House Sitting in Windermere

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Top rated Windermere house sitters

Prices are estimates per night. Pricing may vary based on your search. A booking fee of 11% and taxes will apply.

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Sitter Profile Image: Devona S.
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Devona S.
Star Sitter
from
$30
per night
5.0 out of 5.0 stars
77 reviews
34 repeat clients
10 years of experience
Orlando, FL, 32839

Devona is just the best! Devona truly gives peace of mind when we leave our dogs and our home in her care. She is a great communicator and very friendly.

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Katelyn S.
Sitter Profile Image: Lindsay L.
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Lindsay L.
Star Sitter
from
$38
per night
5.0 out of 5.0 stars
39 reviews
12 repeat clients
22 years of experience
Orlando, FL, 32819

Thank you for being so sweet to Goku and making the trip to come meet him and myself before taking on watching him, everyone should rave about you :)

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Andres B.
Sitter Profile Image: Skylar D.
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Skylar D.
from
$40
per night
5.0 out of 5.0 stars
9 reviews
4 repeat clients
6 years of experience
Ocoee, FL, 34761

This was our first time and Skylar did an amazing job with our cat and put us at ease leaving our cat at home instead of boarding at a facility

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Kim H.
Sitter Profile Image: Alyson F.
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Alyson F.
Star Sitter
from
$50
per night
4.9 out of 5.0 stars
64 reviews
18 repeat clients
30 years of experience
Windermere, FL, 34786

Absolutely amazing - Alyson was one and considerate and helped with my little dog Daisy's severe separation anxiety. She sent so many check-ins - I was very grateful for her help and responsiveness,

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Nina Z.
Sitter Profile Image: Steffanie D.
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Steffanie D.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
18 reviews
5 repeat clients
40 years of experience
Winter Garden, FL, 34787

Absolutely amazing! My girls loved Stephanie. My house was clean when I returned home after two weeks as if I’d never left and the cleaning lady had just come.

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Allison V.
Sitter Profile Image: Nathan B.
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Nathan B.
Star Sitter
from
$100
per night
5.0 out of 5.0 stars
76 reviews
29 repeat clients
9 years of experience
Windermere, FL, 34786

Nathan took wonderful care of our dog, Koda. He checked in with us regularly and sent lots of pictures. He got Koda out on lots of walks, even in the rain. We came home to a clean house and a happy dog!

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Kath N.
Sitter Profile Image: Diahann B.
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Diahann B.
Star Sitter
from
$35
per night
5.0 out of 5.0 stars
17 reviews
6 repeat clients
5 years of experience
Winter Garden, FL, 34787

She was excellent. I highly recommend her. We will be using her, again. Our dogs loved her. Even our timid dog snuggled her. Excellent communication. Left the house very clean and tidy.

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Robert H.
Sitter Profile Image: Sarah H.
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Sarah H.
Star Sitter
from
$62
per night
4.9 out of 5.0 stars
145 reviews
61 repeat clients
15 years of experience
Orlando, FL, 32835

Sarah did an amazing job! Our senior lab is blind and has diabetes, and previously had issues with us leaving her. Sarah was able to come in and make our pup comfortable and kept us updated on how our pup was doing!! I absolutely recommend Sarah.

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Chandler Y.
Sitter Profile Image: Nickolas J.
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Nickolas J.
Star Sitter
from
$50
per night
5.0 out of 5.0 stars
238 reviews
58 repeat clients
25 years of experience
Florida Center North, Orlando, FL, 32811

Thank you, Nick, for another fantastic stay with Ellie and Theo! We came home after two weeks to two happy pups and everything perfectly in order at home.

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Getty A.
Sitter Profile Image: Brittney C.
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Brittney C.
from
$35
per night
5.0 out of 5.0 stars
9 reviews
28 years of experience
Ocoee, FL, 34761

My pup loved Brittney and she made him feel so comfortable! She had incredible communication and updates that left me no questions about my pups care and how his day was while I was away. I would absolutely use her service again and I know Argo is looking forward to it as well.

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Tanielle B.
Sitter Profile Image: Sarah C.
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Sarah C.
Star Sitter
from
$40
per night
4.9 out of 5.0 stars
47 reviews
13 repeat clients
15 years of experience
Metro West, Orlando, FL, 32835

Sarah was absolutely amazing! She took care of our two rambunctious puppies and two older cats while house-sitting, and we couldn’t be happier with the experience. We left her a (very detailed!) schedule for the pups, and she followed it exactly—sending tons of photo updates that gave us peace of mind while we were away. Communication was super easy, and Sarah went above and beyond to make sure our pets felt loved and our home was well cared for. We came back to happy animals and a calm home, which says everything. We will definitely be booking with her again and have already recommended her to our friends and family. Thank you, Sarah!

