House Sitting in Windermere

Find a loving house sitter to watch over your pets and your home.

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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: Karen D.
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Karen D.
Star Sitter
from
$30
per night
5.0 out of 5 stars
26 reviews
6 repeat clients
6 years of experience
Orlando, FL, 32819

Karen takes exceptional care of our senior pack—they absolutely adore her. She’s incredibly attentive to their needs and keeps us regularly updated, which gives us such peace of mind. We always know they’re safe, comfortable, and in great hands with Karen.

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Maria D.
Sitter Profile Image: Alyson F.
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Alyson F.
Star Sitter
from
$50
per night
4.9 out of 5 stars
69 reviews
21 repeat clients
30 years of experience
Windermere, FL, 34786

Alyson watched our two GSP’s for a quick trip to Naples. This was our first time entrusting the care of our girls and home to anyone else and she was great. Communication was great and she left the house spotless and out dogs happy and well cared for. So glad we decided to try out Rover because it’s going to make these quick trips more enjoyable knowing our dogs are being loved and cared for

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Elizabeth B.
Sitter Profile Image: Brittney C.
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Brittney C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
23 reviews
6 repeat clients
29 years of experience
Ocoee, FL, 34761

Brittney was amazing with my fur baby!. She provided tons of updates each day and even a photoshoot! I would definitely recommend Brittney and would book with her again. I came home to a very happy and healthy puppy.

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Celia C.
Sitter Profile Image: Sarah H.
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Sarah H.
Star Sitter
from
$72
per night
4.9 out of 5 stars
174 reviews
72 repeat clients
12 years of experience
Windermere, FL, 34786

Sarah was great. We went away for two weeks and had to find a pet sitter last minute. Sarah communicated well, took good care of the pups, and left the house cleaner than when she arrived.

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Tim & Tess O.
Sitter Profile Image: Thanya M.
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Thanya M.
from
$65
per night
5.0 out of 5 stars
33 reviews
10 repeat clients
16 years of experience
Orlando, FL, 32835

Thanya took great care of Tuco and the house. She is very responsive and sent updates twice a day. With her knowledge and experience with animals I felt very comfortable leaving Tuco in her care.

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Mark B.
Sitter Profile Image: Yelena L.
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Yelena L.
Star Sitter
from
$57
per night
4.9 out of 5 stars
18 reviews
2 repeat clients
40 years of experience
Gotha, FL, 34734

Yelena was great, easy to reach and communicate with. Skai loved her and she even left her a new toy to play with! You can tell she is very experienced with dogs especially being that Skai can be very hyper but it did not seem to bother her at all. I would definitely book again, she made things very easy and smooth thank you :)

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Angie B.
Sitter Profile Image: Shelley R.
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Shelley R.
Star Sitter
from
$35
per night
5.0 out of 5 stars
32 reviews
11 repeat clients
3 years of experience
Windermere, FL, 34786

Shelley was very communicative during her stay. After a rough start for not having the code to our door (completely my fault) things went very smoothly. Daisy and the house were well cared for.

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Lynne T.
Sitter Profile Image: Taylor A.
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Taylor A.
from
$35
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
20 years of experience
Winter Garden, FL, 34787

About: My first sitting job was at 14 for the neighbors across the street, during a month long trip. I have been sitting for friends on and off for the last 4 years, dogs and cats. I have a lot of experience with senior cats and cats who are on medication. I am currently an independent contractor, working as a performer. When in a show, weekends would be difficult, and at most a show run lasts 5 weeks. I also bartend at a theater, those shifts are only 4 hours, and are also only during the run of a show. My schedule always remains very flexible. Growing up I was the designated dog walker in the family, he was a very excitable and friendly dog so I have a lot of experience with dogs who pull on their leashes. I also was responsible for baths. I also have some experience with multiple dogs at a time, of all sorts of personalities. I have owned at least one cat since I was 6, I'm the girl who seeks out the cat at the party to hang out.

Sitter Profile Image: Kaitlyn J.
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Kaitlyn J.
from
$60
per night
5.0 out of 5 stars
21 reviews
3 repeat clients
5 years of experience
Windermere, FL, 34786

Kaitlyn took great care of my dog when I was away. She made sure she had plenty of walks and playtime. My dog seemed very happy when I came home to a clean house. Will be using her again!

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Allison K.
Sitter Profile Image: Nickolas J.
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Nickolas J.
Star Sitter
from
$50
per night
5.0 out of 5 stars
255 reviews
60 repeat clients
25 years of experience
Florida Center North, Orlando, FL, 32811

Nick was the absolute perfect sitter for our pup. This was our first time using Rover and we were a little worried about the process and he put our mind at ease. Now that we are home, our pup keeps going into our guest room to look for Nick, so our pup must have had a great time! Will definitely use again for our next trip!

