Doggy Day Care in Windermere

Drop off your dog at your sitter's home in the morning, and pick them up in the evening.

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Top rated Windermere doggy day care sitters

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Sitter Profile Image: Mayara L.
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Mayara L.
Star Sitter
from
$37
per day
5 out of 5.0 stars
154 reviews
28 repeat clients
10 years of experience
Orlando, FL, 32821

Mayara was great! She responded super fast to any and all questions I had leading up to the booking. She also accommodated my dog’s special needs, as my dog was recovering from an injury. Mayara also sent tons of pictures during my dog’s stay. I highly recommend Mayara for your dog’s stay!

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Lauren A.
Sitter Profile Image: Jared C.
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Jared C.
Star Sitter
from
$30
per day
5 out of 5.0 stars
30 reviews
10 repeat clients
10 years of experience
Winter Garden, FL, 34787

Jared was great! He sent us many pics during Ace’s stay and Ace loved playing with his babies. He was so tired when we got him he went right to bed. So happy we came across Jared. He and his babies are definitely Ace’s new best friends l!!

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Jackie P.
Sitter Profile Image: Poliana D.
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Poliana D.
Star Sitter
from
$55
per day
5 out of 5.0 stars
444 reviews
134 repeat clients
15 years of experience
Windermere, FL, 34786

Poliana was amazing! This was my first time ever using this app and leaving my fur baby with anyone other than family. She eased my fears, sent so my many updated photos and videos! I’m so pleased with this being my first experience and when I come back into the area I will 100% use her services again! If you are hesitant don’t be she will take great care of your baby! Thank you so much me and Pookie appreciate you dearly!

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Gabby M.
Sitter Profile Image: Rennan C.
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Rennan C.
Star Sitter
from
$48
per day
5 out of 5.0 stars
106 reviews
31 repeat clients
6 years of experience
Orlando, FL, 32836

Rennan dogsat for our golden Luke several times over a few weeks we were in town. Luke doesn’t like to be left for long periods of time and Rennan was a perfect fit. It is apparent he loves dogs and takes good care of them and takes them for several walks to the dog park during the day. I feel so fortunate we found him!

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Kim K.
Sitter Profile Image: Kymry G.
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Kymry G.
Star Sitter
from
$35
per day
5 out of 5.0 stars
517 reviews
120 repeat clients
20 years of experience
Florida Center, Orlando, FL, 32819

Kymry was awesome with our puppy! It was our first time leaving our 4 month old puppy with a sitter and she had such a great time. From the moment we dropped her off we felt so comfortable knowing she was in good hands. Kymry kept us up to date through out the day with pictures and updates. She was also so conveniently close to the parks. Our puppy was happy when we picked her up and even dropping her off the next day. We could not have found a better sitter. Thanks Kymry!! We will definitely look to book again next time we are town and need a sitter.

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Madeline C.
Sitter Profile Image: Julie B.
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Julie B.
Star Sitter
from
$40
per day
5 out of 5.0 stars
40 reviews
10 repeat clients
45 years of experience
Winter Garden, FL, 34787

Julie did very well with Daisy. She seems very caring. She sent me pics all thru out the day which I really appreciated. We will use her again for sure.

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Denise B.
Sitter Profile Image: Cheryl O.
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Cheryl O.
from
$35
per day
5 out of 5.0 stars
26 reviews
3 repeat clients
24 years of experience
Windermere, FL, 34786

Cheryl is absolutely amazing and Rafa really enjoyed being in her care. Cheryl was very responsive and kept us updated frequently. Rafa has separation anxiety and needs a little bit more attention and Cheryl was phenomenal in making Rafa feel loved and safe. We will be seeing Cheryl again soon and Rafa is excited! Thank you so much Cheryl for taking such good care of our precious girl.

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Carolina B.
Sitter Profile Image: Angélica S.
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Angélica S.
Star Sitter
from
$30
per day
5 out of 4.9 stars
32 reviews
13 repeat clients
3 years of experience
Ocoee, FL, 32818

Angelica and her family were amazing with my dog. Very kind and gentle. They send updates and also accommodate to the times. We will definitely use the services again.

