House Sitting in Windermere

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

I'm looking for service for my:
Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
Which dates do you need?
What size are your dogs (lbs)?
To ensure accurate availability & pricing, please add your drop-off and pick-up dates.

Search Results

Confirmed availability: Presidents' Day Weekend
Rachel M.
1.
I have a degree in cuddling!Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

Rachel was a knowledgable and experienced sitter. Rocket is not the most laid back dog to care for and sh was ready and willing to tackle making him like her. S… (more)

from
$50
per night
Calendar Recently Updated
Benjamin C.
I really love my job!Orlando, FL, 32809
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Benjamin is excellent, our dogs took to him right away during the meet & greet! He was extremely communicative throughout our vacation putting our family at eas… (more)

from
$65
per night
Calendar Recently Updated
MARK B.
3.
For great pet care, and ExerciseWindermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

Mark was awesome! He sent pictures everyday, and kept us up-to-date on how they were doing together. He made sure she had her allergy medicine daily, taking gre… (more)

from
$37
per night
Confirmed availability: Presidents' Day Weekend
Nickolas J.
Best Home for Lazy DogsFlorida Center North, Orlando, FL, 32811
Boarding, House Sitting, Drop-In Visits, Dog Walking

Nick was fantastic! I was able to book him day of. He was very nice and flexible. He started getting to know my little Hazelnut right away and she took right to… (more)

from
$45
per night
Catherine O.
Quality care by former vet techOrlando, FL, 32835
House Sitting, Drop-In Visits

Wow! I'm always super nervous the first time I use someone new to house sit, especially during this weird time. Catherine was absolutely *stellar* at every step… (more)

from
$45
per night
Confirmed availability: Presidents' Day Weekend
Disney Dog Sitters!Orlando, FL, 32836
Boarding, House Sitting, Drop-In Visits, Dog Walking

Our 1st time having a sitter for our dog. Heather was wonderful with him..walks, golf cart rides, lots of TLC. We were able to enjoy our night out without wor… (more)

from
$75
per night
7.
No furry friend is too big or smallWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

Bailey was fantastic with Butters! She took him on a long walk and took gorgeous photos of our boy. We will definitely try to book her again. (more)

from
$150
per night
Confirmed availability: Presidents' Day Weekend
Attentive care for your pets!Windermere, FL, 34786
House Sitting

This was our second time having Chelsea come to our home for our dog and cat. She did another amazing job and it was so nice, while I was at my daughter’s weddi… (more)

from
$65
per night
Confirmed availability: Presidents' Day Weekend
9.
Cert Vet Asst loves all animals!Orlando, FL, 32811
House Sitting, Drop-In Visits, Dog Walking

So comforting to have Lynzee take care of our pets! I highly recommend her! (more)

from
$65
per night
Confirmed availability: Presidents' Day Weekend
Engineer | Love to Make Tails Wag!Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

Both Gabriella and Kevin were fabulous welcomed Guests in our home. We trusted them quickly. They were very flexible with our hours, and on short notice. We wou… (more)

from
$68
per night
Confirmed availability: Presidents' Day Weekend
Animals are my favorite people!Orlando, FL, 32819
House Sitting, Drop-In Visits, Dog Walking

If I could give Jonathan more than 5 stars I would. He was on time, responsible and very understanding with my dogs' needs. I have an old girl (Border Collie)t… (more)

from
$39
per night
Confirmed availability: Presidents' Day Weekend
12.
Furtopia; Where fur babies vacationWinter garden, FL, 34787
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

Had a wonderful sitter experience with Jasmine while we went on our first big post-pandemic vacation away from our furbabies. Our dogs were very happy and the h… (more)

from
$40
per night
Confirmed availability: Presidents' Day Weekend
13.
vaCATion Oasis for your kittyOrlando, FL, 32819
Boarding, House Sitting

Julia looked after my cat when I had to visit my mother over a long weekend. I knew when I walked into her home that Pippy was going to be fine. Fortunately m… (more)

from
$38
per night
Calendar Recently Updated
14.
Lots of Love for your DogWindermere, FL, 34786
House Sitting, Drop-In Visits

Alyson was great with Lacey. We went to the theme parks and she watched my 6 month old Aussie and took great care of here. She booked under short notice And we’… (more)

from
$35
per night
Calendar Recently Updated
15.
I care for your pets like familyWinter Garden, FL, 34787
House Sitting, Drop-In Visits, Dog Walking

To whom it may concern, Imani Z. is a highly effective motivated pet care worker. I cannot recommend her enough! I have had dog-sitters who are apathetic an… (more)

from
$27
per night
Confirmed availability: Presidents' Day Weekend
16.
From small dogs & cats to large!Orlando, FL, 32819
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
25 years of experience

About: I currently have two dogs of my own, a one year old Pomsky and an eight year old Puggle. Growing up we always had at least 4 pets in the house! My … (more)

from
$35
per night
Confirmed availability: Presidents' Day Weekend
17.
I love animals !Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking
25 years of experience

About: My family had dogs and cats since I was a kid, so I grew up loving them and teaching them how to behave while playing a lot :) I'm available only du… (more)

from
$100
per night
Wag on overWindermere, FL, 34786
Boarding, House Sitting, Doggy Day Care, Dog Walking

Kristine is fantastic! Her attention to detail and her compassion for animals was obvious from the first time we met her. She took great care of our little guy! (more)

from
$40
per night
19.
Animal Behaviorist, the best care!Windermere, FL, 34786
House Sitting, Drop-In Visits, Dog Walking

Heather was INCREDIBLE. She absolutely went above and beyond, took excellent care of our dog and basically trained him in the process. She was so great at check… (more)

from
$150
per night
20.
Professional Dog SitterWindermere, FL, 34786
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking

He’s amazing! Such good care taker of my puppy ane she loves him. Douglas has been going above and beyond to help us with our duties. Late nights and all! Lov… (more)

from
$40
per night

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.

House Sitting