House Sitting in Winter Garden

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

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Top rated Winter Garden 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: Diahann B.
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Diahann B.
Star Sitter
from
$35
per night
5.0 out of 5 stars
21 reviews
7 repeat clients
5 years of experience
Winter Garden, FL, 34787

I am so glad that I found Diahann to pet/house sit while we were traveling internationally. She was great with our 2 pugs. She was extremely responsible and communicative, sending us daily updates about our girls. Our home was also in perfect condition when we returned. Being a veterinarian myself, I can be picky about who takes care of our dogs, but Diahann definitely passed with flying colors. As long as she is available, she will be my go to pet sitter from now on.

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

If I could give Nickolas 10 stars, I would! He was literally perfect. Very professional and an outstanding communicator. The whole time I was gone, he provided daily updates with pictures. I was anxious about leaving my Skye Sissy with anyone whom she didn't know, but she loved him from the minute he met her. I felt confident leaving, I did not worry because I know that she was in capable and loving hands. Bravo to Nickolas for simply being AWESOME!

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Andrea P.
Sitter Profile Image: Joe N.
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Joe N.
from
$20
per night
5.0 out of 5 stars
10 reviews
2 repeat clients
2 years of experience
Winter Garden, FL, 34787

Easy communication and sent me great photos throughout! My cat can be very shy and she warmed up to him pretty fast. Would book with Joe again!

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Mckenna F.
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: Emma B.
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Emma B.
from
$32
per night
5.0 out of 5 stars
5 reviews
2 repeat clients
8 years of experience
Winter Garden, FL, 34787

Such a great feeling to feel confident and at ease in leaving my precious baby with Emma. She is very sweet and took great care of my Pug and my home. She made sure to send me pictures and put my mind at ease. I will definitely be using her again.

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Luisa R.
Sitter Profile Image: Yelena L.
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Yelena L.
Star Sitter
from
$51
per night
4.9 out of 5 stars
15 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: Sarah H.
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Sarah H.
Star Sitter
from
$68
per night
4.9 out of 5 stars
171 reviews
71 repeat clients
12 years of experience
Windermere, FL, 34786

Thank you for caring for our boys... The pictures your sent and all the fun moments and experiences with them kept us calm and relaxed while away. We came home to happy Cats. You are wonderful 😊

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Sasha M.
Sitter Profile Image: Brenda & Dwain K.
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Brenda & Dwain K.
Star Sitter
from
$40
per night
4.9 out of 5 stars
54 reviews
18 repeat clients
25 years of experience
Apopka, FL, 32703

My girl got into some meds while I was at work. Dwain was quick to try to contact me when he stopped by the house and quick to action. They couldn't be in better hands and I'm so grateful.

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Anna B.
Sitter Profile Image: Kaitlyn J.
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Kaitlyn J.
from
$60
per night
5.0 out of 5 stars
20 reviews
2 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: Jezabell D.
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Jezabell D.
Star Sitter
from
$63
per night
5.0 out of 5 stars
26 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: 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 was a fantastic housesitter and we would be happy to have her back at any point in the future. Our large dog and two cats were well cared for and completely chilled out and happy when we got back home. Thanya kept us in the loop with plenty of updates and made sure to communicate with any questions/details we forgot in our initial meet and greet. I know our new kitten was a handful in particular so I really appreciate her patience and attention. Thanks so much Thanya!

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

Alyson stayed at my home x 2 nights with my mischievous Great Dane pup and my 10 year old Doberman. She was prompt with communication and sent updates which allowed me to enjoy my first weekend away in a long time. My dogs were well cared for! I definitely recommend her and will book with her in the future!

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Lory V.
Sitter Profile Image: Karrie M.
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Karrie M.
from
$50
per night
4.9 out of 5 stars
121 reviews
27 repeat clients
45 years of experience
Clermont, FL, 34711

Karrie went above and beyond her call of duty. I always call text and let er know when I am leaving and same when i get back. when she had not heard from me she text and did not get an answer. The air terrific in orland had been shut down and we were in a holding pattern due to the storm that was over Orlando. She went back to my home fed the babies, storming too bad to walk them at the time. Then she came back to walk them, and I had just gotten home. My babies were just as happy to see her as they were me. She loves my babies and treats them like they were her own. If you're looking for someone to trust and take care of your pets like you do, she is the one. I will not use anyone but her. I will reschedule my plans so that she takes care of my babies. I was very nervous at first, now no worries at all.