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Isolina R.
Sitter Profile Image: Shannon Lyver
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Shannon Lyver
from
$65
per night
5.0 out of 5.0 stars
6 reviews
3 repeat clients
13 years of experience
Winter Garden, FL, 34787

Shannon did a great job keeping our dogs and cat. She kept the house clean, was very responsive and sent us pics of our fur babies each day. Highly recommend her 10/10!

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Dani W.
Sitter Profile Image: Anastasiia K.
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Anastasiia K.
from
$44
per night
5.0 out of 5.0 stars
53 reviews
17 repeat clients
20 years of experience
Metro West, Orlando, FL, 32835

So very pleased with Anastasiia‘s service! She was prompt, courteous, and kept my pup constant company . You can tell she has a real passion for pet care! And she sent daily texts with pics and an update on how my dog was doing. I would recommend her highly to anyone.

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Tino S.
Sitter Profile Image: Ariella P.
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Ariella P.
Star Sitter
from
$110
per night
5.0 out of 5.0 stars
24 reviews
9 repeat clients
9 years of experience
Windermere, FL, 34786

Ariela is a total gem, best sitter we’ve ever had! She cared for our dog Belinha at our home for five days while we were out of the country. Our dog has a history of separation anxiety, so we’re always nervous about leaving her, but from the moment we met Ariela, we felt confident she was in good hands. Throughout the stay, Ariela was a fantastic communicator. She sent us regular updates with photos that truly put our minds at ease. We came home to a happy, healthy pup and a spotless house. It’s clear that Ariela genuinely loves and understands the pets she cares for. We highly recommend her and will absolutely be a repeat customer!

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Claudia W.
Sitter Profile Image: Alexis T.
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Alexis T.
from
$50
per night
5.0 out of 5.0 stars
18 reviews
10 repeat clients
7 years of experience
Winter Garden, FL, 34787

Alexis was amazing! She sent us pictures and kept us updated. The dogs looked so happy!! She stayed at our house, and we came back to a beautiful, clean home. We’d definitely use Alexis again!

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Amy B.
Sitter Profile Image: Yelena L.
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Yelena L.
from
$45
per night
4.5 out of 5.0 stars
5 reviews
40 years of experience
Gotha, FL, 34734

Yelena just joined rover, and i was her first booking. She house sat my dog for 2 days. My dog seemed happy on our return, and she communicated well while we were away, and followed his regular routine. I was looking forward to rebooking, and building a familiar dog sitter for my dog however she said she was allergic to my dog (he’s a none allergic breed, and never had issues with anyone else around him…however that being said I guess no dog really is none allergic). This was so disappointing for us as I wouldn’t expect someone with dog allergies to be signing up and doing dog sitting on Rover. For us it’s back to looking for someone we can rebook often, for you she maybe the perfect house sitter, I definitely felt calm leaving my dog with her.

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Karen S.
Sitter Profile Image: Jonathan W.
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Jonathan W.
Star Sitter
from
$75
per night
5.0 out of 5.0 stars
36 reviews
17 repeat clients
13 years of experience
Orlando, FL, 32819

Jonathan was recommended to me by family member and I'm glad they recommended Jonathan. Great communication for planning and during the stay. Will definitely be using Jonathan again.

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Chris H.
Sitter Profile Image: Laura C.
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Laura C.
from
$45
per night
5.0 out of 5.0 stars
3 reviews
1 repeat client
10 years of experience
ocoee, FL, 34761

Laura was exactly what my “needy” fur babies needed — she was patient, super attentive and provided lots of updates along the way. One of my dogs is reactive and takes time to warm up, but Laura quickly won him over! I also appreciated her flexibility in accommodating last-minute medication for my pup and an extended stay when I needed it. Definitely recommend her services!

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Kaleigh W.
Sitter Profile Image: Sherry A.
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Sherry A.
from
$45
per night
1 repeat client
9 years of experience
Ocoee, FL, 34761

Sherry was very good with Daphne. Communicative and very kind and warm. I’ll be using her again in the future.

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Ana A.
Sitter Profile Image: MARK B.
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MARK B.
Star Sitter
from
$75
per night
5.0 out of 5.0 stars
197 reviews
45 repeat clients
3 years of experience
Windermere, FL, 34786

Mark has taken care of our dog several times and is always wonderful to work with. He sends lots of pictures and updates, and does a great job of keeping our older dog active and having fun while we're away!

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Kath N.
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Over 387
pet parents in Windermere have booked house sitting

How Rover works

  1. 1. Search

    Read verified reviews and choose a house sitter who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your house and pets while you’re away
  3. 3. Book & Pay

    All payments are processed through Rover’s secured platform and your booking is backed by 24/7 support. It’s that easy!

The median cost per night for house sitting in Windermere is $45

Why Choose Rover?

  • Cashless payments

    Book and pay through Rover’s secured platform—no cash or checks required.

  • Reservation protection

    It doesn’t happen often, but if your house sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

    We’re friendly, knowledgable, and total pet fanatics. You can get in touch with us anytime.

Sitters in Windermere average 4
repeat house sitting clients

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