Pet Sitting in Windermere

Book a pet sitter to stop by your home a few times a day to feed and play with your pet.

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Top rated Windermere pet sitters

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

1 / 1
Sitter Profile Image: MARK B.
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MARK B.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
219 reviews
48 repeat clients
3 years of experience
Windermere, FL, 34786

My dogs love Mark and he has been taking care of them for the past year! He does a great job of giving them walks and attention while we are away.

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Amanda S.
Sitter Profile Image: Jamie L.
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Jamie L.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
38 reviews
9 repeat clients
20 years of experience
Orlando, FL, 32819

Jamie is very good and very attentive. She is very good with Louis. 100% recommended

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Lysandra A.
Sitter Profile Image: Lindsay L.
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Lindsay L.
Star Sitter
from
$19
per visit
5.0 out of 5 stars
55 reviews
16 repeat clients
22 years of experience
Orlando, FL, 32819

Lindsay is such a gem! She has taken care of our kitties several times, and we always feel so at peace knowing she is with them. Thank you so much! ❤️

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Tashina S.
Sitter Profile Image: Elizabeth R.
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Elizabeth R.
Star Sitter
from
$18
per visit
5.0 out of 5 stars
18 reviews
7 repeat clients
11 years of experience
Windermere, FL, 34786

Elizabeth was great! She was very accommodating when I needed to update the time for the drop in. She communicated promptly and was very sweet and caring with Luna. She made sure Luna ate and had lots of bathroom breaks while walking her. I will definitely book with her again.

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Adriana M.
Sitter Profile Image: Megan W.
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Megan W.
from
$20
per visit
5.0 out of 5 stars
81 reviews
17 repeat clients
8 years of experience
Orlando, FL, 32819

This is our second time asking Megan to watch our cats while we’re out of town— and won’t be our last! 😎 Megan is always very communicative, about everything! She’s proactive with questions, leaves a great and detailed communication card at the end of each check in, and sends the best pictures of our kitties that really captures how well she takes care of them. Always responsive and went above and beyond to help us by assisting with little extra tasks we asked of her while she was checking on our pets. Thanks for everything Megan!

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Andrew P.
Sitter Profile Image: Danielle H.
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Danielle H.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
49 reviews
15 repeat clients
22 years of experience
Ocoee, FL, 34761

I can not say enough good things about or express how much we appreciate Danielle. On several occasions now, she has checked in on and taken excellent care of our two feline girlies. It is so nice to be able to go away and feel sure that they are safe, secure, and well-cared for. Thank you again, Danielle!

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Debra H.
Sitter Profile Image: Samantha F.
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Samantha F.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
95 reviews
35 repeat clients
15 years of experience
Ocoee, FL, 34761

You will absolutely love the expert care that Samantha will give to your pet. As a pet owner herself, she knows what's involved to keep your pet happy in your absence. I trust Samantha with my Persian and my kitty loves when Samantha visits. Don't delay...hire her today!!!

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Roxane L.
Sitter Profile Image: Jenn H.
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Jenn H.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
93 reviews
32 repeat clients
10 years of experience
Orlando, FL, 32835

Jenn was great with our playful cat! She sent pictures everyday and kept me updated. I will definitely use her again. She also quickly let me know when our door battery was low and when there was a change in our cats litter box. I knew our girl was in great hands!

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Mindi S.
Sitter Profile Image: Victoria P.
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Victoria P.
from
$19
per visit
5.0 out of 5 stars
31 reviews
11 repeat clients
10 years of experience
Orlando, FL, 32819

Victoria was amazing! Very patient and understanding when we had key trouble and very informative in the after visit reports. Would recommend and rebook in a heartbeat! Thanks so much!

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Mia M.
Sitter Profile Image: Samantha Y.
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Samantha Y.
Star Sitter
from
$21
per visit
4.9 out of 5 stars
44 reviews
16 repeat clients
7 years of experience
Orlando, FL, 32836

Samantha was a hit with Mulder when they first met! I saw how he immediately accepted Samantha. It gave me peace of mind while we were away for an extended period of time. We have your number Samantha and we will call you again when needed. Thank you!

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Betsy M.
Sitter Profile Image: Shelley R.
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Shelley R.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
18 reviews
6 repeat clients
3 years of experience
Windermere, FL, 34786

She was great in keeping Pumpkin fed and was able to accommodate some extra stays when we had a delay in flights, which we really appreciated! Shelley is very nice and attentive, with good communication as well.