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Kristine M.
Sitter Profile Image: Tim & Tess O.
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Tim & Tess O.
from
$40
per day
5 out of 5.0 stars
60 reviews
4 repeat clients
15 years of experience
Ocoee, FL, 34761

We have rebooked multiple times with Tess and tim! My husband and I get videos and photos throughout the day of lots of play and snuggles! We know our dog is thoroughly looked after, fed, played with, and loved every time we drop off and pick up our dog. Tim and Tess are great at communicating and quick to respond ! Would highly recommend them!

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Allison A.
Sitter Profile Image: Selenia R.
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Selenia R.
from
$30
per day
5 out of 5.0 stars
2 reviews
15 years of experience
Winter Garden, FL, 34787

Always a great experience when I bring my pup to Selenia! She has a great set up in the house for the dogs and a fenced in area for the doggies to play outside! My puppy always comes back exhausted from playing all day with her shih tzu, Gigi!

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Yessenia P.
Sitter Profile Image: Gloria L.
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Gloria L.
Star Sitter
from
$50
per day
5 out of 5.0 stars
45 reviews
11 repeat clients
40 years of experience
Orlando, FL, 32819

Gloria is a very nice lady, she took good care of my dog, sent tons of video so I know my dog was very happy with her. I will definitely request her next time when I come in town. Thank you Gloria ❤️

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Tammy C.
Sitter Profile Image: Lais fernanda l.
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Lais fernanda l.
from
$35
per day
5 out of 5.0 stars
5 reviews
3 years of experience
Orlando, FL, 32819

About: Dogs bring me joy, and I love giving that joy back to them. I offer a warm, safe, and fun space where your dog can feel completely at ease — and have the time of their life! My home has a large fenced yard where pups can run, play, and explore freely. Whether they love fetch, sunbathing, or just being around someone who truly cares, I’m here to make their stay feel like a vacation. I give lots of love, attention, and cuddles — always tuned in to your dog’s unique personality. And yes, I’ll send plenty of photo updates so you never miss a moment of their happy adventures. 💛🐾 I am home all day, and caring for dogs has become one of the greatest joys of my routine. I love welcoming furry guests and giving them all the attention, playtime, and love they deserve. I speak 🇧🇷 Portuguese, 🇪🇸 Spanish and 🇺🇸 English. I have a large fenced yard and one sweet pup named Cora to keep your dog company! She is a small cavapoo very friendly and playful, the reason of our happiness. I am always home and keeping a close eye on our guests — whether they’re playing, resting, or exploring the yard. I follow all your care instructions closely, including feeding routines and walks. My home is calm, safe, and full of love — the perfect place for your dog to feel happy, relaxed, and free. Your dog might never want to leave! 🐾💛

Sitter Profile Image: Garman T.
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Garman T.
Star Sitter
from
$40
per day
5 out of 4.9 stars
22 reviews
4 repeat clients
15 years of experience
Metro West, Orlando, FL, 32835

Garman was amazing with Russell and she is the first person we have allowed to care for him and she did a great job! We hope to continue to have her be Russell sitter (:

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Julia D.
Sitter Profile Image: Kim G.
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Kim G.
Star Sitter
from
$45
per day
5 out of 4.9 stars
56 reviews
23 repeat clients
12 years of experience
Windermere, FL, 34786

We had a meet and greet first and it went well great, You can tell Kim cares about her fur clients and our 2 girls warmed up to her quickly. Even though the dogs have free rein in her home, she actually has a,designated area for dogs if they want to chill on their own. Your dog can leash walk or there is a dog park right in the neighborhood. I would definitely use Kim again.

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Mary Ann D.
Sitter Profile Image: Jerry P.
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Jerry P.
Star Sitter
from
$45
per day
5 out of 5.0 stars
548 reviews
281 repeat clients
15 years of experience
Windermere, FL, 34786

Tucker enjoyed his day with Jerry. He was anxious but the photos during day showed how he relaxed and played. Jerry has a very calm, relaxed manner which is a definite plus! Will definitely return.

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Claude D.
Sitter Profile Image: Briaunna J.
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Briaunna J.
from
$35
per day
5 out of 5.0 stars
6 reviews
1 repeat client
20 years of experience
Ocoee, FL, 34761

About: I’ve grown up with dogs of all sizes my whole life, from tiny pups to gentle giants, and have always had a passion for caring for them. I spent years volunteering at animal shelters, gaining experience with dogs of all breeds and temperaments. Becoming a sitter lets me combine my love for dogs with the joy of giving them the care they deserve. Plus, my mini dachshund would love some new playmates to hang out with! Working remotely allows me to dedicate my full attention and energy to your pets throughout the day. Whether it’s playtime, walks, feeding, or cuddles, I’m always there to meet their needs. My flexible schedule ensures they get all the love and care they deserve, just like my own mini dachshund! In my home, your pets will be treated like family. I provide a safe, loving, and fun environment where they can play, relax, and feel at ease. From daily walks and playtime to cozy nap spots and plenty of cuddles, I ensure they’re happy and comfortable. I follow your care instructions closely so they feel right at home while you’re away.

Sitter Profile Image: Gabby B.
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Gabby B.
from
$30
per day
5 out of 5.0 stars
4 reviews
15 years of experience
Orlando, FL, 32835

About: I have had dogs of my own my whole life puppies-seniors. Not only do I have dog experience care, but I have care experience when it comes to cats and horses! I am currently working as a pet sitter full time for the summer! I am here for all of your fur babys needs! Message me for more info! I will follow all instructions owner has left for me, walk them regularly, feed them on the owner’s schedule, keep a clean environment for them, and spend time with them. You let me know how you want their care to be done and that’s how I will do it!

Sitter Profile Image: Journey F.
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Journey F.
Star Sitter
from
$47
per day
5 out of 5.0 stars
32 reviews
10 repeat clients
7 years of experience
Windermere, FL, 34786

First time using this service and Journey was the best! I didn’t want to leave my fur baby alone while my family and I were at Disney World and booked with Journey. She kept me updated constantly sending pics and videos of my baby having the best time! Knowing she was well taken care helped enjoy my day at Disney even more! Thanks Journey!!! :) will definitely be booking again with her next trip!

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Karla L.
Sitter Profile Image: Amanda B.
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Amanda B.
from
$40
per day
5 out of 5.0 stars
86 reviews
23 repeat clients
5 years of experience
Orlando, FL, 32835

Amanda was fantastic!!! This was my first time ever using a dog sitter for my Doberman & I was very nervous leaving him with someone else, but she made me feel so secure & comfortable with my decision immediately!! She has the best set up at her home & is extremely loving & caring with the dogs! I truly felt like she took care of him as if he was hers! He is such a happy boy coming home & super tired so I know he got a lot of energy out with her at her place playing with her & all the other dog’s! I will definitely be using her again anytime I am in need!! Highly highly recommend Amanda for your precious fur babies!!

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Nikki L.
Sitter Profile Image: Lauren R.
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Lauren R.
Star Sitter
from
$25
per day
5 out of 5.0 stars
21 reviews
5 repeat clients
12 years of experience
Windermere, FL, 34786

Lauren was great! Sent updates throughout the day and Winnie had a great time running around in the backyard. Will definitely book Lauren again in the future.

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Samantha S.
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Sitter Profile Image: Mayara L.
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Sitter Profile Image: Mayara L.
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Mayara L.
Star Sitter

5-20 min from all parks!!!
Orlando, FL, 32821
7.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care
from
$37
per day
5 out of 5.0 stars
154 reviews
28 repeat clients
Profile image

Mayara was great! She responded super fast to any and all questions I had leading up to the booking. She also accommodated my dog’s special needs, as my dog was recovering from an injury. Mayara also sent tons of pictures during my dog’s stay. I highly recommend Mayara for your dog’s stay!

