn to Rover for your Winding Wood, Clearwater house sitting needs. On Rover, it's easy to find a loving dog sitter in Winding Wood, Clearwater, FL who'll give your dog one-on-one attention while you're away, and your dog can enjoy a sweet staycation, right at home. Search from hundreds of trusted Winding Wood house sitters near you, 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. Then, when you're ready, book and pay for your dog's stay all through Rover: it's easy, safe, and cashless. You get free premium insurance, a team of safety experts available 24/7, and cute photo updates throughout the stay. It's the easiest way to find trustworthy house sitters in Winding Wood, Clearwater, FL for your dog: people who'll treat him like family.

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: