House Sitting in Winter Park

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. Christopher

Extremely flexible schedule!

Baldwin Park, Orlando, FL, 32814

House Sitting, Drop-In Visits, Dog Walking

"Chris is AMAZING! My dog, Daisy, took to him right away and he has been reliable, helpful, flexible and super friendly. I would definitely recommend him! (more)"

Confirmed availability
This weekend
2. Oriana

Elite Pet Sitting, LLC

Winter Park, FL, 32789

House Sitting, Dog Walking

"Oriana did a wonderful job. She was very professional and for along with our dog very well. I would definitely use her again when we need a pet sitter. (more)"

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3. Geraldine

Home Full Time for Puppy Love!

Winter park, FL, 32792

House Sitting, Drop-In Visits, Dog Walking

"G.G. Is amazing!! My dogs have never been this calm and healthy to come home too. I have a special needs dog that requires a strict schedule and medication a... (more)"

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4. Maria

Traveling dog sitter and lover!

Altamonte Springs, FL, 32701

House Sitting, Drop-In Visits, Dog Walking

"This was the second time Maria stayed at our house with the girls. We were gone much longer this time and it was wonderful to never have to worry about our ... (more)"

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5. Madison

Ultimate Dog-Mom

Orlando, FL, 32804

House Sitting, Drop-In Visits, Dog Walking

"She came before to meet our boys. Left the house looking just as tidy as when we left. Sent us pictures and communicated with us during the time we were away... (more)"

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6. Ally

Dogs are family. We <3 our furkids

Winter Park, FL, 32792

House Sitting, Drop-In Visits, Dog Walking

"There are not enough words to express how happy I am with the care Ally gave to my dog (Rocky). He is a rescue w special needs and cannot be left alone. I ha... (more)"

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7. Michael

Natural caregiver and energetic!

Colonicaltown South, Orlando, FL, 32803

House Sitting, Drop-In Visits, Dog Walking

"Michael did an amazing job watching my dog. He provided frequent updates and truly catered to my dog’s needs! I will be using Michael whenever I need a sitte... (more)"

8. Austin

Professional Animal Care Exp

Winter Park, FL, 32792

House Sitting, Drop-In Visits, Dog Walking

"It went very well. The app made it (more)"

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9. Melissa

Loving, Experienced Dog Caregiver!

Winter Park, FL, 32789

House Sitting, Drop-In Visits, Dog Walking

"Melissa was outstanding with our two big dogs. They quickly got acquainted with her on the meet-and-greet, so we felt very comfortable having her stay in our... (more)"

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10. Alexandra

Reliable and Doting Dog Lover!

Winter Park, FL, 32789

House Sitting, Drop-In Visits, Dog Walking

"Alexandra is so fun for the girls! I think they behave better after she’s stayed with them! They love her! A very responsible and responsive sitter!! You roc... (more)"

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11. Gabriella

Friends for AF Base personnel too!

Winter Park, FL, 32792

House Sitting, Drop-In Visits, Dog Walking

"Gabriella was wonderful with my cherished pets. From I’m all the wonderful pictures that she sent wh n I was way they all loved spending time with her shey... (more)"

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12. Alexsis

A Dog’s Best Friend

Colonial Town Center, Orlando, FL, 32803

House Sitting, Drop-In Visits, Dog Walking

"Alexsis took great care of my pups while I was away! I received photos and updates every day. Both pups, who are normally very anxious, were happy and stress... (more)"

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13. Becky

Large Fenced Yard - Home Full Time

Winter Park, FL, 32792

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

About: As a lifelong dog lover, I know how important dogs are in our lives. That’s why I’ve taken care of them for so long! Nothing gives me more joy than... (more)

14. Amy

Home full time, LOVES dogs

Colonial Town Center, Orlando, FL, 32803

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

"Amy is fantastic! I had to leave for a last minute trip and needed someone to care for my dog. She responded quickly and was able to care for him while I wa... (more)"

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15. Ashlynn

5 min walk from dog park!

Baldwin Park, Orlando, FL, 32814

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

"Ashlynn watches my pets whenever I leave town. She does everything I ask her of her and more. When I return home my pets are just as happy as if I had never ... (more)"

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16. Chawney

Stay-at-Home Dog Mom

Winter Park, FL, 32792

House Sitting, Drop-In Visits, Dog Walking

About: Hello! I’m currently home full-time and taking online classes so I’m quite flexible with my schedule. I’ve had a pet in the house practically my en... (more)

17. Renay

Dog lover.

Maitland, FL, 32751

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

"I have known Renay for five years. Few months after we met she found an old poodle in her parking lot, abandoned , neglected and almost dead. I never thoug... (more)"

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18. Keirsten & Paula

Home Full Time for Puppy Love!

Orlando, FL, 32792

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

"She was wonderful! Handled muffin very well, and that’s hard to do because muffin (my cat) needs A TON of attention. She even sent me pictures while I was ... (more)"

Confirmed availability
Christmas and New Year
19. Kanisha

Was raised with animals I love them

Winter Park, FL, 32792

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

"Kanisha is very kind and loving when it comes to animals. She is a regular volunteer at SPCA ( animal adoption center). All the animals love her and are exit... (more)"

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20. Sarah

Every Dog Is My Type Of Dog!

Winter park, FL, 32828

House Sitting, Drop-In Visits, Dog Walking

"Our two dogs loved their weekend with Sarah. It was so comforting to know that they were taken care of and loved on. Sarah is very accommodating and I can te... (more)"

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