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Gabriela C.
Sitter Profile Image: Poliana D.
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Poliana D.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
555 reviews
149 repeat clients
15 years of experience
Windermere, FL, 34786

Poliana is fantastic!!! She treats my pets as her own ❤️ I highly highly recommend her for her kindness and care and attention to details regarding special needs pets as well 🐶🐟😻🦎especially as our fur babies who start to get older ❤️

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Kimberly C.
Sitter Profile Image: Karen R.
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Karen R.
from
$22
per visit
5.0 out of 5 stars
289 reviews
81 repeat clients
30 years of experience
Winter Garden, FL, 34787

As always Karen was amazing taking care of my babies! Our cats 🐈‍⬛ absolutely love Karen and I know they are being taken great care of! My mind is at ease having you watch the kitties, thank you again for an amazing experience!

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Breana N.
Sitter Profile Image: Grey G.
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Grey G.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
63 reviews
15 repeat clients
3 years of experience
Winter Garden, FL, 34787

Grey is always communicative, punctual, and just does a wonderful job with my cats. I know they’re in great hands when I am out of town. Thank you Grey!

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Araena G.
Sitter Profile Image: Taryn N.
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Taryn N.
Star Sitter
from
$25
per visit
5.0 out of 5 stars
42 reviews
18 repeat clients
23 years of experience
ORLANDO, FL, 32819

I hired Taryn for a drop-in midday to let out and play with our Goldendoodle. She was on-time, communicative, took lots of pictures, and very easy to deal with! Would highly recommend!!

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James G.
Sitter Profile Image: Nicholas G.
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Nicholas G.
from
$22
per visit
5.0 out of 5 stars
16 reviews
6 repeat clients
15 years of experience
Orlando, FL, 32836

Our pup was very well cared for while we were away. We will definitely be using Nicholas again in the future. He did and amazing job and I love that he washed the dogs bowls before he fed him each time.

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Candace R.
Sitter Profile Image: Brittney C.
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Brittney C.
Star Sitter
from
$20
per visit
5.0 out of 5 stars
17 reviews
4 repeat clients
28 years of experience
Ocoee, FL, 34761

Great experience! Brittany was timely, provided photos, and provided results of visit! Will book again.

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Katie L.
Sitter Profile Image: Samanntha Q.
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Samanntha Q.
from
$15
per visit
4.6 out of 5 stars
33 reviews
11 repeat clients
19 years of experience
Orlando, FL, 32811

I booked Samanntha to look after my cat Sam for a week while I was on holiday. We emailed back and forth a few times to discuss what I was looking for and when she came to meet Sam he fell in love with her, even offering her his belly for rubs by the end of the meeting. Right then I knew she was the one!! Plus she and I had a wonderful conversation as well! She was great at communicating, cleaned his litter every day, played with him, and sent pics and videos each day, even doing a video chat one day! I would definitely recommend her services, as she is friendly, kind and clearly loves animals!! Thank you, Samanntha!!

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Susan A.
Sitter Profile Image: Tracy W.
Verified Enhanced Background Check
Tracy W.
Star Sitter
from
$15
per visit
5.0 out of 5 stars
8 reviews
3 repeat clients
20 years of experience
Winter Garden, FL, 34787

Tracy did an excellent job caring for my achnauzers. She was attentive, responsible, and went above and beyond by keeping the crate area clean and organized after every visit. I truly appreciated her professionalism, communication, and the care she showed to my pets and my home. I would absolutely recommend Tracy to anyone looking for a reliable and thoughtful pet sitter.

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Gloria C.
Sitter Profile Image: Cassia V.
Verified Enhanced Background Check
Cassia V.
Star Sitter
from
$30
per visit
5.0 out of 5 stars
97 reviews
15 repeat clients
25 years of experience
Windermere, FL, 34786

Cassia is wonderful and my dogs love her. She cares so much & has excellent communication. I will def be using her services again for my babies. Thank you! 💕

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Ashley R.
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Over 420
pet parents in Windermere have booked pet sitting

Windermere pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Jamie is ALWAYS WONDERFUL with Louis. She’s very attentive and always great communication. Thank you Jamie for taking care of our baby.

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Lysandra A.
Drop-In Visits
5.0 out of 5 stars

Hailey was super helpful to us last minute! She shared great info and photos about our dog and was very responsive.

