Pet Boarding in Winter Garden

Find a loving Winter Garden pet sitter to watch your cat or dog overnight at your sitter’s home.

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Top rated Winter Garden pet boarders

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: Andrew M.
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Andrew M.
from
$45
per night
5.0 out of 5 stars
315 reviews
138 repeat clients
30 years of experience
Clermont, FL, 34715

Highly recommended! Daily pictures and updates. When we picked them up they (our pups) were not even that excited to see us since they were having so much fun. Will definitely leave them again with Andrew and fam! Thank you!

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Michelle S.
Sitter Profile Image: Roseli G.
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Roseli G.
Star Sitter
from
$45
per night
5.0 out of 5 stars
342 reviews
97 repeat clients
40 years of experience
Winter Garden, FL, 34787

Roseli is truly passionate about dogs. Her home is totally decked out and pet friendly. Sunny loves to go there. She cooks special food for the dogs and takes them to the dog park multiple times a day. We have loved having her take care of Sunny. Highly recommended. She can do long term dog sitting for many nights or short term.

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Dallas T.
Sitter Profile Image: Denys H.
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Denys H.
Star Sitter
from
$30
per night
5.0 out of 5 stars
78 reviews
24 repeat clients
17 years of experience
Altamonte Springs, FL, 32714

This was my first time using Rover and I love it . Denys was so nice and kind . She kept us always with and update and makes us feel secure . Thank you so much Denys for taking care of Choco . If you ever need a pet care Denys definitely is the one . ☺️☺️☺️☺️☺️

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Katherine C.
Sitter Profile Image: Jared C.
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Jared C.
Star Sitter
from
$45
per night
5.0 out of 5 stars
55 reviews
18 repeat clients
10 years of experience
Winter Garden, FL, 34787

This is our second time using Jared and what can I say except that he is exceptional. I love all the updates to what my two huskies are up to while under his care. He understands the energy of a husky and my girls love hanging out with his dogs. I would definitely hire again with full confidence that my girls are being well cared for

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Mary R.
Sitter Profile Image: Kallee & Daniel C.
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Kallee & Daniel C.
Star Sitter
from
$39
per night
5.0 out of 5 stars
6 reviews
2 repeat clients
10 years of experience
Orlando, FL, 32808

"I recently boarded my dog at Kallee and Daniel twice, and I couldn't be happier with the experience. Kallee was very warm and welcoming at our first Meet & Greet and took the time to get to know my dog. During our two boarding occasions, she provided daily updates and shared photos multiple times a day, which eased my mind while I was away. My dog came home happy with no signs of anxiety. I appreciate Kallee to provide loving environment and accommodate our request to pickup and drop off time change at the last minute. I highly recommend Kallee and Daniel to any pet parent☺️

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Archana K.
Sitter Profile Image: Kristin O.
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Kristin O.
from
$36
per night
5.0 out of 5 stars
16 reviews
1 repeat client
20 years of experience
Clermont, FL, 34714

Kristin was so caring and loving with my senior dog. I knew he was in great hands the entire time I was away and did not need to worry about him. I will definitely be booking with her again in the future.

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Sharon G.
Sitter Profile Image: Bryan G.
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Bryan G.
Star Sitter
from
$30
per night
5.0 out of 5 stars
10 reviews
5 repeat clients
10 years of experience
Maitland, FL, 32751

Bryan always does a great job taking care of our cat and dog. They are very comfortable with him and we will continue to book with Bryan whenever we need a sitter.

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Stephanie S.
Sitter Profile Image: Carilyn & Jorge M.
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Carilyn & Jorge M.
Star Sitter
from
$44
per night
5.0 out of 5 stars
265 reviews
85 repeat clients
15 years of experience
Orlando, FL, 32808

Carilyn and Jorge were very caring to my Boy, Poppy! I was so impressed about their process of getting Poppy acclimated into the new environment for him. This was Poppy's first (Ever) Pet sitting situation, and I now feel more comfortable about allowing him (and myself) some away time! Thank you for his great care :)

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Chana T.
Sitter Profile Image: Tisha F.
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Tisha F.
from
$28
per night
5.0 out of 5 stars
10 reviews
3 repeat clients
1 year of experience
Apopka, FL, 32703

Great communication and you can tell she has a real passion for dogs overall. She was open to watching my new untrained puppy with no hesitation. Will definitely request her again!

