House Sitting in Windermere

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

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Boarding
House Sitting
Drop-In Visits
Doggy Day Care
Dog Walking
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Sitter Profile Image: Jerilyn B.
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Sitter Profile Image: Jerilyn B.
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1.

Jerilyn B.

I grew up with all kinds of pets!
Ocoee, FL, 32818
7.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
29 reviews
9 repeat clients
from
$40
per night

Jerilyn was great! She came out to take care of our pup who was having anxiety staying alone in our hotel room. Bella was sad when she had to leave! I would 10/10 recommend Jerilyn to take care of your fur babies!

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Sitter Profile Image: Sharon S.
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Sitter Profile Image: Sharon S.
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2.

Sharon S.

I had a monkey as a pet!
Orlando, FL, 32836
7.0 mi. away
House Sitting
5.0 out of 5 stars
22 reviews
6 repeat clients
from
$42
per night

Sharon watched my baby girl for 4 days and 3 nights. My dog took to her very well. She communicates great, provided multiple daily updates, and followed my instructions. Would definitely recommend.

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Sitter Profile Image: Sarah C.
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Sitter Profile Image: Sarah C.
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3.

Sarah C.

Creating loving experiences!
Orlando, FL, 32835
4.2 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
25 reviews
8 repeat clients
from
$35
per night

Sarah was great with her communication with us. Always prompt with responses and kept us up to date with lots of pictures. We appreciate her enthusiasm. She followed feeding instructions for Ellie and Theo carefully. We came home to a well ordered house and dogs that were happy and healthy. :)

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Sitter Profile Image: Alyson F.
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Sitter Profile Image: Alyson F.
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4.

Alyson F.

Lots of Love for your Dog
Orlando, FL, 32819
3.1 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
36 reviews
8 repeat clients
from
$40
per night

Alyson did a great job with Chloe!! Alyson provided me with pictures and numerous updates on how Chloe was doing. I am looking forward to booking her again.

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Sitter Profile Image: Nickolas J.
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Sitter Profile Image: Nickolas J.
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5.

Nickolas J.

Best Home for Lazy Dogs
Florida Center North, Orlando, FL, 32811
5.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
186 reviews
49 repeat clients
from
$45
per night

We would 100% recommend Nickolas. He was super communicative over the three days he sat with our pups and was sensitive to their needs as senior dogs. We will definitely use him again!

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Sitter Profile Image: Ava A.
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Sitter Profile Image: Ava A.
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6.

Ava A.

Sincere and honest care for pets!
Orlando, FL, 32836
4.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
39 reviews
16 repeat clients
from
$56
per night

Ava did an excellent job caring for our 2 dogs! Her calm approach was perfect and we appreciated her flexibility. I would highly recommend Ava, she’s a natural with animals. Thank you Ava!

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Sitter Profile Image: Chandrika B.
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Sitter Profile Image: Chandrika B.
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7.

Chandrika B.

Fur Mom Who is Here to Help!
Orlando, FL, 32819
5.0 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
4 repeat clients
from
$49
per night

Super impressed with Chandrika! Our dogs are not easy! We have 2 BIG puppies and our malinois Bella is very standoffish. Bella doesn’t even like 2/4 people who actually live here. She eats and destroys everything. She steady barks at everyone, but doesn’t bite, still she seems scary because of how she looks. We also have a happy-go-lucky bloodhound mix, Jethro, who is a complete mess. Chandrika took the challenge. She watched them for a complete week. She sent frequent updates and pictures. She somehow won Bella’s trust very quickly so she must have good dog vibes. Our dogs were well taken care of and were happy upon our return. Thwy didn’t even damage as much of our atuff as usual. If she is brave enough to return we would absolutely hire her again!

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Sitter Profile Image: MARK B.
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Sitter Profile Image: MARK B.
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8.

MARK B.

For great pet care, and Exercise
Windermere, FL, 34786
0.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
63 reviews
30 repeat clients
from
$45
per night

Mark is a great pet sitter and I highly recommend him! He took care of our two English Bulldogs who have eye drops…skin issues..and various pills. He did an excellent job following all of our instructions and taking care of them. They looked great when we returned! He is also very good at seeding pictures and letting you know how they are doing. Mark is the best pet sitter we have ever had!

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Sitter Profile Image: Imani Z.
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Sitter Profile Image: Imani Z.
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9.

Imani Z.

I care for your pets like family
Winter Garden, FL, 34787
4.8 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
8 reviews
1 repeat client
from
$27
per night

Imani was wonderful! She came over the day before to meet Fred and Sophie. She played with them she snuggled with them. She took them outside to play fetch. The puppies really enjoyed spending the day with her. I’ll definitely be booking with her again. I highly recommend her to anyone needing a pet sitter.

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Sitter Profile Image: Olivia K.
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Sitter Profile Image: Olivia K.
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10.

Olivia K.

I am a dog and cat purr-son
Orlando, FL, 32819
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$27
per night

My brave cat fell in love with Olivia immediately. The shy one, hiding under the bed, took a little more time before following suit. Now they both come to her right away whenever she comes over.

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Sitter Profile Image: Kayla H.
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Sitter Profile Image: Kayla H.
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11.

Kayla H.

Dogs > Everything
Windermere, FL, 34786
0.1 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
2 reviews
from
$55
per night

About: I have grown up always having a dog who I loved and cared for always. My dogs were my best friends & I know first hand how important a dog is in someone's life & promise to take care of your dog(s) like i would take care of mine - with love, respect, kindness & extra kisses, cookies and toe rubs if they're extra well behaved ;) I am patient, I understand most dogs very well and provide plenty of love and attention along with ability to follow a tinkle time schedule, give them exercise and of course feed them and rub their bellies. I am comfortable with most breeds, sizes and genders of dogs and would be honored to help care for your dog(s) while you are unable to. My daily routine and lifestyle revolves around making sure my pets are given plenty of love, attention, exercise, and food/water. I make social plans and work commitments around them, and I would do the same for your pets should you grant me permission to care for them in your absence. I do have a fenced in yard which I enjoy for extra precaution in case anyone feels particularly wild and gets the zoomies. My cats stay inside, but dogs can play in the outdoor fenced in space. I would do whatever you are comfortable with, as every pet and owner are different.

Sitter Profile Image: Iliana K.
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Sitter Profile Image: Iliana K.
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12.

Iliana K.

Energetic, animal care all my life!
Orlando, FL, 32819
3.4 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
11 reviews
5 repeat clients
from
$40
per night

Iliana did an amazing job taking care of our senior dog, Maggie. She stayed with Maggie at our apartment. She was in regular contact with us via text message and sent several photos and videos to us which we really appreciated given this was our first time leaving Maggie since we moved to Florida. Maggie got her meds as scheduled and seemingly had a great time while we were gone. Based on our experience with Iliana, we can give her our highest recommendation. She’s great!

Sitter Profile Image: Julia L.
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Sitter Profile Image: Julia L.
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13.

Julia L.

vaCATion Oasis for your kitty
Orlando, FL, 32819
2.9 mi. away
Boarding, House Sitting
5.0 out of 5 stars
17 reviews
3 repeat clients
from
$38
per night

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 my cat is friendly and has become somewhat used to location changes throughout his life. Once he explored the downstairs room and patio he settled quickly. I was very grateful for the short video clips that Julia sent daily, showing that Pippy was eating and drinking well. I highly recommend her peaceful vacation home for cats.

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Sitter Profile Image: Adam C.
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Sitter Profile Image: Adam C.
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14.

Adam C.

We are all living in a dogs world
Orlando, FL, 32819
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
17 reviews
3 repeat clients
from
$35
per night

Adam was great! He came and met Capi before hand and communicated very well. Capi doesn't usually warn up to people very quickly but she couldn't wait to see him after the first time.

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Sitter Profile Image: Nathan B.
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Sitter Profile Image: Nathan B.
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15.

Nathan B.