Availability updated today
Sitter Profile Image: Jared C.
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Sitter Profile Image: Jared C.
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Jared C.
Star Sitter

Your dogs other best friend
Winter Garden, FL, 34787
6.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5 out of 5.0 stars
30 reviews
10 repeat clients
Profile image

Jared was great! He sent us many pics during Ace’s stay and Ace loved playing with his babies. He was so tired when we got him he went right to bed. So happy we came across Jared. He and his babies are definitely Ace’s new best friends l!!

Availability updated today
Sitter Profile Image: Poliana D.
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Sitter Profile Image: Poliana D.
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Poliana D.
Star Sitter

Real home away from home 🐾
Windermere, FL, 34786
4.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$55
per day
5 out of 5.0 stars
444 reviews
134 repeat clients
Profile image

Poliana was amazing! This was my first time ever using this app and leaving my fur baby with anyone other than family. She eased my fears, sent so my many updated photos and videos! I’m so pleased with this being my first experience and when I come back into the area I will 100% use her services again! If you are hesitant don’t be she will take great care of your baby! Thank you so much me and Pookie appreciate you dearly!

Availability updated today
Sitter Profile Image: Rennan C.
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Sitter Profile Image: Rennan C.
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Rennan C.
Star Sitter

Animal lover! Disney area
Orlando, FL, 32836
3.7 mi. away
Boarding, Doggy Day Care
from
$48
per day
5 out of 5.0 stars
106 reviews
31 repeat clients
Profile image

Rennan dogsat for our golden Luke several times over a few weeks we were in town. Luke doesn’t like to be left for long periods of time and Rennan was a perfect fit. It is apparent he loves dogs and takes good care of them and takes them for several walks to the dog park during the day. I feel so fortunate we found him!

Availability updated yesterday
Sitter Profile Image: Kymry G.
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Sitter Profile Image: Kymry G.
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Kymry G.
Star Sitter

Animal lover/close to local attract
Florida Center, Orlando, FL, 32819
4.4 mi. away
Boarding, Doggy Day Care
from
$35
per day
5 out of 5.0 stars
517 reviews
120 repeat clients
Profile image

Kymry was awesome with our puppy! It was our first time leaving our 4 month old puppy with a sitter and she had such a great time. From the moment we dropped her off we felt so comfortable knowing she was in good hands. Kymry kept us up to date through out the day with pictures and updates. She was also so conveniently close to the parks. Our puppy was happy when we picked her up and even dropping her off the next day. We could not have found a better sitter. Thanks Kymry!! We will definitely look to book again next time we are town and need a sitter.

Availability updated today
Sitter Profile Image: Julie B.
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Sitter Profile Image: Julie B.
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Julie B.
Star Sitter

Enjoy Florida, I got your fur baby!
Winter Garden, FL, 34787
5.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 5.0 stars
40 reviews
10 repeat clients
Profile image

Julie did very well with Daisy. She seems very caring. She sent me pics all thru out the day which I really appreciated. We will use her again for sure.

Availability updated yesterday
Sitter Profile Image: Cheryl O.
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Sitter Profile Image: Cheryl O.
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Cheryl O.

Experienced, mature, trustworthy :)
Windermere, FL, 34786
4.0 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 5.0 stars
26 reviews
3 repeat clients
Profile image

Cheryl is absolutely amazing and Rafa really enjoyed being in her care. Cheryl was very responsive and kept us updated frequently. Rafa has separation anxiety and needs a little bit more attention and Cheryl was phenomenal in making Rafa feel loved and safe. We will be seeing Cheryl again soon and Rafa is excited! Thank you so much Cheryl for taking such good care of our precious girl.