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Colton B.
Sitter Profile Image: Jezabell D.
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Jezabell D.
Star Sitter
from
$63
per night
5.0 out of 5 stars
27 reviews
7 repeat clients
20 years of experience
Winter Garden, FL, 34787

Jezabell was great with Gabby and Romeo! This was our first time leaving them alone with someone outside our family since adopting them 7 months ago. Jezabell shared multiple photos a day with us and updates on how they were doing. We were concerned with Gabby eating as she can be picky and has not had her appetite when left before. Jezabell was very successful getting her to eat and kept to their routine. She has given us peace of mind when leaving town without them. Definitely found a great sitter to stay overnight with them and will definitely use her again!!!

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Jessica G.
Sitter Profile Image: Jonathan W.
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Jonathan W.
from
$75
per night
5.0 out of 5 stars
41 reviews
18 repeat clients
13 years of experience
Orlando, FL, 32819

Jonathan did an incredible job again! He has become our “go-to” sitter for our cat and dog. Our animals are so excited to see him and I suspect a little let down when they see us return. Lol. Jonathan provides such wonderful care and attention, sends updates and pics regularly, and it makes taking a family trip so much more relaxing knowing our fur babies are in great care. Can’t recommend him enough!

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Jim E.
Sitter Profile Image: Lindsay L.
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Lindsay L.
Star Sitter
from
$58
per night
5.0 out of 5 stars
61 reviews
20 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: Nathan B.
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Nathan B.
Star Sitter
from
$100
per night
5.0 out of 5 stars
80 reviews
32 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: Elizabeth D.
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Elizabeth D.
from
$40
per night
5.0 out of 5 stars
9 reviews
1 repeat client
10 years of experience
Windermere, FL, 34786

About: I was a Guide Dog Foundation puppy raiser and volunteer throughout college, and raised a working service dog! I've volunteered with my local humane society since I was a teenager and have fostered multiple dogs and cats as an adult and with my family. I have experience in bottle feeding newborn pups, and put all animals before myself! I became a cat lady later in life, and I've never looked back. I've transported many cats by plane, and treat my cat like the king he is, and I would do the same for yours. I am well versed in providing medicine to senior cats and know the signs to lookout for when they are distressed. I work from home with a flexible job so I am available to care for pets with ease! I currently have two fur kids (one cat and one dog) so I already am in petcare mode at all times. If staying at my home, I live in a townhome with lots of walking trails and even a private, fully enclosed courtyard that your pup can sunbathe in! I have a fully enclosed bedroom for cats to stay (and dogs if required). In addition, I have an enclosed courtyard in my townhome that your pup can sunbathe in! I have two fur-friends with me so your pet will always have a buddy. My neighborhood has many walking trails to walk with your pet. I am always nervous when I board my pet, so you can rest assured yours will be in safe hands and all precautions taken!

Sitter Profile Image: Kira S.
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Kira S.
from
$29
per night
5.0 out of 5 stars
3 reviews
1 repeat client
14 years of experience
Orlando, FL, 32836

About: I own multiple pets and am willing to work with any pet. I also work at Disney so flexibility is very important but I am part time there I'm 25 years trying to make some extra cash. A lot of people call me an animal whisperer. Animals mean so much to me and I will not be cruel. I will follow all directions given. I'm not in college right now so my schedule is very flexible. I am not allergic to anything. And can deal with anything. I love all dogs and cats. I am easy to work with and won't put up a fuss for any of your instructions. I am good at giving medications as well. Animals deserve the best care so I am willing to achieve that goal. I enjoy playing with cats and dogs. A few little scratches don't bother me.

Sitter Profile Image: Tiffany P.
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Tiffany P.
from
$50
per night
5.0 out of 5 stars
5 reviews
3 repeat clients
20 years of experience
Metro West, Orlando, FL, 32835

Tiffany was excited! Kept me updated every time she came over to walk, feed and play with my pup. I am very pleased with her service.

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Justin S.
Sitter Profile Image: Liz M.
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Liz M.
Star Sitter
from
$70
per night
5.0 out of 5 stars
6 reviews
3 repeat clients
10 years of experience
Windermere, FL, 34786

Our doggy enjoyed another wonderful sitting with Liz! We are so pleased to have found such a loving and attentive caregiver that loves spoiling our doggy as much as we do!

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Jenna K.
Sitter Profile Image: Devona S.
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Devona S.
Star Sitter
from
$30
per night
5.0 out of 5 stars
99 reviews
39 repeat clients
10 years of experience
Orlando, FL, 32839

Amazing! Devona stayed with my pup when i was away for a weekend. She kept me informed of everything, sent me photos daily, and was very quick to respond. I will definitely call her again for house sitting.

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Luciano S.
Sitter Profile Image: Jocelyn D.
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Jocelyn D.
from
$65
per night
4.9 out of 5 stars
60 reviews
24 repeat clients
11 years of experience
Orlando, FL, 32835

Jocelyn was exceptional. She made our vacation even better knowing that our animals were happy. And our arrival back home confirmed that. She was a great communicator as well.

