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. Jessica

Full-time Pet Lover! Available Now!

Clearwater, FL, 33765

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

10 repeat clients

"Jessica is awesome! She took pictures, sent text and even cleaned our house on her last day. She will be our pet sitter of choice in the future. You could te... (more)"

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2. Joanna

I will love on your dog

Dunedin, FL, 34698

House Sitting, Drop-In Visits, Dog Walking

3 repeat clients

"Joanna is a gem! She sat for us while we were on holiday and was wonderful with our 2 dogs and 2 cats. One of our dogs is afraid of new people, and Joanna w... (more)"

Confirmed availability
Memorial day
3. Troy

Active and Available Dog Lover!

clearwater florida, FL, 33759

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

1 repeat client

"Troy was great! Will absolutely use him again, we felt very comfortable leaving our pups with him. (more)"

Confirmed availability
Memorial day
4. Meaghan

Will work for puppy cuddles!

Dunedin, FL, 34698

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

1 repeat client

"Meaghan is a great pet sitter. She has regularly watched my dog and bearded dragon over the last several years. She has always sent me lots of pictures and u... (more)"

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5. Katie

Active young professional

Palm Harbor, FL, 34685

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Katie took great care of my little fluff ball. She was very communicative before and during the stay. She has such a sweet and gentle energy she is definitel... (more)"

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6. Kelli

Very active and equally patient

Clearwater, FL, 33759

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kelli is a very caring and responsible pet sitter. She is comfortable taking care of multiple animals and special needs. I have several cats and 1 with diab... (more)"

Confirmed availability
This weekend
7. Melissa

Experienced & Special Needs Care

Palm Harbor, FL, 34685

House Sitting, Drop-In Visits, Dog Walking

32 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)"

8. Emily

I'll be your pets bestfriend!

Oldsmar, FL, 34677

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

1 repeat client

"Emily stayed overnight with our fur-babies so we could attend an event. The girls loved her, she was a good communicator and sent pictures during her stay w... (more)"

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9. Karen

I'll treat your dog like Family!

Dunedin, FL, 34698

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

2 repeat clients

"Karen was awesome!!! She took great care of my dogs and my home! Very responsive with photos and updates. Will definitely use her again! (more)"

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10. Brian

Home full time and a 100% committed

palm harbor, FL, 34684

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

1 repeat client

About: I am 100% committed to the dogs needs and very reliable. I love all nature and understand, "Dogs do speak but only to those who know how to listen"... (more)

11. Shannon

One On One Care For Your Dog

Clearwater, FL, 33759

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

10 repeat clients

"So happy to have found Shannon! She was great with our pets providing lots of love and playtime. She was very responsive to us with messages and photos. We w... (more)"

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12. Pamela

fit and retired dog lover

Dunedin, FL, 34698

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

3 repeat clients

"Pamela was tremendous. I was very happy with how she communicated with me about how Louie was doing throughout the weekend. Louie was mean to her, yet she ... (more)"

13. Brandy

Humane Society Volunteer/Runner

Palm Harbor, FL, 34684

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

3 repeat clients

"Brandy watched my pets in my home over the weekend. She was very attentive to their care and communicated timely. This being her first time watching my “mini... (more)"

Confirmed availability
Memorial day
14. Matt

Your dog will love me!

Northwood West, Clearwater, FL, 33761

House Sitting, Drop-In Visits, Dog Walking

"My two dogs are my family. What I liked most about Matt is not only his obvious love for my animals (my babies fell for him immediately) but his professiona... (more)"

Confirmed availability
This weekend
15. Rebecca

Looking for walking & play buddies

Safety Harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

2 repeat clients

"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 availability
Memorial day
16. Kendall

Available to watch your dog!

Clearwater, FL, 33759

House Sitting, Drop-In Visits, Dog Walking

1 repeat client

"Kendall has been great. We have a pup who is shy and she was his friend right away. When we have Kendall help us we know our boy is being well cared for. ... (more)"

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17. Katrina

Let your dog to love me

On Top Of The World, Clearwater, FL, 33763

House Sitting, Drop-In Visits, Dog Walking

"Katrina is our neighbor and has watched our dogs on several occasions. We often ask her to check in on them when we are going out on the boat for a long day ... (more)"

Confirmed availability
Memorial day
18. Martha & Brett

Work from Home-Large Fenced in Yard

clearwater, FL, 33761

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

20 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)"

19. Robyn

Purebred Animal Lover

Clearwater, FL, 33765

House Sitting

6 repeat clients

"Robyn sitted our two American bullies and did a great job! She responded to our request in timely manner and sent pictures and updates on the pups while we w... (more)"

20. Janice

Hugs & Attention!

Dunedin, FL, 34698

House Sitting, Drop-In Visits

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)"

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: