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
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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
41 reviews
15 repeat clients
from
$40
per night

Jerilyn did a great job caring for my two cats and dog! They were very comfortable with her, even my shy cat! She left our home impeccable. I would recommend her services!

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
7 repeat clients
from
$42
per night

Sharon took wonderful care of our puppy!! He was so happy and comfortable with her. We will definitely be using her again next time we are in Florida!

Sitter Profile Image: Adriana R.
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Sitter Profile Image: Adriana R.
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3. Adriana R.

Love spending time with pups!
Ocoee, FL, 34761
7.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
16 reviews
6 repeat clients
from
$40
per night

Excellent care, super nice and personable, friendly and knowledgeable. Magic loved her and I felt very comfortable leaving him in her care. I would definitely call on her again!!

Sitter Profile Image: Chandrika B.
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Sitter Profile Image: Chandrika B.
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4. 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
21 reviews
5 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!

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
191 reviews
50 repeat clients
from
$45
per night

Nick did an amazing job taking care of our pups! The pups LOVED him and were a little sad that he had to leave 🤣. Hope to be able to have Nick visit again in the future!

Sitter Profile Image: Alyson F.
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Sitter Profile Image: Alyson F.
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6. 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
41 reviews
10 repeat clients
from
$42
per night

Alyson was great with our four large dogs! We had a last min cancel and she was timely in response to help us out. She kept us posted on the dogs and ensured our requests were met.

Sitter Profile Image: Sarah C.
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Sitter Profile Image: Sarah C.
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7. Sarah C.

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

There are no words! Sara is one in a million. So kind, professional, responsible a nd caring. We usually experience such anxiety over leaving our pets in vacation, but no more! I know they are in the best hands. Thank you so very much for everything!??

Sitter Profile Image: Nathan B.
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Sitter Profile Image: Nathan B.
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8. 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
55 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

Sitter Profile Image: Chelsea D.
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Sitter Profile Image: Chelsea D.
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9. Chelsea D.

Attentive care for your pets!
Windermere, FL, 34786
3.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
39 reviews
12 repeat clients
from
$65
per night

Chelsea did a fabulous job staying at our house and taking care of our dog and cat for 5 days. Chloe and LuLu were well taken care of and Chelsea kept us updated over our holiday. Will definitely book in with her again!

Sitter Profile Image: Tathyana  F.
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Sitter Profile Image: Tathyana  F.
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10. Tathyana F.

Pets Care Inn
Windermere, FL, 34786
3.1 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
54 reviews
17 repeat clients
from
$35
per night

Tathyana was incredibly accommodating and took such good care of our two pups. She sent pictures/videos of each drop in and we felt very comfortable having her watch our pups during our trip. Will definitely rebook.

Sitter Profile Image: Ava A.
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Sitter Profile Image: Ava A.
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11. 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
40 reviews
17 repeat clients
from
$56
per night

Ava is fantastic! She sat our house and Cane Corso (no easy feat as he can be very intimidating for most people). She gave us daily pics of our babies while we were away and we came home to a very happy dog and cat. I would 1000% recommend her to anyone. She is very responsible and someone you can trust.

Sitter Profile Image: Lynzee M.
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Sitter Profile Image: Lynzee M.
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12. Lynzee M.

Cert Vet Asst loves all animals!
Orlando, FL, 32811
4.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
3 repeat clients
from
$50
per night

We used Lynzee for 3 nights/4 days in our home recently and couldn’t be more pleased. We will definitely be calling her again!

Sitter Profile Image: Kelly H.
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Sitter Profile Image: Kelly H.
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13. Kelly H.

I love dogs and running! 🐾
Windermere, FL, 34786
3.0 mi. away
House Sitting, Dog Walking
from
$27
per night

Kelly is a reliable person who loves dogs. She is dependable and enjoys going on long walk/runs and would be a wonderful pet caregiver. She loves our 90/pound golden retriever and is very good with him. Highly recommend Kelly.

Sitter Profile Image: Taryn N.
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Sitter Profile Image: Taryn N.
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14. Taryn N.

Worry free pet care!
ORLANDO, FL, 32819
3.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
1 repeat client
from
$55
per night

Taryn has the absolute biggest heart and is the most dog-savvy person I know! She currently has 2 pups of her own, has fostered countless dogs, and regularly volunteers at the animal shelter. Taryn has a special way of understanding a dog’s unique needs and working with even the most fearful or “difficult” dogs. She will always ensure that your dog is safe, comfortable, and loved! She is a great communicator and she takes tons of pictures & videos so you will never be left wondering what your pup is up to while you’re away. I would absolutely trust that Taryn would take the best possible care of my fur baby!

Sitter Profile Image: Adam C.
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Sitter Profile Image: Adam C.
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15. 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
20 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.

Sitter Profile Image: MARK B.
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Sitter Profile Image: MARK B.
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16. 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
77 reviews
34 repeat clients
from
$45
per night

Mark took excellent care of our dog! He checked in with us regularly and sent lots of pictures and updates while we were away, which gave us such peace of mind. He took our dog on frequent walks and spent quality time with him. Mark is very friendly, kind, and reliable and we would definitely recommend him, and use his services again.

Sitter Profile Image: Kaitlyn M.
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Sitter Profile Image: Kaitlyn M.
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17. Kaitlyn M.

Animal Lover: Patient, kind, caring
Windermere, FL, 34786
2.5 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
10 reviews
3 repeat clients
from
$55
per night

Thank you for loving our boy while we are away.

Sitter Profile Image: Jonathan W.
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Sitter Profile Image: Jonathan W.
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18. Jonathan W.

Animals are my favorite people!
Orlando, FL, 32819
3.6 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
19 reviews
11 repeat clients
from
$75
per night

Jonathan has a clear love for animals and he did a tremendous job with our dog and cat. Great updates, very timely and house was spotless. Would highly recommend, in fact, we are already hiring him for a second job in a few weeks!!!!

Sitter Profile Image: Alexis T.
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Sitter Profile Image: Alexis T.
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19. Alexis T.

I love animals more than anything
Winter Garden, FL, 34787
2.9 mi. away
House Sitting, Drop-In Visits, Dog Walking
5.0 out of 5 stars
9 reviews
5 repeat clients
from
$50
per night

Alexis is amazing. She goes above and beyond. When one of my dogs had an accident she took our carpet to her own place to clean it. We’ve tried several pet sitters but no one leaves our kitties as happy and our place as clean as when Alexis comes to watch them. We will be using Alexis again and again!

Sitter Profile Image: Susie M.
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Sitter Profile Image: Susie M.
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20. 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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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.

Rover also offers House Sitting in:

Rover also offers other services in Windermere:


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.

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