Dog Boarding in Winter Park

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Sitter Profile Image: Deanna B.
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Sitter Profile Image: Deanna B.
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1. Deanna B.

Star Sitter
A home away from home
Maitland, FL, 32751
2.5 mi. away
Boarding
from
$35
per night
5 out of 5.0 stars
19 reviews
12 repeat clients
Profile image

I’m afraid to say how wonderful Deanna was with our Tilly because then she might be booked when WE need her! 🤣 Deanna was wonderful! Tilly enjoyed vacationing with her!

Availability updated 3 days ago
Sitter Profile Image: Osmel G.
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Sitter Profile Image: Osmel G.
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2. Osmel G.

Your fur babies are like family to
Baldwin Park, Orlando, FL, 32814
2.2 mi. away
Boarding
from
$30
per night
5 out of 5.0 stars
7 reviews
2 repeat clients
Profile image

Osmel was amazing with my dogs, Sunny and Diva! He took such great care of them—attentive, kind, and clearly experienced. I felt totally at ease knowing they were in good hands. Sunny and Diva were happy and relaxed when I got back, which says it all. Highly recommend Osmel to anyone looking for a trustworthy and caring pet sitter!

Availability updated yesterday
Sitter Profile Image: Andrew & Krista O.
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Sitter Profile Image: Andrew & Krista O.
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3. Andrew & Krista O.

Loving dogs since the 90s!
Winter park, FL, 32792
2.4 mi. away
Boarding, Doggy Day Care
from
$30
per night
5 out of 5.0 stars
12 reviews
2 repeat clients
Profile image

Krista and Andrew gave me peace of mind while I was away. They communicated well, and sent many pictures. Will definitely book with them again.

Availability updated 7 days ago
Sitter Profile Image: Carla B.
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Sitter Profile Image: Carla B.
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4. Carla B.

Rover 101
Star Sitter
Winter Park Puppy Play
Winter Park, FL, 32792
3.3 mi. away
Boarding, House Sitting
from
$40
per night
5 out of 5.0 stars
81 reviews
33 repeat clients
Profile image

Carla is the absolute best! I never regret trusting Carla with my fur baby and Bella loves her. Bella always seems so at ease and comfortable with Carla.

Availability updated yesterday
Sitter Profile Image: Michael A.
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Sitter Profile Image: Michael A.
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5. Michael A.

Star Sitter
I love walks and dogs!
Winter Park, FL, 32792
1.3 mi. away
Boarding
from
$50
per night
5 out of 5.0 stars
12 reviews
5 repeat clients
Profile image

Michael is the best and took amazing care of our dog Henry! We could tell that he and his wife love dogs as soon as we met them, and we knew our pup would be in great hands. Their house and fenced in backyard are perfect for dogs and they were flexible with drop off and pickup times. Henry loved his visit and can’t wait to stay at Michael’s house again! 10/10 would recommend ?

Availability updated 17 days ago
Sitter Profile Image: Christina W.
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Sitter Profile Image: Christina W.
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6. Christina W.

Star Sitter
Experienced SAH dog handler
Orlando, FL, 32810
6.8 mi. away
Boarding, House Sitting, Drop-In Visits, Dog Walking
from
$35
per night
5 out of 5.0 stars
80 reviews
31 repeat clients
Profile image

Christina was wonderful with the care of my dog QC. Our dog's are our children , which some do not understand. So I was pretty nervous due to past experiences with close friends. Christina kept me well updated & sent me pictures of him. My boy is very energetic & sometimes I need him to calm down .. lol. After coming back from Christina's he was very calm. Went straight to the bedroom & layed out on the carpet snoring loud 😂. I would Definitely recommend & definitely rebook with her.

Availability updated 2 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Zuleica c.
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Sitter Profile Image: Zuleica c.
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7. Zuleica c.

Star Sitter
Looking for a four legged friend
Winter park, FL, 32792
3.2 mi. away
Boarding
from
$30
per night
5 out of 5.0 stars
30 reviews
7 repeat clients
Profile image

Zuleica did such a wonderful job watching our dog, Leia. She sent plenty of photos throughout the week and always assured her safety and comfort.

Availability updated 15 days ago
Sitter Profile Image: Kevin S.
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Sitter Profile Image: Kevin S.
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8. Kevin S.

Rover 101
Star Sitter
Experienced Dog Handler & Dog Lover
Fern Park, FL, 32730
3.7 mi. away
Boarding, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
541 reviews
211 repeat clients
Profile image

My dog loved her stay. Kevin sent pictures multiple times per day. Jazzy was care for very well during her stay we'll definitely board her with Kevin again!

Availability updated 4 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Melanie & Troy W.
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Sitter Profile Image: Melanie & Troy W.
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9. Melanie & Troy W.

Need our dog fix
Audubon Park, Orlando, FL, 32803
2.5 mi. away
Boarding
from
$50
per night
5 out of 5.0 stars
16 reviews
5 repeat clients
Profile image

Melanie and Troy took great care of our pup while we were away for a weekend vacation. Their proactive communication allowed us to enjoy our trip. We’ll be checking with them again next time we need someone to watch her.

Availability updated 3 days ago
Sitter Profile Image: Gabriela D.
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Sitter Profile Image: Gabriela D.
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10. Gabriela D.

Star Sitter
Your fur babies are like family to
Central Business District, Orlando, FL, 32801
4.8 mi. away
Boarding
from
$30
per night
5 out of 5.0 stars
21 reviews
7 repeat clients
Profile image

Gabriela did such a great job with our puppy! Chuck can be kind of picky when it comes to the people who watch him but it appears he grew very fond of gabriela and her family! We got daily updates with pictures while we were away and we will 100% be asking her to watch our dog again! She is an incredibly sweet, responsive, and responsible sitter:)

Availability updated yesterday
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Jennifer B.
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Sitter Profile Image: Jennifer B.
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11. Jennifer B.

