Dog Boarding in Winter Park
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Top rated Winter Park dog boarders
“Joan is beyond wonderful. She treats our dogs, Trooper & Brody like they were her own four-legged fur babies. They so enjoyed the daily adventure walks and all the sights & sounds they experience. We love the daily activities report along with photos. She makes our time away from Trooper & Brody very special since we know they are loved and happy while spending time with Joan. She is truly a very special person. ❤️🐾🐾”
“Shanik took such great care of our Aussie Shepherd -- she was communicative, prompt, sent photos along the way, overall just made sure our fur baby was safe & happy! Will definitely use her again! Thank you, Shanik!”
“Jenna took such good care of my dog, taking him on a great hike for the day I needed her to watch him (even with a short notice of needing her sitting help) Very happy and would recommend!”
“Ellyn was amazing! She took care of our dog during our wedding week and was able to accomodate our special requests with no questions asked. Our dog (Denver) was in our ceremony so she made sure he was nice and tired and CLEAN before the big day. She treated him like her own and I could tell how much fun and love Denver received while in her care. I will be booking again next time Denver needs special care!”
“Sue was absolutely wonderful with my 10-year old GSD. She was very flexible on arrival and pickup times, and never left her by herself alone. I’ll definitely be reaching back out.”
“Michaela was amazing!! She sent me lots of pictures and kept me updated on my dog throughout his stay. I could tell he was having a great time and was safe and cared for which really helped me to enjoy my trip!”
“Justin took great care of my dog. He updated with pictures, which was greatly appreciated. My dog came home exhausted in the best kind of way - she had a lot of fun with Justin and his dog!”
“Amanda was great! She responded quickly and was able to accommodate on short notice. She sent pictures and took Maggie on one of her favorite walks! I had a tired pup when I picked her up, which is always a guarantee that she had a good time. I will definitely be using Amanda again!”
“Addison was so accommodating, easy to communicate with and sweet with my dog! She sent updates and pictures, and took great care of her. Highly recommend and hope to book with her again in the future :)”
“Tracy has been amazing, I don't know what I would do without her! She has taking the absolute best care of Bell, she has been always responsive and always kept me updated. Tracy has made my out of town trips not as bad my making sure I know Bell is doing well and sending lots of pictures. I would highly recommend Tracy!”
“This was our second stay with Nicole and Craig. Not only does their family provide love and care for our precious Shibas, but they are patient with their quirks and persistent food hunting! Thank you Nicole, Craig, and your boys for keeping Winnie and Rocky safe and loved while we are away!”
“Mitzi is organized and professional. She responds quickly. We felt confident in her services for our first boarding opportunity for our seven month old puppy and she delivered in every way. She showed interest and proactive action regarding our concerns about where we thought he might have trouble. He had a great stay and she sent some fun photos!”
“Robyn was great with our pup. She sent pics every day so we could be reassured all was well. Off leash time to get the crazy out is something our dog needs, so it was fantastic that there is public land across the street where the dogs could run around together. When we picked our dog up, she was having a great time and didn’t even notice us at first. I’m so glad she had a relaxing and social experience while we were gone. We will be back!”
“By all accounts Maple had a great time with Fred! I enjoyed the pictures and could tell she was in a dog lovers home! Peace of mind, while out of town, is priceless.”
“Excellent experience with Missy and Evan. Great communication, flexible schedule, and clearly a loving home. Thanks and if you’ll have my pup again, we’ll be back!”
“Chelsea was FANTASTIC!!! She always made sure to take so many pictures of my baby. She took my dog for a walk and let her run around on such beautiful green grass fields every day! She went out of her way to drop my dog off to me as well. 10/10!!!”
“Della is absolutely incredible! She will always be my first stop for dog boarding, and I have already recommended her services to my friends. I cannot say enough good things about her thoughtfulness, structure, and approach with the dogs. Seriously, use her. Trust me.”
“Jessica is the BEST! She made sure to check in everyday, sometimes multiple times because I missed my little one so much, she sent pictures, videos, and adhered to Kona’s raw diet flawlessly. When I go on trips, Jessica will definitely be my go to!”