Availability updated 10 days ago
Sitter Profile Image: Angélica S.
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Sitter Profile Image: Angélica S.
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Angélica S.
Rover 101
Star Sitter

Loving pet sitter, Home full-time
Ocoee, FL, 32818
4.4 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5 out of 4.9 stars
32 reviews
13 repeat clients
Profile image

Angelica and her family were amazing with my dog. Very kind and gentle. They send updates and also accommodate to the times. We will definitely use the services again.

Availability updated 2 days ago
Sitter Profile Image: Tim & Tess O.
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Sitter Profile Image: Tim & Tess O.
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Tim & Tess O.

Walk/run or sleepover for your pup
Ocoee, FL, 34761
4.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 5.0 stars
60 reviews
4 repeat clients
Profile image

We have rebooked multiple times with Tess and tim! My husband and I get videos and photos throughout the day of lots of play and snuggles! We know our dog is thoroughly looked after, fed, played with, and loved every time we drop off and pick up our dog. Tim and Tess are great at communicating and quick to respond ! Would highly recommend them!

Availability updated 3 months ago
Sitter Profile Image: Selenia R.
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Sitter Profile Image: Selenia R.
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Selenia R.

Your baby is my baby. ❤️
Winter Garden, FL, 34787
4.5 mi. away
Boarding, House Sitting, Doggy Day Care
from
$30
per day
5 out of 5.0 stars
2 reviews
Profile image

Always a great experience when I bring my pup to Selenia! She has a great set up in the house for the dogs and a fenced in area for the doggies to play outside! My puppy always comes back exhausted from playing all day with her shih tzu, Gigi!

Availability updated 23 days ago
Sitter Profile Image: Gloria L.
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Sitter Profile Image: Gloria L.
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Gloria L.
Star Sitter

I love animals and they love me 💕
Orlando, FL, 32819
2.6 mi. away
Boarding, Doggy Day Care
from
$50
per day
5 out of 5.0 stars
45 reviews
11 repeat clients
Profile image

Gloria is a very nice lady, she took good care of my dog, sent tons of video so I know my dog was very happy with her. I will definitely request her next time when I come in town. Thank you Gloria ❤️

Availability updated yesterday
Sitter Profile Image: Lais fernanda l.
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Sitter Profile Image: Lais fernanda l.
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Lais fernanda l.

🐶 A life of cuddles, care & tail.
Orlando, FL, 32819
2.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per day
5 out of 5.0 stars
5 reviews

Lais is now our go to pet sitter when we are out of town. My baby Miley absolutely loves her. She sends us updates and pictures all the time. Plus, she has a fenced backyard so I don’t have to worry about Miley. She has stayed with Lais on four different occasions, two overnight (4 nights each time) and twice when I had an all day long conference and couldn’t leave Miley alone. It’s a blessing to be able to trust someone with my little angel.

Availability updated 5 days ago
Sitter Profile Image: Garman T.
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Sitter Profile Image: Garman T.
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Garman T.
Rover 101
Star Sitter

Tiny paws, EPIC awws 🐾🌎🎢🧙🏻‍♂️
Metro West, Orlando, FL, 32835
3.9 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 4.9 stars
22 reviews
4 repeat clients
Profile image

Garman was amazing with Russell and she is the first person we have allowed to care for him and she did a great job! We hope to continue to have her be Russell sitter (:

Availability updated yesterday
Sitter Profile Image: Kim G.
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Sitter Profile Image: Kim G.
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Kim G.
Rover 101
Star Sitter

A fun stay - Close to Disney!
Windermere, FL, 34786
3.4 mi. away
Boarding, Doggy Day Care
from
$45
per day
5 out of 4.9 stars
56 reviews
23 repeat clients
Profile image

We had a meet and greet first and it went well great, You can tell Kim cares about her fur clients and our 2 girls warmed up to her quickly. Even though the dogs have free rein in her home, she actually has a,designated area for dogs if they want to chill on their own. Your dog can leash walk or there is a dog park right in the neighborhood. I would definitely use Kim again.