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Tiffany M.
Sitter Profile Image: Katie c.
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Katie c.
Star Sitter
from
$37
per night
4.9 out of 5 stars
94 reviews
41 repeat clients
20 years of experience
Windermere, FL, 34786

Katie took great care of my fur baby! My dog was exceptionally cared for and warmed up quickly with Katie. I felt very comfortable leaving my doggy in her hands! I will definitely be returning. :)

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Shaneece S.
Sitter Profile Image: Venessa T.
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Venessa T.
from
$40
per night
5.0 out of 5 stars
88 reviews
35 repeat clients
20 years of experience
Orlando, FL, 32818

Venessa was wonderful! She stayed in constant communication with us and sent lots of pictures and videos of our pup. We would definitely book with Venessa again!

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Anthony M.
Sitter Profile Image: Maria A.
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Maria A.
Star Sitter
from
$38
per night
5.0 out of 5 stars
70 reviews
35 repeat clients
17 years of experience
Groveland, FL, 34736

Will definitely contact Maria for all future fur-sitting needs. I was skeptical of using Rover but was in a last minute pinch. Maria was so great! Fred looked happy upon pick up. He looks well taken care of and she also sent me daily pictures and updates throughout the week.

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Janessa L.
Sitter Profile Image: Rennan C.
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Rennan C.
Star Sitter
from
$48
per night
5.0 out of 5 stars
155 reviews
51 repeat clients
6 years of experience
Orlando, FL, 32836

Rennan takes care of our dog like his own! He goes above and beyond to help us and accommodate us. He is the BEST and we use him every time we need someone to take care of our dog!

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claudia
Sitter Profile Image: Ariana C.
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Ariana C.
from
$36
per night
5.0 out of 5 stars
17 reviews
7 repeat clients
35 years of experience
Ocoee, FL, 34761

Ariana took wonderful care of my Poppy. She made her feel comfortable and happy. She also sent us pictures of her every day. I am extremely pleased with the care she took of Poppy and will definitely use her again if needed.

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Joan P.
Sitter Profile Image: Jerarlin C.
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Jerarlin C.
Star Sitter
from
$43
per night
4.9 out of 5 stars
111 reviews
33 repeat clients
11 years of experience
Mount Dora, FL, 32757

Jerarlin was super! Cooper took to her right away. She took us on short notice but was very accommodating. Sent some great pics of Cooper having a good time. This was our first time using Rover and Jerarlin. We will definitely use her again if she will have us.

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Kress M.
Sitter Profile Image: Feliksa Z.
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Feliksa Z.
Star Sitter
from
$35
per night
4.9 out of 5 stars
81 reviews
39 repeat clients
25 years of experience
Apopka, FL, 32712

Feliksa has watched my dog several times since the beginning of the year. She is attentive to my dog's needs and provides a stress-free environment. I highly recommend her if you are in the Apopka area.

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Sheila W.
Sitter Profile Image: Jordan B.
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Jordan B.
Star Sitter
from
$40
per night
5.0 out of 5 stars
11 reviews
3 repeat clients
7 years of experience
Metro West, Orlando, FL, 32835

Jordan did a good job, she communicated & sent me videos concerning my dog daily. I would definitely use her again.

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Mrs Shelia L.
Sitter Profile Image: Selenia R.
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Selenia R.
from
$48
per night
5.0 out of 5 stars
10 reviews
1 repeat client
10 years of experience
Winter Garden, FL, 34787

We were very happy to have Abby stay with Selenia when we took a week long cruise. We received great reports and pics. Will definitely use Selenia's service again! Thanks Selenia!

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Douglas P.
Sitter Profile Image: Nathaniel R.
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Nathaniel R.
Star Sitter
from
$33
per night
5.0 out of 5 stars
16 reviews
2 repeat clients
20 years of experience
Orlando, FL, 32806

This was our third time using Rover, and once again, it was a great experience! We left Zeus with Nathaniel, and we couldn’t be happier with the care he gave him. He is very kind and friendly, and he made both of us feel completely at ease from the very beginning. Nathaniel is reliable, responsible, and honest—everything you could hope for when leaving your pet with someone. He treated our furry friend like his own, which we truly appreciated. A big plus is that he’s located very close to the airport, which made drop-off and pick-up super easy and convenient on our way home. We highly recommend him to anyone looking for a trustworthy and caring sitter, and we would definitely leave our big dog with him again!

