House Sitting in Windermere

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.

Search Results

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Whitney  & Emily L.
I can’t wait to meet my new friendsWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Very nervous leaving our babies ? for the first time but was pleasantly surprised! We received photos every day and updated text messages. Will be using Whitney… (more)

from
$50
per night
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Kevin & Gabriella B.
Engineer | Love to Make Tails Wag!Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

Kevin and Gabriella are amazing. We felt totally at ease with them watching our pair of puppies. We got a ton of pictures and regular updates. Our dogs liked th… (more)

from
$60
per night
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Kristi A.
3.
TLC offeredWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Kristi is amazing!!! I truly recommend her to anyone looking for a reliable, in-home sitter for their pets! Communicative, responsive, and ALL the pics of your … (more)

from
$60
per night
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Nickolas J.
Best Home for Lazy DogsFlorida Center North, Orlando, FL, 32811
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

The best!!! Trust him completely! I felt very comfortable having my dogs with Nick and they were comfortable too, which is something! He's very flexible and sup… (more)

from
$40
per night
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Jasmine C.
Furtopia; Where fur babies vacationWinter garden, FL, 34787
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Such amazing peace of mind knowing Jasmine was on the job watching our fur babies. She really took the time to make sure all three felt comfortable and loved. I… (more)

from
$45
per night
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Responsible Teacher Who Loves PetsFlorida Center North, Orlando, FL, 32811
Dog Boarding, House Sitting, Drop-In Visits, Dog Walking

Shannon was wonderful! My puppy doesn’t warm up quickly to new people, but she warmed up to Shannon and even sat in her lap! Shannon also sent me photos through… (more)

from
$38
per night
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7.
Beautiful connection with animals!Orlando, FL, 32818
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Dawn checked in on our puppies twice per day while we were gone. She was great with communicating with us the entire time. She came to the house before we left … (more)

from
$50
per night
Confirmed availability: Christmas and New Year
Attentive care for your pets!Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

Chelsea is a sweet person and took great care of Ava and Mochi while I was gone. She sent me photos during the weekend, asked questions and made me feel good th… (more)

from
$50
per night
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Walks, pets, & play....OH MY!Winter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Sabrina was wonderful! She was extremely responsive, flexible, and made me feel at ease with someone new in our house to watch our two dogs. I absolutely plan t… (more)

from
$40
per night
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10.
Any Animal & Any Need!Kirkman South, Orlando, FL, 32835
House Sitting, Drop-In Visits, Dog Walking

Chelsey was the sweetest! Knowing Pearl was in good hands made the weekend away relaxing. I would highly recommend her to anyone looking for a sitter for their … (more)

from
$70
per night
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11.
Trustworthy and experienced sitterOrlando, FL, 32819
House Sitting, Drop-In Visits, Dog Walking

She took an excellent care of our dog while we were out. She literally saved us at the last minute, because we were in a family trip and we were in need for som… (more)

from
$30
per night
Experienced with a true ♥️ For DogsOcoee, FL, 34761
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Had a great experience with Candilynn and her team. I had them stay overnight with my dog for a few days and everything went great. Thanks! (more)

from
$65
per night
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13.
Looking For A Reliable Sitter?Metro West, orlando, FL, 32835
House Sitting, Drop-In Visits, Dog Walking

Bonnie is always amazing with my dog, follows instructions and he absolutely loves her. There are very few people I allow to watch my animals but I never worry … (more)

from
$70
per night
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14.
Dog FatherOrlando, FL, 32835
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Naif was amazing! Super easy, great with our dog, and sent lots of photos. I could not recommend him enough for anyone in the area needing a sitter - and especi… (more)

from
$30
per night
15.
Ray 
Verified Background Check
I love animals!Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

I had to go on a work trip for a week and Ray watched my chihuahua! He sent me pictures and videos throughout my time away which I so appreciated! I will defini… (more)

from
$27
per night
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16.
Patient Pet Parent and FosterWinter Garden, FL, 34787
House Sitting, Drop-In Visits

Carlye was very professional, communicated and sent pictures of Akela during our trip. She came over ahead of time to meet Akela and they bounded immediately. Y… (more)

from
$23
per night
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17.
I Just Wanna Hangout with Your PetWindermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

We cannot be more thrilled that we found Kelsey! We had a friend cancel on us last minute for dog sitting right before we were about to leave on our trip. I qu… (more)

from
$40
per night
18.
I’ll love your animal so much :)Winter Garden, FL, 34787
House Sitting, Drop-In Visits
4 years of experience

About: I’ve been taken care of dogs since I had my own dogs. I clean after my dog, feed him and bathe him and most importantly take him out so I’ll treat yo… (more)

from
$45
per night
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19.
Love is a four legged word ❤️Windermere, FL, 34786
Dog Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Emily was fantastic! She took such good care of our pup and sent us picture and video updates. Will definitely contact Emily again the next time we need someo… (more)

from
$40
per night
20.
Happy to watch your furry babies!Orlando, FL, 32819
House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Very friendly and responsible! My dog loved her... my cat too! She wasn’t hiding from her. (more)

from
$48
per night

Rover also offers in:


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.