Star Sitter
Runs with dogs 🐕 🏃‍♀️
Maitland, FL, 32751
3.4 mi. away
Boarding
from
$50
per night
5 out of 5.0 stars
33 reviews
17 repeat clients
Profile image

Jennifer provided excellent care for my dogs while away for a long weekend staycation. She provided pictures and updates daily, and I know the dogs enjoyed their time with her and her family. Now they need a few days to recover from the extra fun and attention!! Would recommend, and book, again without any hesitation!

Availability updated today
Sitter Profile Image: Debra R.
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Sitter Profile Image: Debra R.
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12. Debra R.

Two Sisters that LOVE Dogs!
Casselberry, FL, 32701
4.6 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$45
per night
5 out of 5.0 stars
194 reviews
83 repeat clients
Profile image

We will happily bring our dogs to Debra again. It’s always a little scary leaving our dogs with someone else, but Debra put our minds at ease right away. She sent daily updates including pictures and/or videos. It was a bonus that she genuinely seemed to love our dogs. Plus, her dogs seemed to get along well with ours. She was flexible when I had to update care instructions for one dog due to a medical issue. Debra went above and beyond for our babies. We are very, very grateful.

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Sara S.
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Sitter Profile Image: Sara S.
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13. Sara S.

Rover 101
Aspiring Vet Student
Winter Park, FL, 32789
1.3 mi. away
Boarding, Doggy Day Care
from
$42
per night
5 out of 5.0 stars
8 reviews
3 repeat clients
Profile image

Sara was fantastic and kept me well informed during my pet’s stay with her. She is very warm and friendly and understood my dog and her needs. Thank you Sara! I will certainly use your services again!

Availability updated 2 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Lauren E.
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Sitter Profile Image: Lauren E.
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14. Lauren E.

Star Sitter
Energetic animal lover near dogpark
Maitland, FL, 32751
2.5 mi. away
Boarding, House Sitting, Drop-In Visits, Doggy Day Care, Dog Walking
from
$36
per night
5 out of 5.0 stars
15 reviews
5 repeat clients
Profile image

We felt very comfortable leaving our puppy in the care of Lauren! She has great communication and sent multiple updates every day! She cared for our dog as her own and we will definitely be returning to her when we need pet sitting again!

Availability updated today
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Leda B.
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Sitter Profile Image: Leda B.
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15. Leda B.

Star Sitter
I love animals,
Lawsona-Fern Creek, Orlando, FL, 32801
4.2 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$37
per night
5 out of 5.0 stars
77 reviews
22 repeat clients
Profile image

My girls absolutely enjoyed their time with Leda! She took amazing care of them and even provided photos of them, which put us at ease. I would definitely recommend Leda to anyone in the area.

Availability updated today
Sitter Profile Image: Martha D.
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Sitter Profile Image: Martha D.
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16. Martha D.

Star Sitter
Who Wants a Belly Rub?
Monterey, Orlando, FL, 32807
4.6 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$35
per night
5 out of 5.0 stars
30 reviews
14 repeat clients
Profile image

Martha & her family took great care of my little yorkie. It was our first time using Rover and her first time not staying at a family members home. We couldn’t be more happy with the care and updates we received! If we’re in the Orlando area again we would definitely feel comfortable leaving her with Martha & her sweet family!

Availability updated 25 days ago
Confirmed availability for Juneteenth Weekend
Sitter Profile Image: Tia W.
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Sitter Profile Image: Tia W.
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17. Tia W.

Star Sitter
I'll run, cuddle & play with ur PUP
Casselberry, FL, 32707
4.4 mi. away
Boarding, House Sitting, Doggy Day Care
from
$38
per night
5 out of 5.0 stars
128 reviews
77 repeat clients
Profile image

It was very easy to communicate with Tia about our dogs' needs and our schedules. She is flexible, accommodating, and above all, loves pets. We felt comfortable leaving our dogs from the moment we met her and think her home is also good for pets.

Availability updated today
Sitter Profile Image: Heather G.
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Sitter Profile Image: Heather G.
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18. Heather G.

Experienced dog (and cat) mom
Winter Park, FL, 32792
1.8 mi. away
Boarding, Drop-In Visits, Doggy Day Care, Dog Walking
from
$50
per night
5 out of 5.0 stars
16 reviews
3 repeat clients
Profile image

Heather was an awesome sitter for our Lily. Her dogs mingled well with our 15lbs princess! The two night stay went well. We highly recommend Heather !

Availability updated 14 days ago
Sitter Profile Image: Marie T.
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Sitter Profile Image: Marie T.
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19. Marie T.

Star Sitter
Fenced dog yard w/ toys & chickens!
Orlando, FL, 32817
6.6 mi. away
Boarding, Doggy Day Care
from
$34
per night
5 out of 5.0 stars
57 reviews
21 repeat clients
Profile image

Marie was amazing at taking care of my 2 yrs old pit, Bella. She had a great time staying with Marie and her dog and they went for walks everyday which Bella absolutely love. Definitely recommend her for your pup stay.

Availability updated 4 days ago
Sitter Profile Image: Bruce C.
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Sitter Profile Image: Bruce C.
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20. Bruce C.

Rover 101
Star Sitter
A Doggies Heaven on Earth
Oviedo, FL, 32765
8.9 mi. away
Boarding, Doggy Day Care
from
$40
per night
5 out of 5.0 stars
536 reviews
151 repeat clients
Profile image

I'd like to thank Bruce to take care of Charlie well. Many pictures sent by the time frame make me peaceful and assure that he is doing fine. I appreciate all he did for Charlie?

Availability updated today

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