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Yiseth G.
Sitter Profile Image: Tia R.
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Tia R.
from
$40
per night
5.0 out of 5 stars
33 reviews
9 repeat clients
30 years of experience
Ocoee, FL, 34761

There’s some people you meet and right away you have a good feeling about them, that’s how it was with Tia. This was my first time using her and my feeling was correct, she was great! I will use her every time I need someone to watch my English bulldog Winston.

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Mandy P.
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Winter Garden pet parents share their Rover experiences

1 / 1
5.0 out of 5 stars

This was our girl’s first stay with Mimi and it was great! Mimi was kind and welcoming and our girl seemed happy and relaxed at pickup. Mimi walks her guests, her home is clean and the backyard is large and fenced in. We received picture updates and she responded quickly when I had a question. Thank you Mimi for caring for Ruthie while we were away. We look forward to seeing you again. Blessings

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Leticia S.
Boarding
5.0 out of 5 stars

Monica was absolutely fantastic while caring for our dog, Willa. She was so easy to work with, dependable, and kept us updated every day with messages and photos, which gave us tremendous peace of mind while we were away. It was obvious that Willa was well cared for and receiving lots of attention and love. Monica treated Willa like one of her own, and we could tell how comfortable and happy she was in her care. We are so grateful for everything Monica did and would highly recommend her to anyone looking for a caring, trustworthy pet sitter.

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Laura M.
Boarding
5.0 out of 5 stars

Connor was fantastic with Grace so much so she’s knocked out. He treated her as if she was his, he sent lots of photos and made me feel very comfortable leaving her with him. We will be returning.

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Martha F.
Boarding
5.0 out of 5 stars

Fantastic dog sitter. Plenty of photos to see how Dory was enjoying her stay. Excellent communication as well, I’d be happy to book again!

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John H.
Boarding
5.0 out of 5 stars

This is our second booking with Caroline (first time boarding) and could not recommend her enough! She is phenomenal with our 1 year old lab, Sailor. We loved the video update of Sailor and her pup, Olive, running around in their yard playing!

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Kallee & Daniel C.
Boarding
5.0 out of 5 stars

5 stars! Lani was very responsive and sent a lot of pictures. She had our fur baby for over a week and he came back happy and healthy!

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Nicole G.
Boarding
5.0 out of 5 stars

Our Boston Terrier loves Julie & her family, they treat her like their own. She sends us photos everyday and follows all medication instructions. We have recommended her to others and will continue to do so.

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Leonard B.
Boarding
5.0 out of 5 stars

Tula had a wonderful time and I recieved photos and communication everyday. The photos speak for themselves about how well they treated Tula. Definitely will recommend them for friends!

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Margaret L.
Boarding
5.0 out of 5 stars

Denise was amazing! She sent daily pictures and updates which we appreciated. We highly recommend Denise if you’re looking for someone to care for your pup!

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Lauren K.
Boarding
5.0 out of 5 stars

Sara and her family took great care of our dog Baymax while we were away! She sent frequent photo updates, and gave him a weekend full of playtime and snuggles. I wouldn't hesitate to book again!

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Ashley M.
Boarding
5.0 out of 5 stars

Linda was great as always! We really appreciate her and the care she takes with our dog. She always keeps us up to date and sends a lot of pictures and videos of his stay.

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Erin B.
Boarding
5.0 out of 5 stars

Cary and her husband provided EXCELLENT care of our older dog Bella! Cary sent almost daily updates, with pics, and when we returned after 6 nights Bella was HAPPY! That, in and of itself, let us know she was treated with lots of love!! They are professional, considerate caretakers and natural dog people. We would 100% recommend!! 😃👍👍

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Carrisa D.
Boarding
5.0 out of 5 stars

Our dog Toby had the best time with this family! They were so attentive to him and good with communicating with us during the 2 week stay at their home. We will soooo be using them again when we have to go out of town.

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Jodi D.
Boarding
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How Rover works

  1. 1. Search

    Read verified reviews by pet parents like you and choose a boarder who’s a great match for you and your pets
  2. 2. Meet & Greet

    Meet either virtually or in-person with a boarder 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!

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 boarding sitter has to cancel, we’ll work with you to find a new pet boarding sitter.

  • World-class support

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

Pet Boarding FAQs

Frequently asked questions about Rover

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

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

Typically, pet boarding sitters on Rover respond in under an hour, so you should be matched with the perfect sitter for you and your pet in no time!

Experience can vary widely from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when comparing sitters available in Winter Garden.

Rover makes it easy to find Winter Garden pet boarding sitters to provide loving care from their own home. The background-checked, 5-star 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 boarding is great for:

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

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