“Maggie was an amazing sitter. Maggie (my dog) had a great stay and was so happy and well cared for. I received photo updates throughout her stay and communication was great.”
Loving dog boarding sitters in your neighborhood
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Joan C.Star Sitter
“Joan is beyond wonderful. She treats our dogs, Trooper & Brody like they were her own four-legged fur babies. They so enjoyed the daily adventure walks and all the sights & sounds they experience. We love the daily activities report along with photos. She makes our time away from Trooper & Brody very special since we know they are loved and happy while spending time with Joan. She is truly a very special person. ❤️🐾🐾”
Jan R.Star Sitter
“We left Croix with Jan and her husband for a week. He was well cared for and taken for multiple walks and hikes. Thanks for taking such great care of our boy.”
Shanik C.Star Sitter
“Shanik took such great care of our Aussie Shepherd -- she was communicative, prompt, sent photos along the way, overall just made sure our fur baby was safe & happy! Will definitely use her again! Thank you, Shanik!”
Jenna & Paul C.
“Jenna took such good care of my dog, taking him on a great hike for the day I needed her to watch him (even with a short notice of needing her sitting help) Very happy and would recommend!”
Ellyn A.Star Sitter
“Ellyn was amazing! She took care of our dog during our wedding week and was able to accomodate our special requests with no questions asked. Our dog (Denver) was in our ceremony so she made sure he was nice and tired and CLEAN before the big day. She treated him like her own and I could tell how much fun and love Denver received while in her care. I will be booking again next time Denver needs special care!”
Sue D.Star Sitter
“Sue was absolutely wonderful with my 10-year old GSD. She was very flexible on arrival and pickup times, and never left her by herself alone. I’ll definitely be reaching back out.”
Mychaela R.
“Michaela was amazing!! She sent me lots of pictures and kept me updated on my dog throughout his stay. I could tell he was having a great time and was safe and cared for which really helped me to enjoy my trip!”
Justin E.
Star Sitter
“Justin took great care of my dog. He updated with pictures, which was greatly appreciated. My dog came home exhausted in the best kind of way - she had a lot of fun with Justin and his dog!”
Amanda P.
“Amanda was great! She responded quickly and was able to accommodate on short notice. She sent pictures and took Maggie on one of her favorite walks! I had a tired pup when I picked her up, which is always a guarantee that she had a good time. I will definitely be using Amanda again!”
Addison E.
“Addison was so accommodating, easy to communicate with and sweet with my dog! She sent updates and pictures, and took great care of her. Highly recommend and hope to book with her again in the future :)”
Tracy B.Star Sitter
“Tracy has been amazing, I don't know what I would do without her! She has taking the absolute best care of Bell, she has been always responsive and always kept me updated. Tracy has made my out of town trips not as bad my making sure I know Bell is doing well and sending lots of pictures. I would highly recommend Tracy!”
Nicole & Craig K.Star Sitter
“This was our second stay with Nicole and Craig. Not only does their family provide love and care for our precious Shibas, but they are patient with their quirks and persistent food hunting! Thank you Nicole, Craig, and your boys for keeping Winnie and Rocky safe and loved while we are away!”
Mitzi & Klifton K.Star Sitter
“Mitzi is organized and professional. She responds quickly. We felt confident in her services for our first boarding opportunity for our seven month old puppy and she delivered in every way. She showed interest and proactive action regarding our concerns about where we thought he might have trouble. He had a great stay and she sent some fun photos!”
Robyn S.Star Sitter
“Robyn was great with our pup. She sent pics every day so we could be reassured all was well. Off leash time to get the crazy out is something our dog needs, so it was fantastic that there is public land across the street where the dogs could run around together. When we picked our dog up, she was having a great time and didn’t even notice us at first. I’m so glad she had a relaxing and social experience while we were gone. We will be back!”