Availability updated 2 days ago
Sitter Profile Image: Jerry P.
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Sitter Profile Image: Jerry P.
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Jerry P.
Star Sitter

Lake Butler Doggy Daycare
Windermere, FL, 34786
2.2 mi. away
Boarding, Doggy Day Care
from
$45
per day
5 out of 5.0 stars
548 reviews
281 repeat clients
Profile image

Tucker enjoyed his day with Jerry. He was anxious but the photos during day showed how he relaxed and played. Jerry has a very calm, relaxed manner which is a definite plus! Will definitely return.

Availability updated today
Sitter Profile Image: Briaunna J.
Verified Enhanced Background Check
Sitter Profile Image: Briaunna J.
Verified Enhanced Background Check

Briaunna J.

Where Your Dog Feels at Home!
Ocoee, FL, 34761
3.4 mi. away
Boarding, Doggy Day Care
from
$35
per day
5 out of 5.0 stars
6 reviews
1 repeat client

Briaunna has cared for my dogs numerous times with excellence. Her love for my animals (and their love for her) are exactly what they need while we are away. She is an intentional, responsible , attentive and a very doting sitter. I appreciate her dedicated service and communication with the our family while apart from our animals. Definitely would recommend her to Rover and anyone needing above and beyond care and devotion to their dogs!

Availability updated 86 days ago
Sitter Profile Image: Gabby B.
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Sitter Profile Image: Gabby B.
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Gabby B.

@GhostWatchPetServices on FB/IG
Orlando, FL, 32835
2.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$30
per day
5 out of 5.0 stars
4 reviews

Gabby was wonderful with my pets. They were so loved and cared for when we had to go out of town. I highly recommend Gabby. Gabby walked, brushed and , bathed my pets l, they looked great!

Availability updated today
Sitter Profile Image: Journey F.
Verified Enhanced Background Check
Sitter Profile Image: Journey F.
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Journey F.
Star Sitter

Take a Journey in Pet Pampering !
Windermere, FL, 34786
2.5 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$47
per day
5 out of 5.0 stars
32 reviews
10 repeat clients
Profile image

First time using this service and Journey was the best! I didn’t want to leave my fur baby alone while my family and I were at Disney World and booked with Journey. She kept me updated constantly sending pics and videos of my baby having the best time! Knowing she was well taken care helped enjoy my day at Disney even more! Thanks Journey!!! :) will definitely be booking again with her next trip!

Availability updated 2 days ago
Sitter Profile Image: Amanda B.
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Sitter Profile Image: Amanda B.
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Amanda B.
Rover 101

Your Pet’s Favorite BabySitter 🐾
Orlando, FL, 32835
2.1 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$40
per day
5 out of 5.0 stars
86 reviews
23 repeat clients
Profile image

Amanda was fantastic!!! This was my first time ever using a dog sitter for my Doberman & I was very nervous leaving him with someone else, but she made me feel so secure & comfortable with my decision immediately!! She has the best set up at her home & is extremely loving & caring with the dogs! I truly felt like she took care of him as if he was hers! He is such a happy boy coming home & super tired so I know he got a lot of energy out with her at her place playing with her & all the other dog’s! I will definitely be using her again anytime I am in need!! Highly highly recommend Amanda for your precious fur babies!!

Availability updated 2 days ago
Sitter Profile Image: Lauren R.
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Sitter Profile Image: Lauren R.
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Lauren R.
Star Sitter

Work from home dog mom!
Windermere, FL, 34786
1.4 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$25
per day
5 out of 5.0 stars
21 reviews
5 repeat clients
Profile image

Lauren was great! Sent updates throughout the day and Winnie had a great time running around in the backyard. Will definitely book Lauren again in the future.

Availability updated 4 days ago

How Rover works

  1. 1. Search

    Read verified reviews by dog parents like you and choose a sitter who’s a great match for you and your dogs
  2. 2. Meet & Greet

    Meet either virtually or in-person with a sitter to discuss the level of care needed for your dogs 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 dog sitter has to cancel, we’ll work with you to find a new sitter.

  • World-class support

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

Doggy Day Care FAQs

Frequently asked questions about Rover