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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.

Tip: Contact sitters now to confirm availability.
Confirmed 4th of July Availability
1. Jessica

Full-time Pet Lover! Available Now!

Clearwater, FL, 33765

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

"Jessica was fabulous!!! She bonded with my very shy chihuahua during her drop in visits and really took the time to get to know her and gain her trust. Jessi... (more)"

Confirmed 4th of July Availability
2. Connie

No pets of my own for the 1st time.

Dunedin, FL, 34698

Drop-In Visits

"CONNIE WAS THE BEST WITH MY CHICKEE. SHE AND I HAVE BECOME FRIENDS TOO!! Chickee Love Connie too!! If we need a sitter again it will be Connie!! I recomme... (more)"

3. Dianna

It's a dogs world

Bonaventure, Palm Harbor, FL, 34684

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

"Dianna was great to work with. She responded quickly to me and was happy to help with Newman on short notice. She kept me informed and I know Newman was well... (more)"

4. Martha & Brett

Work from Home-Large Fenced in Yard

clearwater, FL, 33761

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

"I️ am absolutely thrilled how well taken care my Dog was while I️ was away I️ received multiple texts and pictures assuring me that Henry was walked and fed:... (more)"

5. 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)"

6. Angie

Angie's Furry Family Retreat

Oldsmar, FL, 34677

Dog Boarding, Drop-In Visits

"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 4th of July Availability
7. Alana

Sanchez Family Dog Boarding

North Bay Hills, Safety Harbor, FL, 34695

Dog Boarding, Drop-In Visits

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)

8. Rebecca

Looking for walking & play buddies

Safety Harbor, FL, 34695

House Sitting, Drop-In Visits, Dog Walking

"Becca has been taking care of my golden retriever, Beau, for two years now whenever we travel out of town. She is a very caring and responsible pet sitter w... (more)"

9. Vicky

Pets are Our Family

Palm Harbor, FL, 34684

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

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

10. Emily

Adoring and devoted dog lover

Palm Harbor, FL, 34684

House Sitting, Drop-In Visits, Dog Walking

About: Hello, my name is Emily! I feel that I would make a great dog sitter for you because my passion for dogs is deeply rooted. I have grown up surround... (more)

11. Janice

Hugs & Attention!

Dunedin, FL, 34698

House Sitting, Drop-In Visits

"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)"

12. Brian

Home full time and a 100% committed

palm harbor, FL, 34684

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

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)

Confirmed 4th of July Availability
13. Jenny

Dog lover works from home

Clearwater, FL, 33759

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

About: Hi! I want to take the dog out for some fun outdoor activities such as dog parks and beaches (if your dog likes the beach and water), a running ... (more)

14. Troy

Active and Available Dog Lover!

clearwater florida, FL, 33759

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

"For the first time in Max's life - 14 years - I needed to find an option for his care while I was out of town, which didn't include a family member. I was ... (more)"

15. 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)"

Confirmed 4th of July Availability
16. Brandy

Humane Society Volunteer/Runner

Palm Harbor, FL, 34684

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

"Brandy not only walks Cooper but is incorporating some training tools to help us along as well. I feel very secure in knowing that our baby is in great hands. (more)"

Available this weekend
17. Stacy

I’ll Run with your dog!

Clearwater, FL, 33761

House Sitting, Drop-In Visits, Dog Walking

"Used Rover.com for the first time. My husband & I went out for the evening & planned to be out of the house for 7-8 hours. Stacy came by for a meet & greet... (more)"

18. Danielle

Caring Animal Lover

Dunedin, FL, 34698

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

About: I have had dogs and cats since I was little and I love their personalities and love they bring to any home! I got my own dog about six years ago wh... (more)

19. Simone

Dogs Cats and Exotics OH MY!

Northwood Estates, Clearwater, FL, 33759

Drop-In Visits, Dog Walking

"This is the second time I used Simone's service. I could just tell my kitties loved her. They came out waiting for her and greet her. I feel at ease to ha... (more)"

Confirmed 4th of July Availability
20. Lina

I will care for your dog as mine <3

Clearwater, FL, 33759

Drop-In Visits, Dog Walking

"Lina is such an amazing animal lover. She took care of my dog and cat like if they were her own. I asked for her service on two occasions and I have no words... (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:

All stays booked on Rover receive our Rover guarantee, 24/7 support, and our reservation protection.

How it works

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1) Browse Sitters

We make it easy to find affordable & reliable sitters near you.

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2) Contact Sitters

Chat about your dog and your specific needs. Even meet in person before booking if you really want to.

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3) Book & pay

Our platform makes it easy and secure. No cash necessary.

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4) Enjoy your trip

Drop off your dog without feeling guilty. Relax with regular photo updates from your sitter.