Fred A.Star Sitter
“By all accounts Maple had a great time with Fred! I enjoyed the pictures and could tell she was in a dog lovers home! Peace of mind, while out of town, is priceless.”
Missy & Evan Z.Star Sitter
“Excellent experience with Missy and Evan. Great communication, flexible schedule, and clearly a loving home. Thanks and if you’ll have my pup again, we’ll be back!”
Chelsea B.Star Sitter
“Chelsea was FANTASTIC!!! She always made sure to take so many pictures of my baby. She took my dog for a walk and let her run around on such beautiful green grass fields every day! She went out of her way to drop my dog off to me as well. 10/10!!!”
Della S.Star Sitter
“Della is absolutely incredible! She will always be my first stop for dog boarding, and I have already recommended her services to my friends. I cannot say enough good things about her thoughtfulness, structure, and approach with the dogs. Seriously, use her. Trust me.”
Jessica L.
“Jessica is the BEST! She made sure to check in everyday, sometimes multiple times because I missed my little one so much, she sent pictures, videos, and adhered to Kona’s raw diet flawlessly. When I go on trips, Jessica will definitely be my go to!”
Maggie G.Star Sitter
“Maggie was an amazing sitter. Maggie (my dog) had a great stay and was so happy and well cared for. I received photo updates throughout her stay and communication was great.”
Over 26 pet parents in Winter Park have booked dog boarding
Popular requests near you
Select a filter and find qualifying Winter Park sitters!How Rover works
1. Search
Read verified reviews by dog parents like you and choose a boarder who’s a great match for you and your dogs
2. Meet & Greet
Meet either virtually or in-person with a boarder to discuss the level of care needed for your dogs while you’re away
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 dog boarding in Winter Park is $72
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 boarding sitter has to cancel, we’ll work with you to find a new dog boarding sitter.
World-class support
We’re friendly, knowledgable, and total dog fanatics. You can get in touch with us anytime.
Sitters in Winter Park average 4 repeat dog boarding clients
Dog Boarding FAQs
Frequently asked questions about Rover
As of Aug 2025, the median cost of dog boarding in Winter Park is $72 per night, including service fees. Boarding your dog for one week typically costs $504. Sitters on Rover set their own rates based on their qualifications, your dog's needs, and their space's amenities. As a result, most Winter Park dog boarding rates can be found as low as $29 to as high as $66 per night.
As of Aug 2025, 90 sitters provided dog boarding in Winter Park. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect sitter near you. As a reminder, dog boarding sitters joining Rover must pass a background check for you and your dog’s safety.
Rover makes it easy to reach out to multiple sitters about your booking. Typically, 92% of Winter Park dog boarding sitters respond in under an hour.
Sitters who provide dog boarding in Winter Park have an average of 17 years of experience. Dog boarding sitters with repeat customers have an average of 4 repeat clients. Experience can vary from sitter to sitter, but you can view reviews, years of experience, and number of repeat clients when you compare sitters in Winter Park.
Rover makes it easy to find Winter Park dog boarding sitters to provide loving care from their own home. The background-checked, 5-star sitters you can find on Rover will welcome your dog into their home when you’re away—whether it’s just for the weekend or longer. Dog boarding is great for:
- Dogs of all ages and abilities, including puppies
- Pet parents looking for a safe, loving alternative to a kennel
- Dogs who’d love to socialize with their sitter’s pets
There are 90 dog boarding sitters in Winter Park on Rover, so you’re sure to find the perfect match for your dog! In Winter Park, 100% of sitters offer daily exercise, 100% offer medication administration, and 100% have experience with senior dogs and dogs with special needs. We know each dog is unique and may have specific care instructions. You can filter, sort, expand your radius, read reviews, and compare pricing to find the perfect dog boarding sitter near you. As a reminder, sitters joining Rover must pass a background check for you and your dog’s safety.
Yes! Sitters joining Rover must pass a background check before offering their services. You can also easily keep in touch with your dog 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 dog 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 dog boarding service. You can cancel an upcoming booking directly from the Rover app or your computer, in accordance with your sitter’s cancellation policy.
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