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Tonie T.
Sitter Profile Image: Imani Z.
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Imani Z.
from
$32
per night
5.0 out of 5 stars
30 reviews
5 repeat clients
10 years of experience
Winter Garden, FL, 34787

Imani did an outstanding job caring for our 4 dogs. She was communicative, professional and very sweet with our pups. They responded positively towards her right away. We are happy to have Imani for our pet sitting needs!

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Christina M.
Sitter Profile Image: Zoe R.
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Zoe R.
from
$60
per night
5.0 out of 5 stars
23 reviews
5 repeat clients
5 years of experience
Colorado University, Winter Garden, FL, 34787

Zoe did a wonderful job taking care of my scared pup. He surprisingly opened up to her right away. She was very responsive and I'll certainly be booking again.

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Eric B.
Sitter Profile Image: Taylor A.
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Taylor A.
from
$35
per night
5.0 out of 5 stars
5 reviews
2 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: Skylar D.
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Skylar D.
from
$40
per night
5.0 out of 5 stars
11 reviews
6 repeat clients
6 years of experience
Ocoee, FL, 34761

Skylar arrived on time and sent photos to reassure me that my dogs were doing well. Just a short booking but I felt safe leaving my dogs with her.

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Katherine B.
Sitter Profile Image: Steffanie D.
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Steffanie D.
from
$50
per night
5.0 out of 5 stars
24 reviews
6 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: sofia a.
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sofia a.
from
$50
per night
5.0 out of 5 stars
8 reviews
1 repeat client
10 years of experience
Winter Garden, FL, 34787

Sophia was excellent from our initial contact through until she left after completing the job. We received updates and photos throughout her time with Coleman. She was prompt, polite, and just the caregiver our boy needed for the night. Will not hesitate to call her again!

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Coleman C.
Sitter Profile Image: Aaliyah R.
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Aaliyah R.
from
$33
per night
5.0 out of 5 stars
2 reviews
1 year of experience
Ocoee, FL, 34761

Aaliyah was very friendly and communicative with the dogs. She was very attentive and available and kept sending updates each day. Aaliyah was also very clean and left no messes behind after housesitting for us. We would definitely hire Aaliyah again.

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Mario C.
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Over 722
pet parents in Winter Garden have booked house sitting

Winter Garden pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

Jezabell was such an amazing dog sitter! She gave frequent updates and sent lots of pictures. She also took excellent care of our home and left it spotless. She is trust worthy and I already booked her for future drop ins! I highly highly recommend her!!

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Emma H.
House Sitting
5.0 out of 5 stars

I can’t say enough good things about Delanie. She went above and beyond in every way. From the moment we booked, communication was effortless, updates were thoughtful, and the level of care she gave Oliver and Sophie was exceptional. I came home to a happy, relaxed fur babies. Absolutely perfect, thank you Delanie for everything!

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Dana W.
House Sitting
5.0 out of 5 stars

I never used Rover before and was nervous, but Chelsea eased my mind. She was so nice, great communication, and sent lots of pics of Morty.

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Desiree G.
House Sitting
5.0 out of 5 stars

Emma was absolutely wonderful from start to finish. She was so kind, caring, and attentive, and I immediately felt comfortable leaving Cosmo in her care. Her communication throughout the stay was excellent, and she consistently kept me updated which gave me so much peace of mind. On top of that, she was incredibly adaptable and flexible when my AC unexpectedly went out. I felt terrible about the situation, but Emma remained so positive, understanding, and accommodating through it all. Because of her, I was able to stay with my family without worrying about Cosmo and knew he was being very well cared for. I’m beyond thankful for Emma and truly could not recommend her enough. Anyone would be lucky to have her care for their pets!

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Lauren D.
House Sitting
5.0 out of 5 stars

Mirella was great! She kept in communication throughout our entire trip and sent pictures and videos of our pups. We came home to a nice clean house

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Jose H.
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

Karen is so good to our pup! He loves getting to spend time with her and she gives us great peace of mind. She is an excellent communicator and sends pics during her stay. Can’t say enough good things about her!

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Deanna C.
House Sitting
5.0 out of 5 stars

Callie was great and so easy to work with. Took great care of my dog and house during some crazy weather!

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Jaimy T.
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

Diahann is a blessing to have caring for our dogs! They are comfortable with her and she’s very attentive to their needs. Lots of communication while we are away. Respectful of our home.

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Jane B.
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 Winter Garden 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 Winter Garden 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 Winter Garden 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 Winter Garden 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 2,861 house sitters in Winter Garden. 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 Winter Garden house sitters respond in under an hour.

House sitters in Winter Garden have an average of 14 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 Winter Garden.

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. Winter Garden 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.