RoverGO
Rover 101
Much Love for dogs (and cats too!)
Windermere, FL, 34786
3.5 mi. away
House Sitting, Drop-In Visits
5.0 out of 5 stars
53 reviews
20 repeat clients
from
$97
per night

Nathan was AWESOME!! He came to our home to care for my 3 pups while we were on family vacation. He had his hands full with 2 young boxers & my older senior shih

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Sitter Profile Image: Kevin F.
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Sitter Profile Image: Kevin F.
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16.

Kevin F.

Energetic dog? I'll tire them out.
Windermere, FL, 34786
3.7 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
5 reviews
from
$24
per night

For the last couple of years I have routinely relied on Kevin to take care of my dogs, Tara and Ike, while traveling on business or vacation. He is extremely conscientious and reliable. Whereas many dog sitters can be counted on to just meet basic expectations, Kevin consistently goes above and beyond, walking and entertaining them. The only negative is that Tara and Ike seem to do so well in his care that they are not nearly as excited to see us when we get back.

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Sitter Profile Image: Rachel C.
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Sitter Profile Image: Rachel C.
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17.

Rachel C.

Flexible schedule, animal lover
Windermere, FL, 34786
2.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
3 reviews
1 repeat client
from
$25
per night

Rachel is definitely my dog’s favorite babysitter. My little one is always so excited to see her. She has experience caring for senior dogs, and I can always trust her to give medicine on time. She truly loves animals, and she will be your fur baby’s best friend. Another huge plus is she always sends pictures (:

Sitter Profile Image: Chelsea D.
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Sitter Profile Image: Chelsea D.
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18.

Chelsea D.

Attentive care for your pets!
Windermere, FL, 34786
3.5 mi. away
House Sitting
5.0 out of 5 stars
38 reviews
11 repeat clients
from
$65
per night

Chelsea arrived on time and we went over our steps for watching Fergie. She sent us pictures in the afternoon and let us know how Fergie was doing. We again received a message in the morning providing details of how the night went and how Fergie did in the morning. It was a great experience and we felt very safe in leaving Fergie in the hands of Chelsea.

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Sitter Profile Image: Susie M.
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Sitter Profile Image: Susie M.
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19.

Susie M.

Caring for your pets like my own
Orlando, FL, 32819
3.1 mi. away
Boarding, House Sitting, Drop-In Visits
5.0 out of 5 stars
9 reviews
1 repeat client
from
$50
per night

About: I have been pet sitting since childhood. I am the type of sitter who will take the time to love on your pet, play with them, and spend time with them while you are away. Whether I’m staying with them or I’m doing drop in visits, I will spend quality time with your pets. I’m experienced with and have personally owned cats, dogs, rodents, and snakes. I also have experience caring for birds. I work M-Th in the office from about 8-5, but have a flexible schedule and can work remotely if required. I’m off every Friday-Sunday. I am available to do boarding, house sitting or drop in care up to twice a day (I am not able to support 3 or more times a day unless it is a weekend only). I have a fenced back yard with a dog door that can be locked if not appropriate for your pet. I have a large shaded neighborhood to take your pet for walks in. I have two cats that can be separated from boarders if required. If your pet needs isolation, I have a guest room that can be a dedicated space for your pet.

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Sitter Profile Image: Claire G.
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Sitter Profile Image: Claire G.
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20.

Claire G.

Near downtown Winter Garden!
Windermere, FL, 34786
1.8 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
5.0 out of 5 stars
6 reviews
1 repeat client
from
$28
per night

Claire used to pet sit for my dog all the time when we lived in the same state. She is thoughtful and reliable. At one point I had to be in another state for about three weeks, and Claire was the only person I even considered leaving my dog with. She took care of her, and I had confidence that she does what was in Nala’s best interest. Claire is an animal lover and has two pets of her own. As far as work ethic goes, Claire and I were former coworkers. I find her to be reliable and straightforward in her communication.

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Windermere House Sitting ratings

Overall Rating:
4.9 out of 5 stars

House sitters in Windermere are rated on average 4.9 out of 5 stars based on 206 reviews.

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