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Caroline P.
Drop-In Visits
5.0 out of 5 stars

Lena was wonderful! She provided great attention to our two kitties, always arriving on a regular schedule to feed, clean their litter boxes and tend to their special needs. I would highly recommend her and plan on booking her again for our future trips.

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Emy Y.
Drop-In Visits
5.0 out of 5 stars

Miranda was very great to work with and very attentive to caring for our kitties. She was very consistent with her service, went above and beyond and was very helpful. Definitely would book again!

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Adam M.
Drop-In Visits
5.0 out of 5 stars

Cheyanne never disappoints me in her ability to provide great service. Her level of care and trustworthiness is exemplary. Thank you again, Cheyanne, for your help with Stormy.

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David L.
Drop-In Visits
5.0 out of 5 stars

Taryn, was excellent. I was able to contact her last minute and she was able to come to the house twice a day for me. She let me know how he was doing every day and really put me at his thank you so much highly recommend.

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Gustavo C.
Drop-In Visits
5.0 out of 5 stars

Katherine is absolutely wonderful! She was very responsive and reliable. I also appreciate that she would grab our packages if we had any sitting and bring them in. I will absolutely schedule care with Katherine again in the future!

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Jessica M.
Drop-In Visits
5.0 out of 5 stars

Thank you Jessica for taking such good care of our babies! We will definitely call on you in the future 😊

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Janet R.
Drop-In Visits
5.0 out of 5 stars

Wonderful and caring. Entertained our pups and made sure they had fun while we were out. Definitely will be calling on Nathan again.

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Shannon A.
Drop-In Visits
5.0 out of 5 stars

She’s awesome did a great job very trustworthy and respectful to my home . I will only use her when needed .

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Lance L.
Drop-In Visits
5.0 out of 5 stars

Alexis has been taking care of our cats since they were kittens. The cats are familiar with her, and we love the pictures that she sends to us. We will definitely ask her to sit for us again!

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Carmen H.
Drop-In Visits
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Find pet care near you

How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a 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 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 pet sitting in Windermere is $20

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 pet 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 6
repeat pet sitting clients

Pet Sitting FAQs

Frequently asked questions about Rover

Pet sitters on Rover are free to set their rates. The median cost to hire a pet sitter in Windermere on Rover as of Mar 2026 was about $20 per night, after factoring in Rover’s service fees. A pet sitter’s rate may also change as you customize your booking to fit your and your pet’s needs.

If you’re searching for a Windermere pet sitter for the first time, visit the pet sitter’s profile and select the Contact button.

If you have an active request or have booked a service with a pet sitter before, learn more about how to do this in the Rover app or on your computer.

As of Mar 2026, there are 1,302 pet sitters in Windermere. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass a background check for you and your pet’s safety.

Rover makes it easy to reach out to multiple pet sitters about your booking. Typically, 89% of Windermere pet sitters respond in under an hour.

Pet sitters in Windermere have an average of 15 years of experience. Pet sitters with repeat customers have an average of 6 repeat clients. Experience can vary from pet sitter to pet sitter, but you can view reviews, years of experience, and number of repeat clients when you compare pet sitters in Windermere.

Rover makes it easy to find Windermere pet sitters to provide loving care from their own home. The background-checked, 5-star pet sitters you can find on Rover will welcome your pet into their home when you’re away—whether it’s just for the weekend or longer. Pet sitting is great for:

  • Pets of all ages and abilities, including puppies
  • Pet parents looking for a safe, loving alternative to a kennel
  • Pets who’d love to socialize with their pet sitter’s pets

There are 1,302 pet sitters in Windermere on Rover, so you’re sure to find the perfect match for your pet! In Windermere, 98% of pet sitters offer daily exercise, 94% offer medication administration, and 90% have experience with senior pets and pets with special needs. We know each pet is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect pet sitter near you. As a reminder, pet sitters joining Rover must pass background checks for you and your pet’s safety.

Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your pet sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your pet sitter has access to advice from qualified veterinary professionals. In the rare event of any issues during a booking, rest easy knowing your pet is covered by the Rover Guarantee reimbursement program for eligible veterinary care.

Note: If your pet sitter requested to cancel this booking, then they need to cancel from their account. Please contact them via Rover Messages.

We get it—sometimes plans change and you may need to cancel your pet service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.