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Josh P.
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Over 85
pet parents in Windermere have booked house sitting

Windermere pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Elizabeth was incredible! She took such good care of our pups and was a pro! We will use her every time we need a sitter! You will not be disappointed

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Rysan W.
House Sitting
5.0 out of 5 stars

First time using Rover, super nervous to leave my dog with someone I didn’t know in my hotel but felt it was a better option over doggy daycare! I choose Thanya because of her current work history working with animals as a vet tech! I felt my dog would be safe in her hands with her additional knowledge in her field of work! She made the entire process so easy, she did a meet and greet which she does not have to do which was KEY to meet us, our dog and see the location of where she needs to go vs just showing up the day we needed her. She was very friendly, flexible and on time! She took the trash out which was not asked of her and cleaned up after herself. I know my dog liked her because day 2 he didn’t bark at her when she walked in the door she had gained his trust! She followed eveything asked of her in regards to spuds needs, schedule and my little extra crazy about germs with shoes off in the hotel and washing her hands every time she walked the dog and returned back to the apartment hotel. Highly recommend, we will be using her again the next time we come to Florida and sending her info to friends and family. She is Mahoney & Spud Approved! Worth every penny! Took the best pictures of my dog too one I actually plan to frame when I get home! 🐾

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Heather M.
House Sitting
5.0 out of 5 stars

Taylor was amazing! We are new to pet-sitting and have pups that have only ever been watched by friends and family. She was very professional in all interactions from first text to first meeting with us and our dogs, to being able to do a second meet and greet right before our planned vacation to get some alone time with our grumpy older dog. She sent us photos, videos and daily updates. And everything went awesome! House was taken care of, she even watered our plants. I would 100% recommend her and she will be our go-to pet-sitter for future trips.

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Melanie N.
House Sitting
5.0 out of 5 stars

Lilly is awesome! She took care of Ellie in our home for 5 days and was flexible enough to stretch it a full day when our flights were delayed. She's conscientious, friendly and extremely mature, and she sent us frequent updates and pictures throughout the week. Ellie seemed to love spending time with her, and we felt confident leaving both our pup and our home in her hands. We would not hesitate to use her again!

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John S.
House Sitting
5.0 out of 5 stars

Nathan took such great care of our pup Winston! He communicated frequently with pictures and updates. Winston seemed very happy and at ease with him. I definitely recommend Nathan!

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Natasha L.
House Sitting
5.0 out of 5 stars

Everything went smoothly, the girls were well cared for, and the pics showed they clearly enjoyed being with Hailey. Thanks for giving me peace of mind while traveling!

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Kyle S.
House Sitting
5.0 out of 5 stars

Miranda did a great job. She sent pictures and my 4 dogs were well taken care of. I would recommend Miranda for pet sitting! Lisa

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Lisa S.
House Sitting
5.0 out of 5 stars

Alexis is an amazing sitter! She truly cares about all the animals we have. My old dog had an accident and she cleaned it up before we got home. Sorry I know what was gross.

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Randy M.
House Sitting
5.0 out of 5 stars

Laura was amazing. On time and sent tons of photos. Our dog loved her and was so comfortable with her from the moment we met her. Extremely respectful of our house and a great communicator. We look forward to having her sit for us again!

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Daniel G.
House Sitting
5.0 out of 5 stars

Handled some complicated medicine for elderly dog well. Also managed some oddball behaviors for both of them without issues.

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Julie G.
House Sitting
5.0 out of 5 stars

Aries was wonderful with my two large dogs. She sent photos daily to make the stay away less stressful. I highly recommend her!!

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Dani C.
House Sitting
5.0 out of 5 stars

Maddie was a godsend with all of our pets. We hired her for drop ins to take care of cats while we were on vacation. We emergently needed her to come additional times for dogs as well and she was able to assist while we were out of the country! Pets were well taken care of and I had peace of mind! Would 100% recommend and use her again!!!

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Jennifer O.
House Sitting
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Find pet care near you

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

House Sitting FAQs

Frequently asked questions about Rover

House sitters on Rover are free to set their rates. The median cost to hire a house sitter in Windermere on Rover as of Jun 2026 was about $45 per night, after factoring in Rover’s service fees. A house sitter’s rate may also change as you customize your booking to fit your needs.

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

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

As of Jun 2026, there are 3,062 house sitters in Windermere. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect house sitter near you. As a reminder, house sitters joining Rover must pass a background check for you and your house’s safety.

Rover makes it easy to reach out to multiple house sitters about your booking. Typically, 87% of Windermere house sitters respond in under an hour.

House sitters in Windermere have an average of 15 years of experience. House sitters with repeat customers have an average of 4 repeat clients. Experience can vary from house sitter to house sitter, but you can view reviews, years of experience, and number of repeat clients when you compare house sitters in Windermere.

Heading out of town? It’s easy to book a 5-star house sitter to take care of your home. Book a house sitter to take care of your dog and cat, while keeping an eye on your property. And the best part? Your best friend gets to stay on their home turf. Windermere house sitters are great for:

  • Dogs who’d prefer to stay on their home turf
  • Cats and caged pets
  • Pet parents on a tight schedule
  • Keeping an eye on your home and plants while you’re away

Yes! House sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your house sitter through messages on Rover for delightful photo updates. The Rover team is available 24/7, and your house 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 house 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 house sitting service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your house sitter’s cancellation policy.