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House Sitting in Windermere

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

Confirmed availability
 Christmas and New Year
1. Rachel Verified Enhanced Background CheckRover 101

All pets, all shapes, all sizes...

Millenia, Orlando, FL, 32839

House Sitting, Drop-In Visits, Dog Walking

"This was the first time leaving our new puppy for the day, and we couldn't have found a more perfect person in Rachel. She was incredibly communicative, warm, … (more)"

Confirmed availability
 Christmas and New Year
2. Jasmine Verified Background Check

Fur mom to two beautiful cats

Winter garden, FL, 34787

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

"Jasmine was so sweet to our precious Maggie! We already have her next booking scheduled. Highly recommend Jasmine! (more)"

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3. Kaitlyn Verified Background CheckRover 101

Purrfectly splendid to meet you!!

Winter Garden, FL, 34787

House Sitting, Drop-In Visits, Dog Walking

"Kaitlyn did such a great job taking care of my little Maltese while I was away on vacation. She even house sat for me and did other things around my house whil… (more)"

Confirmed availability
 Christmas and New Year
4. Kristi Verified Background CheckRover 101

TLC offered

Winter Garden, FL, 34787

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

"We were on a 3-week trip out of the country and 2 of our 4 dogs had never been left with anyone else. We were nervous but decided to hire an overnight sitter f… (more)"

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5. Allen + Laurie Verified Background Check

Semi Retired Professional Couple

Orlando, FL, 32836

House Sitting, Drop-In Visits

"Allen and Laurie are amazing! They watched our dogs while we went on a week long cruise and sent us updates the whole time! (Even though we couldn’t view them … (more)"

Confirmed availability
 Christmas and New Year
6. R'Riana Verified Background Check

Providing Cuddles & Care

Metro West, Orlando, FL, 32835

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

"She was a great help and my dog loved her. I would definitely recommend her to others. (more)"

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7. Tristan & Drew Verified Background CheckRover 101

Safe home environment for dogs/cats

Ocoee, FL, 34761

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

"We are so happy with the care Tristan provided for our girls! We received pictures daily and they looked so happy! We will definitely use him in the future and… (more)"

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8. Shahlaa Verified Enhanced Background Check

Vegan|Animal lover | Active |Caring

Kirkman North, orlando, FL, 32811

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

About: i’ve had 2 dogs in my lifetime, Skyy (cane corso) & chancellor (hound/lab mix) unfortunately i had to leave them at home in delaware with my family. … (more)

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9. Cristina Verified Background Check

I already love your dog(s)

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

"Cristina was wonderful and our dogs were very sad to see her leave! (more)"

Confirmed availability
 Christmas and New Year
10. Samantha Verified Background Check

Happy and fun pet lover!

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

About: Although I have little professional experience with pets, I have cared for my own cats, dogs, turtles, chinchillas, lizards, and guinea pigs for the … (more)

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11. Mari-Kate Verified Background Check

BIG fan of dogs of all sizes :)

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

"Mari-Kate is a qualified and excellent candidate to be a loving dog caregiver associated with Rover. Every time my family goes on vacation, Mari-Kate watches m… (more)"

12. Jaklyn Verified Background Check

An animal lover and fur baby friend

Winter Garden, FL, 34787

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

"Jakalyn is so wonderful, I think my pup loves her more than she loves me:) I feel so comfortable and safe having Jaklyn watch and walk my furr baby. She is so … (more)"

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13. Candilynn Verified Background Check

Experienced with a true ♥️ For Dogs

Ocoee, FL, 34761

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

"Candilynn has a very patient warm welcoming energy. Really understands and tunes in to the animal for a happy safe connection. She is consistent and trustworth… (more)"

Confirmed availability
 Christmas and New Year
14. Lisa Verified Background Check

Animal lover & treat ur dog as min

Ocoee, FL, 34761

Dog Boarding, House Sitting, Doggy Day Care, Dog Walking

"Rocky and Thor love it at Ms Lisa’s (more)"

Confirmed availability
 Christmas and New Year
15. Cami Verified Background Check

Home FULL TIME w/ dog park

Orlando, FL, 32819

House Sitting, Drop-In Visits, Dog Walking

About: I absolutely love dogs and I STRIVE to make your pup feel loved and secured. Located 5 miles from Orlando airport; perfect for last minute trips.I am… (more)

Confirmed availability
 Christmas and New Year
16. Michael Verified Background Check

Pro-belly ruber. No big deal.

Windermere, FL, 34786

House Sitting, Drop-In Visits, Dog Walking

"I have known Michael Lee White for over 2 years, and throughout that time I have seen him as a dog owner and a pet lover in general. He is an exceptional fathe… (more)"

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17. Andrea Verified Background Check

Will provide lots of love

Orlando, FL, 32819

House Sitting, Drop-In Visits, Dog Walking

"Andrea did a great job. We hired her to house sit with our dog, and were more than pleased. We always feel nervous about hiring people to stay in our home, but… (more)"

18. Ella Verified Background CheckRover 101

Count on me when a pets in need!

windermere, FL, 34786

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

"Ella is trustworthy which is the most important aspect which I would expect from someone that I would ask to come into my home and take my dogs out. (Hard to … (more)"

Confirmed availability
 Christmas and New Year
19. Anna Verified Enhanced Background Check

Taking Great Care of Your Pet!!

Orlando, FL, 32819

House Sitting, Drop-In Visits, Dog Walking

"Anna is a huge dog lover and animal lover in general. Since she was a child she has always loved animals. She takes wonderful care of the dogs she has and they… (more)"

Confirmed availability
 Christmas and New Year
20. Tracy Verified Enhanced Background CheckRover 101

dedicated to pets wellbeing

Windermere, FL, 34786

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

"Tracy was amazing, we went on vacation and knew that our fur baby was going to be well taken care of. Tracy was very professional, prompt, kind and most impor… (more)"


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 Windermere house sitting needs. On Rover, it's easy to find a loving dog sitter in Windermere 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 Windermere 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 Windermere for your dog — people who'll treat him like family.